This is a document I’ve shared at the last two companies I took on the CTO role. I sent it right when I started and refined it very lightly recently. Overall, I've had good feedbacks on the concept.

I believe it’ll help us cover a lot of ground in term of communication, leadership and expectations. This is a living document that can — and should — be challenged. It’s supposed to serve as a “moral contract”, so as with any contract, it needs to work for both parties.

A note with which I’d like to preface the entire document:

I try to always lead by example. Every expectation I have for you, you can have for me. It’s only fair.

Me as a person

I’ve been working with a coach for 3+ years now and worked with a mentor for a year. They helped me figure out a lot of aspects of my personality and how these aspects can affect the way I work and interact with my teams. They have helped me figure out a path on which I’m comfortable taking risks and moving forward while staying true to my core values.

Here are 2 extracts from various sources in which I especially recognise myself in this regard and that illustrates some key aspects of the path I just mentioned:

As managers, Advocates may dislike wielding their power. They prefer to think of everyone as equals, no matter what a person’s business card might say. Rather than micromanage their subordinates, Advocates often prefer to empower them to think and act independently. They work hard to encourage others and promote an atmosphere of mutual respect.

This will transpire into this entire document.

Another extract from this article in which I find myself:

“I can be confrontational at times. It’s never personal. I expect you to call me out when I’m wrong. I expect you to be able to defend your choices and reasoning. I expect you to take initiative and responsibility. I expect you to take pride in your work.”

I’m here to help you succeed in these expectations, but know that this is where I want you and the team to go.

My role as a CTO

⚠️ A note: I tailor this part with specifics I gather from pre-onboardings, such as discussions and objectives set during the recruitment process. I’ve removed such specifics for clarity purposes. ⚠️

My role in term of leadership is to make sure that everyone in the team feels heard, proud of what they do on a day-to-day basis and eager to get to the next step.

My role in term of product is to make sure that we all deliver a product that is both something to be proud of and that matches the needs of our clients so much that they’d be willing to pay for it 😉.

My role in term of tech is to ensure that we continue to use the right tool at the right place for the right reason. A tech choice is not just using a library or a given pattern, but need to be part of a more global approach: How much time/money/street cred are we going to gain from it? How easy will it be for newcomers to be trained on it? Is the job market favorable to this tech?

If I had to order those three pillars, it would be like above. People need to be in a good state-of-mind to perform, be creative enough to thrive and take the product to the next level, thanks to technology. These principles are at the core of my character – inside and outside of work.

If you have an idea to better any of the 3 aforementioned pillars, to help me help you better, be sure to let me know.

Management style

Hands-Off

I don’t like to micro-manage, so I won’t. I’m available to discuss and help you come to decisions if you want, but I won’t intrude into your day-to-day to make sure that you’re going into the right direction. I expect you to take a step back whenever you’re starting something and assess wether you should see with me first or not. I trust your judgement.

Understand that at first we’ll need to calibrate though, so over-communicating is always better when in doubt.

Accountability

We’re accountable. It starts with me, so call me out if you think I’m not leading by example. That being said, it does not alleviate yours. We say what we do, and do what we say. This is the basis of our collaboration.

Failing to meet a deadline is fine as long as:

• You should not realise you’re not making a deadline the day after but before: communicate at that time. It’s not my job to chase down this behaviour but rather to help you get the next deadline.
• You share this openly with me and the rest of the team. We don’t hide our failures, but dissect them together, as a team, so everyone learns. It’s a work in progress and not everyone will be comfortable doing so in such a public manner, which is fine. The minimum is to share it with me, and we’ll move from here.

Decision Making

I believe that a good decision is based on three things:

• All people making the decision share the same context, otherwise they need to make sure about it beforehand. “You can’t improve what you don’t measure.”, so make sure we have the data first to make an educated decision.
• Its process is documented. Don’t document for the sake of documenting (#processParalysis), but based on the potential of the decision we should be able to refer to the thought process
• Its outcome is communicated across the organisation. We shift the strategy? Plan on offering a new service next year? Support should know about it and should understand it as Engineering does in a small organisation as ours. It does not mean that everyone should be around the table though.

When disagreement happens, which it will – let’s not put our head in the sand – I do believe that the person assuming the responsibility of the decision outcome should make the final call. Let that be me or anyone else. This call needs to be made once the parties were heard: I’m not advocating full dictatorship, but I believe in moving forward.

With a decision making process as inclusive as this, I expect everyone to commit to the final decision, even if they disagreed at first.

If you start disagreeing with a number of them, this needs to trigger a warning for us both. Maybe I’m turning into a dictator or your vision is splitting from mine and the company’s. This should warrants action in term of communication, education or the need to take a step back from this issue to look at the bigger picture – on both ends, mine and yours. Communication is – once again – key into defusing potential tensions.

Recurring Meeting – 1:1s

1:1s are at the core of our communication. Their time is sacralised in my week and except if there is a literal fire, we won’t cancel it.

• They last 45 minutes max, once every 2 weeks. If we don’t have a lot to talk about, I’m not taking you hostage, but know that this time is yours, use it.
• You can prep them or wing them, I don’t care, but know yourself: if we’re talking about the last 3 days every session, we’re both loosing time. You will have a shared document with me with notes from our last session, use it if necessary. They are the only meetings I take without an agenda.
  • The first 4 are somewhat special, as they follow these questions: First 1on1s
• You can come with whatever you want. I will lead a bi-yearly session about your career and performance, but we’re not limited at those 2 to talk about these subjects. Bring it 🙂
• They will happen once every two weeks but they can move. Don’t hesitate to suggest a new time directly in the calendar. No need for 42 Slack messages (see the Communication part below in this doc.

This is the only meeting I work with. The rest is on-demand – from me or a team member – and can be suggested with a thorough agenda. A 1.5-hour meeting with 5 people costs 7.5 hours, almost a work day. Use these times wisely.

Communication

• I tend to prefer async communication via Slack/Discord. Everyone is in charge of its own notifications. If I send you a message, you don’t have to reply immediately, especially not on weekends or holidays. I send it whenever I come across it and trust you to get back to me. The expectation here is that you will 🙂 At the latest though, I do expect an answer at the start of your next working day. These expectations are aimed at you, and you can have the same towards me.
• Whenever I’m in a call, I prefer to have everyone’s cameras on. Remote communication is already hard as it is, so I feel like removing all non-verbal is not necessary.
• I believe that good management goes hand-in-hand with strong connections with people. I’m not trying to intrude into your personal life but I believe that if we understand each other better, we can better build the necessary empathy for one another.
• I will send you an event through our calendar app directly. It does not mean that it’s a final time-slot, you can suggest another one if it does not work for you.
• A meeting should have an agenda, otherwise it’s a chat but should not require mandatory presence. Call me out if I’m setting up one without, I’ll do the same!
• Start a message with FYI to easily communication that this is informational and not expecting an answer. I love this.
• I like to joke around, chat about video games, sports or else, no need to always be 100% about work. I like a good tier 3 meme every now and then too, I’m somewhat of a meme enthusiast myself (#sfw… at least in the company slack channel).

Inspirations

I’m heavily inspired by:

• Claire Hughes Johnson’s – ex Stripe COO – very own “How to work with me” that inspired me to write this one.
• Servant Leadership philosophy
  • My role is to help you become better, more efficient and happy at what you do
• Radical Candor book
  • If something is wrong, I’ll just go ahead and say it. There is nothing personal, ever. If I challenge you, it’s in your and the company interest.
• Turn the ship around book
  • From Leader → Follower to Leader ↔︎ Leader. Fascinating stories to illustrate this shift in paradigm from the classic 80’s top down management to a more modern approach.

Latest update: July 8, 2024 by @Stan