Monthnotes – May 2026

Monthnotes – 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 as a business from scratch is a good reminder of the hard work and grind that comes from a standing start – and probably gives me a bit more perspective on the earlier experiences of the founders that I work with!

I’m also working on a fascinating operating model consultancy project with a mid-size experiential agency. The early, learning-heavy parts of a new client engagement like this are interesting – it’s where the nuances of each client business start to emerge and where the intellectual challenge starts to become clearer for me when I’m working as a consultant.

The middle of the month was a particularly intensive period, with clients across timezones spanning Los Angeles to Dubai. That meant I was getting pretty exhausted and didn’t do the 120 mile bike ride I had planned, which was disappointing but probably the right call. I need to get better at planning out client blocks of time to better manage this kind of thing.

Last week I facilitated a team awayday for a client who I’d helped operating model and organisational design last year. I enjoyed seeing a new organisation emerge and start to make the thinking I’d been part of a reality. Plus they’re a nice bunch, doing valuable work and I got to ride my Brompton through some lovely Sussex countryside. And there was a micro-pub on the station on the way home too!

I do a lot of calls. Once in a while one of them really throws my mind into overdrive – and this month a regular catch-up with former colleague and friend Ronald Ashri really did just that.

Ronald’s been doing some thinking about AI, knowledge and how people work that blew my mind. It resonated very well with my emerging thinking about how humans and AI work together coherently in organisations in 2026 – there are some clear patterns emerging that I am using in operating model and organisation design work. Ronald’s thinking felt highly complementary to my approach and that first call with him led to several more as he’s building out some fascinating tech to underpin his thinking. Interesting to see where this early thinking and experimentation leads to.

We had two public holidays this month in the UK. We took our motorhome away locally for a couple of nights on the second one, camping in a field with friends. The sun shone, we played padel and badminton, drunk beer and ate lots in celebration of my upcoming 50th birthday.

Yesterday I ran a 50k ultra along the river Medway in Kent with my friend Paul. It was a hot one but nice to not be running solo and to do an ultra somewhere a bit less mountainous than some others I’ve done. Was glad to get to do this after not feeling up to the cycle sportive a couple of weeks ago.

And finally today’s our 23rd wedding anniversary, so a very happy anniversary to my lovely partner-in-crime Jo Wakeman. With our eldest son finishing uni this week, our youngest heading off to uni soon and me turning 50 next month, life’s got a big transitional feel to it in many ways – but I’m pretty excited about what Jo and I have got coming up together in the next few years as life unfolds in new directions. And I should really thank her for putting up with me and my foibles for so long – here’s to another great year ahead xx.

Music this month…

Discovered Remark on Soundcloud when looking for some Pet Shop Boys. His tune selection and great mixing is superb. Here’s the Pet Shop Boys mix I have had on repeat a lot this month. And weirdly he lives about 20 miles from me.

Podcasts this month…

Not too many podcasts this month but this episode of the Operations Room was good food for thought on the AI & org design stuff I’m ruminating on after my Ronald chat.

Reading this month…

I enjoyed reading Alchemy: The Surprising Power of Ideas That Don’t Make Sense by Rory Sutherland. Lots of interesting ideas around marketing that are very transferable to my work too. Then I’ve started reading Johnson at 10: The Inside Story and it’s just making me cross.

Cycling this month…

100.9 miles.

Running this month

86.2 including yesterday’s 50k’er.

About SIMON

I work as a fractional Chief Operating Officer (COO), consultant and advisor. I created the B3 framework® for company building and I also write a newsletter called Build for leaders who care about creating resilient and sustainable businesses.