Earlier in my career, in my first week as CTO, a customer service agent came running across the hall.

Systems down. Orders not processing. I leaned over to Marcus, one of the founders, the one who built everything, and asked if he was handling it. He said yes. Fifteen minutes later the agent was back. I turned to Marcus again.

He hadn't started yet.

That moment told me everything I needed to know about where the company was. Marcus was brilliant. He was also in the critical path of everything. If Marcus was unavailable, distracted, or just slow to respond, the whole operation felt it. We were completely dependent on one person who wasn't going to scale with the company.

Brad, the other founder, had been direct about what he needed from me: make the technology independent of Marcus. That was the job.

It took me only six months. By the end of it, we had a real team, real systems, real processes. Then I suggested Marcus take some time off. He drove to Florida for two weeks and didn't take his phone.

It scared the hell out of me. We were fine.

I've spent the last fifteen years helping founders work through the same thing. The goal isn't to be indispensable. The goal is to build something that works whether you're there or not.

Most founders never get there. Not because they can't. Because they don't really want to.

The Most Common Succession Plan Is No Succession Plan

A founder will tell me, casually, that if something happens to them, someone will step in. There’s an assumption that the business will figure it out.

There’s no plan. No structure. Just confidence that it will somehow hold together.

At the same time, they’re getting more embedded in the day-to-day, not less. More decisions run through them. More of the business depends on them.

It feels manageable. Until it isn’t.

Then something happens. A health issue. A key person leaves. The founder gets pulled away longer than expected.

And the business isn’t ready for it.

It’s never a question of whether something will disrupt the operation. It’s a question of when, and whether the business can absorb it.

Most can’t.

Because nobody built it to.

What Making Yourself Dispensable Actually Requires

There's a version of this conversation that sounds simple: document your processes, hire well, delegate more. It's all true. It misses the harder parts.

The first thing you need is the right people in the right seats.

Not people who are loyal, or people who've been around longest, or people you like working with.

People who can actually do the job without you in the room.

This is harder than it sounds. Most leaders are good at reading people like themselves.

Hiring for a role you don't fully understand, or for a stage the company hasn't reached yet, is a different skill. Most of us learn it the hard way.

The second thing is systems.
Repeatable ones.
Not how you do things when you're there and paying attention, but how things get done when you're not.

This applies to operations, to product, to delivery, and critically to sales.

I worked for two years building a repeatable sales process for my own business.
Found one.
Then the pandemic hit and the behaviors it relied on changed overnight.

Which leads to the third thing: you have to maintain and revisit people and systems regularly, because everything around them keeps changing.

There's a piece that doesn't show up in any framework though.
You have to actually want it.

The Identity Problem Nobody Talks About

Most founders built their business from nothing. They were the product, the salesperson, the decision-maker, the culture.

The company exists because they willed it into being.
Somewhere along the way, being needed became part of who they are.

That's not ego in the pejorative sense.
It's human.
We find meaning in being useful, in being the person others turn to.
When a client calls you directly, when your team can't move without your input, when the business stops if you stop, that feels like proof of something.

That you matter. That what you built matters.

Making yourself dispensable asks you to give that up before you have something to replace it with.

I've watched founders stall on succession planning for years, and it's rarely about the mechanics.
They know they need a plan.
They know they need to document, delegate, hire for scale. They just can't quite get there.

When we dig into it, the real question underneath is: if I'm not the one holding this together, what am I?

That's not a business question. It's a harder one, perhaps existential. It doesn't have a clean answer. It has to be asked.

The Stress Test

The most honest way to know whether you've actually made yourself dispensable: leave.

Not permanently. Take two weeks. Don't check in. See what happens.

A lot of leaders won't do it. Some because the business genuinely can't absorb it yet, which is useful information. More often because they're not sure it can, and not knowing is easier than finding out.

The sabbatical isn't the goal. It's a diagnostic. What breaks tells you exactly where to focus next. What holds tells you the work is real.

When I suggested Marcus take time off, I wasn't being generous. I needed to know if what we'd built actually worked. The team was new, the systems were in place, and we were heading into the holiday season, the most critical stretch of the year for our e-commerce company.

He drove to Florida. No phone. Two weeks.

We were fine.

Something else became possible because of it. The CEO came to me a few months later and asked me to take over customer service, to do for that department what I'd done for technology.

I had no background in customer service. And I love learning and mastering new skills. And I could say yes because I had a team that didn't need me anymore.
Directors in place.
My head of software could step into my CTO role.
I could move because I'd made myself moveable.

Making yourself dispensable doesn't diminish what you've built. It frees you to build what's next.

Marcus came back from Florida. The company was fine. We were both better for it.