One of the hardest transitions a leader ever has to make is realizing that your job is no longer to do the work.
It’s to create an environment where other people can.
This is surprisingly difficult in practice. If I’m being honest, it’s still something I struggle with because I genuinely enjoy doing the work. There’s a certain satisfaction that comes from solving problems, innovating, making decisions, and jumping in to help when something needs attention.
Most businesses begin because someone is good at something. They know the craft. They understand the customers. They make the important decisions and guide the vision because, at first, they’re usually the only person capable of making them.
Eventually, though, the business grows beyond what the founders can carry. More clients arrive. More employees join the team. More decisions need to be made. Suddenly, everything still funnels back through the same people. Growth slows, not because the business lacks opportunity, but because leadership has become the bottleneck.
Ironically, the very habits that helped build the business begin limiting it.
Letting Go is Uncomfortable
Early in my career, I believed that being a good leader meant having the answers.
If there was work to do, I did it.
If someone had a question, I answered it.
If there was a decision to make, I made it.
If something wasn’t done correctly, I stepped in and fixed it.
On the surface, that looked like leadership. In reality, I was unintentionally teaching people to depend on me. Every time I did the work instead of allowing someone else to solve it, I made myself a little more necessary.
It felt productive and helpful.
It wasn’t productive for the long-term success of the company.
Over the years we’ve adopted a couple of phrases at Sanctuary that constantly remind us of this.
The first is, “We don’t take other people’s monkeys.”
It sounds a little silly, but the idea is simple. When someone brings us a problem, our job isn’t to take ownership of it. Our job is to help them think through it, coach them, support them, and then hand the monkey back. Whether it’s a client issue, an internal conflict, an important decision, or even an emergency, we want the person who owns that responsibility to continue owning it. The moment a leader takes someone else’s monkey, they also take away an opportunity for that person to grow.
The second phrase is, “Let go of the vine.”
Imagine swinging through the jungle. You can’t reach the next vine until you’re willing to let go of the one you’re already holding. For a brief moment, you’re suspended between the two. It’s uncomfortable because you’re giving up something familiar before you’ve fully secured what’s next.
Leadership often feels exactly like that.
Every time we hold onto work because we can do it faster, better, or with less risk, we prevent someone else from growing into that responsibility. But when we intentionally let go of the vine, we create space for another leader to grab hold. They gain experience. They build confidence. They make mistakes, learn from them, and eventually accomplish things that no longer depend on us.
This is another lesson that’s hard to learn, and that is, mistakes are generally “ok” in hindsight. Sometimes you just have to let people make mistakes. Then support and encourage them after the fact. In my personal experience, this can be one of the most important things that a leader can do. The result is that people end up learning, improving, innovating, being more responsible, more accountable, and ultimately, doing better work next time. This can feel like you’re intentionally allowing your company to take a step back in the moment when you “let go”. But what you’re really doing is enabling your team to take a giant leap forward in the long run.
Ownership Changes Everything
There’s an important difference between assigning tasks and assigning outcomes.
A task tells someone what to do. An outcome gives someone responsibility for what needs to happen and holds them accountable for achieving it. While those ideas sound similar, they produce very different behaviors.
When people are simply completing tasks, they naturally wait for direction. They ask permission before making decisions. They become cautious because success is measured by whether they followed instructions correctly. Their focus shifts toward checking boxes instead of successfully achieving the result.
Ownership and accountability changes everything.
When someone owns and is accountable for an outcome, they begin thinking differently. Instead of asking, “What do you want me to do next?” they start asking, “How can I improve this?” “Is there a faster, better way?” “What problem are we really trying to solve?” Those questions rarely come from someone who’s simply working through a checklist. They come from someone who believes they’re accountable for the results.
I believe that most people actually want this level of responsibility. They don’t want someone looking over their shoulder all day. They want clear expectations, confidence that leadership trusts them, and the freedom to use their own judgment. When they’re given that opportunity, most people rise to it.
Research into human motivation supports this idea. One well-established theory identifies three universal psychological needs that drive engagement and performance: autonomy, competence, and relatedness. People want the freedom to make decisions, the opportunity to become good at what they do, and the feeling that they belong to something larger than themselves. When those needs are met, motivation and performance tend to increase. If you don’t provide these things to your team, you’ll likely end up losing your best people because they feel micromanaged, untrusted, ineffective and disengaged.
Autonomy Requires Structure
None of this means people should simply be left alone without direction and support. Autonomy only works when people understand the mission, the priorities, and the boundaries they’re operating within. They know where they sit within the organization and why, and they clearly know what they’re going to be held accountable for.
Freedom isn’t the absence of structure.
Freedom exists because of structure.
When expectations are clear, values are understood, priorities and performance measures are visible, and communication is consistent, people can make decisions without constantly asking for permission. This can be really powerful.
Honestly, over the last 20 years, one of the most rewarding parts of leading a growing company has been watching people exceed my expectations.
Some of the best ideas in our company didn’t come from the owners. They came from people throughout the organization who were trusted enough to lead in their area of accountability.
Instead of one person carrying the organization forward, dozens of people begin contributing ideas, solving problems, serving customers, and making decisions every day. The organization has become smarter and stronger because it no longer depends on a few people.
My lesson is that leadership isn’t measured by how many ideas you have, decisions you make, or how helpful you are. It’s about creating a culture of empowerment and autonomy. This is the engine of growth.
And when enough people begin leading this way too, the company becomes more successful and resilient than any one leader could ever make it.