What Got You Here Won't Get You There: Why Success Can Sabotage Leadership

Welcome to Deep Read, a podcast where we dive into books that change how we think and work - and I should mention upfront, this entire episode is AI-generated, including the voices you're hearing, brought to you by FlexDesk Pro, the standing desk that automatically adjusts to your posture throughout the day.

Today we're exploring Marshall Goldsmith's "What Got You Here Won't Get You There," a book that's fundamentally changed how we think about leadership development. I'm joined by Michael Chen, an executive coach who's been applying Goldsmith's methods with C-suite leaders for over a decade.

Thanks for having me, Sarah. This book hit me like a lightning bolt when I first read it because it explains something we see constantly but rarely talk about.

Which is what exactly?

Why so many successful people plateau or even derail as they move up the organizational ladder. The skills that made them stars as individual contributors often become liabilities when they need to lead others.

Marshall Goldsmith has this incredible background as an executive coach to Fortune 500 CEOs. What gives him the credibility to make these claims?

He's coached over 200 major CEOs and worked with companies like GE, Ford, and Goldman Sachs. But what's unique is his 360-degree feedback approach where he gets brutally honest input from peers, subordinates, and bosses.

So he's seeing patterns that the executives themselves can't see?

Exactly. When you're successful, people stop giving you honest feedback. Goldsmith created this systematic way to surface what everyone knows but won't say directly.

What problem was he trying to solve when he wrote this book?

The fundamental disconnect between technical competence and interpersonal effectiveness at senior levels. Most leadership development focuses on adding new skills, but Goldsmith realized the real issue is subtracting behaviors that no longer serve you.

That's counterintuitive. We usually think about growth as addition, not subtraction.

Right, and that's why this book was revolutionary. Traditional leadership training says learn more strategies, attend more seminars. Goldsmith says your problem isn't what you don't know - it's what you do that you shouldn't.

So what's the core thesis here?

The higher you go in an organization, the more your problems are behavioral, not technical. A VP of engineering who micromanages every code review might be brilliant technically, but that behavior will kill their effectiveness as they move up.

Why does this happen so predictably?

Success creates superstition. If you got promoted because you were always the smartest person in the room, you start believing you need to prove you're the smartest person in every room.

And that worked when you were an individual contributor?

Absolutely. Being right, having all the answers, winning every argument - these behaviors got rewarded early in their careers. The problem is they don't scale.

What's Goldsmith's evidence for this thesis?

He analyzed thousands of 360-feedback reports and found the same behavioral patterns showing up again and again among derailed executives. The data was overwhelming.

Was he the first to identify this pattern?

Not entirely. Peter Drucker had talked about executive effectiveness, and there was research on derailment from the Center for Creative Leadership. But Goldsmith was the first to create a systematic taxonomy of specific behaviors.

What was he responding to in the leadership development field?

The competency model craze of the 90s and 2000s. Everyone was focused on what leaders should do more of, but nobody was talking about what they should stop doing.

How is his approach different from traditional leadership coaching?

Most coaching tries to fix weaknesses by building strengths. Goldsmith says if you're already successful, you probably have enough strengths. Your issue is that you have interpersonal habits that undermine your effectiveness.

And these habits are invisible to the person doing them?

Completely. That's why the 360-feedback is so crucial. You might think you're being decisive, but everyone else experiences you as dismissive and closed-minded.

Let's dive into the specific behaviors. Goldsmith identifies twenty habits that hold leaders back. What are the big ones?

The first and most common is "winning too much." This is the need to win at all costs, in all situations, even when it doesn't matter.

Give me a concrete example of what this looks like.

I coached a CEO who would argue with the restaurant server about wine recommendations during client dinners. He had to be right about everything, even when being right damaged relationships and served no business purpose.

How does this behavior develop?

These are typically people who got ahead by being smarter and more driven than everyone else. They've been rewarded for winning so consistently that they can't turn it off.

What's the cost of this behavior at senior levels?

Your team stops bringing you ideas because they know you'll pick them apart. Innovation dies because people learn to only present ideas they're certain you'll approve.

What's another major behavior?

"Adding too much value." This is when you can't let someone else have a good idea without making it better or adding your input.

That sounds like it would be helpful though.

Here's the thing - even if your input improves the idea by 5%, you've just reduced that person's commitment to it by 50%. They no longer own it.

Can you walk me through a real scenario?

A marketing director comes to you excited about a campaign idea. Instead of saying "Great, run with it," you say "I love it, and here's how we can make it even better." You've just stolen their ownership.

And ownership matters more than the marginal improvement?

At senior levels, absolutely. You need people to execute with passion and commitment. That only happens when they feel true ownership of the initiative.

What about "making destructive comments"?

This is the sarcastic remarks, the cutting observations, the need to be the smartest person in the room at someone else's expense. Leaders think this shows their intelligence.

But it doesn't?

It destroys psychological safety. I worked with a CFO who was brilliant but would make these devastating one-liners during meetings. People stopped contributing because they were afraid of being his next target.

How does Goldsmith suggest people recognize these behaviors in themselves?

That's the challenge - you can't. By definition, these are blind spots. That's why he's so insistent on 360-degree feedback from multiple sources.

What does that process look like practically?

You get confidential feedback from your boss, peers, and direct reports. The key is asking specific questions about behaviors, not general "how am I doing" questions.

Such as?

"Does Michael listen without interrupting?" "Does he give credit to others for their ideas?" "Does he admit when he's wrong?" Very specific, observable behaviors.

Then what happens with that feedback?

Goldsmith has this four-step process. First, apologize to the people you've impacted. Second, advertise that you're working on changing. Third, listen to suggestions. Fourth, follow up regularly.

Wait, you start by apologizing?

It's counterintuitive but essential. You have to acknowledge that your behavior has impacted others negatively. Most leaders want to skip this step, but it's what creates buy-in for the change process.

What would that conversation sound like?

"I've gotten feedback that I interrupt people and don't really listen to ideas that aren't mine. I know this has been frustrating for you, and I apologize. I'm committed to changing this behavior."

That must be incredibly difficult for successful people to do.

It's the hardest part of the whole process. These are people who've built their identity around being right and having the answers. Admitting they've been wrong about something fundamental is terrifying.

What's the "advertise" step about?

You tell people what you're working on changing. This serves two purposes - it creates accountability, and it helps people interpret your new behaviors correctly.

Why does interpretation matter?

If you suddenly start listening more without announcing you're working on it, people might think you're sick or distracted. When you advertise the change, they understand it's intentional growth.

The third step is listening to suggestions. How does that work?

You ask people for specific ideas about how you can change the behavior. This is crucial because it makes them partners in your development rather than victims of your bad habits.

And the follow-up?

Monthly check-ins where you ask "How am I doing on listening without interrupting?" The key is you don't defend or explain - you just listen and say thank you.

That sounds almost mechanical.

It has to be. Your natural instinct will be to justify or explain your behavior. The discipline is just listening and acknowledging the feedback.

Let's talk about implementation. If someone recognizes themselves in these behaviors, where do they start?

Goldsmith is very clear - pick one behavior and focus on it completely. Don't try to fix multiple things at once.

How do you choose which one?

Usually it's the behavior that shows up most consistently in your 360 feedback. If eight people mention that you interrupt, that's your target behavior.

Walk me through what changing "winning too much" would look like day-to-day.

You start by catching yourself in the moment. When you feel the urge to correct someone or prove you're right, you pause and ask "Is this worth it?" Most of the time, the answer is no.

What are some practical techniques?

One client put a rubber band on his wrist and snapped it every time he caught himself winning unnecessarily. Another kept a tally on his phone.

How long does it typically take to see change?

Goldsmith says it takes about six months of consistent effort. The behavior change happens faster than that, but it takes time for people to trust that the change is permanent.

What are the most common mistakes people make when trying to implement this?

The biggest mistake is trying to change too many behaviors at once. The second biggest is not doing the follow-up. People think if they change the behavior, that's enough.

But it's not?

Not at all. You have to actively manage other people's perceptions. They have years of experience with your old behavior - they need evidence that the change is real and lasting.

What about contexts where these behaviors might still be useful?

That's a great question. Goldsmith acknowledges there are times when you need to win at all costs - like a genuine crisis or a make-or-break negotiation. The key is choosing consciously.

How do you know when it's appropriate?

Ask yourself "What's really at stake here?" If it's just your ego or the need to be right, let it go. If it's the company's future or someone's safety, then engage fully.

What about different organizational cultures? Does this advice work everywhere?

The specific behaviors might vary by culture, but the underlying principle is universal. Every culture has ways that successful individual contributors sabotage themselves as leaders.

If someone could only implement one thing from this book, what should it be?

Stop adding value to every idea that crosses your desk. Just try going one week where when someone brings you an idea, you either say yes, no, or ask clarifying questions - but don't improve it.

That's harder than it sounds, isn't it?

It's excruciating for high achievers. But the results are immediate - you'll see people's energy and ownership increase dramatically.

Let's shift to evaluation. What does this book do brilliantly?

It's the first book to systematically catalog the specific behaviors that derail successful people. Before this, coaching was much more generic and theoretical.

The taxonomy of twenty behaviors is pretty comprehensive.

Exactly. And it's based on real data from thousands of executives, not just theory or anecdotes. When you read the list, you immediately recognize people you've worked with.

What about the methodology? How sound is the 360-feedback approach?

It's become the gold standard in executive coaching. The key insight is that behavioral change requires external perspective - you literally cannot see these patterns in yourself.

Where does the book fall short?

It's very focused on senior executives in large corporations. The advice doesn't necessarily translate to entrepreneurs, small business owners, or non-profit leaders.

What else does it miss?

It doesn't really address systemic issues. Sometimes toxic behavior is rewarded by organizational culture, and individual change isn't enough.

The book also assumes people have the self-awareness and motivation to change.

Right. Goldsmith is clear about this - his methods only work with people who genuinely want to change. If someone is defensive or in denial, this approach won't work.

How does it compare to other leadership books?

Most leadership books tell you what to do more of. This book tells you what to stop doing. It's much more actionable than books about leadership philosophy or vision.

Any other limitations?

The book doesn't address skill deficits. If you genuinely don't know how to do something, stopping bad behaviors won't fix that. You need actual training or education.

What has been the broader impact of this book?

It fundamentally changed executive coaching from a general development conversation to a focused behavioral change process. Most coaching today uses some version of Goldsmith's methods.

Has it influenced how organizations think about leadership development?

Definitely. Companies are much more aware now that promoting high performers without addressing behavioral issues is a recipe for disaster.

What criticism has the book received over time?

Some people argue it's too focused on conforming to organizational expectations rather than challenging systems that might need to change.

That's an interesting point about power dynamics.

Yes, there's a valid question about whether we should always adapt to existing organizational cultures or sometimes push back against them.

How has the leadership landscape changed since this book was written?

There's much more emphasis now on psychological safety, emotional intelligence, and inclusive leadership. But the core behavioral issues Goldsmith identified haven't gone away.

Do these behaviors show up differently in remote or hybrid work environments?

Absolutely. "Winning too much" now happens in Slack threads and email chains. "Adding too much value" happens when you edit everyone's documents before they're shared.

As we wrap up, what's the single most important insight from this book?

That success can be your enemy if you're not careful. The behaviors that got you to your current level might be the very things preventing you from reaching the next level.

And the practical takeaway?

Get honest feedback about your interpersonal behavior, pick one thing to change, and systematically work on it with the same discipline you'd apply to any other business challenge.

Michael, this has been incredibly useful. Thanks for helping us understand why what got us here won't get us there.

Thanks, Sarah. The book is a wake-up call that I think every ambitious person needs to read.