People often wonder when the best time is to hire a Fractional COO, an ops specialist, a glue person, a ME! I know it’s not always the most obvious decision. You’ve been in the weeds of it for so long it’s hard to see exactly what the solution is. What is going to pull you out of this funk, slump, or flat-line? (Yes, I am still watching The Pitt this week.) There is a weird category of startup problem that is too important to ignore, but also probably doesn’t require a $150,000 salary to clear up.
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.”
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.
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.
Wait a minute - are you listening to the voices in my head? Cause we apparently think in the same way.
Which may or may not be a scary comparison for you.
Great idea - love the use of your time and the potential outcome.