First, let me say that my client have a wonderful relationship, love working together, and have been together for a very long time. We have worked through many changes over the years. For the purpose of this article, my client will be names James and the DOO will be named Sally.
James hired Sally as a Director of Operations, someone he had known for years and trusted completely, to build out his company her own way. This was a big decision for him and the company. I kept running everything I always had, and Sally and I met every week. She would walk me through what her plans were, what she was working on, and what she needed from the team. She was genuinely excited about it, and so was I. Sally truly believed in what she was building. I hoped she could make it happen.
On paper it made complete sense to James. Loyalty. Trust. Someone he’d known for years, sharp, hungry, good with people, the kind of hire everyone around him liked immediately. Sally was not a bad hire. Hardworking, well-liked, genuinely believing in what she was building. James told the team we would all step back, let her do things her way, and support her where we could. She had a year make it happen. Her growth projections were lofty. James believed she could deliver what she had promised.
Here is what I knew from the beginning and did not push hard enough on: Sally’s entire career, as successful as it was, had been in a completely different kind of business, one with different economics. High volume, more room to absorb overspend, product-based, the next sale always right around the corner. James’ business was a much smaller, founder-led, service-based business. While it was multi-faceted, there were thinner margins, no inventory to fall back on, not much cushion built into the model.
Sally did not want to operate the business the way it had been running. She wanted to build something bigger, planning for considerably more than a 25% increase in revenue in the first year. There is nothing wrong with ambition, nothing wrong with vision, and nothing wrong with wanting to take a business to the next level. And most often you have to break the systems that got a you to one level to build it to the next level. But she replaced the processes that existed with systems built for the business model she understood, not the one she was actually operating in.
I watched budgets climb. I watched revenue decrease. Sally, the bookkeeper, and I discussed it each month. We discussed it after any big events. We discussed it with James. We expressed concern to the new DOO. She said the plan was working. Growth takes time and she just needed a little more of it.
By the end of the year, the losses had reached more than six figures. That happens in business. Being a business owner is risky. There is risk with any new venture, with any new investment. Financial loss is one of them. So this was not a shock to anyone. We had just hoped it would have went the other way.
| A title does not transfer competence. A résumé from a different industry doesn’t either. The business hired confidence. What the business needed was fit. |
After careful thought and many conversation with all involved, the decision was finally made to let Sally go. It was a hard one for everyone for many reasons. We truly like the Sally. Then it was time for James and I to work on how we could recoup the losses and how fast we could do it.
James decided to put me in the Director of Operations seat for his business. Titles do not really mean anything but it is a title I earned the slow way, after years working of side-by-side with James and working in his business, learning first-hand what happens when a position gets filled by the wrong person for the wrong reasons.
Why a Title Isn’t the Same as Fit
A Director of Operations is the highest-leverage hire a founder makes, and the most high-stakes one to get wrong, because by the time you have decided you need this seat filled, you have usually stopped checking the person in it as closely as you checked everyone before them.
That is the trap. The earlier stages force you to build visibility: workflows, decision rights, accountability rhythms. A DOO hire tempts you to hand all of that over and stop watching, because the whole point of the seat is that you’re not supposed to have to anymore.
| A Leadership IQ study tracking more than 20,000 new hires found 46% failed within 18 months, and only 19% were considered unequivocal successes. The higher the seat, the more expensive that failure gets, and the longer it takes anyone to admit it’s happening. Source: Leadership IQ, “Why New Hires Fail (Emotional Intelligence vs. Skills),” Mark Murphy |
What Actually Went Wrong
Not character. Sally was well-liked, hardworking, had a strong record on business success, and never acted with anything but good intentions. Not ambition either, wanting to build something bigger was not the problem. Not effort, she worked constantly. What was missing was not good intentions. It was fit.
What was missing:
- No domain fit check. Leadership experience is not the same as experience in this kind of business. A large, product-based, high-volume model and founder-led, service-based education model don’t share a playbook.
- No spending guardrail at the top. A person in this seat still needs a threshold above which they can’t move money alone, especially in the first year.
- No real path for a concern to change the plan. Sally spent real time with me and the rest of the team, asking sharp questions, doing the homework, getting the right information about how the business actually worked. But information is not oversight. When questions were raised, there was no structure that required it be weighed against the plan.
What This Stage Actually Requires
Director of Operations is not a reward for loyalty or confidence. It is a seat that has to match the person to the specific business, with real limits until trust is earned with evidence.
1. Check for domain fit, not just leadership experience. A résumé that says “ran an operation” isn’t the same as “ran this kind of operation.” Ask what economics they actually understand, cash cycles, margins, customer relationship, before you ask what they’d change.
2. Set a monthly spending threshold before day one. Even, especially, for the most senior operational seat in the business. No one should be able to outspend revenue without a conversation happening first.
3. Give concerns a real channel, not just an open door. Gathering information from the team members who already knows the business is not the same as having a structure that requires their concerns be weighed before the plan moves forward. If there is a red flag, there needs to be a check in place.
4. Judge the plan against the numbers, not the confidence behind it. “This will pay off eventually” is not a plan. A specific, time-bound target is.
Where This Is Not You
If you have not built Operational Clarity™, Foundation™, or Leadership™ yet, a Director of Operations is not your next move at all, that is the whole point. Hiring for this position before the business has those three in place just gives someone a title to inherit chaos with.
And if you have a strong operators in place, ask for their feedback. Have a team meeting for eveyone to express concerns or ask questions. Then, give it serioius thought. This will go a long way to support success in future decisions.
The Bottom Line
A title did not fix anything. It gave one problem a bigger paycheck and a longer runway before addressing issues. What fixes a business at this stage is the same thing that fixes it at every other stage: the person in the seat matches what the business actually needs, and somebody is still watching the numbers.
| A Director of Operations is not a solution. It’s a milestone. |
Frequently Asked Questions
What is a Director of Operations™, and when is a business ready for one?
A Director of Operations is the fourth stage of the Operations Ascension Ladder™, meant to sit on top of Operational Clarity™, Foundation™, and Leadership™ already being in place. Hiring for this seat before those stages exist gives someone a title to inherit chaos with, not a business ready for them to run.
Should a Director of Operations have unlimited authority to make changes?
No. Even the most senior operational hire needs a spending threshold and a check-in rhythm early on. Full authority without evidence of results isn’t trust. It’s an absence of structure.
How do you know if a DOO hire is the right fit?
Check the plan against the numbers, not the promises behind it. A specific, time-bound target with real checkpoints is verifiable.
| Confirm your stage. Clarify your next move. The Operations Ascension Ladder™ Assessment helps you confirm your current stage, identify the gaps keeping the business from progressing, and clarify which operational priorities deserve your attention now. you. → Take the Assessment — done4u.vip |
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