The First Thing A Startup CTO Must Do
Perhaps you are a technical co-founder who has managed to raise funding and you have been catapulted into the startup life. Perhaps you have just been brought in to handle the startup’s tech after the first round came in.
As the CTO, or the most senior technology person in the company, there are so many calls on your attention at this stage.
There is plenty of interesting new tech to build. There are potential customers to speak to (hopefully). There are investors to keep updated, who will want to know when the company is going to grow. There are people to hire. It can feel like you are drowning in possibility.
In the midst of all of that, we neglect this one thing at our peril.
Work on your relationship with your CEO
Nothing else matters as much at first. If there are communication problems, work on them. Figure out the kind of company you want to build together.
It is likely there are few other team members at the moment. There will never be a smaller company or fewer relationships to manage than now. Make the most of this precious focus time while you have it. It does not last.
Get to know your CEO well. Learn about their family, what they love, what they hate, what gives them energy. This journey will be a rollercoaster, and you will be strapped into the same car together. Find out what that will be like.
Figure out what you do not agree about. Fissures in your relationship will become deeper cracks under pressure. Understand whether this is likely to be a strength or a weakness for the business.
Part ways now if you cannot be friends
Patrick Lencioni says that out of every five people we meet, four will generally like us, be happy to get to know us and help us out, one of those four will be especially keen to become friends.
Figure out whether your CEO is someone you like. Ideally they are the one out of the five that you get on especially well with. It is even better if they feel the same about you, but this won’t always happen. In any case, a little constructive friction between you is useful and keeps you at your edge. A self-affirming pairing without challenge does not serve your startup.
So much for the first four people. The fifth person just will not work out. Try as you might, you cannot seem to get along and will not be friends. That is ok in general, and not usually their fault, or your fault. Not everyone gets along. It is not ok when it comes to your CEO.
If either of you are that “fifth person” for each other, this relationship will not work. If you persist, your startup will fail.
This is not like a regular office job where you might be able to tolerate a co-worker that you do not like much. If you come to realise that person is your CEO, save yourself a huge amount of heartache by finding something else to do as quickly as possible.
Solo founders
If you are a technical person founding a company on your own, the first person you hire is the most important relationship in your business. Your relationship will define the interactions between all the team members coming after you.
Before your first hire, think deeply about the kinds of interactions and values you want in your company. During the hiring process make sure that this person will accept and build on those values.
Your new hire should have have complementary skills to you, and therefore will have a different perspective on the world. Once you have established the basic mindshare on values, learn as much as you can about what that perspective is, and embrace it. It will enhance the company you want to build.
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Why Hybrid Work Works
As someone who lives an hour and a half from my London office, I love working from home. I can help my teenagers out of the door in the morning, and I am present when the family comes home. I can have coffee with my wife Ellie before we start work. I prepare dinner during my lunch break, and receive deliveries. I can contribute more effort during my day to Cherrypick, free from distractions, interruptions and the long commute. I would struggle to work effectively five days a week in London.
I also love working from the office. It is an opportunity to spend real time with the people I work with. Communication is easier and I spend less time on screens. I can train less experienced colleagues much more efficiently than video chat. I can ask for and give advice and help in person, cutting down long feedback cycles. I would struggle to work effectively five days a week from home.
Much of the debate around hybrid working appears to be a zero sum argument about why working from home is “better” or “worse”, and why working in the office is “more” or “less” productive.
One is not better than the other; they are just different. I think we need both for a balanced life.
Here are some pointers for how to have a productive conversation about hybrid in your team.
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Startup CTOs or founding developers are the first technical people in the business. It is natural to think your job is to write code and build software. This is backwards.
Your first job is not to build software. Your role is to use your technical expertise to help the startup figure out fast if you have a valid solution to a compelling problem, and then a valid product for a big enough market.
You might do this through building software, but you might not need to.
Here is a story of how I did this wrong, and how you can do it right.
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It has been a long time since I wrote on this blog. Roughly 10% of the world’s population wasn’t even alive yet when I last posted - that’s sobering!
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Every chunk of code you commit is more for someone else to read, digest and understand.
Every complex “clever” expression requires another few minutes of effort for each of your team. They must now interpret what you wrote and why you wrote it.
Every line you add limits your project’s responsiveness to change.
Your code is a liability. Never forget this.
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