With Martin G. Moore

Episode #295

My Biggest Executive-Level Mistakes: And how I turned them into strengths

One of my recent social media posts went viral, as I outlined the three biggest mistakes I made when I was finding my feet in my first few senior leadership roles.

The good news is that, once I was aware of them, I was able to put some strategies in place to fill the holes. This had the surprising outcome of turning some of my biggest mistakes into genuine strengths.

They became part of the rock solid foundations of my leadership repertoire and, for at least one of these weaknesses, it became an unqualified strength, which gave me a competitive edge over my peers.

In this episode, I take a closer look at the three biggest mistakes I was still making when I stepped into senior leadership roles, and how I managed to turn these around.

I’d love you to be able to do the same, without having to get quite as many scars as I did!

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Episode #295 My Biggest Executive-Level Mistakes: And how I turned them into strengths


We posted a brief piece on social media recently outlining the three biggest mistakes I made as I was finding my feet in my early senior leadership roles. To say that the post went viral is an understatement.

The response to social media can be the most useful feedback we receive because it’s a reasonably accurate reflection of the topics that are resonating with you the most. Given that you’ve sent us such a strong message about this particular subject, I decided to go a little deeper on these three critical areas of performance in this podcast episode.

The good news is that, once I was aware of them, I was able to put some strategies in place to fill the holes. This had the surprising outcome of turning my biggest mistakes into genuine strengths. They became part of the rock-solid foundations in my leadership repertoire, and for at least one of the weaknesses, it became an unqualified strength, which gave me a competitive edge over my peers.

In this episode, I take a closer look at the three biggest mistakes I was making when I stepped into more senior level roles, and how I managed to turn these into strengths. I’d love you to be able to do the same without having to get quite as many scars as I did.


The first mistake that really hurt me when I was new to the ranks of senior leadership was not reading the political play. I thought that just delivering superior results would overshadow everything else, as long as it was done ethically and didn’t go outside the company’s risk envelope.

Well, apparently not!

I was blindsided several times by political attacks from peers that I didn’t see coming, and they cost me and my team dearly. We were able to recover, but it took a huge amount of energy on my part to undo the damage. And, even when I did, I think there were some residual question marks that we couldn’t erase.

Despite all the talk about collaboration, life at the upper echelons of most businesses is incredibly competitive – executives vying for favor with the CEO and the board, all hoping that they’ll be the next anointed one.

Many behave more like politicians than they do business people. They evaluate their own performance, not based on the results they achieve for the company, but how much favor they curry with the power brokers at the top. And look, it’s easy to fall into this trap. I’ve seen many otherwise capable executives do so.

But this is when you have to ask yourself a few important questions:

  • What type of leader do I want to be?

  • How do I want my contribution to be remembered?

  • When people say things at my farewell, will they be heartfelt and genuine, or will they have to lie through their teeth for the sake of protocol?

When it comes to politics, the tone is set at the top – the leader sets the tone. I think of this tone as a behavioral continuum: on one end, you have the behavior of self-seeking, ego politics; on the other end you have selfless pursuit of the best outcomes you can possibly deliver for the business.

Very few people are at either extreme, but everyone falls somewhere on this continuum.

I decided that for me, I wanted to be as close to the selfless end as I possibly could. Why? Because I highly value my self-respect. And, from what I can tell, unless you’re a sociopath, it’s hard to maintain your self-respect when you know deep down that you’re a manipulative liar.

But I also know that some people will just choose to believe their own bullsh!t, and that’s going to keep their conscience squared away for the most part. Political animals behave the way they do for all sorts of reasons.

I just want to share a couple of the most vivid examples that come to mind for me:

One woman, who I’ll call Jane, must have realized in the early part of her career that she wasn’t as smart as the average bear, but she was still incredibly ambitious. So, she worked out that the best use of her skills would be to learn how to mold, manipulate, and satisfy her boss… very chameleon-like. She was driven purely by what made her boss happy, and she would carry out his desires without question.

The problem was, when she detected a threat from someone else who was receiving positive attention from that boss, her insecurity would force her to undermine that person. And although that’s really obvious (and very freaking ugly), Jane managed to get away with it. She also did the dirty jobs for the CEO, which further ingratiated her in his eyes.

Another woman, who I’ll call Greta, was just a self-righteous yes-person. Her deal was simply to protect her relationship with the CEO by being as fawning and obsequious as she could possibly be. Whenever I had to watch her hanging on his every word in an executive meeting, I’ve got to tell you, I used to throw up in my mouth just a little bit.

When I challenged her assessment of one of her people in a talent management discussion, she took great exception to it, and decided to exact revenge. She couldn’t stand the fact that I’d called bullsh!t on her in an executive meeting. So, she set about to covertly destroy my reputation. And, to give her her due, she did a pretty good job.

It wasn’t until a loyal HR business partner confided in me about what she was doing, and why, that I woke up to what was going on. And after those experiences, I realized just how naïve I had actually been!

I developed a three-pronged approach to being more aware of politics. Fortunately, because I had such an aversion to it and such a distaste for political players, I was able to do it without sinking to their level:

  1. I created cross-business unit alliances. Nothing is really achieved these days in companies of any size without some form of cross-team collaboration. So, I made sure I developed strong alliances with the people who I knew were relying on me to deliver for them. And in turn, this created incredible loyalty. In the rooms that I wasn’t in, I believe I had people with significant influence protecting my interests and speaking on my behalf.

  2. I had direct conversations with the rumor mongers. On the occasions where I had reasonable intel on what was being said behind my back, I would confront the individual directly. Before this revelation, I used to think it was best to take the British monarchy approach – never complain, never explain. But I learned that there were times when I’d be better off going head to head.

    So, I would just drop into their office casually and say something like this, “Hey, Greta, I’ve heard along the grapevine that you’ve been saying X about me and my team. I just want you to know in case you don’t already, that it’s not true. Now, I wouldn’t embarrass you by sharing this with the CEO, but I’d just appreciate it if you come to me directly next time when you hear something like that.

    Believe it or not, this can be quite effective to put a shot over the bow. If nothing else, they know after a conversation like that, that you won’t be inclined to take any sh!t from them… and that normally slows them down just a little.

  3. I let the CEO know my position. I’d be careful not to let the conversation descend into a he said / she said, but I’d be pretty clear that I knew what was going on, that I wasn’t interested in playing the political game, and that I would deal with it myself. The message I wanted to get across was, Hey look, boss, I don’t want you to do anything, but I also don’t want you going off half-cocked and believing this idiot.

    My dialogue would go something like this. “Look, I know Greta is trying to undermine me, and no doubt you’ve heard plenty of rumors. I don’t want you to intervene. I can fight my own battles, but I just wanted to let you know that I don’t play games. I’m just going to continue to focus on producing results. So, if you’re ever wondering where I am, I’ll be off working with my team on how to deliver the most value for the company.”


My second big mistake when I was new to the ranks of senior leadership was being too slow to deal with poor performers. I used to give people a really long time to hit the standard of performance I was expecting.

Doing this when you’re at the lower levels isn’t such a big deal, but the higher up you go, the greater the impact your direct reports can have – and, at this altitude, leaving a poor performing leader in place can risk the performance of the whole company.

Early on, when these leaders clearly weren’t hitting the mark, I would give them the benefit of the doubt. For me, this wasn’t driven by the things that caused most leaders to hesitate or avoid performance issues. It wasn’t about me being afraid of conflict, or even about feeling sorry for the individuals involved. I certainly wasn’t squeamish about difficult conversations, and I can’t even tell you how many people I’d terminated for underperformance up to that point in my career.

My lack of speed was driven by two things, which were subtly different:

  1. My overdeveloped sense of fairness and equity. I found myself giving people more time than was reasonable to demonstrate acceptable performance.

  2. I knew the pain of having to start again, after investing a lot of time, energy, and money into getting a direct report to the current level of performance even if it was still substandard. I was a slave to sunk cost.

The bottom line is that I kept several poorly performing leaders in their roles far longer than I should have. Once I realized this, I shifted my tactics to move way faster. I got much more diligent in the first weeks and months of a new leader’s tenure. I would scrutinize their work much more closely. I would start the informal correction and calibration process much sooner. I would expect the best, but prepare for the worst so that I could nip any performance issues in the bud one way or another.

I would also spend more time with the people below them, to get some much needed insight into what that leader looked like from below. I asked them fairly innocuous questions, but they were super useful:

  • “What messages is Peter giving you?”

  • “What do you think is most important to the company right now?”

  • “Where are you focusing your energies?”

  • “Are you really clear on what Peter is aksing you to do?”

If you aren’t diligent about doing that calibration work – in other words, looking at individual performance from all angles – it’s easy to be fooled by the rhetoric.

As they say, organizational structures are like a tree full of monkeys: when you’re looking down from the top of the tree, all you can see is smiling faces; but if you are looking up from the bottom of the tree, all you can see is a bunch of assholes.

I learned to move quickly, diligently, and fairly on performance issues. And, by the end of my corporate career, I can confidently say that I was at least three times faster than other executives at dealing with poor performance… but I also knew that, despite that fact, I was still 30% slower than I could have been!


My third big mistake when I was new to the ranks of senior leadership was giving people too much rope. This was a huge flaw in my execution. I would give people the trust and space to do their job, but I wasn’t diligent enough in inspecting their outputs.

I got into the nasty habit of trusting without verifying.

I was too intent on two things: the first was not being a micromanager, and the second thing was giving my people 100% trust to do their job competently.

Think about the dynamics here: when you’ve hired someone, they’ve just spent a considerable amount of time and energy during the hiring process to convince you that they have the skills, experience, and attitude to handle the role. So, you feel as though they deserve the opportunity to show you what they can do – unconstrained freedom to stamp their mark on the job was always my go-to for a new direct report.

However, this led to surprises that I wasn’t prepared for: missed deadlines and off-track projects. It forced me to think about how to do this better. I didn’t want to not trust my people, but by the same token, I needed to manage the outcomes more diligently.

Once again, I changed three things:

  1. I spent more time front-loading my expectations. What was I after specifically, in terms of the outcomes? I set really clear expectations for quality, time, and value delivery. This process was an invaluable learning experience for me too. I would tune in really closely to how each person responded, and having honed my leadership craft through thousands upon thousands of one-on-one conversations, I was pretty decent at reading people’s reactions.

  2. I decided how frequent my touch points should be. How often did I need to check in, and how deep did my inquiry need to be? In my head, I was sliding up and down the scale of engagement styles based on Situational Leadership Theory: Sure, I trust you… but based on my assessment of your capability and maturity, I’ll take either a more or less interventionist approach.” Ideally, I’d just love to leave them to it, but some people, especially if they’re new to the company or industry, really needed short interval control – that is, frequent check-ins.

  3. I upped my level of diligence on single-point accountability. How could I remove any uncertainty about who was accountable for which outcomes? This gave people the expectation that they needed to behave like corporate adults. It was a no blame / no excuses culture, which I know takes a little while for people to get comfortable with. But this was everything. It completely changed the energy of the individuals involved, when they knew they were singularly accountable for the outcomes. I also realized that very few people will admit to being in trouble: they’ll try to fix it, or sometimes they’ll just hope it’s going to get better. And, when it doesn’t, they rely on excuses.

With these three changes, I managed to circumvent the vicious circle of the unpredictability of outcomes. I gave everyone the trust and autonomy to do their job, but I didn’t just take their word for it. I worked out how to be more diligent at inspecting progress, while still trusting them and not micromanaging them.

So, instead of hearing them tell me how they were going, and me saying, “That’s awesome!“, instead I learned to say, “That’s awesome… show me what you mean!


Making the mistakes was one thing, but learning how to fix them was a revelation.

Combining some of these skills enabled me to put together my model for execution excellence, balancing accountability and empowerment in just the right measure.

At the end of the day, the proof of the pudding is in the eating. This underpinned the stunning results that my teams were able to achieve in my last few executive roles, and it later went on to form the basis for my No Bullsh!t Leadership framework.

We all make mistakes, at each new level that we move to in our career. It’s an essential part of our growth and development. But the higher up you go, the bigger the impact that those mistakes have. I was really lucky: I learned how to cover my three biggest gaps before I found myself in a large CEO role, where those mistakes would’ve been really costly.

It was these learnings, which really only came to me after the age of 45, that enabled me to excel as a business executive and leader. So if you are still young and working your way up, it’s unlikely you’ve even discovered your biggest challenges yet.

But, don’t worry. Keep learning and keep growing. And when your biggest challenges come for you, you’ll work out how to deal with them just as I did – and that will make you unstoppable!


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    Ep.63: Reading the Play


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