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Simon Wakeman

Build is my free email newsletter for founders interested in building sustainable and resilient businesses.It features insights, techniques & thinking for those navigating the ups-and-downs of the growth journey and developing their own leadership along the way.

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Build 55 - valuable voices, mining metaphors and storytelling skills

Build 55 - valuable voices, mining metaphors and storytelling skills Hey there, It’s Simon here with your Wednesday dose of Build. This week I’ve got three fascinating articles that grabbed my attention plus a quick recap from last week’s issue: 1. What you see is what you get… Geoff Marlow has a nice piece on how we use organisational metaphors in business. He explains how the use of four dominant metaphors can affect the emergence of organisations, often without much conscious thought about...

Build 54 - avoiding OKR fails Hey there, It’s Wednesday so time for this week’s Build newsletter for founders. A couple of years ago I was being asked to do a lot of work to help founders with objectives / key results (OKRs). That led me to investing my own time and money in becoming a Workboard accredited OKR coach. And what I learnt on that course led me to question the value of OKRs in the founder-led growing businesses that I work with. I'm sure that wasn't their goal with the course...

Build #53 - reflective leadership and organisational containers. Hello, Today I've got three interesting founder-friendly links worth your time: 1. Four keys to leading today Not another leadership article, surely Simon? In this one Rishad Tobaccowala sets out what he considers important leaders in 2025 through four components.He explores these areas in some depth and provides a refreshing candidness about what good leadership really looks like in the new era of work. My take: Regular Build...

Build #52 - the grip paradox Many years ago I remember a founder in a company we acquired. He was charismatic, bright, forceful and outwardly hero leading his business. But once we stripped back the layers, we saw toxicity, dysfunction, an unhealthy culture and a failure to spot and get hold of the real issues holding it back. We’d uncovered a leader without grip - a performative leader who seems to be taking superficially plausible actions. But in reality they’ve not got a true grip on the...

Build #51 - rebuilding better, BOS design and discomfort with feedback Hello, After the joys of last week’s look back at 50 issues of Build, normal service resumes today. Here’s my round-up of the most interesting things I’ve read recently: 1. Rebuilding better Michele Zanini explores some high level directions that might be taken in rebuilding US government organisations after Musk has wreaked havoc. He recognises that refreshing organisations involves a certain amount of trauma, but that...

Build #50 - the journey so far Hey there, Today’s Build has a slightly self-indulgent feel. I’m taking a look back over the last 50 issues of my newsletter for founders. I was going to title it “the greatest hits” but I bailed. Build began in November 2022 as an exploration of how businesses can scale better – becoming sustainable organisations for the long term, not grown too fast upon weak foundations. Then as I went independent in January 2023, it became an opportunity to capture...

Build #49 - coaching, measuring and disaggregating work Hello, Hope your week’s going well and you’ve got a little corner of brain space for three interesting articles I spotted recently: 1. Measuring knowledge work is hard Cal Newport has an interesting article that segues neatly from Elon Musk through management by objectives to its modern day counsin OKRs. The common thread is the challenge of measuring the unmeasurable - how knowledge work is inherently unmeasurable, despite a lot of...

Build #48 - why you need a BOS Hey there, I’ve worked closely with founders in growing businesses since 2014. Over those years I’ve noticed a few patterns that hold true almost everywhere. One is about the founder’s ability to devolve the right to make meaningful decisions. The sad version of this pattern is where the founder holds decision-making power close and doesn’t really enable others to genuinely take decisions. As the business hires good people into leadership roles, they work out...

Build #47 - place, governance and the ego toll Hey there, It’s Wednesday which means a quick canter through three interesting things I spotted this week: 1. We are shaped by place Jindy Mann explores how place shapes who we become on our journey through life. Through the lens of his own experience, he considers how the contexts in which he has worked and travelled might have shaped the people he met along the way. My take: I love Jindy’s writing. It's beautiful. It never fails to transport me...

Build #46 - the case for curiosity Hello, I hope your week’s going well so far. In this week’s Build I’m asking you to take a step back and join me in an exploration of why curiosity matters. Our life experience shapes who we are and the way we work. It strongly influences the way we perceive those around us and our interactions with them. Yet we rely too much on our experience and this leads us to make flawed decisions. Psychologists Emre Soyer and Robin Hogarth have a great book about this...