You Already Know. You’re Just Waiting | Aug 2026

One of the hardest decisions a founder will ever make isn’t hiring someone.

It’s admitting they hired the wrong person. And often, the hardest part isn’t figuring out what to do. It’s accepting that you already know what needs to happen.

A recent Entrepreneur article put words to something many founders experience but rarely talk about. Kerry Benjamin, founder and CEO of StackedSkincare, described having a head of marketing who had been with her since the early days of the business. She felt loyal to her, but could feel the gap widening. “I knew for almost a year before I acted,” Benjamin said.

That sentence is worth sitting with. Because the delay is rarely about not having enough information. More often, it’s about everything else getting in the way: loyalty, history, guilt, ego, fear of making the wrong call, or simply hoping the situation will improve on its own.

I’ve seen this play out with companies we work with, and I’ve experienced it myself.

Earlier in my career, there was someone on our team who simply wasn’t a fit. It wasn’t subtle. People outside the company were even questioning the decision. And yet, I kept giving it time.

Looking back, there were signals I should have paid more attention to.

The problem wasn’t that the information wasn’t there. The problem was that I wasn’t ready to act on it.

That’s an uncomfortable lesson for a founder: sometimes you don’t need more data. You need the courage to trust what the data is already telling you.

The person who got you here may not be the person who gets you there

This becomes especially difficult as a company grows.

Someone may have been exactly the right person when the company was smaller. They may have helped build the function, hired the first team and figured things out when there was no playbook. Then the business grows. The team gets bigger, the complexity changes and the expectations change with it.

Suddenly, the person who was instrumental in getting you from A to B may not be the person who can get you from B to C.

That doesn’t make them a bad employee, and it doesn’t erase what they contributed. It means the business changed. The mistake is assuming that because someone was right for the business once, they must always be right for the role.

As Benjamin put it, “Keeping someone in a role they’ve outgrown doesn’t serve them either.” That’s an important distinction.

Sometimes the answer isn’t simply to let someone go. It may be possible to find a different role where their strengths still make sense. But sometimes the business genuinely needs a different leader.

When that’s the case, delaying the decision doesn’t protect the person. It can actually make things worse for everyone.

Loyalty can become a liability

Founders understandably feel tremendous loyalty toward the people who helped build their companies. They remember who took the risk early, who stayed late, who believed in the company when there wasn’t much to believe in yet, and who was willing to do five jobs when there was only budget for two.

That history matters. But a business decision can’t be made entirely on the basis of history.

The longer a leader stays in a role they’ve outgrown, the more expensive the decision can become. The impact may show up in missed opportunities, frustrated employees, poor decision-making or a team that has quietly stopped believing in the direction of the company.

Kat Schneider, founder and CEO of Ritual, described a similar lesson in the Entrepreneur article. She had someone who was hitting their KPIs but repeatedly falling short as a people leader. The short-term numbers looked good, but the leadership impact was damaging trust.

Performance isn’t only what someone delivers. It’s what their leadership leaves behind.

A high-performing individual can still be the wrong leader. And sometimes the cost of keeping them is paid by everyone around them.

Then there’s the founder’s ego

This is the part nobody likes to talk about.

What if I made a mistake? What if everyone else saw it before I did? What does it say about me that I hired this person?

Founders are expected to make good decisions, so admitting that a senior hire isn’t working can feel like admitting a personal failure. I’ve seen founders hold onto people because they don’t want to acknowledge that the original decision was wrong.

But a hiring decision isn’t a referendum on your intelligence. You made the best decision you could with the information you had at the time. The question is what you do once you have new information.

This is where founders need to separate the personal from the organizational.

You can care deeply about someone and still recognize that they’re not the right person for the role. You can be grateful for what someone has contributed and still make a change.

You can be wrong about a hire and still be a good leader.

The bigger leadership failure is knowing something isn’t working and allowing the business to absorb the consequences because the conversation is uncomfortable.

As Job van der Voort, cofounder and CEO of Remote, put it simply in the Entrepreneur piece: “It rarely does.” He was referring to problems leaders hope will resolve themselves. Usually, they don’t.

Don’t confuse the wrong hire with the wrong timing

There’s another side to this conversation that founders need to consider. Sometimes the problem isn’t that you’re keeping the wrong person. It’s that you’re waiting for the perfect person.

I see founders who want to hire someone who will completely transform the business. They’re looking for the person who will 10x revenue, build the perfect function and solve every problem at once. The result is often analysis paralysis. They don’t make the hire because the person they’re imagining doesn’t exist at the level they can realistically attract or support.

Sometimes the better question is: who can help us get two or three times further?

That person may not have every skill you’ll eventually need. They may not have built a $500 million organization. But they might be exactly the leader you need for the next stage of growth. You don’t always need to hire for the company you imagine five years from now. You need to hire for the business you’re building next, and then give that person the opportunity to grow with it.

Stop making people decisions in isolation

There’s one more lesson I’ve come to believe strongly: founders shouldn’t make every people decision alone.

Founders bring context and instinct that nobody else has. But they also bring history, familiarity and personal relationships, and those things can create blind spots. The people around the leader may see things differently. They may see the impact on the team, notice behaviours the founder has normalized, or simply be less emotionally attached to the original hiring decision.

That perspective matters.

A good people decision should consider the organization, the role, the team and the individual, not simply whether the founder personally likes or trusts someone. The question isn’t whether you still believe in the person. It’s whether they’re still the right person for what the business needs next.

Those are two very different questions.

The decision you’re avoiding is already a decision

Founders often think that delaying a difficult people decision means they’re buying themselves time.

They’re not.

They’re choosing to maintain the status quo, and the status quo has a cost.

Every month you keep the wrong person in the wrong seat is another month of missed potential. Another month where the team adapts around the problem. Another month where the business operates below what it could be.

And sometimes, the most compassionate thing you can do for the person, the team and the business is to make the decision you’ve been avoiding.

The hardest part may be admitting that you already know.

Once you do, the question changes. It’s no longer, “Am I sure?”

It’s, “What is the business waiting for me to do?”

That’s where leadership gets real. Not when the decision is easy, but when you finally make the decision you knew you needed to make.