Many founders bring me in because they believe their team isn’t the right fit.
On the surface, that conclusion makes sense — if goals aren’t being hit, someone must not be performing.
But here’s the hard question almost no one asks before replacing people:
Is this a skill problem or a will problem?
The Cost of Skipping the Question
Hiring is expensive. Replacing someone comes with severance, recruiting costs, training, and months of lost momentum.
Worse, if the problem isn’t the person but the system they’re working in, the next hire is doomed to the same failure.
That’s why this distinction matters. Founders save themselves massive time, money, and team morale by pausing to diagnose: is it can’t or won’t?
Skill = Can’t
A skill problem means the person doesn’t currently have what they need to succeed. This can look like:
Missing training or unclear expectations
Tools that slow them down instead of helping
Processes that create confusion or duplicate work
Workload that exceeds capacity
I once walked into a SaaS company where project managers were missing deadlines every week. Leadership assumed the PMs weren’t strong enough and started lining up replacements.
But the real issue wasn’t their talent — it was the system around them. Work was scattered across disconnected tools, requests came in from every direction, and priorities shifted daily without a source of truth.
No project manager — no matter how skilled — could succeed in that environment. Once we streamlined workflows, implemented a single system, and clarified ownership, the same team started delivering consistently.
In other words: this was never a people issue. It was an ops issue.
Will = Won’t
A will problem is different. This is when the systems are clear, the tools are in place, the expectations are realistic — and yet the effort, ownership, or attitude isn’t there.
That’s when you’re no longer dealing with capability, but motivation and alignment. A project manager who has a clear roadmap but continually avoids accountability. A team member who has the training and tools but resists using them.
Ops can support will, but it can’t create it. If the will isn’t there, no process will change the outcome.
The Quick Diagnostic
Before making a replacement decision, I run through four simple questions:
Clarity — Do they know what’s expected of them?
Tools & Training — Do they have what they need to succeed?
Capacity — Is the workload achievable with the resources available?
Ownership — With all the above in place, are they still falling short?
If the first three are missing, you’re looking at a skill (or system) issue.
If all three are true and performance doesn’t shift, then it’s will.
Why This Matters for Founders
The Skill vs. Will question saves founders from the most common trap: assuming underperformance = wrong person.
Sometimes it is. But often, it’s the environment around them that’s broken.
And if that’s the case, swapping the player without fixing the system is just rearranging deck chairs on a sinking ship.
The best founders know this. They don’t jump straight to replacement. They ask the harder question first.
All the best,
Natalie
Fractional Strategic Operations Leader
If you’re a CEO missing your numbers and your team’s stretched too thin, let’s talk — I can fix it.
If you’re ready to start a fractional business, The Fractional Launch Lab will get you there in 10 weeks.
Thank you for reading.
This newsletter is new, and I’d love your feedback.
What worked? What didn’t?
Just hit reply and let me know. I read every one.