Almost every startup sets the same trap, and almost every founder and executive falls for it. I certainly did. And I’ve watched friends and colleagues do the same.

It’s not immediately obvious that you’re trapped. A lot of the symptoms just feel like the challenges of scale. In a sense, that’s all they are. But the way they act on you makes you put off solving them. And the more you put them off, the deeper you get stuck.

How many of these feel true to you?

Your meetings are too big. They mix people from a variety of departments and seniority levels. They are often 12–15 people wide or more. You defend this as being about a diversity of input, and avoiding top-down groupthink. Whatever the reason, the result is slow and ineffective meetings, which leads to slow and ineffective teams.

They mix people from a variety of departments and seniority levels. They are often 12–15 people wide or more. You defend this as being about a diversity of input, and avoiding top-down groupthink. Whatever the reason, the result is slow and ineffective meetings, which leads to slow and ineffective teams. Your calendar is a mess. Where you spend your time tells me what your priorities are. Yours should be the long term health and direction of the business. Instead your day is full of ad hoc conversations and deep dives into details. You’re extremely available to your people for quick questions but nobody can get your undivided attention when they need it. You never have the kind of time needed to make big, thoughtful decisions unless you hide in a meeting room or a coffee shop.

Where you spend your time tells me what your priorities are. Yours should be the long term health and direction of the business. Instead your day is full of ad hoc conversations and deep dives into details. You’re extremely available to your people for quick questions but nobody can get your undivided attention when they need it. You never have the kind of time needed to make big, thoughtful decisions unless you hide in a meeting room or a coffee shop. Your bus factor is too high. That’s always true for execs, and doubly so for founders. But you make it worse for yourself. Your team could step into broader ownership and accountability, but they never have to. You’re always right in there. That’s great for alignment, but awful for organizational growth and a direct barrier to scale.

That’s always true for execs, and doubly so for founders. But you make it worse for yourself. Your team could step into broader ownership and accountability, but they never have to. You’re always right in there. That’s great for alignment, but awful for organizational growth and a direct barrier to scale. Your company isn’t where it needs to be. There are other people who can sweat the details, but few who can set direction. You are doing good work, but it’s work others should do. And the result is that you aren’t where your people need you most.

Feeling trapped yet?

Stuck

The trap is sticky for two reasons. First, it sticks because all the symptoms are inter-related. You could put a cap on meeting size, but without trusted delegates you’ll still need to attend every one. And because you attend them, it’s a place for people to get your uninterrupted time and so they’ll all want in. And now your meeting is too big again. You can’t fix any one thing without fixing all the things, and that feels so big.

The second reason the trap is so sticky is that escape feels like failure. Having an assistant feels haughty. Telling people they need to book time with you feels arrogant. Asking, “Is this presentation ready for me?” or “Does this meeting actually require an executive to be present?” feels so pompous. So you tell yourself that those things are the trappings of ego, and you stick to what has worked in the past.

Only it’s not working now, or you wouldn’t still be reading this.

Fallacy

There’s a popular concept bouncing around these days called the Stack Fallacy. Maybe you’ve heard of it. The Stack Fallacy observes that companies consistently underestimate how hard it is to build products higher up the technology stack. Mobile OS vendors think apps are easy and they’re wrong. Database providers think CRMs are easy and they’re wrong. That sort of thing.

To unstick yourself, you need to recognize that a related thing happens with leaders in an organization experiencing rapid growth. Because we are hilarious people, let’s call it the Stuck Fallacy. 😉

The Stuck Fallacy: Growing startups consistently undervalue the support roles and structures present in larger organizations.

I understand that you don’t want to be a pampered corporate stereotype. No one does. When you were small, the wholesale dismissal of operational supports felt lean and agile. But you’re bigger now. Staying stuck in that way of thinking is now the biggest thing slowing you down.

Escape the Trap Without Hating What You’ve Become

Growth happens when you let go of the behaviours and attitudes that no longer help you. You can keep to your values, but recognize that they need different expressions as your team gets bigger. Let me give you an example.

I know a founder whose real concern as his organization grows is that he remains accessible to the team. He’s a great strategic thinker, but doesn’t want to just sit in a leather chair strategizing all day. He wants to be where his people are. He feels the importance of having the founder voice be present and approachable. And he’s drowning.

For him, the way to express that value is to take lots of meetings, and get involved early in every process. The result is that he often sees early, junior work, and feels the need to make it better. He answers questions other people can answer, and solves problems other people can solve.

My advice to him was to admit how big his organization has become, and what that means for his role. To give away his legos, as Molly says. He doesn’t have to give up being accessible, but he might have to put some structure around it. Friday hosted lunches, or scheduled skip-level 1:1s, or town hall sessions. He shouldn’t stop being involved in developing work, but it’s fair for him to ask if it’s ready for his attention.

It isn’t sustainable for hundreds of employees to expect daily affirmations from the founder. He knows it. I think mostly he needed permission to say so without feeling like a pretentious ass.

This Generalizes

Your trap might look different than his. You might be hung up on a different word than accessibility. Maybe performance, or mission, or “hustle”. It’s still a trap if you’re trying to do all the heavy lifting on your own. You’re still stuck if your systems haven’t grown as your team has.

I have worked with people who over-correct on this point. Who feel that being an executive entitles them to conspicuous privilege, and more still in secret. Who impose their status instead of reluctantly accepting it. I’ll be honest, I find them much harder to love.

But the rest of you need to cut yourselves some slack. It’s hard work doing what you do. It’s okay to set some boundaries about how your time gets spent. It’s okay to invest in process and people support to let you focus on the right things. It’s more than okay. It’s your new job.