Leadership is Discovery, not Invention

Growing up, I was pretty good at most sports. In the 80s, being good at sports and being unafraid to tell people what to do often put you in the captain’s seat. Score a few points, yell at your teammates, and just like that, you’re a born leader.

That model of leadership seemed to be pervasive among my coaches too — very few of them were anything but yellers. It’s certainly something. But that something is closer to being an entitled dick lacking in empathy than what anyone would call good leadership.

My off-court models of leadership weren’t exactly perfect, either. Toy Soldiers, a movie from the early ’90s starring a charismatic Sean Astin and a bunch of scrappy kids using their diverse skills, guts, and determination to overcome and defeat a band of terrorists, was, I’m embarrassed to admit, responsible for shaping my early definitions of what leadership should look and sound like. Hey, I could have done worse than a young Samwise Gamgee! But here’s the thing: charisma is great, but it only gets you so far.

A Still from the 1991 movie, Toy Soldiers. Mr. Frodo, I’m so charismatic.

Being an authentic leader means discovering what you want, developing clarity around your values, and creating a context for how you and your team can be most effective in the service of your goals.

Leadership Makeover

I had reached a point in my business where I knew I didn’t want to run it as a series of projects and wanted to have a breakthrough in revenue, but I couldn’t really articulate that goal nor did I have a great idea for how to get there. I wasn’t sure why, but I felt anxious about moving forward.

It took time and some introspection to get to the point where I could admit to myself that all the doubt and anxiety I was feeling was rooted in being an ineffective leader. Never one to leave things in a grey area, I knew I needed to solve this problem.

I threw myself into a leadership makeover by way of coaching, books, podcasts, and a supportive community. Over the next 12–18 months, I slowly began to understand that leadership wasn’t a role to play; it was a mindset. It wasn’t a title; it was a way of operating, regardless of title.

leadership wasn’t a role to play; it was a mindset. It wasn’t a title; it was a way of operating, regardless of title.

Beginning to understand authentic leadership gave me an appreciation of just how hard leadership is. Beyond its difficulties, I recognize that to elevate my team, it’s more to do with what they see leadership do, rather than what they hear leadership say. It’s on me to take responsibility for the context I create, to communicate effectively with clear expectations of what is and isn’t acceptable, and to be consistent with all of it. Getting all of the ambiguity out of the way frees your team up to operate more effectively and with a greater sense of accountability.

To be sure, my leadership style has changed pretty significantly. Teammates have commented on what ‘old-Steve’ would do and how ‘new-Steve’ is easier to work with. I like that they feel I’m easier to work with, but that’s not my key takeaway. Here are some main ideas that changed my perspective on leadership. I hope you get some value from my experience because, really, who wants to wear the struggles of leadership like a badge of honour?

Show Vulnerability

For me, it was exhausting pretending that I knew exactly what to do all the time. It was a delicate house of cards. On one hand, I was actually trying to make good decisions, but my thoughts were clouded by second guessing and wondering if my team had finally figured out that I haven’t a clue.

The irony is that being vulnerable and asking for help rather than letting everyone think you got this creates opportunities for your teammates. By giving them the opportunity to contribute and generate ideas, the bus goes where it needs to go. Call it lazy-leadership, servant-leadership, whatever you want. You’re doing exactly what a leader should do: clearly identifying the goal, crystallizing the context, and highlighting the gaps so your team can figure out the best way to fill in those gaps and get the bus rolling.

By including my team in the process of solving challenges, they started to feel like they were a part of something that they help create. With this shift towards empowerment, they became more accountable to each other, had a greater sense of ownership around outcomes, and thrived in an environment underscored by a greater degree of autonomy and stronger social bonds.

“He who thinks he leads, but has no followers, is only taking a walk.” — John C. Maxwell

Showing your vulnerability takes a bit of confidence and a leap of faith that your team won’t hold your vulnerabilities against you. Your mileage may vary, but for me, it was hard to think of the positive outcomes when so much of my leadership identity was rooted in being right. If I’m not right, I’m wrong. If I’m wrong, what good am I to my team? It’s a sham. If you show trust, your team will reciprocate. I wish I had learned earlier that being authentic rather than playing into my own ill-defined models of leadership is a much better way to go. If your team is given the opportunity to rise to a challenge knowing that they have your full support and trust, they will do exactly that. Continue to invalidate them by solving all their problems for them, you’ll be on an island.

Be Responsible for the Context you Create

You can’t control everything but you can control your own actions. Those actions determine how you show up for your team and how they react to you.

I learned very early into my leadership coaching experience that the easiest thing that I could do as a leader is set context. I used to get so caught up in trying to really understand what setting vision meant, looking to larger than life figures like Steve Jobs or Elon Musk. I’d think, Jeez, can I have a vision like those guys? Am I a fucking imposter because I don’t have that kind of vision? But looking to them and their accomplishments, you’re really just seeing the outputs. Setting context, on the other hand, is what you need to get through every day; it’s how you get to the output. It’s about being consistent with your actions, identifying what people need to be successful, and showing them that you’ll follow through on what you say.

Communicating requests with a clear picture of what success looks like, when the thing needs to be done by, and how the thing fits into the bigger picture is a great way to treat people like adults. Once ambiguity is gone, there’s very little wiggle room to miss the mark. A switch flicked for me. Maybe a good amount of instances where I might have been frustrated by a teammate’s lack of delivery or poor performance was, in fact, partly due to my role in the relationship by not setting the right context for my people to operate within.

I don’t have exact stats, and this is hard to measure, but it’s my post and my experience so I’ll just say that anecdotally, 80% of being a leader is communicating effectively about what today looks like, what tomorrow should look like, and identifying where the gaps in the journey between today and tomorrow exist — then trusting that your team will get you there.

Develop a greater sense of self

Developing a greater sense of self doesn’t mean being selfish. Just being more aware of yourself. You aren’t perfect and you’ll do really stupid stuff that you’ll punish yourself for. Own it and don’t shy away from it. Take responsibility when you say the wrong thing — you’re human. Having said that, pay special attention to the kinds of on-going behaviour that limits results or closes off possibilities. Also, try to understand how your own tendencies can be a real strength and weakness for your leadership style.

For example, I’d like to think that I’m a critical thinker. Often, I’ve found myself in conversations or in brainstorms where I’ll jump a few steps ahead and can see how an idea might play out before the other person has even finished. Good skill, right? Maybe, maybe not. Like all skills, it really depends on how you wield it.

Poking holes has a time and place, but learning to embrace all the possibilities of what the seed of an idea could turn into is a leader’s job. Asking questions rather than shutting down suggestions lets your team make their own decisions about the worth of an idea. You can help steer them into your line of thinking in a way that isn’t disempowering by being more curious than certain.

I know that when people are able to bring up ideas or ask for feedback without thinking that someone is going to shit on it, trust and innovation can truly exist. You never know from whom or from where the next big idea will come. If I hadn’t understood how my own behaviour was limiting my team and my business, we’d be missing out on these ideas.

It’s never going to be perfect

Your people are like a farm; you have to tend to them to help them produce. — Jen Dary.

You’re human. You’re flawed. That’s OK. Feedback, and how we deal with it, tends to tap into our insecurities at the best of times, but when interpretation trumps facts, we all to retreat to an emotional state that won’t do anyone any favours. The trick that, if I’m being honest, I haven’t mastered, is trying to remain objective and focus on the facts. If someone says something that’s cutting or gives you feedback on work you felt personally invested in, it’s hard not to let the ideas reinforce background conversations that happen in your head about how you’re not good enough or smart enough.

The truth of the matter is that someone had an opinion on something. How you let that opinion play out is entirely up to you.

Even recognizing that your background conversations will drive your interpretation of the world and how it occurs for you, is enough to change your response. It’s like the Hawthorne effect but for your own head. A background conversation from your past telling you that you’re not good enough or smart enough is just a background conversation and it has no place shaping your behaviour as a leader.

You have to tend to yourself, tend to your team, and understand that you’ve all got shit from your past that affects how you show up for other people. Recognize your own shit and understand that your past limits what’s possible for the future. Get out of that loop. It’s lonely and filled with fear.

Build a culture of gratitude.

There are ways of expressing gratitude that don’t require any resources beyond your time and attention. Humanity is free and doesn’t take up too much time. I’ve found that just paying attention to what people do and acknowledging that effort goes a long way.

Humanity is free and doesn’t take up too much time.

Taking a page from a friend who runs an incredible agency in South Carolina, I’ve developed a way of recognizing my team’s effort while ingraining our values at the same time. We call them Friday 🖐 fives, and it’s really just a way of publicly acknowledging the behaviour and actions teammates have displayed over the course of the week that exemplify our values of courage, collaboration, curiosity, and persistence. If someone stayed a little later to push a feature, they showed persistence. If they helped unblock someone to ensure that a project stayed out of risk, great job collaborating. You get the idea.

Friday 🖐 fives look like this and generate healthy reactions and positive vibes while reinforcing our values.

Some comments and feedback that I’ve received have been overwhelmingly positive — one person even said it was like a hug before the weekend.

Publicly acknowledging positive teammate behaviour wasn’t something that I was used to doing regularly because I was always so focused on the next job or the next deadline. As an entrepreneur or leader, always thinking that your next opportunity is going to be your best doesn’t make the team feel great about the effort they are putting in today. Appreciate the accomplishment because no matter if it’s your best work or not, your team worked hard. Don’t invalidate them because you’re already on to the next thing.

It’s important to note that you shouldn’t expect gratitude back. I mean, it’s nice when your team acknowledges you, but you shouldn’t expect them to fall over themselves because you did your job. Align your expectations and you won’t be upset.

Don’t go it alone.

My coach was instrumental in helping me through this personal transformation. She allowed me to see that fear was running the show. Fear of being found out, fear of fucking up, fear of not knowing how to be effective. Unless you want fear to be the cork in the champagne bottle of possibilities, at some point you just have to acknowledge the fear, move past it and let the cork fly. Yeah, you’ll get a little uncomfortable, but after you settle into your discomfort, you’ll marvel at how quickly all of it will feel like a comfy sweater in contrast to all of the amazing challenges you and your team are tackling, together.

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