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The Mysteries of Leadership
How do we get a realistic view of the role?
The complexity and pressures of leadership are hard to grasp. Misconceptions about leadership abound. I know this from experience. Despite spending years working with executives, I wasn’t prepared for the challenges of being a COO. Leadership takes many of us by surprise, presenting a speed bump, slowing our progress.
How do we know what something will be like before we embark on it? Marathon runners have regimented training plans to help them prepare. Leadership is quite different. What comes before a leading role can approximate it, but what comes after is not the same.
After my role as a COO, I wondered if others' experience of being in a high profile, high responsibility, a high-pressure role was like my own. I long to know which parts were common and which parts were my own singular experience. I’m curious if the gap between their expectations and reality were as big as my own. After interviewing others, I discovered most had a similar experience. It highlighted how unprepared most of us are for organizational roles that have more impact.
Now I want to give future leaders a glimpse to help them make informed decisions about whether it’s the right path. If they do, I hope this information eases the transition.
How perceptions about leadership form
How do we close the perception gap? First, we need to understand how these perceptions form. There are plenty of ways our awareness develops, I’ll focus on three of them.
Profiles of famous people in the media are everywhere, there’s even a popular substack devoted to it. Many who aspire to bigger roles pore over these pieces, looking for common threads. Early in my career, before I became a COO I did too. Later I understood these profiles served PR purposes. What I read was a constructed image and practiced answers. While there are useful bits, these interviews don’t provide a full picture. We see what the company’s PR team wants us to see; the messy bits left out until they become scandalous. We can underestimate the rigors of leadership, how hard it can be mentally.
Reality tv is everywhere these days. Shows about work abound, most relevant are ones that are the extended job auditions or offer a peek into a CEO’s life. They might be execs, but they're also here to entertain. Stories need tension, producers amp up the drama, lines become blurred in a way they aren't in real life. We know they're contrived, a facsimile of real life.
Still, some sell themselves as giving an understanding of the demands of business and leadership. The most obvious of this genre is The Apprentice — so contrived we take little from it other than the danger of blunt, egocentric leaders. Worse, it highlights competition over the more powerful multiplier of collaboration. Many that followed highlighted similar tropes. We know these shows bear little resemblance to reality still, they reinforce the image of the strong, directive leader. While reality tv didn’t create this image, it does little to prove other, equally effective ways to lead.
The rare exception is Stylish with Jenna Lyons which was originally designed as a documentary-style show. It offers a more nuanced view, mirroring some of the challenges leaders face in the real world.
The advantage of using our observations is having a closer view. Having a direct line of sight and frequent interactions is useful. Yet, seeing a leader in action every day can lead us to overestimate how much information we have. Most folks in a company can’t see the whole picture, sometimes not even those in leadership roles. We fail to recognize we’re missing context. We can underestimate the difficulties or write off some leaders as incompetent. We become overconfident, fail to recognize the complexities until we run straight into them. This leaves us with the Instagram effect for leadership — it looks more glowing and tidy than the real experience.
When in the role we discover we have less control than we expect, collaboration more important than ever. We might have a say in a decision but aren’t always the final answer. We must consider many points of view. If we haven’t considered other work styles, stress grows, conflict rises, goals get delayed. We become disillusioned when our imagined future doesn’t work out the way we expect.
While social media can be detrimental, it’s also a powerful tool for sharing information. It also creates another way to see leadership in action. Leader's errant tweets give a glimpse into how they handle mistakes. We see how they deal with pressure when thousands or even millions are watching. It’s easy to criticize their responses, the observant reflect on how they might react to the scrutiny.
More entrepreneurs are attempting to work in public. It’s an attempt to peel back the layers, sharing low moments, not just the high points. One example is Sahil Lavingia, the CEO of Gumroad. Sahil shares his successes and failures, the company’s roadmap, and his thoughts on entrepreneurship on Twitter. This method is generally best for understanding the business demands of leaders without less focus on the messy collaboration and people bits.
There are a few good examples of those who open up about the messy people bits like Alex Lieberman, former CEO and Executive Chairman of Morning Brew. While Alex’s episode is particularly good, the entire The Talk Therapy podcast by Nathan Baschez and Dan Shipper is illuminating. Being so public means being mindful of being watched. This is the Observer Effect in action — the awareness of being observed changes how we act. The self-preservation instinct is powerful which takes bravery to be vulnerable which limits our view.
Execs who are working in public come the closest to approximating the demands of leadership, sharing the impossible choices, pressure, and overwhelming responsibility they face.
Better preparing people for leadership
Can we ever predict how something will feel (be) before we experience it? Can we accurately represent what something will be like to someone who has not experienced it before? Or must we experience it to understand? Will it always be a superficial understanding without life experience? And is a superficial understanding enough to attempt it?
None of these methods are 100% accurate. It isn’t realistic. We can give a better sense of the challenges, the confusion, the complexity that go with any role with organizational influence. Rather than a fun thought experience, it’s essential. When under stress humans tend to go back to what they know. Leadership is quite different from what you’ve done before. What worked in the past isn’t likely to work now, it might even make things worse. Having a better understanding of the rigors. allows new leaders to grasp key skills faster, make fewer mistakes, and harm others less.
We can do more to give more accurate and transparent views. A few suggestions:
Some companies have folks perform the role before they get the title. This can work though there are questions. On the negative side, it can be used to circumvent increasing pay or awarding titles. This path should be carefully considered, structured and expectations communicated upfront.
Be as transparent as possible about the challenges you face as a leader, especially for those who may be considering moving into larger organizational roles. Having a more realistic view of the role can ease the transition, making it a better experience for everyone they interact with.
Provide leadership development coaching and courses for all leaders including those who are up and coming. For example, my Leadership Masterclasses offer real-world opportunities to reflect and work through friction (hello self-promotion).
Later this month I’m giving a talk on this topic at enter JS. Hope to see you there.
Until next time, be well.
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