30 Observations About Leadership
I should have a glass of something bubbly in my hand as I write this to celebrate the 30th edition. When I started this substack I never thought I’d be able to keep up with writing a weekly substack.
In honor of that, I’m sharing 30 of my observations about leadership. They come from my experience as a COO and my work with leaders. This isn’t the authoritative list on leadership, nor is it an exhaustive list. I’m always learning so my thoughts may change over time. Think of this as a snapshot of my thoughts now. As a collection of my thoughts on the topic, there are tons of resources in this edition. I hope you find these observations useful or at least intriguing.
#1 Complex is not the same as complicated. From the outside, leadership seems complicated, a puzzle you can solve. There are some problems you can solve. There are also more unknowns, ambiguity, and less obvious answers. This makes leadership complex and much harder than expected.
#2 Leadership is more subjective than stereotypes might make us think. Being a compelling leader depends on a host of different variables. Don’t believe the myth there is one right way to be effective. It’s false.
#3 The pressure of being a leader is overwhelming. It’s easy to carry the stress with you. Managing your emotions is paramount for well-being and can stave off burnout.
#4 Leadership and org strategy are intertwined. Some fail when they focus only on what’s best for their area, even if it causes pain for other functions. Everyone flourishes when we let go of the myopic view in favor of thinking about organizational success.
#5 Management and leadership are not synonymous. We often conflate these terms. They need different skills and mindsets. Not all leaders manage others and not all managers are leaders. Yes, I said that. Leadership is more than a conferred title or managing work.
#6 Learning to work well with your peers is a powerful multiplier.
#7 Leaders don’t always need to have all the answers. Tap into the team's wisdom. Leaders who share idea generation and decision-making come up with a more creative solution, boost morale, and build trust.
#8 Working on yourself allows you to have more impact.
#9 Adopting a false persona is the fastest way to fail. Trying to be something you’re not is exhausting. Worse, people see through the act — reducing trust. There is no one right way to lead, there are oodles of ways. Don’t get a personality facelift, find situations requiring your expertise, values, and approach.
#10 The strongest leaders aren’t always the toughest ones. Being open when in the spotlight like leaders takes inner strength and courage. Leaders willing to share their humanity create a bond with their teams the way a stoic leader can’t.
#11 People leadership isn’t for everyone. Those who prefer to have a different path can have just as much impact. These folks add incredible value that helps the team thrive. Don’t let organizational structures and mindsets penalize them.
#12 Phase of business fit is more important than expertise. True for most anyone but especially for leaders. Experience leading a function at a large company is quite different from leading one at a scaling startup. These situations need different approaches, attitudes, and know-how. Even the most experienced leaders can fail when what they bring doesn’t match what the company needs.
#13 Learning to be with discomfort is essential. The roles offer massive growth. If you’ve ever tried to learn a new skill that doesn’t come naturally, you know this isn’t always comfortable. You will misstep, make poor decisions
#14 Leadership immerses you in hard conversations. There’s no way to avoid them in the role. If you embrace it, this kind of communication will teach you to more comfortably navigate conflict. You may never enjoy it but at least it won’t be as upsetting.
#15 Perfectionism will make you miserable. It also drives the team away. The pressure might tempt you to be perfect but don’t take the bait. It’s an impossible task. Get a coach or even a therapist if needed.
#16 Discernment is essential. You know the adage… if everything is a priority means nothing is a priority. To elevate the most critical, other items fall to the bottom of the list. Even in the face of pressure, leaders must resist the urge to push forward on too many fronts.
#17 Trusting your instincts leads to better outcomes. That doesn’t mean ignoring facts, it means using both. Many leaders let a difficult decision linger despite their instincts screaming at them. Using data and instincts yields a far better result than either alone.
#18 The foundation of leadership rests on three legs. Great leaders know how to use all three.
Intrapersonal (how we relate with ourselves)
Interpersonal (how we relate with others)
Organizational (dynamics within the entity)
#19 Perceptive leaders find confidantes. They recognize that these connections offer a place to let their guard down helping them stave off loneliness.
#20 Knowing your principles helps others know what you consider important. While the team may not agree, stating your values bring them to light so we can negotiate friction points. When they’re too far apart, it’s a signal we’re not a work match, smoothing the way for us to find a better fit.
#21 Autonomy as a leader is a mixed bag. We expect to have more autonomy as a leader. This is why many of us get into the role, we want to make a difference. In some ways, there is more autonomy, especially in the area you’re directly responsible for. Outside of that, it becomes murky. Having to share decision-making with peers across the organization diminishes that autonomy. This creates a tricky speed bump for many new leaders.
#22 Unspoken expectations lead to loads of pain. Talking about the talking — how we communicate and work together — sets expectations, reduces friction. Don't just do the work, talk about how you'll do it.
#23 Prioritizing the connection over being right builds stronger relationships. Relationships are one of the strongest levers in this role. Effective relationships multiply the impact more than your effort alone. Always remember that.
#24 Being flexible with your style is better than having a strong style. There’s a fallacy that you need to be a strong leader to succeed. Playing to your strengths is helpful, but be wary of clinging too hard to one style. You can get out of balance. As my dad says, “Your assets in excess become your liabilities.” Knowing how to flex your style makes for more effective collaboration.
#25 Resist the urge to build a wall around the team. Unless done with extreme care, this well-meaning behavior can have negative second-order effects.
#26 Advice often focuses on tactics but the people bits are the hardest. Reading books about strategy, developing good OKRs, and holding good meetings is helpful. Navigating human behavior is more difficult. Multiply your impact by focusing on leveling up these skills. Start with Multipliers by Liz Wiseman.
#27 The best leaders recognize the outsized impact of the role. They take care of what they say and how they say it. They pay attention to their actions knowing they set an example for others.
#28 Wise leaders know there aren’t perfect decisions. Given the uncertainty, ambiguity, and changing information inherent in leading, they do their best. These folks recognize that an imperfect decision is better than no decision.
#29 Prioritizing well-being brings dividends. Perceptive leads know that few people perform well under long periods of pressure. They structure in release valves and rest opportunities for the team, and themselves.
#30 Leadership is the biggest challenge most of us have taken on. Despite the sometimes bumpy ride, the ability to have a positive impact was worth it. I’d do it again.
Until next time, be well.
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What else to read
How I nearly burned out as a leader (and why I’m not alone)
The critical difference between complex and complicated
The cost of workaholic leaders