The software may be doing its job. The handoff around it may not be.

That gap is especially easy to miss when you’re close to the product. You see a workflow that makes sense: information comes in, the system matches it, the right person reviews it, the next step happens. You’re so close to the product you can no longer see them, but the people using the system experience the seams. A clinic needs to know what to do. An operations team needs to explain the process. A technical partner needs to investigate an exception. Someone has to make the call when the normal path doesn’t work.

If nobody knows who owns that next step, the customer feels it.

The company is the workflow, too

Picture a growing health tech company selling software that helps information move between healthcare organizations. The product depends on integrations, permissions, data quality, and people following the right steps (and boy do we know this part is fallible). Not to mention all the regulations and red tape you have to navigate. Its customers aren’t all doing the same job. A front-line user needs practical instructions. An operations lead needs to understand the workflow. A technical team needs enough detail to diagnose what went wrong.

The founder knows all of this. She has spent years in the industry and can explain the product, the customer problem, and the edge cases in mega-impressive detail.

She’s also become the person everyone asks to translate. Whomp. Whomp.

A customer asks what happens next. The internal team checks with her. A technical question turns into a Slack thread. A process decision lives in someone’s memory. The same explanation gets rewritten for different audiences, sometimes slightly differently each time.

This is a made-up composite, based on patterns I’ve seen with 15+ years of health tech operations experience.

The problem in this example isn’t that the founder failed to communicate. She’s communicating constantly. The problem is that the company has made her the place where communication has to pass through.

That works for a while. Eventually, it becomes part of the product experience, whether the company meant for it to or not.

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Find the seam where the work changes hands

The first step isn’t to buy another platform or write a giant process document. It’s to find the moment the work changes hands.

A customer completes one step. It’s time to ask:

• Who owns the next one?

• What information do they need?

• Where does it go?

• How do they know it’s complete?

• What happens when the usual path breaks?

Those questions sound basic. And you know what, they are basic! They’re also where a lot of operational ambiguity hides.

In health tech, the answer may differ depending on whether the person is a clinic user, an implementation lead, a partner or an internal technical owner. A single “how it works” document may not help any of them. It can leave the people doing the work to interpret what applies to them, then ask the founder when they’re unsure.

A clearer system gives each person the information they need at the point they need it. The end user gets the next steps in plain language. The internal team knows who owns the follow-up. The technical team knows what information to include when something needs investigation. The founder can still handle exceptions and important decisions without being the default route for every question.

Make the work legible to the people doing it

Start by walking through the customer journey with the people closest to the work. Not to create a perfect map for a binder, but to see where real people pause, repeat themselves or have to ask for help.

Then the team could make a few practical changes:

• Write separate, role-specific guides instead of one document for everyone.

• Name an owner for each handoff, including what they receive and what they’re expected to do next.

• Clarify what counts as a routine question, an exception and an issue that needs technical review.

• Give the team a shared place to record decisions and unresolved questions, so answers don’t disappear into chat.

• Set a regular time to review what keeps getting stuck and decide whether the process, product or guidance needs to change.

None of that is especially glamorous. It is also the work that helps a good product feel dependable.

In an early-stage company, the founder should still be close to customers and important decisions. We aren’t trying to make them fully unavailable. The goal is to stop routing ordinary work through one person simply because the rest of the system is unclear.

A founder becomes a bottleneck when the same question keeps finding its way back to her. That’s a signal about the company’s design, not a reason to blame the people asking.

The customer experiences your operating system

Health tech founders carry an extra kind of responsibility because it's so personal. A confusing handoff can affect a busy clinician, a patient waiting for information, or a partner trying to do the right thing without knowing which step comes next. The internal process may look like “just operations” from the inside. From the customer’s perspective, it’s part of whether the product feels safe to rely on.

That doesn’t mean every workflow needs layers of governance. It means the human path around the technology deserves the same care as the technology itself.

Your product may be the software. The experience is everything required to make the software useful: the instructions, the ownership, the follow-through, and the way the team handles exceptions.

Founders (in health tech and beyond), try tracing one important workflow from the customer’s first action to the moment they get value. Notice every place where someone has to ask, “Who has this now?” or “What am I supposed to do next?”

That’s probably where your operating system is showing through.

If you’re feeling too close to the situation, an extra set of outside eyes can be really helpful. I love sitting with founders to plot this out and make it simple for all.

If you’ve been here a while, you know I love AI. Can’t overstate how much it has improved my ability to start and run a solo biz. Most days, I am on an AI high, my friends, but then I’ll read something about where AI could be headed and think: holy s*** are we on the edge of WALL-E? Blade Runner? Something that explodes? Okay, maybe my imagination has a flair for the dramatic, but the underlying question is real: what happens when technology moves faster than our ability to understand or govern it?

I don’t think stopping scientific progress is simple, or even the right answer. I can see how much good AI could do. I’m excited by what it might make possible for my 3-year-old daughter. I also catch myself wondering whether she’ll have a career, and you know, who the heck gets to decide what these systems are allowed to touch.

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I think that uncertainty is what makes me feel untethered lately. I don’t trust that the people making decisions at the top always know what they’re doing, or that they’re thinking first about what’s best for people. When the stakes feel that big, “just stay curious” doesn’t quite settle me.

I do know what uncertainty looks like in a startup. I seem to crave that world (15 yrs and I can’t quit you.): the risk, the figuring it out as you go, the constant change. It also means I know how much it helps to build some structure around the uncertainty. Clear ownership. Systems people can follow. Boundaries around what gets automated and when. Those things don’t give you control over everything. They do give you a better chance of seeing what’s happening and responding before the chaos gets wild.

I think about AI in business the same way. I want to be an empathetic leader first. People are what keep a company running, and they should know how valuable they are. At the same time, I believe people need to learn how to use AI in their work. It’s becoming part of how companies operate, and teams that refuse to adapt will fall behind.

Those ideas can sit beside each other. People can learn the tools and still be essential because they bring context, judgment, oversight, and an understanding of what a customer actually needs. The human role can change without becoming disposable.

There’s one line I keep coming back to: we should only automate workflows we trust and are proud of. Automating a broken process can make the confusion happen faster and at a much larger scale. Some customer issues may eventually be handled well by AI. I still firmly believe customers should still be able to reach a person quickly when they need one. That matters to me.

I don’t have a reassuring prediction about where AI is going. I’m not giving up the ways it helps me, and I’m still uneasy about the people deciding how it gets used in government, the military, and everywhere else. I also wonder whether we’re sitting with what this current generation of tools can do before rushing to make the next one smarter.

Maybe the thing I can hold onto is smaller than a prediction. In the company I help build, I can keep asking who benefits, what happens when the system gets it wrong, and whether a person can still get help from another person.

I can’t give my daughter certainty about the world she’ll work in. I can keep insisting that the businesses we build remember there are people inside them, and people on the other side of every system. Those people matter.

That’s not an answer to all of this. It’s something I can stand behind while I figure out what I think.

As you build or lead out there, what are you choosing to keep human?

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By the end of this you’ll have:

✅ A way to spot the handoffs hiding inside your day-to-day work

✅ A simple rule for who owns the baton until the next person is ready

✅ A clearer idea of what context actually needs to move with the work

✅ A downloadable worksheet to audit and redesign one of your own handoffs

Before we get into the template...

A lot of handoffs do not look like handoffs. They look like someone saying, “Can you send that over?” or “I told her in Slack,” or “CS should have that.”

It is a deal changing stages in HubSpot. Product makes a decision that creates work for Engineering. One person goes on vacation, and everyone realizes they were manually connecting three departments without anyone noticing.

If you are the operator or glue person, these can be especially hard to see because you are often the one filling the gaps. You chase the missing context, remind someone to update the CRM, tell Customer Success what Sales promised, and make sure the client does not have to repeat themselves.

After a while, that starts to feel normal. (Exhausting, but still, normal.)

That is usually when I start paying attention.

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Somehow, she still found herself personally calling ice cream trucks to save a company event.

That was one of my favorite stories from our Substack Live today, mostly because I’ve seen some version of it happen at nearly every growing company I’ve worked with.

The founder is still solving problems they shouldn’t have to solve. Not because they’re incapable of delegating, but because the team, roles, and ways of working haven’t quite caught up with the business.

Carly was refreshingly candid about the mistakes she’s made getting there. We talked about:

• Why hiring the impressive résumé doesn’t always mean hiring the right person.

• How staying too scrappy can actually start costing you money.

• Why delegating isn’t the same as handing someone a giant document of instructions.

• How to build a team that can make decisions without constantly pulling the founder back in.

One thing Carly said really stuck with me: As she prepares for her next maternity leave, she’s spending less time explaining how she would do things and more time making sure her team understands what outcomes they’re responsible for.

Pretty meaningful shift!

It’s also the difference between building a team that can follow instructions and building one that can actually operate without you.

Our conversation was a continuation of the first installment of Operator Questions for Founders, and I loved getting to compare what she’s learned in the founder’s seat with what I’ve seen from the operator side.

If you’re growing a team, making your next hire, or wondering why everything still seems to land on your desk, I think you’ll get something out of this one.

And if you missed our original article, What Nobody Tells You About Scaling a Lean Team, you can catch up here.

A huge thanks to Carly for being so generous with her experiences, especially with baby number two arriving soon!

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• What did you hire too early?

• What did you hold onto too long?

• Where did “scrappy” stop working?

• What did growth expose that you couldn’t see when the company was smaller?

For the first issue, I talked with , founder of Beekeeper’s Naturals.

Carly has spent nearly a decade building Beekeeper’s from the founder seat, which means she has the kind of operating scar tissue I care about: expensive hiring lessons, places where running lean worked brilliantly, places where it became an overcorrection, and a very real test of whether the company could keep moving when she stepped away.

I’ve spent most of my career walking into companies after the “we’ll figure it out as we go” phase starts showing cracks.

So when Carly and I started comparing notes, we kept coming back to the same thing:

Founders can spend an extraordinary amount of money trying to solve problems they haven’t actually diagnosed yet.

A big hire. An agency. Another tool. Another layer of management.

Sometimes that absolutely is the answer.

Sometimes somebody just needed to ask: Wait. What exactly is broken here?

That’s what I wanted to get into with Carly: the decisions founders usually understand much better after they’ve already paid for the lesson.

More people can make a messy system more expensive

I asked Carly:

When you think back over almost 10 years of building Beekeeper’s, where have you spent money because you thought adding a person would solve a problem that you later realized was actually a structure or clarity problem?

Her answer immediately went to marketing.

“It’s challenging because sometimes the skillset for creativity and strategy is very different from organized and execution oriented. Also it can be very compelling to work with agencies who have amazing pitches and specialize in areas you need to grow but you can quickly drain cash if you aren’t crystal clear on what you want the agency to solve, how they have an edge or create value you can’t generate on your team and they require ongoing oversight.”

She also said:

“People can have the best ideas but if there isn’t follow-through on who does what throughout a campaign; things can come out half-baked. Another issue can be lack of tracking. Results need to be analyzed and used to inform future decisions and sometimes that’s not intuitive for creatives who want to move quickly to the next exciting idea.”

This was the part I underlined:

“Sometimes adding an extra person actually creates more of a bottleneck.”

That is one of the biggest patterns I see from the operator side, too.

A vague problem creates a vague role.

Then you have an expensive person trying to invent their own job while the founder is sitting there six months later wondering why nothing feels easier.

Before I recommend adding headcount, I want to know:

• What is actually breaking?

• Who owns it today?

• What outcome are we trying to change?

• Is this truly a capacity problem?

• Or is it an ownership, process, or decision problem?

Headcount can cover up operational problems for a surprisingly long time, but it makes them a heck of a lot more expensive.

The big logo on the resume is not the job description

This is one Carly and I are both a little spicy about.

I asked her:

You mentioned seeing founders get excited about candidates with huge companies on their resumes, and how they spend aggressively without really knowing whether that person can build in an early-stage environment. What have you learned about evaluating people for a lean team?

Her first point was simple:

“Step one is understanding the holes on your team.”

She said not to assume someone has been through the thing you need just because they worked somewhere impressive or at a place that scaled the way you hope to.

“One independent person is not necessarily responsible for the whole, so try to get a sense of the team and structure they had around them, and then try to see how similar that is to what you have currently.”

She also wants to understand “what tactical elements from the previous company they were personally accountable to and responsible for.”

That distinction matters a lot.

A recognizable company on someone’s resume tells you where they worked.

It does not tell you what they personally built, what support they had around them, or whether they can operate inside your current environment.

At a large company, a senior person may have specialist teams, mature tools, established budgets, deep data, agencies, and layers of support around them.

At an early-stage company, that same person may need to find the problem, make the spreadsheet, talk to the customer, stand at the booth, and build the system from scratch and more.

Those are different jobs.

When I asked Carly what “gritty” actually looks like in practice, she said:

“Trying things yourself before throwing money at the problem.”

And:

“Getting things wrong a couple of times and being okay with that.”

She gave me one example I loved:

“I’ll still go to events and stand at a booth. I’ve never been above that. It might not always be the best use of an expensive person’s time to always be doing that type of work, but it’s a mentality thing. If a senior person does what they may call ‘grunt’ work once in a while, it sends a major signal to everyone else on the team that the work they’re doing is important. It also keeps them connected to different facets of the company and helps them ladder up to the goals in a real way.”

That is the part founders should be screening for.

Not “have you worked somewhere impressive?”

More like:

Tell me about something you had to build when there was no team, limited resources, no playbook, and no obvious owner yet.

Scrappy has an expiration date

Of course, there is a very important counterpoint here.

Sometimes the expensive senior hire is exactly the right answer.

I asked Carly:

You said there have been moments where you looked up and thought, “How have I been doing this this way for five years?” What’s an example of something that worked because you were close enough to it, until suddenly it absolutely did not?

She went straight to supply chain.

“We have a very complex supply chain. At the start I couldn’t afford an expensive hire, and I needed to do it myself at first to really get a good understanding of it.”

Doing it herself gave her context. Then came the in-between stage.

“There was this weird in-between time where the cost of hiring someone who knew more than me would have been so astronomical. But once I made the decision to make that hire, they more than paid for themselves.”

She knew she had hit the limit when shipping costs went up and maintaining margin became a real business problem.

“It would have taken pretty much all my time to solve that problem. Once I brought that hire on they solved so many other challenges that I realized I could have been way more efficient way sooner.”

That is the tension of running lean.

Scrappy is useful when it buys speed, learning, and resourcefulness.

Once it starts creating repeat confusion, missed opportunities, or founder dependency, the math changes.

Carly’s line on this was probably the cleanest:

“Periodically gut-checking your thesis on how you're spending your time is so important.”

Just because you can do the work does not mean you should still be the person doing it.

This is where I think founders often overreact in the other direction and assume “more structure” means bureaucracy. When it really does not.

Usually the team just needs clearer ownership, one place to find the answer, cleaner handoffs, and a predictable way to make decisions. (Oh hello…this is what I write about every week!)

Carly made another point I think is worth sitting with.

“I was so obsessed with running lean I think I overcorrected but I would still do 90% of it again.”

Still, she said there were select areas, “like supply chain and finance,” where specialists, a more built-out team, and better process or structure would have been useful sooner.

That is the distinction.

Lean is not the real goal. A company that can execute well with the right amount of people and structure is the goal.

The final test: can the company work when you are not in the room?

I asked Carly:

Your first maternity leave gave you a pretty unforgiving test of whether the company was actually set up for you to step away. What did that experience expose?

Her answer was candid:

“It exposed a lot of gaps in our org structure. There were certain areas of the business where it was a lot harder to function without me than it should have been.”

She said they saw a real decline in KPIs in some areas, and that it showed her two things she had been doing wrong.

“1. Not delegating enough and 2. I had too junior of a team that could follow a step-by-step game plan but couldn’t decipher when a pivot was necessary or when to ramp up.”

Following a plan is not the same thing as being able to interpret what is happening and make a call.

For this upcoming mat leave, she has prepared differently.

“This time I’ve brought on more senior leadership who are really strong in the areas we saw weakness last time.”

She has also been more deliberate about pressure-testing leadership before she steps away.

“I’ve also been more specific with feedback. Brought on people who have similar instincts and have had them partner with me on multiple projects prior to mat leave so I could validate that hypothesis. I’ve been clear with people in leadership roles where I think things could go wrong, and I’ve had ongoing conversations about possible challenges and pitfalls I see, and we’ve all strategized and pressure-tested possible scenarios. Obviously, you can’t plan for everything.”

You cannot plan for everything, but founder absence is one of the cleanest stress tests of an operating system.

You can be deeply involved in your company without being the answer key for your company.

And this applies well beyond maternity leave.

Vacation. Illness. Fundraising. A giant launch. Or simply needing enough headspace to do the actual CEO job.

Before you make the next big hire

I asked Carly one last question:

What would you tell a founder who is growing quickly, has money to spend, and feels like the obvious answer is “we need more people”?

Her answer:

“Really understand the gaps in your growth, what could go wrong, and what could slow you down, what could lead to a missed opportunity. Don’t just bring on fancy people from fancy places thinking they’ll know what to do.”

She also said to consider the challenges the business is facing right now and how that hire’s skills relate to the strengths and gaps of the team you already have.

That is exactly where I would start too.

Go to the people closest to the work.

Map where things are getting stuck.

Clarify ownership.

Fix the obvious repeat friction.

Then decide whether the answer is another person.

Sometimes it truly is, but when it is, you will know what you need them to own, what success looks like, and what kind of environment they need to operate in.

That gives the company a better shot.

It also gives the new hire a fighting chance.

Join Carly and me Thursday, October 15 at 2 PM PT for a live conversation here on Substack. We’ll go deeper on all of this: hiring, founder dependency, scrappy systems, and what actually needs to be in place before you scale.

Bring your questions. We’ll get into the messy stuff.

A quick gut check before you hire

• Name the actual problem. “We’re overwhelmed” is a symptom, not a job description.

• Talk to the people doing the work. They usually know where the friction is.

• Clarify who owns what before adding another owner.

• Fix the repeat confusion first. A cleaner handoff, one decision rule, or simple documentation can go a long way.

• Hire for the company you actually have, not the company you hope to look like three years from now.

A lean team is incredibly powerful when clarity is high.

Without clarity, lean starts looking a lot like everyone doing three jobs and hoping the founder remembers the answer.

That gets expensive fast.

I might spend the morning rebuilding an entire customer onboarding journey, figuring out where Sales is handing off incomplete information, where customers are getting stuck, and what needs to change to make the experience better. Thennn an hour later, I’m helping a finance team figure out how to name and organize their documents so leadership can actually find the financial information they need.

Both of those things are operations. Both are important. One sounds considerably more impressive when I tell people what I do for a living. I’d say that’s probably a pretty good introduction to fractional COO life.

You get invited into someone else’s mess

When I start working with a founder, they usually have a pretty good idea of what they think is wrong with their company. They’ve been living with the problems, feeling the friction, and probably personally compensating for a lot of it.

I listen. I empathize. I try not to immediately assume they’re right.

Not because founders don’t understand their businesses, but because the view from the founder’s seat is only one view. The really interesting stuff tends to surface after I’ve talked with the people doing the work or been unleashed on the company Slack.

That’s when I start finding the gaps between what leadership thinks is happening and what is for real happening.

Sometimes a founder thinks they have a performance problem, but the team has never been given clear ownership. Sometimes everyone is frustrated with communication, but the real issue is that nobody knows where decisions get made. Sometimes a process looks perfectly reasonable on paper until you talk to the three people who have developed entirely different ways of working around it.

I weirdly love this part. It’s a little like being a detective, except the mystery is why five very smart people are having the same conversation every Tuesday.

The nice thing about having spent more than 15 years inside startups is that very few of these situations are completely new to me. The people and products are different, but the patterns start to look familiar. I can usually get to something useful much faster than someone who has to learn every lesson from scratch.

That speed is a MASSIVE part of what founders are actually buying.

Sometimes I’m working on things I never expected to touch

My background leans heavily toward the commercial side of businesses. I’ve spent a lot of time in marketing, communications, revenue operations, customer experience and the messy places where those functions meet.

Yet one of my health tech clients needed help establishing better rhythms and communication cadences for an engineering team.

Engineering! Not exactly where I expected my marketing and communications background to take me.

Except the underlying challenge wasn’t really about engineering. It was about how people communicate, make decisions, surface blockers and coordinate work across functions. Those problems show up everywhere, even when the technical work itself is completely different.

I didn’t need to become an engineer. I needed to understand how that team worked, where things were getting stuck, and what structure would actually help them.

This is one of my favorite things about being a generalist operator. You learn that so much of what makes a company function well is transferable. You just have to be willing to learn enough about the people and their work to apply it thoughtfully.

Occasionally that means going from a high-level strategy conversation to reorganizing a folder structure because nobody can find the numbers.

Sadly, there is no glamorous way to explain that last part. Still matters though!

The relationship can feel surprisingly close to having another co-founder

I think one of the biggest misconceptions about hiring a fractional COO is that you’re buying a certain number of hours of operational advice.

You can certainly structure an engagement that way, but the work I enjoy most is much more embedded.

A founder brings me into the business because they’re carrying too much of it themselves. They’re making decisions that other people should be able to make, keeping track of work that should be visible to the team, and spending time solving problems that keep coming back.

When the relationship works, I become another person who can hold some of that weight.

I can get into the details, have the uncomfortable accountability conversations, follow up on things that aren’t moving, and make decisions about what deserves attention RIGHT NOW versus what can wait. I can also tell a founder when I think they’re contributing to the very problem they’re frustrated by. Lovingly, of course. 😘

I don’t have the founder’s equity or their history with the business, and I’m not pretending those things are interchangeable. But I can bring a level of ownership and investment that feels a lot closer to an operating partner than an outside consultant.

For a founder who has been the default answer to every question for years, having another experienced person who can see the whole picture and actually do something about it can be an enormous relief.

Since I’ve been inside so many different versions of startup chaos, we don’t have to spend six months getting to that point.

There’s also the business of being fractional

Now for the part that doesn’t make it into the dreamy posts about fractional careers.

You still have to find the clients.

And unless you happen to have an enormous network of people waiting to hire you, that is a whole job in itself.

You’re building a brand, explaining what you do, creating content, meeting people, following up, nurturing relationships, and trying to stay visible enough that someone thinks of you when they finally realize they need help.

Then you sign a client, get wonderfully busy doing the actual work you love, and suddenly remember that you’re also responsible for keeping your own pipeline alive.

It’s a fascinating little cycle. (I spoke more here about how I discovered I am a lot like my founders when it comes to running my own biz.)

The irony of being an operations person running a fractional business is that you can be extremely good at building structure and accountability for other companies while having to remind yourself to apply the same discipline to your own.

Client acquisition has been one of the hardest parts for me. Not the actual operating work, which is where I feel most at home, but continually making the case for why someone should bring me into their business. (I find it very hard to sing my own praises. In an attempt to get over this, I recently asked some clients and past co-workers to recommend me as a little exercise. Highly suggest you do this as well!)

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Then there’s also the emotional investment.

I care about my clients. I care about their teams, their customers, their goals, and whether the things we’re building actually work. I’m still learning how to care deeply about a business without carrying every one of its problems home with me.

Being fractional doesn’t automatically make you emotionally detached. Sometimes it just means you have several companies to worry about instead of one.

This my friend is a very efficient way to diversify your anxiety.

The people might be my favorite part

For all the challenges, one of the biggest surprises has been how much I enjoy the people I get to meet.

I get to work with founders who have built things I never would have thought to build, teams solving problems in industries I might otherwise never have encountered, and incredibly talented people with completely different areas of expertise.

I get to learn how other people think. I get to see how different businesses operate from the inside. And I get to bring something I’ve learned in one environment into another where it might make a real difference.

That last part is especially satisfying.

Every company feels unique when you’re inside it. And of course, in many ways, it is, but after enough time moving between them, you start to realize how many challenges are shared. A founder struggling to delegate, a team with unclear ownership, a customer journey full of unnecessary friction. The details change, but the underlying problems often rhyme.

I think that’s what makes fractional work such a good fit for the way my brain operates. I like variety, I like figuring things out, and I like being useful. I especially like the moment when something that has felt impossibly complicated to a team suddenly becomes manageable.

I don’t need to be the permanent person in the room to help create that change.

So what does a fractional COO actually do?

Some days I help founders think through the next stage of their business. Some days I hold teams accountable to decisions they’ve already made. Some days I build the systems that allow people to do their jobs without constantly asking for permission.

And some days I organize financial documents.

The through line is that I help a company work better, whatever that happens to require.

For anyone considering a fractional career, I’d say the freedom and variety are real, but so are the responsibilities of building a business around your expertise. You have to be good at the work and willing to keep putting yourself out there so people know that work exists.

For the founders wondering what it would feel like to bring someone like me into their company, I think the biggest difference is that you don’t have to figure out every operational problem alone before asking for help.

You can invite someone into the mess while it’s still messy.

In fact, that’s generally where I do my best work.

Just please don’t make me guess which spreadsheet is the real one. 🤪

Want to get into the weeds together?

Whether you’re a founder trying to figure out what to hand off, an operator navigating a particularly messy challenge, or someone exploring a fractional career of your own, I offer paid Office Hours for exactly these kinds of conversations.

Bring me one thing you’re trying to untangle. We’ll spend 60 minutes working through it together, and you’ll leave with a clear, actionable plan for what I’d do next.

Book your Office Hours session here.

There is a wild thing happening these days with our access to AI and agents who can amplify all of the angles of our work. We’re choosing to lay AI on top of workflows that make ZERO sense. We want to keep moving fast and breaking things and boy are we cruising.

Sales has to ask CS exactly how to do the new client handoff every time.

Marketing has new sales enablement docs, but no one knows where to share and prep the sales team.

No one knows who owns renewal follow up.

There are important decisions stuck in 10 different Slack channels.

Obviously the natural and ideal next step for this is: LET’S GIVE ALL OF THESE JOBS TO AN AI AGENT!

We’ve made it to this new spot where we aren’t just asking AI to write us emails. Now we’re actually handing them the work. Which in some ways is pretty cool. As a solopreneur, I can truly say AI has done absolute wonders for my ability to make an impact and move fast. However, I’m not layering that agent on top until I’ve got clarity on what the actual F the agent should be doing. What’s that outcome supposed to be?

Your AI agent is the world’s most literal new hire

Imagine hiring a new employee and explaining that when a deal closes, Sales hands it off to CS. Usually. There is technically a process documented in Notion, although you’re not positive it’s the current one. Sarah knows what actually happens, so they should probably ask her. Enterprise customers are different for reasons no one has written down, and Mike knows about those. Billing has its own thing going on entirely.

Then you send this poor person off to work and three weeks later you’re annoyed that they’re not performing. (Not gonna lie, I have seen this exact situation an alarming amount of times.)

We would (or at least should) recognize pretty quickly that the new hire isn’t the problem. We handed them a scavenger hunt and called it onboarding.

Yet we’re starting to do essentially the same thing with AI agents, except our expectations are somehow HIGHER. We’re expecting them to walk into years of tribal knowledge, conflicting documentation, weird exceptions, and half-decided workflows and somehow emerge with a beautifully automated company on the other side.

The technology may be smarter than your average new hire, but it still cannot read Sarah’s mind. Which is unfortunate, because Sarah is apparently holding half the company together.

Humans have been hiding how broken some of this is

I actually think this is one of the more interesting things AI is exposing. Humans are remarkably good at compensating for bad systems. We just kind of remember that one customer gets special pricing. We know that when the founder says something is “approved,” there is still one more unofficial check before it actually goes out. We know which spreadsheet is the real spreadsheet and which one everyone continues updating for reasons lost to history.

None of that feels particularly dramatic when you’re a team of eight people. Everyone talks constantly, the founder is sitting in half the meetings anyway, and when something gets stuck, you yell across Slack until the right person fixes it. The company keeps moving, so you assume the system works.

Except there isn’t really a system. There are a bunch of smart people filling the spaces where one should be.

That distinction becomes much more obvious as the company grows, but AI is giving us another way to see it. The second you try to hand one of these workflows to an agent, you have to explain what actually happens. Suddenly “Sarah knows” isn’t enough. You have to decide what triggers the work, where the agent gets the information it needs, which version of that information it can trust, what it’s allowed to do on its own, and when a human needs to get involved.

Basically, you have to make all of the decisions you’ve been successfully avoiding while everyone was busy moving fast.

Oops.

AI might be the best operations audit we’ve gotten in years

This is where I think things get genuinely useful.

If you’re trying to build an agent and find yourself unable to explain exactly what it should do, I wouldn’t immediately assume you have an AI problem. You may have just discovered an existing operational problem that your humans have been politely working around for the past two years.

An agent forces those shadow things into the open because it needs more than “you know what I mean.” It needs an outcome and enough structure to reliably get there.

This is the part of the AI boom that makes me laugh a little.

For years, the decidedly unsexy side of startup life has been documenting how work happens, creating clear ownership, cleaning up information, and making sure people know what happens next. Startups wanted to talk about growth and innovation and speed. Nobody was breathlessly posting about their newly clarified decision rights.

Now we want fleets of intelligent agents moving work seamlessly through our companies, and what do those agents need?

They need us to know how the company works.

We have somehow built some of the most sophisticated technology humans have ever had access to and automated ourselves directly back to basic operations.

(Gosh, I love a Seinfeld-style full-circle moment.)

I still want the agents

None of this is an argument for being precious about AI or waiting until every process is perfect. That would be equally ridiculous, and very much NOT how startups work. There will always be some mess. There should probably be some mess. A ten-person company does not need to spend six months documenting itself before anyone is allowed to automate an email.

I am extremely bullish on what this technology can do for small teams. I’m already living a baby version of it myself. As one person, I can research, create, organize, analyze, and execute at a level that would have required considerably more time or help even a few years ago. I don’t want to give that back.

I just think we’re getting the order of operations wrong when we expect the AI to create clarity we haven’t created ourselves.

The companies that get the most leverage out of AI probably won’t be the ones with the greatest number of agents running around. They’ll be the ones that understand their work well enough to know exactly where an agent can make it better. They know what outcome they’re trying to create, what information matters, where human judgment still belongs, and what can safely disappear into the background.

That’s when AI gets really exciting to me. You’re no longer asking technology to compensate for the chaos. You’re giving it something good to amplify.

If your Sales-to-CS handoff makes no sense today, giving it to an AI agent doesn’t magically make it a system.

You’ve just given your chaos a company email address.

And let’s be real, it already had enough access.

Still, I know the patterns. Five projects going at once. 47 tabs open on their three different types of browsers. (One of them is running agents! Because AI.) Three new projects before launch. A Slack message at 11:42 pm because they finally put together what we have been trying to work through all week.

Mad ability to move between multiple often unrelated things at once. Slightly less impressive ability to close the loops on all of these killer ideas. I’ve spent 15 years helping train and harness the power of that brain.

Then last year, I started my own fractional business. And BOOM. Turns out when it’s my baby, I am exactly that human.

I didn’t realize how much structure was holding me up.

I was diagnosed with ADD after starting my business.

Looking back, I assume it had probably been there for a very long time. I just functioned really well. Actually, some of the things I now recognize as part of how my brain works were things I considered strengths. I am fantastic at multitasking. In fact, it’s a real challenge for me to only work on one thing at a time.

I was always the glue person. Holding a million things at once. I could move from finance to marketing to CS without ever losing the plot. It even helped me connect the dots across departments for others. I could see relationships between things happening in totally different parts of a business. (This is, BTW, extremely useful when your entire career is basically: walk into messy company, figure out why the hell everything is connected, fix it.)

Once I started my own company, though, it wasn’t just connecting those dots across one company. It was connecting cross-functional dots across several companies at once.

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There was a point in my first 6 months of building this where I had a real breakdown moment. I was completely overwhelmed and unsure how to get myself out of this spiral.

This is where I tried to listen to all of my own advice. Set up my own structure. Take time for me. (Yoga and breathing exercises work wonders…) Don’t be afraid to ask for help.

I talked about founder ADD in my recent live appearance with . The more we talked about it, the more I realized it shows up in my work.

Most founders are fantastic at opening loops. They can see the thing that no one else can see. They connect an issue CS is having with something happening in sales, which then reminds them of the product idea, that then leads to the partnership they’ve been thinking through. Which obviously then needs to be Slacked to their other glue person before they forget.

That brain can build a hell of a company.

The issue begins when the rest of the team is forced to react to ALL of these ideas and paths. At some point, your team cannot tell where you want them to go or how they can contribute to the success of the company. Meanwhile, the founder is wondering why the heck no one can follow at their pace, and they have to hold it all.

This is also why I’ve changed the way I think about my role with founders.

For a long time, I thought I was simply the Type A operator or integrator keeping a visionary person organized. There is definitely some of that. We all know how much I LOVE a system.

Actually, though, I think I’m good at working with these brains because I understand them.

I can follow the five jumps you just made in a conversation. I see why Idea #4 suddenly feels incredibly important. I can usually see the connection you’re seeing between three completely different parts of the company. My job is then to help you decide what we are actually going to DO about it.

So if you’re in one of those moments right now where EVERYTHING feels important, here’s what I want you to try.

Get it all out of your head first. Every project, weird idea, customer issue, Slack message you need to answer, thing you swear you’re going to remember later.

Put it somewhere you can see it. (Yep, literally on a doc.)

Then ask yourself three questions:

• What actually needs me?

• What can someone else own?

• What am I willing to deliberately NOT do right now?

The goal is NOT to stop having ideas. Please, please don’t. Some of your very best founder instincts probably come from the same brain currently making you want to launch six things before Friday.

You just need somewhere for all of that energy to go besides directly into the operating system of the company.

I’ve had to learn the same lesson about myself. I don’t need to become a person who only has one tab open. Frankly, that seems unrealistic and a little boring.

I DO need systems that help me close the important ones.

Turns out that’s pretty much what I’ve been building for founders all along.

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If you’re sitting in one of those moments where your brain has 47 tabs open, and you can’t tell which one actually matters, bring me one messy thing.

One process. One bottleneck. One project you cannot seem to close. One “I know this needs fixing but I don’t even know where to start.”

In Office Hours, we’ll spend 60 minutes pulling it apart together. You’ll walk away with a clear document outlining what I would do next, what matters first, and what can wait.

No giant consulting engagement required. Just one hour, one mess, and a plan.

Snag your hour

So before you turn your annoying little startup problem into A Whole Thing, here are the three questions I would ask.

Did this happen once, or is there a pattern here?

One weird customer handoff or bumpy employee onboarding might just be one weird day. If the same question keeps getting asked, the same client problem keeps surfacing, or you have fixed some version of the same issue five times, okay. Now I am on the hunt for the chaos gremlin.

Patterns usually mean something underneath the individual incident is broken. Ownership is fuzzy. The handoff is unclear. Information lives in someone’s head. The process technically exists, but no one follows it.

Is the problem actually what you think it is?

Founders will often tell me one department or one person is the problem, and then once we actually follow the workflow, the root cause is somewhere completely different.

Customer Success looks messy, but Sales is making promises nobody documented. Someone looks like they are dropping balls, but three different people are assigning them work in three different places. The team wants to automate something nobody can even explain the same way twice.

This is where an outsider helps. I am not attached to the story everyone inside the company has already agreed on. I can just ask annoying questions and follow the REAL workflow.

Does this need execution, a decision, or something else?

This one can save you a LOT of money.

There are times when you absolutely need someone to come in and do a full rebuild. A new onboarding flow, a real renewal process, a meeting cadence that works. There are other times when you do not need a six-month project or another software subscription. You just need someone to look at the mess and say, “Here are the three things I would change first.”

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I have spent 15+ years as a second-in-command for early-stage teams, working across customer success, sales, marketing, product, finance, and engineering. I have seen a LOT of weird little places where problems hide and fester. At this point, pattern recognition is probably one of the most valuable things I bring into a company.

I have followed one weird thread and found $30K+ in recurring revenue a company simply was not collecting. Other times I have watched everyone get frustrated by a supposed “people problem” that turned out to be one busted handoff. Sometimes the answer is even simpler: please do not turn this into a giant project.

That is why I am officially opening Operator Office Hours.

You bring me one messy thing. A team issue, a customer journey problem, some weird lil thing between Sales and CS, a process you want to automate, the spreadsheet you hate looking at. We spend 60 minutes pulling it apart, I ask the questions, poke at your assumptions, and help you figure out what is actually going on.

Afterward, I will send you a short Operator Triage note with what I think is happening, what I would do next, and what I would NOT spend time or money on yet.

Office Hours are $250.

No big prep required. Please do not make me a deck. Truly. Bring the ugly spreadsheet, the Slack screenshot, the questionable org chart, or the process everyone swears exists somewhere in Notion.

Let’s get our hands dirty.

BOOK AN OPERATOR OFFICE HOUR

Not sure if your thing fits? Reply with one sentence about the mess. I’ll tell you.

KB

P.S. If the answer turns out to be, “Katie, this is a much bigger ops problem,” I will tell you that too. You do not have to sit there spinning on it by yourself.

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One thing kept coming up: founders often think they’re sharing an idea, while the team hears an instruction.

Cory talked about this from his own experience as a founder with ADHD. Things connect quickly in his head, but that does not mean the team knows which idea is a real priority, which one is brainstorming, or what just got bumped off the list.

That’s why I’m such a fan of simple systems like decision logs, parking lots, clear owners, and visible priorities. Nothing fancy. Just enough structure so the team can answer: What are we actually doing? Who owns it? What changed?

We also got into a topic I think about constantly: tasks vs. ownership.

You can tell someone they “own” onboarding, but if you still make every decision around timelines, client communication, exceptions, tools, and process changes, they do not actually own onboarding.

Real delegation means handing over some judgment, not just assigning work.

We also talked about mistakes, accountability, and why a bad outcome is rarely one person’s fault. Sometimes the process was broken long before the employee ever touched it. The point is to find where it broke, fix the system, and not keep stepping on the same rake.

Very Systems & Side Eyes. 😂

Cory and I covered a lot more in the live, including neurodivergence, yes-people, founder accountability, and how much process is actually enough.

Thanks again to Cory and team for a fun convo. I kind of think we agreed on far too much… so next time we may need to come prepared with some opposing opinions. 😈

KB

P.S. If your company has reached the “everyone is smart but everything still somehow routes through me” stage, that is very much my lane.

Get more from Katie Barnes in the Substack app

Available for iOS and Android

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By the end of this you’ll have:

✅ A clearer definition of what “ownership” actually means

✅ A way to spot where ownership is getting fuzzy inside your company

✅ A simple test for what your team should be able to decide without the founder

✅ A downloadable worksheet to identify and map your biggest ownership gaps

Before we get into the template...

One of my favorite startup conversations goes something like this:

“Oh, you did that?”

“I thought I was doing that.”

“No, I thought YOU were doing that.”

“Wait, who told the client?”

Cool.

Love this for us. We are thriving.

Usually, I start noticing ownership problems before anyone calls them ownership problems.

There are a million questions flying around Slack.

Meetings get added because nobody is quite sure who should make the call.

Two people do the same thing.

Something else gets done by nobody.

A handoff happens halfway.

Someone tells a client one thing while another person is working from completely different information.

Eventually, yes, you get an angry customer, but usually the internal mess shows up first.

Read more

Naturally, we wandered into A LOT.

Including the fact that my first few fractional clients came from Substack. One of my favorites literally found my writing, messaged me because she liked my voice, and asked if we could work together. Which remains a pretty strong argument for showing people what it would actually be like to work with you.

We also talked about something I’ve been thinking about a lot lately: portfolio careers.

For years, the conventional wisdom was that the “safe” option was one full-time job.

I’m not entirely convinced that’s true anymore.

Having a few clients, your own audience, maybe a product or two, and multiple places your income can come from feels like a different KIND of security. The danger, of course, is deciding you need 17 revenue streams by Thursday. (Oh hi. It me.)

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My current lesson is much less exciting:

Pick one thing. Actually work it long enough to know whether it works. (Thanks to my friend and fantastic growth advisor, Sibi!)

We also got into:

• why a good operator sometimes has to be the professional killer of shiny objects

• how I’m using AI to keep multiple client worlds straight without outsourcing my brain to it

• why Substack DMs still feel surprisingly human compared to the LinkedIn garbage heap

• what I’d tell someone thinking about going fractional

• the systems I rely on to keep my own business moving

• my extremely sophisticated Substack growth strategy of “post Notes and talk to actual humans” 😂

And Philip made me give one piece of advice for fractional work, one for Substack, and one for LIFE at the end. No pressure…

If you missed it live, you can watch the whole conversation below.

Get more from Katie Barnes in the Substack app

Available for iOS and Android

Get the app

Welcome to triage. Scrub in and join me for the ride.

PATIENT ONE: “My Team won’t take any ownership”

Patient enters ER at 8:12 am.

Founder visibily agitated.

Primary complaint: “I just need my team to take more ownership.” The patient’s crew nods their heads politely while biting their lip. One department head stares at the floor. Another has 15 outstanding Slack messages from the patient.

Initial vital signs look normal. Upon further examination, we discover the team has been attempting to make decisions for months. Recently, the crew stopped adhering to the decision-making treatment plan as they were not seeing progress in the patient.

Dr. Katie steps in with questioning:

Who is actually allowed to make a decision?

What happens if they make the wrong one?

When was the last time someone made a call without you?

What decisions still NEED to go through you?

What decisions just do?

Founder pauses.

BINGO! We found the blockage. Very common condition called founder bottlenecking.

Treatment is straightforward. Doctor prescribes:

• Define ownership

• Define decision rights

• Clarify what needs founder input and what does NOT.

Harder part of treatment…the founder needs to let someone make a decision that isn’t identical to the one that they would have chosen. Patient is frustrated, but agrees to try treatment.

Prognosis is excellent!

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PATIENT TWO: Active Revenue Leak

Patient arrived at 12:01 am.

Complaint that “Sales are slower than we expected.”

Founder requests new pipeline strategy immediately. Sales team would also like more leads. Everyone is chatting about outbound.

We begin the routine labs.

Before ordering any new campaigns or strategic moves, Dr. Katie asks a highly annoying question. (Yes, this made the chart.)

Are we collecting all of the money we have earned?

Met with silence. We inspect invoicing, renewals, contract dates, failed payments, billing systems, and arrangements.

Surfaced many items that rely on one person knowing to execute something based on memory or a calendar event.

Found it…Revenue already sold, but wandering around the hospital unattended. (I once found over $30k in unbilled revenue a startup didn’t realize existed.)

Treatment as follows:

• No new funnel needed.

• Find the leak.

• Assign ownership.

• Create a super boring and repeatable process.

• Automate where it makes sense.

• Put an actual human in charge of noticing when something goes wrong.

Patient is discharged with improved cash flow and mild embarrassment. Should clear within one to two weeks.

PATIENT THREE: Customer Success Trauma

Patient arrives via ambulance.

Chief complaint: “Customer success just keeps dropping balls.”

CS has been informed they need to be more proactive. Morale is low. Sales appears to be doing mysteriously well.

Dr. Katie unleashes the boring questions.

Walk me through the last deal you closed.

What did sales promise?

What info did CS receive?

When did they receive it?

Where does it live?

What does “onboarded” mean here?

How do we know the customer is healthy?

Who owns the renewal?

One member of the crew slowly backs toward the exit.

Diagnosis made. Customer was sold one thing, but the handoff to CS never existed. Or was frankly a Slack message and broken link to a gdoc. Onboarding seems to vary across all clients. Success milestones do not exist. CS did not create this wound.

Treatment as follows:

Trace the entire customer journey.

Identify all handoffs.

Define what information travels with the customer.

Assign owners.

Decide what “good” (or even better “great”) looks like for your team.

Then we make sure the systems support the process instead of forcing the team to be amateur detectives whenever a customer asks a question.

Patient will recover. Sales has been asked to stay for observation. (Click here for more information on this treatment.)

PATIENT FOUR: Accute Mettingitis.

Patient arrives out of breath at 10:10 am after 3 scheduled meetings.

Primary symptom:

“We have a communication problem.”

Current treatment plan includes:

Monday leadership meeting.

Tuesday department meeting.

Wednesday project meeting.

Thursday cross-functional sync.

Friday “quick check-in.”

Three standups.

Two recurring “touch bases.”

One mysterious calendar event called ALIGNMENT.

Exhaustion is evident.

Before administering further meeting treatment, we again unleash the boring questions to the patient and their entourage.

What have the last few weeks looked like?

Show me your calendar.

What changed recently?

Where do decisions get made?

Where do updates get shared?

What happens after meetings?

This is the ops triage I really love. Talking to the founder. Get their side of the story. Then we step away, and I meet with the people around the founder. Connecting the dots between what I hear from leadership and what I hear from those in the day-to-day is the fix.

Patient diagnosed with Severe Communication Without Architecture.

Treatment:

No added recurring meetings.

Establish a regular operating rhythm. (I shared my preferred one here.)

Meetings should be where decisions get made. Not where everyone reads updates off an agenda live.

Several meetings are removed. Patient immediately relaxes.

PATIENT FIVE: The Startup Hypochondriac

3:30 pm Friday afternoon. Patient bursts through the ER doors shouting. “We are a DISASTER!” Full trauma team is called upon.

Founder reports:

Everything is broken. Nobody knows what they are doing. This company cannot scale. Ops are a mess. Series A is doomed before it starts.

We begin examination…

Revenue is growing. Customers really like the product. Team is capable. There are some documented processes. Founder has delegated many decisions. Meetings are a bit messy. Handoffs aren’t totally clear, and there are four tools doing jobs Claude could handle.

Dr. Katie looks up from chart. Ma’am I am happy to say you have a startup.

This is one of my favorite diagnoses. Growing companies are messy! We aren’t going to get away from that fact. Sometimes a founder spent so long in the weeds with every imperfection they forget that normal chaos and growth is painful.

No emergency transplants needed.

Treatment:

A few conversations with the right people.

Maybe a revised written process or two.

Probably fewer Slack channels.

Hydrate & rest.

Call me if the founder starts approving every invoice again.

QUICK NOTE FROM TRIAGE

Funny thing about startup ops. My clients almost never arrive saying “Hello, I believe we have an unclear ownership model creating downstream customer lifecycle issues.”

They arrive complaining of all the things above. This is why my first move is ALWAYS talk to the people. Do the actual digging to find the real diagnosis. Not the thing one person is screaming about.

Sometimes the company needs surgery. Other times it needs a few lil stitches. And sometimes at the end of the day, I tell the founder to stop googling symptoms.

The waiting room remains full.

The operator washes her hands.

If your startup would like to be seen by the Dr. Robby of operations, my waiting room is open.

See you in triage.

KB

✅ A simple framework for deciding where company information should live

✅ A way to separate conversation, action, and long-term company knowledge

✅ The questions I use to find communication gaps when I first join a team

✅ A downloadable Notion worksheet to audit your own communication architecture

Before we get into the template...

In the first few weeks with a new company, I ask a lott of real annoying questions.

“Where does that live?”

“Okay, but where would I find it?”

“Who updates that?”

“What happens after this meeting?”

“Wait. So that decision is only in this Slack thread?”

(I really am delightful.)

I ask because one of the fastest ways to understand how a company actually operates is to follow the information.

How it literally moves, not how the founder TELLS me information moves.

There is usually a pretty big difference.

The founder might tell me:

“We keep everything in Notion.”

Then I talk to the team. And the answers are really more like:

“Oh, I usually just ask Sarah.”

“We have a doc somewhere.”

“I think that’s in Slack.”

“Maybe Jira?”

“Let me find the link.”

Boom. There it is.

That’s the real “system”

.

Read more

The fifth and whiniest “just one more,” proved I had absolutely nothing left in the tank.

This month has been...a lot.

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My Mimi passed.

We moved.

Kiddo decided this was the perfect time to completely regress on potty training. (I’ve gotten real friendly with that new washer and dryer.)

I’m onboarding a new client.

Turns out our new garage leaks.

I somehow still have things at the old house that need to be cleaned up.

I’m supposed to keep prospecting because businesses don’t magically grow while you’re unpacking boxes.

Oh...and apparently lettuce is trying to kill us this summer? So I’ve been eating cold pizza and leftover Chinese food like I’m back in college.

Somewhere in the middle of all of that, I stopped working out.

Stopped reading.

Started waking up in the middle of the night.

Then I sat down to write this newsletter and realized I didn’t even care what I wrote this week.

That was the biggest kick in the gut. I love writing; this is my little safe space, and I could barely face it.

How was I going to get myself out of this funk? People hire me to bring order to chaos.

That’s LITERALLY my job.

When a company starts dropping balls, I laugh when they tell me they or their team just need to work harder. Do more.

I don’t encourage them to build some elaborate new operating system.

I send them right back to the basics.

What’s actually on your plate?

Where is it all living?

What can leave your brain?

So...I stepped back and decided to take my own advice.

Whipped out the old checklist.

Actually put things on my calendar instead of trusting my brain to remember.

Brain-dumped into GPT instead of trying to carry every loose end around in my head.

Again, nothing genius here, just back to those key basics.

I think founders, operators, and truthfully, a lot of parents have the same bad habit.

We convince ourselves that everyone feels safer if we keep holding everything.

As if carrying more somehow makes us more responsible.

It really doesn’t. It just makes us heavier.

Last night I asked myself what I would say to my daughter, Sloane, if she were my age, running a company, moving houses, trying to build something meaningful.

Feeling like she was dropping balls everywhere.

I’d tell her,

“Girlfriend...you’re rocking it. I’m really proud of you.”

It’s probably time I started talking to myself that way too.

While building my fractional company and this newsletter, I’ve been clear with my audience: I LOVE AI. I feel fortunate that it’s at my fingertips while I launched this portfolio career of mine. Truly couldn’t have seen the success I’ve seen in the last year without the help of these tools.

Last week I sat down drafted, edited, and posted my newsletter. Breathed a sigh of relief. Then went to my Substack notes feed and immediately saw a post from saying Substack rolled out AI detection.

WTF??? My heart dropped. Panic ensued. I hadn’t received any heads-up this was happening. What does this mean? Where does that show up? Who sees that? Can I turn it off? Will I be punished for how I just used AI?

I felt like I was about to be outed as a fraud to my audience. My first thought was far from “Oh wow this is an interesting and helpful feature!” It was “What if my readers assume everything I do is GPT with my name at the top?” That is incredibly uncomfortable when you’ve spent countless hours of energy and heart working to build trust. This complete flip of a belief that you’re not valuable if you use AI was foreign and felt like an attack.

As the dialogue progressed and my nervous system chilled out, I realized I would love to be super open about how I use AI in my work. So I want to take this opportunity to offer a deeper peek behind the curtain into how I use the tools. If you’ve been here a while, you know my brand is transparency and human-first. Even in my LinkedIn banner, I make it clear that I am about human-first, AI-powered systems. I consider this to be a huge benefit to my clients and readers. AI is NOT going anywhere. I strongly believe if you don’t adapt and use it in your practices, you will be left behind. I still believe this after feeling like I was stripped down naked and the Substack lords yelled “Shame” upon me. (God, does being a Game of Thrones fan just age me now?)

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Anyway, I am going to share my process for using AI in my content here. The process is a lot like working with another human in the room, but as a solo, I don’t have that luxury. When I sit down to write my newsletter for the week, there are a couple of ways it goes.

Sometimes I have the fully fleshed-out idea for an article.

Sometimes I have a vague idea of where I want to go with an article

Sometimes I sit down with severe writer’s block and stare at the screen for a hot minute.

Whatever the case, I usually will still have my GPT or Claude (depending on who is on my good side that day) interview me. Ask me about what I am seeing with clients, what’s being talked about in my world, and what I am feeling lately. For this piece of the process, I like using Wispr to speak it out. It feels more natural.

Once I get that out, I outline, draft, rewrite, edit. Then I hand it back to my robot buddy for feedback.

The journalism kid in me despises being called out for grammar issues, so I make sure that it’s checking me on my grammar. (I’m not perfect but damn my brain sure thinks I should be.) If there’s research that I need to do for the piece, I work back and forth with Claude to help me surface that. I still go through and click on the sources and articles that Claude’s giving me to verify because it’s not always accurate. It’s like your well-meaning and hard-working, but still rather young, intern.

Then, at the end of all this, I’ll put it on Substack and do one last pass on it myself. Okay, let’s be real: 10 passes because aren’t we all afraid to commit to clicking the send button only to send something horrifically wrong? (Anyone else previewing all 3 formats a stupid amount of times before send? Anyone??) Eventually, I finally fire away.

The stories, frameworks, and witty quips 😬 start in my brain first. But, YES, the AI does help me clean this up and give the final product you’re reading. I don’t know what grade I’m going to get from that detector, but it’s fair to say it’s not 100% human these days. It’s also not close to 100% AI.

Which is why I am still not sure what the detector is measuring. I’ve read thoughtful arguments from both the supporters and the haters. Maybe this removes some of the low-effort “AI slop” out there. And I am all for that! I don’t think there is a single person out there asking for more generic content. But I keep finding myself coming back to the negatives. False negatives. False positives. Then something I didn’t even think about before: there is a whole set of people out there who speak English as a second language, and they’ve suddenly been able to access a whole new market. This feels like a punishment to them. My friend, speaks about this extensively in his publication, Slow AI.

I'm just not convinced we've figured out how to measure "human" in a way that's actually fair.

Other AI tools I am using to streamline my business because it doesn’t stop here:

Claude

ChatGPT

Whispr

Granola

Grammarly

Gamma

Lovable

Probably five more next month because I have absolutely no self-control when a new AI tool drops.

If AI really isn’t your thing?

That’s cool. You can still hang with me.

By the end of this you’ll have:

✅ The operating rhythm I use as a starting point with most growing SaaS companies

✅ The purpose of every recurring meeting

✅ Rules for when meetings should (and absolutely shouldn’t) exist

✅ A downloadable worksheet to audit your own company’s rhythm

Before we get into the template...

The first thing I look at when I join a company isn’t Notion.

It isn’t Jira.

It isn’t Slack.

It IS the calendar.

Because the calendar tells me how work actually moves through a company.

I don’t care how many AI tools you’re using.

If every answer still ends with someone tagging the founder...

If Engineering has no idea what Sales promised...

If Customer Success finds out about product changes from customers...

...your problem isn’t communication.

Your company doesn’t have an operating rhythm.

Most startups think they need fewer meetings.

Most actually need meetings that know what job they’re supposed to do.

Read more

Not the highlight reel.

The actual, messy, three-Slack-threads-deep reality of it. I am incredibly grateful that there are over 4,800 of you here sitting in the mess.

Over time, I realized there are two groups in that 4,800.

The founders living through the chaos.

And the operators helping them clean it up.

Where that’s already showing up

I didn’t plan for both of you to be here, but looking back, it makes complete sense.

More than one founder has read this newsletter, kept reading, ended up on a call with me, and eventually hired me. That part has worked exactly the way I hoped.

But a LOT of you reading this are not the founder.

You’re the operator. The fractional. The generalist. The person someone calls when the company has somehow created four onboarding processes and no one knows which one is real.

You’ve been here the whole time.

I just haven’t been building enough specifically for you.

What stays free

The free newsletter will keep being a place where both groups can see themselves.

The founder still deep in the chaos.

The operator who can already see why the chaos keeps happening.

That is the whole point of Systems & Side Eyes. I’m not changing it.

What’s changing about the paid tier

Here’s the part I’ve been sitting on.

I have an entire Google Drive full of templates, prompts, meeting structures, scripts, and operating tools pulled from real client work.

Built for real problems.

Used inside real companies.

Currently collecting digital dust until I happen to need them again. Very efficient system I have created here.

So the paid tier is becoming The Operator’s Back Room.

This will not be a second set of essays.

It will be the actual stuff I use to do the work, along with the context that makes it useful:

The Notion homebase I set up when company information is living in seven different places.

The meeting cadence that ends the “we need another meeting to discuss this meeting” cycle.

The ownership structure I use when every decision still floats back to the founder.

The scripts, prompts, and frameworks that help turn vague frustration into a problem someone can actually solve.

One tool at a time. Plus when to use it, how to adapt it, and where it tends to fall apart.

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What this is NOT

This is not a course about becoming fractional.

It is not a coaching program.

I am not going to stand at the front of a virtual room and pretend I have discovered the one correct way to build a portfolio career. (The internet has enough people doing that.)

I am opening up the systems I use to do the actual work.

I know how to walk into a growing company, find the friction, get people talking to each other, and build structure that does not immediately get abandoned.

That is what belongs in the back room.

What opens first

The first resource is coming next week.

I’m deciding between:

The Notion operating homebase.

The meeting cadence structure.

The RACI-lite ownership template that helps get decisions out of the founder’s head.

If you are the operator, fractional, or generalist holding everything together for someone else, reply and tell me which one you would use first.

Paid subscribers will get the winner first, along with the walkthrough for how I actually use it.

Founders are welcome in the back room, too. You may not want to build every system yourself, but you might want to see how I approach the problems happening inside your company.

Either way, the free side is staying exactly where it belongs.

Behind the curtain. Looking at the mess. Occasionally side-eyeing the fourth Slack thread.

More soon.

KB

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I sat in my car after my last day and thought: cool, now I just have to convince strangers to pay me for the thing I’ve been doing inside other people’s companies for 14 years. No pressure

.

A year later, I’ve fully replaced my W2 income. This newsletter somehow has over 4,700 of you in it. Most importantly, when my daughter needs me, I’m there.

I could stop the post here and call it a nice little brag, but that’s not actually the interesting part of this year.

The interesting part is that I spent 14 years telling founders what their businesses needed. And then I built one. And it turns out knowing the playbook and living the playbook are two very different things.

So instead of a highlight reel, here’s what I actually learned. The stuff I now understand in my body, not just in a deck.

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The “is anyone going to pay me” panic doesn’t go away. You just get faster at moving through it.

I’ve told founders a hundred times: the fear doesn’t mean you’re wrong, it means you’re doing something that matters. I believed it. I didn’t feel it until I sent my first invoice and refreshed my banking app four times in an hour.

The panic isn’t a signal to stop. It’s just the tax on doing something real. You don’t wait for it to go away before you act. You act with it sitting right next to you.

Sometimes the fix isn’t more structure. It’s less permission for new work to exist.

A founder pulled me into what was supposed to be a quick conversation about shaping the next sprint.

By minute ten, it was obvious the sprint wasn’t the problem. Product was talking in Notion. Engineering was operating entirely out of its own head. Process was trying to stand in the middle, translating between two teams that weren’t actually talking to each other. And the founder was sitting there, acting as the human API between every function in the company.

The instinct in that room was to add more structure. More meetings. More “alignment.” I’ve watched founders do this a hundred times, and as a true ops girl, I’ve felt the pull to do it myself.

The actual call was simpler and somehow a lot harder: no new work until the existing work had an owner, a board, and a deployment plan.

The line I gave was, “If it’s not on the board, it doesn’t exist.”

Boards don’t fix anything by themselves, but the company had reached the stage where invisible work had stopped being harmless and started being dangerous. Every task living only in someone’s head was a task that could secretly die, get duplicated, or get blamed on the wrong person.

If your team can tell you what they’re working on but you can’t see it anywhere without asking them, you are dealing with invisible work. Invisible work is how founders end up back in the middle of everything, even when they swore they’d delegated it.

Boundaries aren’t the opposite of partnership. They’re what make the partnership usable.

Here’s the one I got wrong this year, and I’m not proud of it.

I underestimated how expensive unclear boundaries are when you’re the one embedded inside someone else’s chaos. Not financially, although yes, that too. Cute little bonus consequence.

I mean operationally. Emotionally. I let a few client relationships stay too vague for too long because I was trying to be helpful, flexible, easy to work with. Turns out “flexible” turns into “available for everything” faster than you’d think if you don’t define the edges early.

I know this. I build clarity for a living. I have literally told founders, in these exact words, that the fuzziest relationships in their company are the ones that eventually break. And I still let my own scope stretch because a founder needed help, I could see the path forward, and it felt easier to just do the thing.

The lesson was annoying because it was so obvious once I said it out loud: a boundary isn’t a wall you put up to protect yourself from the people you’re helping. It’s the thing that makes the help sustainable enough to keep showing up.

If you’ve got a hire, a vendor, or a fractional partner whose scope has grown past what anyone actually agreed to, that’s not a them problem. That’s an unclear-edges problem, and it’s fixable in one written conversation.

You don’t need permission to build the thing you already know how to build.

For 14 years I was already doing this work, just without the title, the ownership, or the full credit. I didn’t need a new skill to go independent. I needed to stop waiting for someone to tell me I was allowed to.

If you’re sitting on expertise you’ve been handing to someone else’s company for years, that’s not a reason to wait. That’s the business.

So. One year in. Here’s what I actually know now that I didn’t a year ago:

The fear doesn’t disqualify you. The lack of clarity isn’t a phase you outgrow. Imposter syndrome doesn’t mean you’re a fraud; it means you’re paying attention. And most of what looks broken in your company is actually just an honest conversation you haven’t had yet.

If you’ve hired me, read this newsletter, or just cheered me on this year, truly, thank you. You built this too.

Year two, let’s go!!!

A founder texted me last week: “Can you look at this? I had AI run our retro notes, and I don’t actually know what we decided anymore.”

He read that back to himself before I could even respond. “That’s weird, right?”

Yeah. That’s weird.

He’s not lazy. He’s not checked out.

He’s running a sixteen-person team, closing deals, prepping for a raise, and doing what every founder does when the to-do list eats the day whole: he found the fastest way through it. AI wrote the retro summary. AI drafted the hiring rubric. AI ran point on a comp conversation when his Head of Sales asked for a raise.

None of that is the problem on its own. I use AI for half my day too (and we all know how much I LOVE a good shortcut).

The problem showed up two weeks later, when a client complained onboarding felt disorganized, and he couldn’t tell me why. He hadn’t actually sat inside the retro where his team named the exact reason. AI folded it into a tidy paragraph, he skimmed it, and the texture, the tension, the thing someone almost said but didn’t, all of it got smoothed out before it ever reached him.

He wasn’t in the room for his own company anymore. AI was.

Here’s the part nobody out there is saying out loud

The AI backlash crowd wants you to quit using it. That’s not my advice, and it’s not happening anyway.

My advice: use it AND stay the one doing the thinking.

Those are two different jobs. Lately, founders are only doing one of them.

A recent BCG study of C-suite leaders found that half are already seeing this exact gap show up in their own teams, and most expect it to get worse over the next few years. The skill they flagged as most at risk? Judgment and decision-making. The one thing you can’t hand off and still call yourself the founder.

Judgment isn’t a task. It’s a muscle. You use AI to clear the noise around a decision. You still have to make the call, sit in the discomfort of not knowing, and watch what happens when you’re wrong. That’s the whole loop. Skip the middle two steps and the muscle goes soft, even while your calendar looks more efficient than ever.

What this actually looks like when it’s working

The founders I trust most right now use AI to get to the decision faster, then still show up FOR the decision itself. They read the raw retro notes, not just the summary. They sit in on the hard conversation even when a doc could technically stand in for them. They know the difference between delegating a task and delegating their own understanding of their company.

You didn’t get slower or dumber. You just started mistaking the summary for the thing itself.

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One question before you close this

Where’s the one place in your business right now where you’re reading the AI summary instead of sitting in the actual room? Be REAL, REAL honest.

...

KB