Doctor’s Note — Issue 16 – The Design Leadership Dip

In this issue: Imposter Syndrome and the Design Leadership Dip / Social Distancing for Ideas / The Linkhole / Books /

Welcome to Issue 16 of Doctor’s Note. If you were forwarded this by a friend, you can sign up here. If you love it, you can buy me a coffee and I’ll love you back even more.

Since I’ve just started offering Design Leadership Coaching, I thought I’d share my experience of moving into that role. But first, some background.

A cliché photo of leadership for your pleasure. Credit: Jan Niclas on Unsplash

A journey into Design Leadership

A long time ago, someone once said to me, “The worst thing about growing up is realising adults don’t have all the answers.” I was in my mid–20s at the time, but it’s stuck with me ever since. 

Straight out of university, I co-founded a collective, Antirom with one of my lecturers and several student colleagues. Antirom had a completely flat structure and a very robust—albeit occasionally bruising—critique culture. This was only successful because we wrote that we were there for the “love and support of each other” in our founding manifesto. It also helped that our group of ten included two sets of siblings and a couple, which set the tone for a candour I’ve never experienced in the workplace since.

This structure was my first taste of commercial life as a designer of sorts (we called ourselves “interactive designers” — interaction design wasn’t yet a formed discipline with a name — but we did a lot more than that). I didn’t have an Art Director or Creative Director as my role models or the advantage of an existing agency structure to model any future endeavours upon. We really were making it up as we went along, helped by our friends at Tomato whose structure we borrowed from.

It also fanned my distrust of hierarchy, authority and titles. I could never understand the idea of deference to a Managing Director or CEO. These are just people like you and me. They eat, shit and make mistakes just like you and me. I respected people who had clarity and insight, for the things they had done and created, or who were able to do things I couldn’t. Sometimes that was someone in leadership. Sometimes it was an intern.

We got used to being the young guns, always trying to give the establishment the finger, or preparing to be treated as the kids in the room. Then, one-day several years later, someone asked for my opinion about a problem. I gave it and they replied, “Okay,” and walked off to do what I just said they might think about doing. 

It was a shocking moment of realisation that I was being turned to for leadership and direction. After all, we’re all used to the refrain, “that’s just your opinion.” And it is, but over time it’s one honed by experience. Judges have opinions too, but we trust them to judge wisely.

The dip

Seth Godin wrote a little book about The Dip. It’s about when to quit when something has become too difficult and when to push through the dip to the other side. 

There’s a similar moment that happens for designers moving into leadership positions. You start to let go of some of your “on the tools” craft skills and take on more business and people responsibilities. The result can be a confidence-jarring dip, where you’re not very good at either one. Imposter syndrome can quickly set in. I believe designers have a particular case of this due to the way the arts are treated in the education system.

I can pinpoint the exact moment, 20 years ago, when I realised this was happening to me. It took me a good year or two to become comfortable with the leadership role. Initially, I assumed the team would be just fine without much input from me, because I’d hired talented people. In fact the imposter syndrome kicked in hard, because I had hired people more talented than myself. I was desperately worried they’d respond to my direction with, “You do it then!” And, of course, I would not have been able to. That’s why I had hired them.

Then I saw the work of the team dip. It wasn’t because they were rubbish. It was because they, like all of us, regularly got too close to their work and needed critique, feedback and direction. Without it, the were struggling to move forward.

My feedback either confirmed their existing thoughts and freed them up to move on, or it would trigger them to defend their work. This is a good thing. It means you have a proper debate about the merits and failings of the work in hand. If you really feel you want to defend a piece of work and can successfully do so, the chances are you stand by it for good reason. Having that moment also helps people get unstuck.

The work got much better and I finally realised I was designing teams who design and beginning to understand the nature of design leadership.

Imposter syndrome is a healthy sign

Twenty years later and I’m here to tell you imposter syndrome never entirely goes away. I’ve got a PhD, wrote a book, work with design leaders and executives, regularly keynote at conferences. I still expect someone in the audience to stand up and say, “You’re not who you say you are!” in the middle of my talk.

What you come to realise is that everyone really is making it up as they go along. The key is becoming comfortable with that fact and trusting that your experience is valuable and will help you navigate unknown territory without panicking everyone else.

Leaders who are convinced by their own brilliance and have no imposter syndrome at all can be pretty awful to work for. Imagine if someone like that became the President of the United States.

Becoming comfortable with yourself is a life-long project. It’s what C.G. Jung described as individuation. The good news is that the self-reflection that goes into that process is one of the most useful tools for understanding how designers and teams get creatively blocked and will help you guide them out of the woods.

If you’re interested in having a guide through that process, get in touch. With a brown blanket wrapped around me and my glasses off, I can be a passable Obe-Wan Kenobi.


Social distancing for ideas

Okay, I’ve completely failed to avoid this Doctor’s Note mentioning Covid–19, but one of interesting side effects of the current pandemic is that it’s such a clear demonstration of what it actually means for something to “go viral.” I had been thinking for some time that social distancing also goes for ideas and disinformation. 

Social media allows us to be very promiscuous with the passing on of information, of course. It’s an unhygienic idea cesspool. A second thought about re-posting or forwarding something questionable is the disinformation equivalent of wearing a face mask, washing your hands and keeping your distance. We should all really try it more often.

At the Fondation pour la Recherche Stratégique (it sounds so much better in French) I read an interesting short interview along similar lines with Audrey Tang, Taiwan’s Digital Minister. Tang works to fight disinformation and help to foster open government. Here’s her view on what a digital democracy means:

A digital democracy is a democracy with the use of the digital spaces, so that people can not only be talked to but also be listened to. When we talk about transparency here, we always mean that the state makes itself transparent to the people to show trust. It’s about listening, and it’s about trust. It’s about the government trusting the people without requiring the people trusting back. All the digital technologies are here just to amplify the trust that people can get in a face-to-face setting.

I loved the point that “It’s about the government trusting the people without requiring the people trusting back.” This seems to have been what’s gone so wrong with the policing in the UK. Others might disagree, but it’s one of things I like about living Germany – there is much more trust between the citizens and government and more accountability.

Tang is also optimistic about the power of memes:

Of course, meme engineering — that is, the “package the message in such a funny way that you simply have to share it” — can crucially allow accurate information to be disseminated more quickly. If it is possible for the accurate information to immediately follow disinformation, it can similarly gain just as much traction, a strategy that we call “humor over rumor”.

I am less convinced. As Jonathan Swift wrote:

Falsehood flies, and truth comes limping after it, so that when men come to be undeceived, it is too late; the jest is over, and the tale hath had its effect.


The Linkhole


  • Mark Shayler’s Do Present is very fine indeed. Essential reading for presenters, design leaders and anyone who fears public speaking. His “who stole your voice?” question is so simple, but goes straight to the heart of the matter. There’s also a bonus chapter on presenting virtually on the book’s resources website.

  • In Do Fly, Gavin Strange gives his take on how to “Find your way. Make a living. Be your best self.” It’s a charming and idiosyncratic take on also finding your voice and basically ensuring you still have fun in life.

  • Sticking with my Do Books binge, Do Open is a very human, non-marketing take on “how a simple email newsletter can transform your business.” You’re reading this one, so here’s hoping…

  • Daniel Stillman’s Good Talk is a “step-by-step framework to effect change in your personal and professional conversations.” Daniel and I had a lovely conversation recently that will be a future Power of Ten episode, once I’ve worked through my editing backlog. His “conversation OS” grid is insightful.

  • I also interviewed Jim Kalbach about his Jobs To Be Done Playbook for Power of Ten. He’s got a very clear writing style and successfully manages to be informative without being dogmatic. I used to be a bit of JTBD skeptic, but now I’m a convert. He makes the excellent point that it’s for everyone in the organisation to use and is especially useful that it doesn’t have the word “design” in the name.

  • I’m in the middle of Nine Lies About Work. It covers a lot of ground that The Stupidity Paradox and Brave New Work cover, but so far I’m mostly enjoying it and it’s worth a read if you’re in the middle of corporateland. Here’s a quote worth pondering in the context of Design Leadership:

Culture locates us in the world. It consists of stories we share with one another to breathe life into the empty vessel of “company.” But—and here’s the kicker—so powerful is our need for story, our need for communal sense making of the world, that we imagine that our company and its culture can explain our experience of work. And yet it can’t. So strong is our identification with our tribe that it’s hard for us to imagine that other people inside our company are having a completely different experience of “tribe” from ours. Yet they are—and these local team experiences have far more bearing on whether we stay in the tribe or leave it than do our tribal stories.

That’s it for this issue. If you liked it, please consider forwarding it to a friend or colleague to sign-up. I really do appreciate all the shares and feedback.

Take care,


P.S. You might also like my podcast, Power of Ten, which is all about design operating at different levels of “zoom,” but mainly consists of me talking to people smarter than me from a broad range of disciplines.