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About 35% of current jobs in the UK are at high risk of computerisation over the following 20 years, according to a study by researchers at Oxford University and Deloitte. Go to http://www.bbc.co.uk/news/technology-34066941 and type your job title into the search box below to find out the likelihood that it could be automated within the …
The great jazz trumpeter Miles Davis once said, “Sometimes you have to play a long time to be able to play like yourself.” This is why the best artists are not only masterful at their craft but also distinctive in their voice; they’ve committed themselves to the process of being themselves. Subsequently, this means they committed themselves to the failure that comes along with it also. But that’s the part no one talks about—the work required to “become” who we are or, better yet, who we want to be. It’s as if we’re expected to go to the gym and walk out with a six-pack. That’s not how the gym works, nor is it how work works. And we know this. There’s a process to becoming, and that process inherently requires failure.
Be that as it may, there are no LinkedIn claps reserved for failing. There are no at-a-boys for coming up short, despite the reality that we’ve all experienced failure to get to where we are. But of course, failure is just a natural part of the process of becoming. So why do we omit this truth from our stories when we tell the tale of becoming ourselves? Why do we whitewash the parts that aren’t so flattering and “yada yada yada” our narratives to a flatten expression of self. I get the fact that no one wants to fail, let alone admit to it. However, I also realize that in order to get good at something, we have to work through being not so good first. So, maybe we should practice sharing the entire story more frequently to help folks more successfully navigate this process of becoming. That’s exactly why we invited Courtnee LeClaire onto the FOR THE CULTURE podcast. LeClaire’s career trajectory consists of a who’s-who of brands. She was the head of worldwide app marketing and corporate partnerships at Apple after launching the iPod and iPhone. She’s held executive marketing seats at Disney and Intel before serving as CMO of the Oakland Raiders. But these days, LeClaire boasts a different title. Today, she is a chief “becoming” officer, an executive coach that helps leaders become their best selves, who they truly are, to help them achieve what Paul Coelho’s The Alchemist would call their personal legend. Despite her long list of impressive accomplishments, in this new role LeClaire spends more time talking about her failures, but she makes a pointed distinction between “failure” and “failing” that unlocks many of the challenges we have with failure.
Failure, as LeClaire bifurcates, is a complete sentence. It’s done, and, therefore, it occupies real estate in our lives like a title—I failed, so I’m a failure. Failing, on the other hand, is an active sentence, meaning that there’s something that comes after it. And it’s the something that comes after it that enables us to do something about it. I’m failing, so I need to [fill the blank]. I was failing, so I [fill in a blank some action].
The reframing of failure to failing is what opens the door for success. Whether it’s something new or something new to us, there will be a point when we are failing relative to our ambition and taste. But when we perceive it as an active sentence, we give ourselves room to improve. Failure is something we experience, not who we are. It’s a moment in time, and because it’s something we’re merely experiencing, that means we can change it. This distinction is critical. One is a state of who we are (failure), and the other is a state of where we are (failing). When we reposition failure to failing (or I was failing), we acknowledge the reality of where we are relative to where we want to be and can now honor the fact that this is just a part of the process.
To hear this from LeClaire during our conversation on the pod had a profound impact on me personally because I worked with her during my time at Apple. She was much more senior than I was, and I “totemized” her as the consummate example of having it all together. She wasn’t in my reporting vertical, but I got to engage her from time to time, where she’d drop marketing wisdom and sage advice for how to navigate life on One Infinite Loop. To hear her reveal her moments of failing on her way to becoming, even in those moments when I held her on a pedestal, was like learning that Spiderman is really Peter Parker. That is to say, LeClaire, like all of us, had to play a lot to learn to play like herself. Fancy that.
Hearing this not only humanized LeClaire but also gave me permission to admit to my own failings and accept the fact that we’re all just buffering, even the best of us, as we become our best selves. Imagine how empowering that would be if we all started to share our own processes of becoming, moving from failure to failing; it might help us all navigate the process with a bit more grace—and perhaps even a bit more success.
Check out the full episode of our conversation with Courtnee LeClaire on the latest episode of the FOR THE CULTURE podcast on Spotify or wherever you get your podcast.
Human beings are obsessed with change. As large scale scientific studies show, most of us would like to change at least some aspects of our personality, defined as consistent patterns of behaviors or habits that make us who we are and different from others. For example, I’d love to be less impulsive, excitable, or cynical, which is why I have been working on not being myself for many years. Likewise, most individuals want to grow, to develop new adaptations that make them a better version of themselves, and organizations are equally interested in transforming, which typically depends on their people’s ability to grow and evolve.
At its core, change is not about becoming someone else. Rather, it is about becoming a less exaggerated or extreme version of yourself. Most of our strengths, when overused, become weaknesses. Confidence becomes arrogance, attention to detail turns into obsessional perfectionism, and resilience mutates into stubbornness or “false hopes” in the face of problems and challenges that undermine our potential. Real development is not reinvention but calibration. Think of it as the ability to regulate your natural tendencies so they fit the demands of the situation, or optimize your behavior to develop better adaptations and become a more versatile and effective version of yourself, keeping your limitations and flaws in check, especially in high-stakes or critical situations.
Sadly, left to our own devices, we rarely change.
Human behavior is remarkably stable. Personality traits show high levels of consistency over time, and even when people receive feedback, they tend to interpret it in ways that protect their self-image. We are biased toward seeing ourselves as better than we are, and we systematically underestimate the gap between how we see ourselves and how others see us.
This is where coaching comes in…
The evidence is clear: coaching works, but not always, and not equally for all. A landmark meta-analysis by Tim Theeboom and colleagues found that coaching has significant positive effects on performance, well-being, coping, and goal attainment, with effect sizes ranging from moderate to large. More recent meta-analyses confirm that workplace coaching consistently leads to positive organizational outcomes, particularly when it focuses on behavior change.
The key insight is that coaching is not a placebo. It is a scientifically validated intervention. But like most interventions, its effectiveness depends on how it is designed and delivered, who it’s delivered by, and of course who the recipient of coaching is.
Some coaching relationships are transformative. Others are pleasant but inconsequential, like chatting to a friend of hairdresser. The difference is rarely about whether coaching “works” in principle. It is about whether the right coach is matched to the right person, for the right goal, in the right way.
Four factors
Choosing a coach, therefore, should be treated as a high-stakes decision. Yet most people approach it casually, relying on reputation, referrals, or vague impressions of “chemistry.” That is not enough.
There are four factors that matter most.
1) First, personality chemistry and style fit. Coaching is fundamentally a relationship, and like any relationship, it depends on trust. But chemistry is not just about liking someone. It is about alignment between the coach’s style and the coachee’s needs. Some coaches are direct and confrontational, excelling at telling people what they need to hear, even when they really don’t want to hear it. They challenge assumptions, provide blunt feedback, and push for rapid change. Others are more facilitative and supportive, helping individuals reflect and arrive at their own conclusions. Neither approach is inherently superior. The question is which one works for you. If you are defensive, overconfident, or prone to dismiss feedback, you may need a coach who is willing to confront you. If you are already self-critical or risk-averse, a more supportive approach may be more effective. The goal is not comfort, but progress.
There is also a personality dimension. Research suggests that similarity can build rapport, but difference can drive growth. A coach who mirrors your worldview may feel comfortable but may not stretch you. A coach who is too different may create friction without insight. The optimal point is somewhere in between: enough overlap to build trust, enough difference to challenge your thinking.
2) Second, method fit to goal. Not all coaching is the same, and not all goals require the same approach. If your objective is to improve a specific skill, such as communication or decision-making, a structured, behavioral approach with clear feedback loops may be most effective. If your challenge is more psychological, such as managing derailers, improving self-awareness, or navigating interpersonal dynamics, a deeper, more reflective approach may be required.
Some coaches draw on cognitive-behavioral techniques. Others rely on psychodynamic frameworks, systems thinking, or data-driven assessments. Increasingly, coaching is also augmented by analytics and AI. None of these approaches is universally better. What matters is alignment with the outcome you seek.
Too often, organizations adopt a one-size-fits-all approach to coaching, offering the same intervention regardless of the problem. This is equivalent to prescribing the same medication for every illness. It is convenient, but ineffective.
3) Third, expertise and proficiency. The coaching industry is largely unregulated, which means quality varies significantly. Anyone can call themselves a coach. Not everyone should, and not everyone is qualified.
It is not enough for a coach to have a preferred method. They need to be good at it. This includes formal training, relevant experience, and, critically, a track record of impact. Have they worked with people at your level? Do they understand your context? Can they translate insight into action?
In an era where AI can generate generic advice instantly, the value of a coach lies not in providing information, but in interpreting it, contextualizing it, and applying it to your specific situation. As I have argued in I, Human, the differentiator in the AI age is not access to answers, but the quality of judgment applied to those answers. A good coach enhances your judgment. A mediocre one simply adds noise.
4) Fourth, and avoid stagnation through measurement and iteration. Coaching should not be an open-ended, indefinite process. It should be structured, with clear goals, regular checkpoints, and measurable outcomes. This is where many coaching engagements fall short. They focus on conversations rather than outcomes. They create insight, but not change.
Effective coaching requires experimentation. Try new behaviors, gather feedback, adjust, and repeat. It also requires measurement. Progress should be assessed not only through self-reports, but through observable indicators. These may include improvements in team engagement, changes in leadership behavior as captured by 360 feedback, enhanced performance metrics, or even hard business outcomes. Research suggests that coaching has its strongest impact on behavioral change, which is precisely what should be measured. Indeed, without measurement, coaching risks becoming what much of corporate life already is: well-intentioned but performative.
The AI role
In many ways, selecting a coach is similar to selecting a leader. You are making a bet on someone’s ability to influence behavior and drive outcomes. You would not make that decision lightly in a business context. You should not make it lightly here.
In the age of AI, the stakes are even higher. As machines take over more of the cognitive heavy lifting, the human edge will depend on adaptability, self-awareness, and the ability to evolve. Coaching, when done right, can enhance all three. The right coach will not change who you are. They will help you become a more effective version of yourself. They will challenge your assumptions, expose your blind spots, and help you build the adaptations you need to succeed so that the best version of yourself shows up more frequently, and the worst version is contained or silenced, at least during critical work interactions.
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