If I Were Hiring a Fractional COO, These Are the Questions I'd Ask

How to know when you need one, what good operational leadership actually looks like, and how to find the right person for your business.

I’ve spent more than 15 years working inside growing companies, usually somewhere between the founder’s big vision and the team trying to make it happen.

I’ve seen founders build incredible products, hire genuinely talented people, land customers they never imagined they’d win, and then hit a point where everything starts feeling harder than it should.

Projects take longer. The team seems to need more direction. Customers are waiting on things that should have been done weeks ago. The founder is still answering questions about EVERYTHING.

Naturally, the conversation turns to whether they have the right people.

Maybe they need a better project manager. Maybe the team needs to work harder. Orrr maybe it’s time for a COO?

Here’s where I’d encourage founders to do a little digging before making another hire.

I’ve walked into companies where leadership was convinced they had a people problem, only to discover that nobody had ever clearly established who owned what. The team was working hard. They were also spending an absurd amount of time trying to figure out what everyone else was doing.

I’ve also seen the opposite. Sometimes someone genuinely isn’t right for their role, and clearer expectations make that impossible to ignore.

Both situations can look remarkably similar from the founder’s seat.

So, if I were running a growing company and considering bringing in a fractional COO to keep scaling that revenue, here’s what I’d want to understand first.

First, do you actually need a fractional COO?

Before we get into interview questions, I’d ask yourself some things about how your company is operating today.

1. Why does everything seem to take longer than it should?

This is probably the most common complaint I hear from founders.

They have a roadmap, a team, and plenty of meetings. Yet somehow the work keeps slipping. Product launches get pushed. Customers wait too long to get onboarded. Everyone is busy, but the business isn’t moving at the pace the founder expects.

I’d start by following one delayed project all the way through the company.

Where did it get stuck? Was somebody waiting for a decision? Did one department think another department owned the next step? Were the expectations ever clear in the first place?

You can learn an awful lot by tracing one real piece of work instead of making assumptions about the entire team.

If this keeps happening across different departments, it’s worth looking at your operating structure before hiring another person to manage the chaos.

2. What would happen if you stopped answering Slack messages for a week?

A little uncomfortable, I know.

I’m also not suggesting you disappear on your team for a week to test this. (Although I’m sure a vacation sounds pretty wonderful.)

But think about it.

Would your team know which decisions they could make independently? Could a new customer move from sales to onboarding without someone checking with you? Would projects continue moving?

Or would you return to 47 messages, a few unhappy customers, and a very long list of things waiting for your approval?

In the beginning, being involved in everything is often exactly how a founder builds a successful company.

Eventually, that same approach can become a limitation.

You should absolutely remain close to your business, your customers, and your people. But you shouldn’t have to personally direct every interaction between them.

3. Do you know where you’re losing time, money, or customers?

This one is especially important for companies that have started gaining traction.

Maybe you’re closing deals, but new customers take weeks to get fully onboarded. Maybe your sales team is making promises that the delivery team doesn’t know about. Maybe renewals are handled whenever someone happens to remember they’re coming up.

I’ve worked in a company where auditing the subscription billing process uncovered more than $30,000 in uncollected annual recurring revenue.

The customers were there. The revenue should have been there. The process for collecting it wasn’t doing its job.

We fixed it.

I’ve also helped reduce onboarding time from 18 days to six by getting the right people, expectations, and handoffs aligned.

These aren’t necessarily problems that show up as one big, obvious emergency. They accumulate as a business grows.

If you know something is slowing the company down but can’t quite figure out WHERE, that’s often a good reason to bring in an experienced operator.

4. Have you outgrown the way you’ve been running this company?

There’s a stage of growth where the things that made you successful start making everything harder.

You hired people because you couldn’t do everything yourself anymore. But somehow you’re still involved in everything. You’re reviewing decisions your team should be able to make, connecting departments that should be talking to each other, and keeping track of projects that everyone technically owns.

You’re working just as hard as you were when the company was half its size.

I’ve seen founders reach this point and assume they need to hire more people. Sometimes they do. But adding five more employees to a company where nobody knows who owns what can make things even messier.

This is often the moment when bringing in operational leadership makes sense.

You need someone who can look across the business, connect the pieces, establish accountability, and help your team operate without every decision running through you.

And here’s the part I think founders sometimes struggle with: you can be an excellent CEO and still need help running the company.

In fact, recognizing that you need that support might be one of the most important leadership decisions you make as your business grows.

Okay, so you’re considering hiring someone. What should you ask them?

First, a quick distinction.

A fractional COO is a senior operations leader who works with your company on a part-time or contracted basis.

For an early-stage business, this can be a great way to get experienced operational leadership without committing to a full-time executive salary.

The title alone doesn’t tell you much about how someone will work with your business, and there are some pretty big differences between the person who can manage an established operating system and the person who can build one alongside you.

Here’s what I’d ask.

4. “What would you do in your first 30 days?”

I’d be a little wary of anyone who has your entire operational transformation planned before they’ve met your team.

I’ve worked across healthcare, SaaS, professional services, and other early-stage businesses. The products and customers are different, but the patterns of operational friction are often familiar.

That experience helps me identify things worth investigating quickly. It doesn’t mean I should arrive with a giant playbook and start changing everything.

My first priority is understanding how the company actually works.

I talk to the founder, department leads, and the people doing the work every day. I want to follow the customer journey, understand how information moves through the company, and see where decisions are getting stuck.

There are usually a few obvious fixes we can make quickly, and I LOVE finding those.

The bigger work comes from understanding what is creating the same problems over and over again.

I’d want to hire someone who can tell the difference.

5. “How will you know whether the problem is our people or our processes?”

This might be my favorite question of the bunch.

Because a good operator should be willing to challenge your initial diagnosis.

If I tell someone my team isn’t executing, I don’t want them immediately agreeing that I need to replace three employees.

I want them asking me WHY I think that.

What expectations have we established? How is performance being measured? What happens when something gets delayed? Who’s responsible for moving the work forward?

When those things are unclear, even a great employee can look ineffective.

A strong operator should be able to establish clearer ownership, expectations, and accountability so you can actually evaluate performance.

Sometimes that process reveals that someone needs more support or a different role. Sometimes it reveals that the founder has been accidentally creating half the delays.

Yes, that happens too.

The goal is to understand what’s really going on before making expensive decisions based on frustration.

6. “What will actually be different after working together?”

PLEASE ask this one.

It’s easy to talk about systems, processes, documentation, and all the lovely operational things that make people like me very happy.

In the end, those things should meaningfully change how the company runs.

I’d want an operator to explain what success could look like for MY business.

Maybe that means:

• Customers getting onboarded in days instead of weeks.

• Projects moving forward without waiting on the founder.

• Leadership meetings ending with actual decisions and clear owners.

• A team that understands its priorities and can execute without constant clarification.

• Better visibility into the numbers that drive business decisions.

Those results will look different depending on where the company is struggling.

I’d also want to understand how we’ll measure progress and what the operator will actually own.

You shouldn’t have to wait six months to understand whether the relationship is helping.

7. “How do you work with founders who struggle to let go?”

Ooooh, this is a good one.

Building a company requires an enormous amount of personal investment. Founders have spent years making decisions, solving problems, and knowing every little detail about how things operate.

Then someone comes along and tells them they should delegate more.

Easy enough to say. Much harder to do.

A good fractional COO needs to understand that dynamic.

The strongest founder/operator relationships I’ve been part of are built on trust. The founder needs to feel confident that someone understands the vision, cares about the people, and will speak up when something isn’t working.

That includes having uncomfortable conversations.

I want founders to feel comfortable handing me important parts of their business, but I also want them to know I’ll challenge them when I think we’re heading in the wrong direction.

You should look for someone who can do both.

One more thing: You might not need a fractional COO yet.

I realize that’s a slightly odd thing for a fractional COO to tell you.

But it’s true.

If you’re still figuring out whether customers want your product, or you’re working through one very specific operational issue, an ongoing leadership engagement may be premature.

You might benefit more from a focused project or a few advisory sessions.

On the other hand, if you’ve found traction, your team is growing, and the same execution problems keep showing up across the business, it may be time for somebody to take ownership of how the whole company works together.

That’s the sweet spot for fractional operational leadership.

You get someone who can see across departments, connect the dots, help your team execute, and work alongside you as the company grows.

Ideally, you get back more time to focus on what made you want to build the company in the first place.

Wondering what’s actually slowing your team down?

This is exactly the kind of work I do through Rise & Optimize.

I partner with growing founders as a fractional COO and operating advisor, helping them figure out why work is getting stuck and build the clarity, accountability, and structure needed to move forward.

I’m currently opening space for new partnerships.

I’ve also introduced a free 30-minute diagnostic Get Work Moving session for founders who know their team could be moving faster but aren’t sure what’s getting in the way.

We’ll look at one real execution challenge, talk through where things may be breaking down, and identify where I’d start investigating.

You’ll leave with a clearer direction for what to address next, whether we work together or not.

Book your free 30-minute Get Work Moving session

See you out there,

Katie

Katie Barnes is the founder of Rise & Optimize, where she works with early-stage founders as a fractional COO and operating advisor. She helps growing companies improve cross-functional execution, build systems their teams actually use, and scale with a whole lot less chaos. Learn more at riseandoptimize.com.