As leaders, we all hit a point when things stop going well. A problem emerges that we think we can handle but discover we can’t. The tools that got us this far somehow stop working. We don’t understand; what are we missing? What we don’t see is what we can’t see: we have blindspots.
It’s a known fact that we’re often not great judges of ourselves, even when we think we are. Sometimes we’re simply unaware of a behaviour or trait that’s causing problems. Other times, where we see normal, effective behaviour, others see tremendous deficits. Bottom line: until we uncover these blind spots, we can’t move forward or deliver on our goals as leaders.
The good news is that you can learn to do your own blindspotting. Clinical-psychologist-turned-entrepreneur-turned-business-coach Martin Dubin has spent years learning when and how leaders get in their own way, and he has turned that experience into a deeply practical blueprint to help you identify your professional blindspots and work to overcome them. In his new book, Blindspotting, Dubin provides a framework for understanding six types of blindspots, then takes you inside coaching sessions with profoundly relatable leaders going through the process of learning to recognize their own blindspots.
In this interview I speak to Martin Dubin, a clinical psychologist, serial entrepreneur, business coach, and adviser to C-suite executives and Silicon Valley entrepreneurs. He founded several companies, including a multimillion-dollar health care company where he also served as CEO. A former coach at the Center for Creative Leadership and a partner at talent firm RHR International, he worked directly with hundreds of C-suite senior executives from Fortune 500 companies and with Silicon Valley venture capital firms and their portfolio companies.
Q: Are there any key traits you see psychologically, in great leaders?
[Marty Dubin]: There are definitely some traits that are essential to being an entrepreneur, and we can talk about those. But at the end of the day, what really matters is how well you know yourself — because every aspect of your leadership is expressed through your personality. The more aware you are of who you are, where your strengths lie, and where you have opportunities to improve, the more deliberate and strategic you can be in how you show up and how you manage yourself. I think that single trait — self-awareness — or rather, that skillset, outweighs all the others put together.
You’re filtering every experience you have with others through your own perceptions, your own biases, your own reactions and instincts. So you have to know yourself first before you can truly know anyone else.
Q: Are there any specific traits you see in entrepreneurs?
[Marty Dubin]: I mean, number one is confidence, I think — because as an entrepreneur, you’re often doing things that haven’t been done before, or doing them in ways that break the mould. All sorts of people are telling you, “No, that’s not how it’s done,” or, “You can’t do it that way,” and you’re trying to push the boundaries, so you’re constantly running into obstacles. Without a lot of self-confidence, you can’t even get started.
Then, what naturally goes along with that is perseverance — you just have to keep going at it. But the trick, I think, is knowing when you need to pivot. That confidence and perseverance can sometimes lead you to keep charging ahead headfirst, when what’s really needed is a pause and a course adjustment. I think that’s the challenge — and I talk about that in the book — when strengths get overused.
Q: What are leadership blind spots?
[Marty Dubin]: I’d had this unusual career, and I started wondering — why did I say what I said to those people? Why did I give that particular advice? I really tried to unpack my methodology, because being a psychotherapist and then a coach, a big part of it is the art of relationships and being intuitive. But to be honest, I was pretty frustrated when I shifted from being a clinical psychologist to a coach, because there was no science behind it. I mean, how do you even know what’s really wrong?
As a psychotherapist, you have diagnostic categories for problems. There are specific techniques and therapies to apply. So the book really comes out of that frustration. If you think about science, it progresses from description, to categorisation, then to explanation, prediction, and control — and I wanted to feel like there was some science behind what I was doing.
So Blind Spots is really a taxonomy — a categorisation of where to look. If your arm is hurting but the real issue is in your hip or somewhere else, you need to know where the actual cause is, where you really need to go after. That’s where the whole thing came from.
And as I sat back and thought about my patients as a psychotherapist and my clients as a coach, those six areas just kept showing up. At one point I had five, at another point nine, but eventually I landed on six as the right number — the ones that consistently mattered.
[Vikas: and what are those 6 areas?]
[Marty Dubin]: I wanted no psychobabble or scientific terminology — I wanted everything to be in common, everyday language. Because I think we’re all scientists when it comes to ourselves. We observe, we reflect, and we try to figure ourselves out.
I use a diagram to help make sense of it — think of it as three concentric circles. The outer ring represents what we’re most aware of about ourselves: our behaviour and our identity. We can talk about each of these in more detail, but I’ll just give you the overview. Behaviour and identity are things we can access pretty quickly. We can observe our behaviour. If someone asks, “Who are you?” we have words to describe that.
The middle ring is made up of things that are harder to grasp, but we still have some awareness of them — our intellect, our emotions, and our traits, which we touched on earlier.
Then, at the very core — the bullseye — is our motive. That’s the engine in the system. What’s driving us? Why do we do what we do? As a psychotherapist, that’s often what you’re really trying to get to with people. And it’s often what surprises them the most — when they feel something strongly and have no idea why. Why did you cry at that movie? Why did you instantly like or dislike someone? Those motives are harder to access, but they’re often the real drivers behind our behaviour.
Q: What is the role that your sense of identity plays as a leader?
[Marty Dubin]: …we have multiple identities. And like I said, identity is on the outside because it does change. You become a parent — one day you weren’t, your identity was as a couple with your partner, and then you have a child. Your identity immediately shifts. You’re now a parent, and suddenly you’re paying attention to diaper commercials and all sorts of things you never noticed before, right?
Some of our identities run deeper — other people can see them, sometimes more clearly than we do. I like to talk to business people about this in terms of brand: you work on the brand of your product, and this is like your personal brand. Your identity is your personal brand. Sometimes you know exactly what it is. Other times, other people figure it out and see a version of you — a brand — that you may or may not even be aware of.
And the blind spot happens when your identity and your role aren’t fully aligned. I saw this all the time with entrepreneurs — and I’ve been one myself. Entrepreneurs often start out as innovators. You’re excited about doing something new and different. If you’re lucky enough to gain some traction, and your product finds a market, now you have to build a company. That requires a whole new set of interests and skills. But a lot of entrepreneurs don’t make that switch. They cling to that brand identity of “I’m an innovator,” still tinkering with the product while everyone else is saying, “Hey, it’s good enough — let’s hire our first salesperson,” or do whatever needs to be done. And eventually, you have to make yet another shift — into the role of leader.
So when you’re not really thinking about the alignment between your role and your identity, that’s when problems can start.
Q: is there a big difference between identity and traits?
[Marty Dubin]: We’re complex, and there’s constant feedback happening. Everything inside of us is going on all the time, and everything is influencing everything else. So I say in the book — don’t get too hung up on making fine distinctions. The real point in working with these blind spots is to figure out where you’re having difficulty and what’s most apparent to you.
So, for example, if you think your trait of confidence is getting in the way — maybe it’s turning into arrogance, or you’re becoming so decisive that you move too quickly — that might be a trait, but it could also be part of your identity: “I’m the decider, I know what to do.”
And I don’t think it really matters which piece you start working on, because when you work on one, you’re also working on the others. It’s just a handle — a way for people to start narrowing down what to focus on.
Q: How should we think of motive as leaders?
[Marty Dubin]: We are so influenced by what we think other people want to hear, and we often talk about our motives in that way — just like you’ve described. But I’ve also seen the opposite. I had one entrepreneur who, after a discussion, asked, “Can I talk to you really confidentially?” And he said, “My company has grown bigger than I ever thought it would. I don’t care about the money, but my VCs keep pushing me to make more. I’d really rather just have an easy life and get out now — but everyone’s depending on me.”
So that was an honest conversation about how money, beyond a certain point, really wasn’t important to him. And that’s why it’s so important to get clear on what’s driving you. There’s never just a single motive. I talk in the book about this Harvard organisational psychologist, from quite a while ago, who came up with three universal motives in business: the motive to achieve, the motive for power, and the motive for affiliation.
And I think that’s a great place to start. We all have some portion of each. Different situations pull more strongly on one or another, but the trouble starts when people are really out of balance with them — or when they’re unaware of what’s actually showing up.
You’ve probably heard someone say, “Oh, he just cares about the money, that’s all.” He’s standing up in front of the senior team talking about all these grand ideas, and nobody sees that — all they see is a single motive. So being aware of your motives, and learning to balance them according to the situation — that’s where the key is.
Q: How can we understand where our blindspots are?
[Marty Dubin]: It is kind of a catch-22 — if they’re blind spots, how can you see them? So the first thing is self-curiosity. Just being curious about yourself. My point is that you and I could read the same book on leadership or how to run a good team meeting, and we might take away the same five lessons, but we’d still apply them differently — even if we were trying to do exactly the same thing. That’s because of our different personalities.
So being curious about that — about your personality and how it’s actually a tool for your leadership — is the first place to start. Then, from that foundation of self-awareness, you can begin to ask: Where am I struggling? Where do I feel stuck or confused about why things aren’t improving? And instead of defaulting to “It’s the economy,” or “It’s the product,” or “It’s that other team member,” you begin to ask, “How might I be contributing to this problem?”
One place to often start is by looking at traits that may be overused — because strengths, when overplayed, can become blind spots. I tell people to take something they’re great at and put the word too in front of it. What happens if you’re too decisive? Too creative? Too organised? That can help you start thinking about how these traits might be showing up in ways that aren’t always helpful.
But at the end of the day, we often discover our blind spots through other people. That might be through 360 feedback or simply by listening to what people complain about. And that was the hard part for me as a coach — figuring out how to interpret that feedback. How to see those so-called weaknesses not just as problems, but as reflections of deeper strengths, or aspects of someone’s identity. Often, what people are pushing back on is really just the flipside of something fundamental about who you are.
Q: How does behaviour play a role?
[Marty Dubin]: Your motives show up in your behaviour, your identity — they all push you to act in certain ways. In the book, I talk about three things that are more like complex behaviours: influence, communication, and prioritisation.
Take the example you just gave. You might ask yourself, “Alright, I think this is the right decision — now I need to influence the team, or my co-founder, or whoever it might be.” Then you start thinking through that process: what are the different ways to go about influencing? Because maybe you are 100% right — everything lines up, and it is the right decision — but you stumble in the execution, in the behaviour of influencing. So you need to consider: how do I appeal to the different stakeholders involved in making this happen?
Prioritisation is another one. Are you really doing what you need to be doing as a CEO? And again, you can look at that through the same kind of audit lens.
Q: How do the big-5 personality traits connect with your leadership & blind spots model?
[Marty Dubin]: I mean the first part is know thyself. The exercise is exactly what you just did — to do that kind of quick self-reflection for yourself. And the Big Five is a good place to start. There are lots of other traits, but really knowing yourself well in terms of those Big Five traits is key.
So let’s say you know you’re not that agreeable — you tend to be critical and push back a lot. Now you’re going into a meeting, and things start going haywire. You’re feeling bad about it, and a quick internal check might be: “Am I overdoing my criticality here? Am I pushing back too much? Has anyone in this room felt like I’ve acknowledged their point of view?” Maybe you haven’t shown any agreeableness or created any sense of harmony.
The key is getting really good at being flexible. I make the point in the book — I’ve worked with some very successful leaders. They’re right 95% of the time. They’ve gotten where they are because they’re successful, and the environments they’ve been in have suited them — like a jigsaw puzzle that fits perfectly.
But the real challenge is that 5 or 10% of the time when their automatic, go-to behaviours aren’t working. That’s when they need to be able to say, “Whoa, wait a minute — I need to do some self-reflection here and figure out what changes I need to make.”
I actually start the book with one story like that — a guy who had an unbelievable track record of success, but was completely floundering. He just couldn’t look at himself. For him, it was always someone else’s problem, or something external. It’s sad to see, but those are the kinds of failures that happen.
I’ve had a couple of investors say, “They were great — until all of a sudden, everything blew up.” But that doesn’t just happen. Things don’t just suddenly blow up. It’s a ticking time bomb. And to your point, they were probably just not self-aware. They kept doing the same things that had brought them success in the past — until it stopped working.
Q: What is the role of resilience with leaders?
[Marty Dubin]: When I was an entrepreneur, I had an investor tell me, “We’re reluctant to invest in your company because you haven’t had any failures.” And I thought, what a stupid thing to say. I’d been successful! But later, I realised how wise that actually was — that I hadn’t been tested. We hadn’t been tested as a company.
And I think about my own life — I had a pretty comfortable middle-class upbringing. I mean, we all have challenges growing up, but one question I now ask everyone I’m evaluating is: “Tell me about a failure.” It’s really telling when people don’t want to share, or when they talk about failures but twist them into something they immediately turned around, without really seeing them as failures or learning anything from them.
Because to your point — you can’t get experience until you get experience. And those moments when you’ve been knocked down and had to get back up again — those are often the greatest learnings. But being open to that is tough. In school and in life it’s all about “achieve, achieve, achieve,” “do better, do better.” But we all know we learn the most from the times we didn’t succeed.
Yeah, and you really should unpack that experience. Sometimes people just move on — “I got through it, I learned one thing, and that’s it.” But usually there’s a lot more there if you really reflect. How you relied on others, or didn’t. What you did when you were emotional and couldn’t sleep. All the things going on inside — how you pulled yourself through. Who helped. What insights showed up. What you depended on. What you were telling yourself.
So I think it’s a huge opportunity — to unpack as much as you can from those experiences.