The Evolution of a Leader

Why the Founder's Personal Development Is a Non-Negotiable for Team Health

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A while back my friend had a boss with poor boundaries. My friend would tell me stories about how his boss would talk and talk and talk in their meetings, how she would overshare with my friend about her emotions, and how she would overwork and constantly be exhausted. I felt for him. It sounded to me like his boss used him as an emotional sounding board and since he wasn’t being paid to be her therapist, it was wildly inappropriate. It was an example of someone in a leadership position who wasn’t doing their own personal work and it showed.

Leadership is loaded. It requires holding responsibility and power. It can inspire and create mass movements. It can oppress and demand conformity. And it can be an overvalued role that doesn’t do much of anything. Who becomes a leader and what is valued in a leader is cultural. So much so that Wikipedia deems leadership a ‘contested term’ when trying to define it.

Being a business founder necessitates leadership. It’s one of those many hats founders wear during the building of their business that they may not have much experience or skill with. At least initially.

A while back I was on a finance call with a group of high 6-figure and low 7-figure business owners and their number one pain point at that stage of growth was hiring, retaining, and leading team members. If an entrepreneur wants to grow their business and build a team, developing leadership skills quickly becomes a non-negotiable. And so much of what makes up ‘leadership skills’ is how healthy that leader is in their own sense of self and their relationship with others.

Life Experiences & Relationships

Our personal development is not separate from our business, it is intimately connected. Humans are multifaceted and complex. There are many parts to us. And while people have varying levels of skill at compartmentalizing their work and home lives, we can’t ignore our personal conditioning when we show up for work. The families and cultures we grew up in and the things we’ve experienced up to this point absolutely influence how we show up to work and relationships. 

Relationships are an essential aspect of business, without them a company will fail. So even though ‘personal development’ sounds individualistic, it’s really about the evolution of our ability to show up to relationships in healthy ways. For most of us, this requires ongoing refinement.

Accountability & Growth

In the entrepreneurial world there is a huge emphasis on growth. But what isn’t talked about is the fact that the more a company grows, the more relationships there are to maintain. Relationships with team members, customers, community, and our environments. Additionally, relationships with family and friends often evolve as a business evolves. Maintaining relationships takes care, consideration, reflection, and time. The more people we add into the mix, the more this responsibility grows. Richie Reseda, a producer and abolitionist entrepreneur, sums it up well in this post when he says, “The more you affect, the more you are accountable to.” Growth necessitates an increase in relational capacity. 

Whether a leader is aware of it or not, they have a more-than-average influence on the tone of a group. So the maturity of the group is impacted by the maturity of the leader. The leader isn't the only factor, but they’re an important one because so much of their role is related to holding the group together. Personal development for the leader is largely about developing their ability to stay accountable to the group in a variety of situations.

There is great power in leadership and it’s important to be mindful of that. An interesting example of this is politicians. They are some of the most prominent leaders in the land and we can learn much about what it looks like when they do their own work and when they don’t. Too often I look at politicians and I see people who have too much unresolved trauma to be in a position of power. You know the ones - the terrifying politicians. They aren’t self-reflective, they aren’t collaborative with the people whose lives they impact, they don’t take feedback well, and they use their power to armor up (literally and figuratively). Part of why politics can be so frustrating is because too often there’s little, if any, accountability for these types of leaders. And we see how the population suffers because of it. This is the same for business founders. Team health is directly related to leadership health.

The Value of a Leader

That being said, we need to be careful with how much we value leaders. In the U.S. mainstream culture, there is a power balance implied in the dynamic of ‘leader’ and ‘follower’. Undoubtedly, the role of a leader can be incredibly important for gathering a group together, helping them move in a direction, and shaping how they do that.

Is it more important than other roles? Debatable. Is it one piece of an interdependent system? Absolutely. Humble leaders are often the most beloved leaders because they don’t situate themselves above those they work with, but next to them.

An example of how this can influence team health is in the cultural norms around giving and receiving feedback within a company. When a leader is humble enough to recognize their capacity for mistakes and when they’re willing to listen to feedback, communication channels open up. When healthy communication practices are modeled at the leadership level it helps to normalize those behaviors. Because the reality is, in a work environment where money is being exchanged for labor, there is undoubtedly a power dynamic at play and it’s the responsibility of leadership to understand that. Priya Parker defines power as, “anytime two or more people come together.” Add pay rates, promotions, hiring, and firing into the mix and that power dynamic only heightens. Trust needs to be established so when a team member brings something up they know there won’t be retaliation. 

If the feedback norms aren’t healthy at the leadership level, it will likely create a culture of fear. This could look like defensiveness, deflection, blaming, shaming, or ignoring. These responses will discourage feedback and close communication channels, and will encourage back-channeling and lack of engagement. 

The U.S. mainstream culture doesn’t emphasize healthy feedback skills, so most of us need to make the effort to develop our ability to give and receive feedback. There are plenty of times in my life when I haven’t been skilled at receiving feedback. And plenty of times when I haven’t given feedback very well or avoided it all together. I’ve had to recognize it as a skill that can be developed, rather than something I should inherently know how to do. It’s an ongoing practice, an ongoing work in progress. So much of leadership is.

Leaders Need Support

I once heard Julie Chenell compare leadership to a tomato plant. She made the point that the more the plant grows and produces fruit, the more trellis support it needs. Leadership isn’t an individualistic endeavor, it’s a collective one. You aren’t meant to do it alone. And thank goodness for that because some days being a business founder is hard. 

The thing is, being the founder and being a leader is a role in and of itself. But in the early stages of building a business founders often end up holding the responsibility of multiple jobs. Sometimes it’s out of financial necessity. But sometimes it’s because they don’t even realize they’re doing it. They’re not sure what or how to delegate and it feels easier to keep doing all the things rather than take the time to figure it out. But leaders need support or else they aren't really leading.

If you are one of those founders this is my request - write yourself a job description. Start by brain dumping all the things you are responsible for and all the tasks you’re doing. Time track yourself for a couple weeks if necessary. This will give you a visual of all the plates you’re holding. Leadership responsibilities should be on that list such as casting vision, making high-level strategic decisions, reviewing the finances regularly, inspiring and motivating the team, problem solving, and developing your leadership skills. All of these things take time and energy. 

Crafting a realistic job description can help you clarify your true priorities, identify tasks to delegate, and maybe even support your personal development. Boundaries, work/life balance, and clarity of purpose are all helpful for effective leadership. When we hold a leadership role we hold significant responsibility. But we don’t have to hold it alone.

Related Resources

• Power, Intention, and Gathering with Priya Parker on the Finding Our Way podcast

• A Renaissance of Our Own: A Memoir & Manifesto of Reimagining by Rachel E. Cargle

• Dare to Lead: Brave Work. Tough Conversations. Whole Hearts by Brene Brown

• Nicole McDonough - leadership coaching