What is 'The Deliberate CEO', and why am I writing it?

Introducing my newsletter about my process and experience of learning to be a CEO

I’ve decided to write about learning to be a CEO in a deliberate way, because I think it will let me vocalise and work through the thoughts, quandaries, and questions I have about growing into this role (as co-founder and CEO of Lingumi), many of which I struggle to express in my own head. 

Read enough? If not, plenty of waffle below. If yes, here’s a subscribe button:

I plan to write a monthly article. The writing will give me a tempo and a discipline, which is a pair of characteristics common to much of what I do: with my approach to language learning, to fitness, and various other hobbies, I’m fairly rigorous and structured (to the annoyance of some friends), and so I see no reason not to be rigorous and structured with my approach to becoming a better CEO.  I’m calling it ‘The Deliberate CEO’ because I think being a good CEO requires a deliberate mindset, and this newsletter is a deliberate act in helping myself (and, possibly, others).

A warning I’ll make, loud and clear, to future readers: I’ve never had a job except this one. I’ve never been led by a great CEO, never been a senior exec in a big business, never done anything in the professional world except occupy the (self-appointed) position of CEO of Lingumi, a small company with a big heart and an enormous mission about which I’m extremely passionate.

I’m a firm believer that being a CEO is a skill that must be learned, and is not innate. This sounds blindingly obvious even to write, but forgetting it would be fatal; being a ‘good CEO’ is a journey, and not a sunny land at the end of a rainbow that some people are born in - forgetting that, or getting too comfortable, would slow or reverse one’s progress.

This newsletter will initially be most interesting to CEOs in the ‘growth’ stage of their businesses, and will be focused on strategy, business growth, and team growth for a technology business. As rough proxies, CEOs of technology companies at or approaching ‘Series A’ or who ‘have some semblance of product-market fit’ and sufficient capital to deploy in pursuit of hiring great people, and growing the business on a stable(-ish) foundation. This doesn’t mean I won’t reflect on the earlier or later stages; I hope to both reflect on the earliest stages, and to lean on the learnings of later-stage CEOs to look ahead. However, my principal aim here is a selfish one: to help myself grow at the stage I’m in, and prepare for the next one. For anyone who does read this, being at a similar stage will make it most relevant. I think ‘being good at Seed stage’ is really well-covered, and founders at Seed should focus on all the great writing on finding product-market fit, avoiding running out of money, and so on. If you do want to read this too, I’m flattered.

Founders already get far too much advice. I’m not going to offer much advice here, I’m just going to write about my experience running the business I co-founded, and talking to others at points about running their businesses, too. You can extrapolate from that what you wish.

I’m also doing this in the hope of building a community of CEOs at a similar stage to share learnings and experiences with me, and hope to share more ad-hoc experiences directly or in a group, depending on how it evolves. If you’re a CEO and want to read more frequent, more personal explorations, and have more regular conversations on the themes I cover in a group of peers, then consider me a willing sparring partner on anything. Email me (first name at domain dot com) and I’ll add you to a small group on Telegram or similar.

For now, this will be a free substack newsletter, but I’m considering charging for it one day, once it’s of sufficient value to anyone, for three reasons:

1. I am principally writing to encourage my own reflection and learning. So, the downside to charging is low - I’m not optimising a funnel for massive readership here. 

2. I intend to write some very personal pieces that expose and explore my weaknesses, and pro-actively limiting the access to that to high-intentionality readers seems reasonably sensible.

3. Having even one paid reader will act as excellent extrinsic motivation to keep going. If I ever decide to stop, I’ll simply issue a pro-rata refund and stop.

As a taste of what I intend to explore, I have an approximate monthly agenda, but will change this as my work, and the reflections it creates, changes. A sample of things I am thinking about, which I will address in no particular (or any) order:

1. How I create, and communicate, a company strategy that is non-fluffy and that my team understand and can use as a decision-making tool (and the worries I have about my method)

2. How I communicate with my team, board, and investors, what the results of this consistency are, and what I think I can improve

3. The value of my time, and understand how ruinous it is when I fail to say no to, or delegate, many of the things I do regularly

4. Working effectively with my co-founder (and how wrong I’ve got this sometimes)

5. Building our company’s Senior Management Team, and how I’ve tried to take this team through the ‘forming’ and ‘norming’ stages

6. How I work with my exec coach and what I find useful, and challenging, about our sessions (including some of the strengths and weaknesses in my 360 report...juicy reading!)

7. Deliberately managing my energy (and how rubbish I often am at managing my working energy through misuse of my time, poor planning)

8. How I am trying to find the right balance between ‘stepping in’ and ‘stepping back’ as I watch our team grow and take on the challenge of achieving our mission

9. How I try to push beyond my very non-confrontational nature in situations where confrontation is a useful tool

10. And many more, I hope!

Anyone who chooses to read this stuff, and wants to know how I do a certain something, just message me in the group. I will probably be happy to write about it, or call you to discuss it. None of this is going to be ‘life hacking’ or ‘this one secret trick…’ type stuff. It’s all bog standard, normal, human experiences, but I am probably guilty of trying to over-optimise my life in various ways, and I apologise in advance if I veer into advice territory in my writing.

So, here we go! My first long piece is about creating and communicating our company strategy, how I got to the method I use, and the various anxieties and issues I have about it. I’ve told a lot of friends who are founders about this method, and often they’ve found it fairly useful. Click below if you want to get my ramblings in your inbox.