Writing on the web since 2003

Monthnotes – May 2026

Sunset at Bridge, May 2026

Lots going on as ever this month with a couple of new clients joining the Team Wakeman client roster. The experience of building Team Wakeman … Read More

Build #103 – Your BOS tool won’t save you (but it might just help)

SPONSORED NEWSLETTER Build #103 – Your BOS tool won’t save you (but it might just help) Hey Reader, I talk a lot about operating systems – more specifically business operating systems (BOS) – things like EOS, Scaling Up and their ilk. And even more specifically I’ve been doing a client project reviewing the tooling options to support their BOS – yes, systems to run a system. It’s all getting a bit meta. I’ve been doing a market appraisal of the software tools that have sprung up to help…

Build #102 – Autonomy without boundaries just isn’t autonomy

Build #102 – Autonomy without boundaries just isn’t autonomy Hey Reader, I’ve been thinking about something that came up in a project I’m delivering at the moment (it’s funny how these little moments sit with me for days afterwards). I’m working with a tech SaaS client on building the “practices” component of their bespoke business operating system. I was leading a workshop exploring how decision-making needs to change as they make a fairly rapid push from 35 to 95 people over the next year….

Monthnotes – April 2026

Sundown by the River Stour in Chartham, April 2026

The Easter bank holidays in the UK at the start of the month plus a few days off work gave the first half of April … Read More

Build #101 – A worse version of you?

I’ve been noticing something over the last month that’s been making me increasingly uncomfortable, so I wanted to share that in this month’s Build. Let me give you an example that stuck in my mind. Last Tuesday, I was reading a Slack message from a founder I’m working with. It was perfectly constructed, well formatted with clear bullet points and a nice professional tone. But still it took me reading it three times to realise what was really…

Monthnotes – March 2026

This month’s notes are probably the saddest I’ve had to write since I started writing monthnotes back in 2019. Last Thursday, our beloved labradoodle, Meg, … Read More

Build #100 – Ringing the changes

Build #100 – Ringing the changes Hey Reader, One of the things I seem to do a lot with founders is prioritisation. There’s a real purity in knowing what to focus on and where to place the effort we put into building businesses. And now it’s time for me to take a bit of my own advice and get my house in order. Many of you will know that a real focus for me this year so far has been launching and building my new operating partner business – Team Wakeman, as well as my new founder newsletter The…

Build #99 – Mind the gaps

Build #99 – Mind the gaps Hey Reader, There’s a particular kind of organisational dysfunction that really been bugging me this year – when everything looks right on paper, yet nothing quite works in practice. This week’s Build pulls together three articles exploring critical gaps that separate intention from reality in how we build companies. What makes these gaps so dangerous isn’t that they’re invisible, it’s that we seem to have become remarkably skilled at pretending they don’t exist at…

Build #98 – AI and the workslop epidemic

Build #98 – AI and the workslop epidemic Hey Reader, I’ve been thinking about a particular kind of waste in business a lot recently. Not the obvious kind – where someone clearly hasn’t done the work or has done it badly. That’s easy to spot and easy to fix. No, I’m talking about something far more insidious: work that *looks* perfectly fine but is actually wholly worthless. It’s work that appears plausible, sounds professional and uses all the right language. But when you really examine it,…

Monthnotes – February 2026

I realise I say this most months, but February felt simultaneously short and packed. Maybe it’s the combination of a 28 day month, half-term, illness … Read More