My ‘top tip’ for CEOs


e14 / podcast & show notes, wherein I unabashedly champion Brave New Work

Illo by  dangerlam

Illo by dangerlam


Whew, so that last episode was a (wonderful) doozie. Thank you dearly to those who wrote in with appreciation.

But by golly—I can’t let that be the new standard. Otherwise these things will barely ever get published, and my next book—the thing I tell myself I am ‘meant’ to be writing—will never get writted.

Ergo, here is my valiant attempt to temporarily suspend my tendency to obfuscate the sharing of my ‘truths’ (and to turn any attempt at writing into an unsolicited saga). Watch me as I get straight to the point:—!

In this episode I answer one of the first questions I received when putting out the Call for Questions in the launch of my podcast. I’m not entirely sure if it was a joke, given my avowed allergy to ‘tips’. But, as a Fool, I take humour very seriously.*

* ‘Tis no laughing matter, humour. A lot of truth is said in jest, it is said.

Here’s the question:

“Hi Jason. What are your top tips for CEOs of legacy organisations?” – David, ex-CEO

A subtly profound question. I am not sure that ex-CEO (aka David) really took the opportunity to embrace a mythic title (it’s one of the things I ask of those who gift me with questions), but nonetheless I enjoyed a good rant about Many Things in this episode.

To my horror, though, as I write this (after the podcast was recorded) I realise two things:

  1. I really ought to have highlighted the sheer hubris in my stance of thinking I had any right to answer such a question (though, having worked somewhat deeply with many CEOs and their leadership teams, I feel I have some right, perhaps—but only a smidgen… enough to serve as a provocateur of thought, one hopes).

  2. I kinda misread the question as ‘top tip’ (singular), rather than ‘top tips’ (plural). But in my signature meandering style I don’t think ex-CEO was short changed at all—we covered some good ground. And I kinda liked the challenge of collapsing everything into a singular and almost practical ‘tip’. A rare experience, for me.

But what was my top tip?

Hoho, yes I’m being quite coy in regards to that. It was something to do with enabling CEO’s and their senior leadership teams to better progress deep conversations and to make meaningful progress in complex domains. It’s an incredibly practical tip—though very few really want to hear or contemplate it, and it can be tedious to implement. Mysterious!

Now, onto the show notes.

First and foremost, I found myself unabashedly championing Brave New Work—a new book by Aaron Dignan of The Ready. I have been an admirer of Aaron’s work ever since he wrote Game Frame, and I fancy some minor similarities in our paths.* I was familiar with Aaron’s work—he and his team are very generous in sharing their thinking—but this book encapsulates things wonderfully. I’d recommend it as essential reading for any leadership team, and a primer before any leadership off-site. It’s that good.

* We both started to see the connections between game design and work design, and have both since taken a journey toward greater complexity.

Other things I mentioned on the show:

» Why we dumb things down is an article I mentioned in relation to the crowded channels (and capacity) for leaders to think. It pairs well with my article on the 5 pernicious patterns most leaders cannot see.

» I think I mentioned the notion of ‘teamwork’. Dom Price (Work Futurist at Atlassian, interviewee in The Cleverness Biannual) is the instigator and co-developer of the Team Playbook (a practical guide to unleashing your team’s potential—it’s worth reading). You might also like this article he penned: How Atlassian teams build agility and strength (without silly games)

» The ‘top tip’ I shared in this podcast can easily be misinterpreted or dismissed prematurely. It’s something that requires we keep our wits about us, lest we descend into a new mess. Ergo, I highly recommend much of the writing of Jason Fried (co-founder and co-CEO of team communication software Basecamp). Their new book—It Doesn’t Have To Be Crazy At Workis on the rather ‘pithy’ side, but it makes some very good points. I tend to like Jason’s article writing more, though. For example, here’s an article wherein he shares the literal handbook for everyone who works at Basecamp. This even includes what happens if an employee finds themselves in a situation where their performance has been called into question. “Not knowing where you stand when there is a problem – or not even realizing there’s a problem at all – is an uncomfortable and unproductive place to be. You can’t do your best work when your mind is riddled with anxiety stemming from existential questions about job security. To clarify the process for helping identify and resolve such problems, we recently added a section to the handbook that details our newly formalized performance plan process.”

» I mentioned Scott Adam’s ‘Humour Diversification Rule’. It’s something I have in the back of my mind—to a very minor degree—as I oscillate betwixt topics and domains in the podcast and my writing.

» And finally, I couldn’t help but mention Cal Newport’s two books—Deep Work—Rules for Focused Success in a Distracted World and Digital Minimalism—Choosing a Focused Life in a Noisy World. My good friend Amantha Imber (whom I have interviewed, and vice-versa) recently interviewed Cal to talk all things deep work and digital minimalism, and I loved the added depth and perspective she unearthed. Highly recommended!

I hope you enjoy the show.

Have a question you’d like for me to muse upon in auditory fashion? Subscribe to my museletter and keep your eye out for my next Call for Questions. Or heck: just ask me here. I’m likely to respond.