Kelly talks to Martin Dubin, a clinical psychologist, serial entrepreneur, business coach, and adviser to C-suite executives and Silicon Valley entrepreneurs about his new book: “Blindspotting: How to See What’s Holding You Back as a Leader.”   

There’s a story we tell in the book “Yes, And” about a leader for a group vying to build a new website for Second City and his level of poor communication was the reason we didn’t end up working with his group – it had nothing to do with technical ability. 

“And the natural inclination is not to look at themselves, right? When things go wrong, it’s like, ‘It was the economy,’ or ‘It was the other guy,’ or ‘It was my team,’ or whatever. And sometimes those are the right answers, but there’s probably an answer in there that has to do with the person. And that’s what the book is about. It is a bit of that catch-22 because if they’re a blind spot, how can you know? How can you see your own blind spots? And we can talk a little bit about the clues to doing that – but the first clue is just being open to the fact that you actually don’t know it all. It’s like the alcoholic saying, ‘Hi, my name is Marty and I’m an alcoholic.’ So, the first thing is to say, ‘I need to look at myself and start to get some help doing that.’” 

You also note that sometimes your own success can be a kind of blind spot. 

A positive feedback loop means you’re doing great, keep doing more of it. Whereas a negative feedback loop is self-corrective. So, the more success you have, the more you think it’s due to yourself. And another point I make in the book a number of times is that it’s always the interaction of the person in the situation. There are super talented people – and most leaders that I worked with were leaders at the top – and they were on target 90, 95 % of the time. But that isn’t enough always and getting that extra 5 % or 2 or 3 percentage points can make all the difference. And it is small tweaks at those points to pay attention to what’s getting in the way.” 

I know that when I shifted out of my main creative leadership role at Second City, I struggled with my work identity. 

“When I talked to leaders about this, I saw this a lot in Silicon Valley, where super creative people and their identity is as an innovator, right? They’re launching some new product to the world, and at some point when that catches traction and their business starts to build and they’ve got a market and so on, then they need to make a shift from innovator to business builder and eventually leader. And I don’t know if you experienced this, but there should be some grief about that, right? I mean, you gave up that old identity that brought you so much joy and everything else. And you make the shift to a new identity and comes with a bit of a sense of loss.”