Is It OK to be Ambitious? (Challenge #68)

There’s a bit of conventional wisdom that floats around, especially in mission-driven fields, that the best leaders are the reluctant ones. The ones who never sought power, but accepted the mantle when it was thrust on them, and who rose to the challenge because of, not in spite of, their lack of interest in leadership. And I have seen over the years that people who took that path to leadership often have an innate sense of humility and obligation that serves them well as they work to build a better world. But does that mean that the other side of the coin is true? That people who strive to lead should be avoided as ego-driven power seekers? Are Ambition and Kindness mutually exclusive?

Well, that depends. And we’re going to explore the strengths and weaknesses of both mindsets around power, and how this simple bit of conventional wisdom actually points to a deeper and more complex truth around what makes a kind leader.

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Welcome to the Kind Leadership Challenge, the podcast that empowers leaders to heal their organizations in ten minutes! I’m Dr. Sarah Clark, founder of the Kind Leadership Guild, where I use my PhD in Higher ed leadership and nearly 2 decades of experience in academic libraries to coach educational leaders to sustainably build a better world. 

Kind Leaders aren’t perfect, which is actually as it should be. In our unique ways, We make tough decisions without becoming jerks. We create impactful and burnout-proof systems for our organizations. And we know that once we stop controlling and start collaborating, even the most ambitious vision can become effortless. Kind Leadership’s pretty simple, but that doesn’t mean it’s easy. So if you’re up for a challenge, stick around as I teach you how to create a resilient, thriving legacy that will strengthen your community long after you’re gone.

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So I’m going to reach back to my PhD days as a qualitative researcher and lay out my “positionality” right up front. As the clichéd firstborn kid I was always the strong personality who stood up for injustice on the playground, and tried to coordinate every team project at school because I knew I could do it well and wanted us to get the best grade possible. I had strong opinions and wasn’t afraid to say them. I was always striving to be the best at anything I did, and pushing my friends along with me. Think Hermione Granger, but with really thick glasses. This worked OK for me till puberty or so, when my “spunk” got reframed as “bossiness”, and eventually another word that began with a B. In response to that social rejection, I learned to hide or at least dim my spark through junior high, high school, and to a lesser degree college. 
 
 But as I grew in my career, inevitably some leader would always note my poorly hidden spark after it flared in a meeting or email. Often they would mentor me in one way or another, usually showing me the interpersonal and diplomatic skills I could use to control my spark without snuffing it out. But other than the occasional flare of imposter syndrome about whether others would accept my weird, outspoken self as a leader, there was never anything reluctant to my feelings about leadership. I concluded very early on in life that the world was a messed-up and unfair place, and I felt I had both the opportunity and obligation to use my skills to leave at least a few little corners of our hopelessly broken planet better than I found them. And leadership means you are no longer a lone fighter for a better world. You get to scale your impact by orders of magnitude through the like-minded team, organization, and community you lead. 

In short, I am an ambitious leader, though more around my impact on the world than around my take-home pay, and on my best days I make no apologies for that ambition. But does that ambition make me a worse leader than one who had to be talked into taking the lead?

Well, it certainly makes me a leader who had to overcome my share of bad habits. My spark of passion is a great thing, but a spark can either fuel a city’s power grid or burn that city down. It’s all in how that spark is channeled. And boy howdy have I made some misfires in my career, from telling off powerful people to poorly considered coaching conversations to ignoring the fine line between assertiveness and intimidation. I have chased many a shining pretty butterfly of a vision right over the edge of a cliff. And perversely, my desire to get it right and be the best leader possible can send me into spirals of overthinking and anxiety when things don’t go to plan. But all in all, my passion to make a difference is the foundation I can use to rebuild my confidence when it is battered by the ups and downs of leadership. In any case, it’s not like I can change it, so I try to use it to its best effect. That’s what a leader does with all their strengths and weaknesses.

On the flip side, I’ve known and worked with plenty of leaders who took a more reluctant path to power, some who’ve made it pretty high up in the org chart. In fact, although I don’t think anyone’s done a study, I suspect most educational and library leaders didn’t initially come into this field with a goal to be the boss. In a lot of cases, leadership kind of just happened—either out of a desire for a better paycheck or simply because there was nobody else available who could do the job. There’s also probably some gender/pink collar job stuff mixed up in this dynamic as well. However, I’m going to be bumping up against my ten minute maximum as it is, so we’re saving that conversation for another episode. But whether their reluctance is born of innate personality, systemic biases, or some of both, reluctant leaders have some amazing skills that the world needs more of, not less.

Whereas I described leaders with an ambitious mindset as having an eye-catching (if occasionally hazardous) spark, reluctant leaders tend more toward a steady, welcoming glow. Reluctant leaders to a one, are great listeners. Because they are more cautious, they are open to other ideas, and invite new people to join a team rather than trying to inspire them to follow a movement. 
 
 That said, reluctant leaders can struggle with being overly influenced by others. They can get disillusioned when they see less mission-oriented leaders acting in ways they see as hypocritical or counterproductive to the mission. Because they’re less comfortable with the power they wield, they can struggle with indecision and overthinking. Because reluctant leaders are so collaborative and sensitive to their team’s perspectives, when the inevitable moments come when they are disliked by team members because of their position or just their job title, it can feel like torture. And when reluctant leaders are motivated more by their organization’s needs than their own, they can stay in a bad situation longer than they should. 

Finally, I’m going to say a version of something that I often say when discussing a behavioral binary of this sort—the real world of leadership is always messier than a leader being ambitious or reluctant. The higher up the chain I got, the slower I’ve learned to move, and the less assertive I’ve become. As I’ve been knocked down and climbed back up in my roller coaster of a leadership journey, I’ve become more picky about what I will and won’t sacrifice at the altar of my career, and I draw less of my self worth from my work successes. I’ve also seen initially reluctant leaders blossom not just into good caretakers of their team and mission, but also derive genuine, personal joy from an achievement that drives them toward a bigger and brighter impact. Ultimately, one path to leadership is not better than the other, and we need both approaches to leadership to build the world we all wish to see. 
 
 So my challenge this week is to consider whether you right now are more of an ambitious or reluctant leader. Your gut will tell you pretty quickly. Then ask yourself—what can you learn from the other side of the spectrum? Find a trait you wish you had from a leader you admire but who seems to have a different mindset than you on the ambitious and reluctance spectrum. And intentionally practice that trait this week.  

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Thanks as always for listening to the kind leadership challenge. Before you go, here’s a quick way you can spread the word of kind leadership. I’d like you to take a moment to think of one friend or colleague who could most benefit from this week’s challenge. Then, open your app or head over to kindleadershipchallenge.com/66 and share this episode with them. And add a friendly note as well. Never doubt that day by day, you’re building a better world, even if you can't see it yet. So until next time, stay kind now.