How I work

This is a rough guide to working with me. It’s my best effort to document how to get the most out of me, based on my own reflections and collected observations from former colleagues. Hopefully you don't need to read this to work with me, but it might help.

Communication style

• I am personable and open, but can be quite goal oriented, and I’m often guilty of cutting short the chitchat, and moving on to meeting goals and the main topic.
• Although I might seem outgoing, my inner me is an introvert, and I don’t like competing to be heard in group conversations. If there’s already enough people asking good questions, I’ll probably let them continue while I focus on listening and thinking.
• If the conversation seems a bit one-way at the start, that means I’m trying to gather enough data to form a mental framework to approach the rest of the conversation with.
• I can get frustrated when a meeting is derailed, am known to try to take the wheel to get it back on track.
• Speak freely, and tell me when I’m wrong. I don’t care about being the one who is right, and I won't take offence unless you are explicitly trying to offer it.

Workflow and preferred channels

I’ve been operating the Gettings Things Done (GTD) methodology since the 2000s. Among other things, this means:

• I normally have less than 5 emails in my inbox. Every email gets processed. If you write me an email, you can be sure that I will read it soon, and if it requires action from me, I will translate it into my to-do list and calendar, or delegate/reject and let you know.

• Clear and actionable requests will probably move directly into my to-do list or calendar. Ambiguous emails will likely languish for days before being lobbed right at you for clarification. Requests that I can satisfy in less than 5 minutes will probably get done immediately.

• I am on Slack, Whatsapp and Signal but they are not in my GTD workflow. They are disjointed and ephemeral and I treat them as asynchronous. I might reply immediately, or I might not; I might forget about it, miss the notification, or dismiss the notification if I’m on personal time or it’s inconvenient. If it’s important and you require me to act, you should choose email.

• For work-related chat, please prefer Slack, where available.
• If you need to escalate, start with Whatsapp. If you need to grab my attention in real-time, contact me however you need to, including a phone call.
• I don't check social platforms like LinkedIn or Twitter X, so don't bother trying to communicate with me there.

Some boundaries:

• If I don’t know you, don’t expect a response.
• If you phone me from a number I don’t recognise, I won’t answer.
• Send me a message whenever you like, but I probably won’t respond until I’m next working.

Personal Pitfalls

• I have a tendency to jump deep-dive down interesting looking rabbit holes, which is fun but can be an unplanned and bad use of my time, and could be a waste of yours. If I’m pulling the conversation in a direction out of curiosity, feel free to flag it.

• The perfect is the enemy of the good. People have previously pointed out that I over-invest in building upfront infrastructure rather than just getting a job done in the quickest way. There is a tension between getting things done right vs getting things done quickly. It's okay to hack or bodge something together if it can be quickly replaced later on, but we always have to mind our technical debt and avoid creating shoddy foundations that compromise our future work. However, I definitely like things to be perfect and I get an endorphin hit from 100% completing jobs before I move on. I try to keep that in check.

• I get a kick out of improving any craft, whether that’s coding, welding, woodworking, sewing or gaming. This can sometimes be fun disguised as work. If I seem to have ended up in the weeds but have an inexplicable grin on my face, you might need to intervene.

Meeting Time

Meetings scale badly. As you add people, their cost grows linearly and their quality declines exponentially. Before organising a meeting, consider if some kind of async group chat would suffice instead.

If you want me to join a meeting with more people than you and me in it, bear in mind that some part of me will be asking:

• Is someone chairing this meeting?
• Is there a clear goal that’s achievable in this session?
• Is everyone necessary in attendance? Is everyone in attendance necessary?
• Has everyone done their homework?
• Are we identifying actionable next steps and assigning ownership?

That said, if you just want an open-ended chat, coffee or walk, I'm usually amenable.

About Introductions

Introductions are made possible by reputation and network - two things it takes a lifetime to build. I take them seriously!

• Feel free to ask me for an intro to anyone I know, and I will tell you if I think it’s appropriate.
• I will always ask permission before making an intro, and will always include a paragraph saying why I think they should take the intro. If that paragraph is hard to write, I won’t do the intro.
• Before you introduce someone to me, please ask me first and tell me why.

For advice:

Mentoring, coaching and advising have mixed up definitions, but I'll go by “adviser” as the least exotic of the three. Sometimes I work for an extended period with a startup founder for a few hours a month, sometimes providing tactical or strategic advice based on my own experience, and sometimes just by being an informed sounding board. The interaction should be focused on areas where I can create high value for the startup at low cost to me - normally by contributing experience, knowledge, clear thinking or introductions. It's not about me doing the work. This is a long-term relationship that is a two-way street. It gives me insight into your industry, allows me to learn what you learn, can lead to other opportunities for me, and if all goes well might lead to a longer-term friendship between us. However, it is impossible to push advice - you must ask for it.

If I'm your boss...

I try to be the manager I would like to have. Here’s what I think that means:

• I aim to equip you with clearly delineated but challenging responsibilities, the autonomy to direct yourself, and the resources you need to succeed.
• My main goal is to get obstacles out of your way. Maybe you need training, support, tools or resources, or maybe you just need help making a difficult decision.
• We do 1-on-1s every week, and we check-in every day. Most obstacles should get removed daily. We might schedule time to work together to solve particularly hard problems. The weekly 1-on-1s should prevent things falls between the cracks.
• You send me short async and regular updates on progress and outcomes as you go (email, IM etc). This means we can spend our face-to-face time more productively and I don't spend time chasing progress reports.
• You proactively call in support when the going gets rough. I never want to discover you’re failing because you’re missing something you need to succeed.
• This job is one step in your career. I’ll want you to spend as much of it as possible with the company, but my hope is that you will ultimately outgrow any company you join. We can be realistic about that, and talk openly about getting you the opportunities and experience you need to grow as quickly as you can.

Introspections

On engineering. Not only am I an engineer by training, but I’ve been disassembling and building things since I was a kid. I view nearly everything through an engineering-tinted lens, but I’m not just interested in machines and code. When all you have is a hammer, everything looks like a nail. To me, accounting, marketing, recruiting, org design and politics all look like process problems. At least, that’s where I tend to start. I try to grasp every field from some kind of first principles. Some experts don’t like this and want people like me to stop asking questions and stay in our lane, but I need to have at least an outline understanding of how something works in order to get creative with it.

On problem solving. I work through every-day problems like a computer programmer and think with jargon that is lifted straight out of my education. Ideas get arranged on orthogonal axes, and work gets optimised with short-circuit evaluation and binary searches. If you want to take a closer peek inside my interior monologue I tried to blog some of it here.

On Uncertainty. When doing something new, there will be a need to make fast decisions despite fundamental uncertainty. I am comfortable with this, but I still like to increase my chances. I prefer decisions based on data, when data can be practically obtained. I want to learn whatever is easy to learn, and have a plan about the remainder. How and when to learn it, or where to find an expert. I’d like to try to scope out my unknown unknowns, perhaps with some external advice. When we can’t make decisions based on data, I’d like to check if my intuition is at least based on experience. When there is neither data nor reliable intuition, I try to make the least catastrophic guesses.

On Energy. One of my most popular blog posts is The Energon Methodology (inspired by the 1980s Transformer cartoon, or the Michael Bay movies if you prefer), in which I set out a basic method of accounting for mental energy expended during a day. Hard thinking requires emotional as well as intellectual fortitude, and many days don’t work out as planned because something comes along and steals all your "energons". For me, giving people my full attention is both rewarding but very costly in terms of energons. If I spend a morning consulting, teaching or being an attentive soundboard, I probably won’t spend the afternoon coding. The most expensive energon loss comes from stressful conflict, whether in work, at home or in transport between the two. I have found it’s important not only to know how to be calm when someone else isn’t, but more structurally to avoid spending time with people who cause conflict.

Books

Some book that significantly influenced me.

• Getting Things Done
  A book with a fanatical following of people who feel it saved them from certain insanity. How to run your busy inbox, task list and calendar with a confidence that allows you to put your work down, stop stressing and maintain your creativity, productivity and happiness.

• The Elements of Style (a.k.a. Strunk and White)
  A writing style guide that is 100 years old, out of copyright and incredibly influential. It espouses and practices pithy writing, takes just a couple of hours to read and is free online. If you don’t know "that" from "which" you should read it ASAP, and receive the superpower of being able to write compellingly, precisely and kinetically.

• The Innovator’s Dilemma
  The book that coined “disruptive innovation” is big, dense, often misquoted and a bit of a slog, but it provides a complete framework for understanding how technology and markets interact to create industry waves, and when a David is likely to beat a Goliath, and when he’ll get trounced.

• On Bullshit
  A short, formal and nearly completely straight-faced theory of the existence of bullshit as distinct from lying, which is increasingly relevant in this new age of generative AI.

• The Design of Everyday Things
  A famous book about product design, from just before software ate the world. The design of an object should communicate to its user a model of its capabilities and available interactions. Readers of this book are intolerant of bad door handles, mindful of good teapots and in a wax-on/wax-off kind of way, strongly opinionated about software UX.

• Running Lean
  It’s the short applied version of Steve Blank’s The Lean Startup. If you are short on time and just want to ingest the lessons, spend a few hours with Running Lean.

• Crossing the Chasm
  So widely cited and embedded in every other theory, that simply reading the wikipedia article might remind you that you already know it. But if you don’t, it’s how you go to market with a new technology product, know the difference between an early adopter and the early majority, conquer a beachhead and find a path to the wider market. If that sounds new, go read the book.

• Tom DiMarco’s Peopleware and Slack
  The two first books I read on the topic of managing people and building teams, which were new at the time and made special space for the particular needs of information workers.

• Built to Last
  If you’ve had enough of corporate culture and values, then you can blame this book. But you haven’t actually read this book, you probably don’t get it. It's a kind of split twin study, charting fortune 500 companies that have been around for a long time in comparison to their original rivals who never made it. It’s answer: having a culture and value system (whether for good or for evil) produces efficient group decision making processes and effective organisations. Anti-pattern: trying to invent or impose a culture never works.

• The Challenger Sale
  Based on a study of hundreds of sales teams, a cluster analysis identifies 5 types of sales person including the usual suspects, but also a new type of salesperson who excels at selling complex products by combining some pushiness with unique domain expertise. Convinced me that an engineer can be a great salesperson without selling his or her soul.

• Accounting for non-accounting students
  You can't avoid accounting and bookkeeping. If you're going to be an entrepreneur, it's will be a big part of your life. The best strategy is learn it soon and well so you can use it as a tool to properly manage your business, not just stay compliant. This is the book I used.

• Getting To Yes
  The book that coined BATNA and ZOPA, and showed us that negotiations shouldn't be zero-sum games. Being an agreeable sort of person, I used to dread negotiations, and would often avoid them entirely (and probably missed lots of opportunities as a result). I also witnessed pitbull negotiators irrevokably wreck working relationships in an attempt to "win". This book provided me with a principled and comprehensive framework to calmly approach any negotiation with, with the aim of a mutually agreeable outcome. This has been useful in both business and life.