Before You Decide It’s a People Problem
Your most persistent problem may be unsolvable by design.
This problem sticks around because it’s not the real issue, it’s the buffer that protects you from facing structural chaos or personal growth.
It’s your “favorite problem.”
In my experience, the go-to favorite problem is people.
People are great to blame. If you have a people problem it means the problem:
isn’t you
has a quick fix
doesn’t require any structural changes
We hold on to these problems because familiar battles, however unsolvable, feel better than the unknown that might be lurking at the core of our company.
But when you don’t know you’re holding on to the wrong issue, your company suffers while you grow frustrated and confused.
In reality, the thing we avoid, deeper structural evaluation, is much easier than building the perfect team. Whatever the issue might be—bottlenecking, leadership fears, a blurry growth vision—it's something real. That means it comes with a real solution.
The hardest part isn’t solving, it’s identifying. Helpfully, our favorite problems are great guides to our real problems.
If you are constantly frustrated with your team, they always need you to step in, or you find yourself on the endless search for the perfect hire, “people” might be one of your favorite problems.
Here are five questions to try first when you find yourself wondering “is this the wrong person?”
1. Wrong person, or wrong role?
Sometimes we already have the perfect people, but we’ve put them in charge of the wrong things.
On a recent call, a founder told me she had this weird gut feel about her Head of Product, like she was trying to hammer a square peg into a round hole.
The gnawing feeling that something wasn’t right was spot on, but she assumed the person was the problem.
Reacting to structural chaos—the team wasn’t coordinating, launches were a “train wreck,” and no one owned delivery—she had hired a Head of Product to take product vision off her plate so she could address the execution chaos.
It didn’t work.
Despite the hire, she couldn’t step away from vision, leaving her no time to address that chaos.
But the problem wasn’t her, or the hire. It was their roles.
This founder had hired for strategy when the company was starving for structure.
Once she realized this, the fix was painless: put that new hire in charge of execution while she stayed focused on what she was best at, vision.
No one, not even you, can make the impact you want if you don’t know what that impact looks like or why it isn’t happening. But when you stop to learn exactly what your company is missing, then you have all the power to give it what it needs.
2. Wrong person, or unclear expectations?
When someone is underperforming, it may be a sign that you expect them to solve issues that haven’t been fully understood.
We can all be guilty of designing impossible roles, lumping all our problems together and hoping a magical person will come along and do it all.
In fact, this is what we do all the time with ourselves. Instead of staying focused on vision and strategy, we get bogged down trying to do everything and put out every fire.
Before blaming your team or yourself, try to tease out the many roles you may have merged into one:
What are your real issues?
Where do they begin?
Do they connect or stand alone?
Which can be addressed through automation?
Which need a repeatable system or better communication?
And which form a single position that you can hand off to someone else?
No one can do 5 roles well at once, but lots of people can absolutely crush a single well-defined position.
3. Wrong person, or leadership anxiety?
When the right person comes up against your anxiety, they might look like the wrong person.
This can take many forms.
If you struggle with difficult conversations, you may avoid giving a team member truthful feedback. Without this crucial information, they don’t have a chance to correct, and what’s really a communication problem takes on the disguise of a people problem.
Symptoms of this show up in team performance and behavior.
I have a client who loves his COO’s work, but struggles with his attitude. This person tests boundaries, speaks sharply, and often pushes back.
But my client hasn’t stopped to define leadership expectations or communication norms. With the right context and container, his smart COO might also become a constructive team member.
Founder anxiety often shows up as delegation challenges. When we don’t take a risk on people, we don’t give them a chance to succeed. If we can’t tolerate a learning curve, no one will have the time to thrive. The problem isn’t the team, it’s our own anxiety around mistakes.
When the issue begins with leadership, it’s harder to face but easier to fix.
Rather than finding the perfect person, the company needs you to investigate your own fears and habits. But I think that's much more fun than the endless hiring search.
4. Wrong person, or incomplete on-boarding?
Imagine you hire a new Head of Sales and they immediately start pushing back on pricing strategy.
They may look like the wrong fit, you want someone who gets to know the business first. But they might be working in a vacuum left by unclear expectations, trying to impress you and achieving the opposite.
Or, maybe you hire someone who is eager, hardworking, and capable but their work consistently misses the mark. The tone is off and the priorities feel misaligned.
These could be real mismatches, but they might also tell you that your on-boarding isn’t communicating your company culture.
If people don't understand your company, they’ll revert to what worked in their last job. Your responsibility is to clearly define and communicate your unique mission, values, and goals.
This lets you truly assess if someone is a match. And it gives you a clearer understanding of your company and its needs.
5. Wrong person, or wrong stage?
Sometimes you really have hired the wrong person, or your company has outgrown your team. But if you jump immediately to blaming individuals, you’ll miss important information.
Lots of founders hire wonderful, talented people, just not for the stage they’re actually in. They hire for the company they wish they were running or expect to be running six months.
If you have the wrong people for your current stage, the crucial work is understanding where your company actually is.
Or, if your company has outgrown your team, instead of blaming your team for “not being able to keep up” try identifying exactly what skills and knowledge they lack that have now become crucial.
Only by understanding where you are or how you've already grown can you keep moving forward.
Putting it all together
Your favorite problem, whatever it might be, keeps you from asking more useful questions:
What decisions am I avoiding?
What structure have I outgrown?
What expectations live only in my head?
What kind of leader does this company need me to be now?
But these deeper ideas only feel abstract and threatening because we avoid looking at them. When we decide to face them head on, suddenly they look manageable.
Next time you find yourself battling a too-familiar battle, ask yourself if this is the real issue or a symptom of something deeper.
Your frustration might be pointing you somewhere far more interesting.
See you next week! 👑
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