My Startup is Broken

Whenever I advise (or join!) a startup, one of the first conversations goes something like this:

“Oh man. Everything here is broken! It sucks! There’s so much to do and not enough people to do it. We’re missing so many things, we don’t know where to start! The product needs so much work. Marketing needs all these assets and budget and we don’t know which assets or how much. The sales reps are selling things we don’t have. Engineering can’t find who they need to hire. We don’t even know who has bought what and expense reports.. oh yeah, we should do them!”

I always tell them two things:

First, Take a deep breath.

Yes, you’re right.

Then I describe the pain they’re going through:

Your startup is trying to build product, figure out your target market, figure out how to market to new prospects, figure out how to sell, figure out how to sell consistently, find good candidates, interview them, hire them, onboard them smoothly, raise money, court and update investors, pay the bills, take out the garbage, choose vendors and systems, coordinate product launches, and everything in between. And you’re also trying to do it quickly with minimal disruption to everyone else involved.

And the worst part is that even when one of those things goes perfectly – which is challenging at best – there are always disruptions and everything else feels that much more broken.

And the worst worst part is the thing that broke this week was working last week. In fact, it’s worked smoothly for a while so your team is trying to figure out what in the world just happened.

The good news: Anything breaking is momentary.

The bad news: Anything working is momentary too.

But first – what happened?

At a fast growing company, you’re hiring regularly and consistently. Even if 100% of the people are great hires and will be at the company for years, you have two problems:

  • First, the responsibilities and therefore communication patterns have changed. The person who was in charge of A, B, and C handed off B and C to someone who can focus on them. If those things are tightly coupled, now you have to draw boundaries. If they’re not, everyone still needs to learn who to go to.
  • Second, the team’s average understanding of a topic dropped a little. This isn’t a judgement just a statement of fact because the new person doesn’t know much yet.

For the astute reader, you’ll notice these are key premises from Fred Brooks’ Mythical Man Month which I reviewed here over 15 years ago.

But we have added complexity with a startup: Everything is still a variable.

Every single item I noted above is a variable. It’s a variable we have to identify, measure, tweak, experiment upon, flip upside down, plug in backwards, and re-consider regularly as the other variables change.

A Snapshot in Time

Therefore, when we figure out something that “works” for our company, we have to remember that we’re doing it within the constraints and conditions – people, tools, resources, and market/industry – of that moment. As any of those change, our “brilliant approach” will turn into a “what the crap” in the blink of an eye. The thing that didn’t work when you were 10 people may work when you’re 50 and fail again at 150. And even if you’ve witnessed it before doesn’t mean you can copy+paste a solution. Remember, your current constraints and conditions are different than before.

It hurts but this is how it works and it never ends.

I joined Okta around 700 people and was there for almost five years. At any given moment, about 40% of the company had worked there less than a year. I checked the pattern quarterly and it held true my entire tenure up to 4000 people. That means the process we used last year had to adapt a team almost doubling in size, skills changing, roles and responsibility changing, and everything in between. Now multiply that across every team, department, region, product line, etc, etc and the interactions between those groups and the complexity is unbelievable. This is part of the reason teams, departments, and entire companies re-org. They’re trying to shift to a structure that fits their current constraints and conditions better.

If you’re thinking “700 people!? that’s not a startup!” Fair criticism but the pattern also held when I joined Twilio at 25 people and left 2.5 years later at 250 people and in almost every company who starts becoming successful.

A Better Way of Thinking of It

So while we feel like our startup is broken and we want to scream it out loud, it’s the wrong approach and will just stress everyone out. Instead, think of your company as a child:

When a kid is healthy, and growing, they outgrow their shoes. You don’t blame the kid. You just find new shoes.

So yes, your startup is broken.

Now instead of complaining, realize your constraints and conditions have changed and take advantage of it.