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When Leadership Sucks at Managing Startups

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July 15, 2022

Recently, I’ve written about working in big corporate environments and why I prefer working at startup-like companies. They both have their pros and cons, but what happens when leadership sucks at managing the company.

Why I Won’t Work for Super Corporate Companies Again as a Software Developer

Why I Prefer Working at Startup-Like Companies as a Software Engineer

Optics vs Facts — a.k.a. Perception vs Reality

You interview at a startup and are excited about the opportunity. You talk with the people that started and run the company, and they offer you the job. You take the job and after a week, a developer who has been there for a few years leaves, and leadership tells the team what happened. You find out that the developer was not being productive and not committed to the company, but it sure seemed like it when you spoke with that developer.

After a couple of months, you find out from a co-worker that another developer has put in his two weeks and they overheard leadership say that the developer was not producing results.

Is this developer that’s leaving really a shitty developer??? You’ve worked with him, he seems to be a really cool person and solid developer; he’s just working on a massive project that takes time to complete (facts).

Leadership tells the same story of productivity, commitment, and performance which all started when the first developer left (optics or perception). This happens. You may get someone that is overworked, stressed, and not recognized for the deep work and humungous project they delivered (facts or reality); and all of a sudden they leave. The two stories don’t match up; the optics, or what leadership sees as an end result; versus facts.

Some Leaders Are Not Great Managers

If you ever worked at a startup or built one yourself and got VC funding, you would sometimes see a president or CEO that was hired to manage the company. This person has decades of experience managing large teams and knows how to look at various situations objectively.

More often than not; you will see leadership made up of the people that started the company. They’re not bad people, want what’s best for the company, and will do what they can to make that happen. These people don’t want to give up control of the company and have not been in a management position before. They feel like they can make it work through open communication and having a top-notch team.

But, when someone doesn’t live up to their idea of what great results should look like and have explosive arguments; they will think that everyone is subject to piss poor results and shitty performance. They develop poor optics of the team and believe that one bad apple has spoiled the rest.

The right person will be able to turn bad situations around and make the company better and more profitable. They will find solutions to problems within the company and chalk up one bad apple to just one bad apple and move on.

Managing Managers

Your job description does not entail managing your managers; in this case, leadership. You should not have to moderate disputes between developers and leadership, nor should you have to explain to leadership why their expectations of the team are unreasonable, but it happens… sometimes.

Having to manage leadership while also doing your job as a developer is not only time-consuming, it’s foolish and can lead to leadership thinking you’re trying to take control, which if you remember; leadership does not want to give up control. You’re taking on the role of team lead or manager, which is fine, but in a small company where there are 6 developers, there may not be a need for a manager.

Final Thoughts

I’ve worked at a handful of startups and have seen some shitty leadership and sometimes shitty developers that don’t clean up their code and leave some code that pops up a message indicating “This stupid thing doesn’t work” if a user attempts to open a certain screen under certain conditions. I have also been told that I didn’t do enough when I worked on all of the high-value projects, put in 60–70 hours per week, and was burnt out at the end of a quarter. There was nothing I could do to prove the fact. This will all be a part of your journey and will provide some lessons on how to take feedback, what not to do, and some funny stories.

Don’t be afraid to speak up to leadership when something is not right or if you have an idea to improve the process and/or culture in the company. What’s the worst that can happen; they say no, or even worse than that, they fire you? If that’s the case, then that wasn’t the right company for you; you’ll find another. When the optics match facts, you’ll know you’ve landed a sweet job.

What war stories do you have about working at a startup? Or, any company for that matter??