How to Fuck Up Your Startup’s Founding Team — Part II

Little Habits That Will Help You Ruin Your Startup’s Culture

Abhishek Chakraborty
Startup Grind
Published in
5 min readSep 30, 2016

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This article continues from Part I.

When we refer to company culture, we are not talking about activities like company values and employee satisfaction. We are specifically talking about designing a way of working that:

  1. Distinguishes the startup from other companies.
  2. Ensures that critical operating values persist — such as delighting customers or making beautiful products.
  3. Helps to identify employees who fit with the startup’s mission.

If you’ve read my previous article, you’d know that the points are mostly addressed to the CEO of the company. It is important to understand that even if there are more than one member who started the company, it is the CEO who is the anchor of the founding team.

What the CEO does, how she behaves and what kind of example she sets, knowingly or unknowingly, will define the cultural values of the startup. Chances are if she fucks up, the startup is screwed.

In the last part we had talked about how to be an actual startup, not just pretend like one; how to be a team player instead of a narcissist; how to analyse and understand mistakes; and how to do real work, and not just be busy. In this part, we’ll mostly talk about the interaction of the CEO with her employees. These fundamentals will be applicable even if there is just one guy working with the CEO. It becomes even more important then.

Giving Harsh Feedback.

A lot of the things people are working on might not be good at first, and most of them might even suck. The CEO’s job is to make them go from ‘suck to not-suck’. That means giving constructive and structured feedback.

We must understand that feedback is not equal to criticism. Criticism is more on the lines of disparagement and fault-finding. It is more about pushing things down from the top. Feedback, on the other hand, is about pushing something upward from the bottom.

The purpose of feedback is to elevate, not to demean — which means pointing out areas of improvement with proper reasons as well as suggestions for improvement. Feedback is neither a debate nor an argument. It is a process where a group of people come together to find a better solution.

People often forget to be humble while pointing out issues: “This is not clear” or “This doesn’t work” vs “I don’t understand this” is a much better approach. A slight change in the structuring of words can be enough to convey what you want to say. It takes time and conscious effort.

Your friends might be accustomed to your brashness, but your new team members will not be. They’ll be quick to judge you to be rude or harsh and that will make them extra cautious while dealing with you. When they are extra cautious they might not be willing to share ideas easily. Or they might agree with everything you say — which is even worse.

Prevent people from being a shutout. You don’t need people who agree with you always. You need people who might challenge you and not be afraid of it.

A lot of people think that feedback needs one to be truthful and honest about her opinion. That is only partly true. Feedback needs candour more than brutal honesty. A hallmark of a healthy creative culture is that its people feel free to share ideas, opinions, and criticisms. Lack of proper feedback, if unchecked, ultimately leads to dysfunctional environments.

Promote candour and structured feedback.

Entertaining Bullshit.

A CEO doesn’t achieve perfection all by herself. As a result, a startup needs a team consisting of lots of smart, super-engaged employees who can identify particular opportunities and weaknesses and help improve them.

However, sometimes a really smart employee develops an agenda other than improving the company. You have to admit that sometimes your favourite hire might not necessarily be the best team player. Often, brilliant people can become totally unreliable — partly due to their own fault and partly because they are not ‘culturally comfortable’ in the company.

The cultural misfits can become rebels, however brilliant they might be. A company is a team effort and, no matter how high an employee’s potential, you cannot get value from her unless she does her work in a manner in which she can be relied upon.

But things are not always as bad as you think. A CEO should talk to the employee if she fails to meet the requirements. She should try to counsel her if an employee becomes unreliable due to personal problems. People often need a push or a second chance.

At other times, you gotta do what you gotta do.

When you hire an employee, you paint a beautiful picture of her future in your company. You describe in great depth how awesome it will be for her to accept the offer and how much better it will be than joining that other startup nearby. Then one day you realise you have to fire her.

The truth is that if it comes to that, everybody in your team would know that she needs to go. It’s better if you don’t bullshit yourself into thinking that there still might be some hope left. Do the right thing! Sometimes you just make the wrong hire — accept that fact.

There will always be the embarrassment at your end and she will feel a sense of betrayal — both powerful emotions. So get ready for an intense discussion. To do that, you must be very clear in your mind about what you’ve decided and what you want to do. Truthfully, there is no right way to do it, but this is part of the CEO’s job — she has to do what others can’t.

Don’t entertain bullshit — neither yours nor somebody else’s.

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Abhishek Chakraborty
Startup Grind

I write ‘Sunday Wisdom’, a weekly newsletter on clear thinking and decision making: https://coffeeandjunk.com/newsletter