The Biggest Mistake Founders Make When Hiring for Operations (And Why It Sets Everyone Up to Fail)
If you've ever hired someone to help with operations and walked away thinking that didn't work, this post is for you.
Not because operations people are bad at their jobs. But because there's a very good chance you hired for the wrong half of the job.
When "operations" becomes a to-do list
When non-operations folks hear the word "operations," they think in terms of getting shit done. Someone who comes in, knocks out tasks, sees inefficiencies, fixes them. A doer, by nature. And to be clear — execution matters. You need someone who can actually move.
But this way of thinking sets up a lot of operations hires for failure, because it doesn't take into consideration the massive, underappreciated strategy side of ops.
So founders write job descriptions that are essentially a prioritized to-do list. They interview for hustle, capacity, and willingness to roll up sleeves. They hire accordingly. And then six months later, things are still feeling... off. Busy, but not better. Moving, but not toward anything in particular.
That's not an execution problem. That's a strategy problem.
So what is operations strategy, exactly?
Simply put: an operations strategy is a purposefully designed plan that articulates if we do X, we will get Y. It says how to do X. It defines how to measure whether X is actually getting you toward Y — with real data, not gut feel. It's a constant feedback loop between the work you're doing and the results you're getting. And critically, it tells you when to change course.
Without that layer, you end up with excellent execution of the wrong things. Tasks completed, boxes checked, systems built — for outcomes nobody actually defined.
You're doing inefficiencies really efficiently.
The three questions most ops hires are never asked
When hiring for operations, most founders are laser-focused on are we getting shit done? — which, fair enough, it's a real need. But the more important questions are:
HOW are we getting shit done? Are our methods sustainable, repeatable, and built for where we're going — not just where we are right now?
WHY are we getting shit done? Does every task, project, and initiative ladder up to a specific business outcome? Or are we just staying busy?
ARE WE ACTUALLY getting shit done? Do we have real data — not vibes — telling us our work is producing results?
If those three questions aren't baked into how your ops person thinks, you don't have an operations strategy. You have a very well-maintained to-do list.
Execution and strategy are not the same skill
The clearest way I can explain the difference is through examples, because in the abstract it sounds obvious. Of course you want both. But in practice, most businesses are running almost entirely on execution — and don't realize it until something stops working.
The SOP example
A great operations executor can take a process your business is currently running, document every single step, build a beautiful SOP, and make sure it gets followed day in and day out. That is a real skill. It has real value.
But without the strategy layer, nobody is asking — while that SOP is being built — the questions that actually matter:
Why are we doing it this way?
Is this the most efficient way to do it?
How much time is this actually taking from our team, and could that time be spent on something higher-value?
What is the cost of running this process, and is there a cheaper way to get the same result?
What would we free that team member up for if we automated, eliminated, or simplified this?
You can have a flawlessly documented, faithfully executed process that is the wrong process. Execution without strategy just makes you better at doing the wrong things.
The financial data example
Great execution in financial operations looks like making sure every single transaction is documented so you can report on it. Clean books, consistent categorization, nothing missing.
Great strategy asks: what are we actually categorizing these transactions as, and why does that matter?
Is this spend cost of client acquisition? Cost of goods sold? General and admin? That distinction isn't just accounting hygiene — it's what allows you to pull up all that beautifully documented data and actually answer the questions that run your business: What does it cost us to acquire a client? Can we lower that number? Where is our margin actually going?
You can have perfect execution of your bookkeeping and still have no idea how your business actually works. The data is all there. The strategy to use it isn't.
The email marketing example
Faithful execution of email marketing looks like sending two emails every week, every week, without fail. Consistent, reliable, done.
Strategy asks: do these emails actually ladder up to anything? Are they driving sales? What's the relationship between the content we're sending and the revenue we're generating? Which type of content actually converts — and which is just filling an editorial calendar?
Sending two emails a week is execution. Knowing whether those emails are working, and being willing to change course based on data, is strategy.
Are these roles the same person?
Execution and strategy are genuinely different skill sets. But it's not quite as black and white as "hire two separate people."
Let me use myself as an example. When I'm embedded in an organization as their fractional COO, my job looks like this: identify the problem, identify potential solutions, design the fix, and implement it. Once it's implemented — the right way, the most efficient way, with an SOP behind it — I hand it off. Sometimes to my own operations assistant, who handles the repeated execution of tasks that can't be automated. Sometimes to an internal person on the team. But the repeated maintenance of a process is not where a strategist's time should live, and it's not a good use of company resources to have it there.
So it's less that strategy and execution need to be two separate people, and more that they need to be two separate functions — with someone who can hold the strategy layer, and somewhere for the execution to actually land.
Here's where I see it go wrong: a founder has a $4,000/month budget for operations help. They hire someone to "do operations." That person is an exceptional executor — fast, reliable, high-quality. But they're not an ops strategist. So the strategy has to come from somewhere, and it defaults to the founder or CEO.
Except that's not their skill set either. Founders are typically visionaries. They're setting the course, casting the direction, building the thing. They are not — and shouldn't have to be — the ones asking whether the SOP is the right SOP, whether the email metrics are laddering up to revenue, whether the cost of running a process is worth what it's producing.
What you end up with is a gap. Not an execution gap. An operations strategy gap — the back-of-house operating engine that sits between the founder's vision and the team's daily output. It's not the big-picture direction for the business. It's not the task list. It's the deliberate, data-informed system that connects the two.
And when it's missing, everything feels busy and nothing feels like enough.
So what do you actually need?
Most small businesses don't need to choose between execution and strategy — they need both. But they need to hire with both in mind, and they need a structure that holds both accountable.
That's where the work gets interesting.
Every engagement I take on starts with the Blueprint — a two-week deep dive into your financials, operations, marketing, and overall business structure. The point isn't just to audit what exists. It's to understand whether what exists is actually working, whether it's connected to your goals, and where the real leverage is.
You come out of the Blueprint with two things: a clear picture of where the business actually stands (not where you think it stands), and a prioritized action plan — quick wins you can move on immediately, and higher-effort investments worth making as you grow.
From there, you choose how we work together:
DIY. I hand it off, say au revoir, and you run with it. The Blueprint gives you everything you need to move forward independently, or hand off to a VA or internal team member.
Coaching. We meet weekly. I tell you what to do and how, assign priorities, and hold you accountable to making progress. You — or someone on your team — execute. This works well for founders who have the capacity to implement but need the strategic direction and accountability to stay on course.
Fractional Business Director/ Fractional COO. I work inside your business each week, executing on the strategy alongside you. This is for founders who need someone to not just direct the work, but do it.
The throughline across all three is the same: we start with strategy, then execution. Not the other way around.
The bottom line
If operations in your business feels like a never-ending pile of tasks that somehow never adds up to real progress — it's probably not an execution problem. It's that nobody has built the strategy layer that gives the execution its point.
That's the piece most operations hires are never asked to deliver. And it's the piece that makes everything else actually work.
Ready to start with strategy? The Blueprint is a two-week engagement that gives you the full picture and a clear path forward — whether you run with it yourself or bring me in to help execute.
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Operations execution is the act of doing — completing tasks, following processes, maintaining systems. Operations strategy is the layer above that: the deliberate plan that defines what to do, why to do it, how to measure whether it's working, and when to change course. Most businesses have execution. Many are missing strategy.
Why do small business operations hires fail? The most common reason operations hires fail in small businesses is a mismatch between what was hired for and what the business actually needs. Founders typically hire for execution — someone to get things done — without realizing the business also needs someone to ask whether those things should be done at all, and whether they're producing results. When no one holds the strategy layer, execution runs in circles.
What is an operations strategy for a small business? An operations strategy for a small business is a plan that connects daily work to business outcomes. It defines what the business is trying to achieve, how each operational function supports that goal, what metrics indicate progress, and what triggers a change in approach. Without it, a business can be extremely busy and still not be moving forward.
What is the difference between a visionary founder and an operations strategist? A visionary founder sets the direction — the big picture, the mission, the destination. An operations strategist builds the engine that gets there. They are different skill sets. Visionaries are often excellent at ideation and inspiration but not naturally wired for the systems thinking, data review, and process design that operations strategy requires. Conflating the two roles is one of the most common and costly mistakes in founder-led businesses.
What does a fractional COO actually do for a small business? A fractional COO provides senior-level operations leadership on a part-time or project basis. In a small business context, this typically means assessing the full business — financials, operations, marketing, team structure — identifying where the gaps are between current activity and business goals, building the strategy to close those gaps, implementing systems and processes, and handing off execution to the appropriate people. It's the strategy and implementation layer most small businesses are missing.
How do I know if my small business needs an operations strategist or an operations executor? If your business has reliable people doing the work but nothing seems to be moving at the business level — if you're busy but not making progress, spending money but not growing, or hiring help that never quite works out — you likely have an execution function but no strategy function. You need an operations strategist. If you think clearly in systems, know what needs to happen, but simply don't have the bandwidth or the hands to do it, you need an executor. Many small businesses need both.
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It depends on where the gap is. If your business has people executing reliably but nothing is changing at the business level — if you're busy but not growing, or spending money without seeing results — the missing piece is operations strategy. You need someone who can assess what's actually happening, build a plan tied to real outcomes, and measure whether the work is producing results. If you already think in systems and strategy but simply don't have the time or bandwidth to implement, you need an executor: someone to run the processes you've designed. If you're a visionary founder with neither function covered — no one holding strategy, no one reliably executing — you need both, and hiring a pure executor first is the most common and most expensive mistake. Start by asking: does anyone in this business know whether what we're doing is actually working? If the honest answer is no, strategy comes first.
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The most common reason operations hires fail in small businesses is a mismatch between what was hired for and what the business actually needs. Founders typically hire for execution — someone to get things done — without realizing the business also needs someone to ask whether those things should be done at all, and whether they're producing results. When no one holds the strategy layer, execution runs in circles.
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An operations strategy for a small business is a plan that connects daily work to business outcomes. It defines what the business is trying to achieve, how each operational function supports that goal, what metrics indicate progress, and what triggers a change in approach. Without it, a business can be extremely busy and still not be moving forward.
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A visionary founder sets the direction — the big picture, the mission, the destination. An operations strategist builds the engine that gets there. They are different skill sets. Visionaries are often excellent at ideation and inspiration but not naturally wired for the systems thinking, data review, and process design that operations strategy requires. Conflating the two roles is one of the most common and costly mistakes in founder-led businesses.
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A fractional COO provides senior-level operations leadership on a part-time or project basis. In a small business context, this typically means assessing the full business — financials, operations, marketing, team structure — identifying where the gaps are between current activity and business goals, building the strategy to close those gaps, implementing systems and processes, and handing off execution to the appropriate people. It's the strategy and implementation layer most small businesses are missing.
