The Path of the Paradoxical Leader

authentic leadership Jul 26, 2021

Do you ever get the sense that something is happening around you, maybe even because of you, and everybody else knows it - except for you?

A few months ago, our strategist and marketer Mel decided to go full-time with her own project. We were all very sad to lose her, but I was delighted when another great prospect popped up for the role just a few weeks later: my old friend and collaborator Jason Digges.

When Mel was leaving, she wanted to place our company on good footing. She started working with me and AuthRev's operations mistress, Laura, to take over the leadership. Laura hadn't led before. But I wasn't going to do it solo, right?

Jason joined us a month later. He was relieved to find out that Laura and I were co-leading the company. However, while we were fantastic collaborators on the operations front, Laura and I didn't do well in the joint CEO role. She stepped down. As a result, Jason started to get cold feet, because nobody was going to be in the leadership role - I wasn't going to do it solo, right?

It was around this time that I started wondering:

"Wait a second. This is my company. Aren't I supposed to be leading it?"

This may seem like a dumb question. At the time, it was quite profound. I had always "led" AuthRev in a very laissez-faire way. I wanted everyone to be aligned on decisions, to give input, to define their own roles, and to make just enough money for us to survive while doing good things for the world.

This worked fine while we had a small team who were willing to work for small amounts. During the pandemic, for the first time, money started mattering to me, after it became clear how necessary money was for the safety of myself and those I loved. I also started feeling more confident and passionate about the work AuthRev was doing, seeing the difficulties people were having finding connection without in-person hangouts or events.

To grow, we had to hire people who were more experienced and better at their jobs. Those people wanted to be paid more. Ergo, the business had to change. But who was the person to change it? Me, the one who had let us drift along for the last near-decade? Or did we need someone else at the helm?


Who's running this ship?

My favorite quote on leadership has always been this one, from the Tao Te Ching:

"When the master leads, the people say, "Look, we did it - all by ourselves!""

I have a deep reverence for leading from the back of the room. Leadership by gentle guidance, by Socratic questioning, by emergence and authenticity. I've always seen this as the way to bypass many of the directive, capitalist, masculine, dominant-culture ways of commanding a group or company.

I don't think this is wrong. But...we live in a directive, capitalist, masculine, dominant-culture culture. That's what having a dominant culture means: the people in power set the frames of interaction. My maturity was in learning that leading from behind, gently guiding, and only ever facilitating instead of directing - all that, beautiful as it was, was keeping my company from being able to engage in any of the business interactions that would lead us into the mainstream.

Mainstream companies have a vision and goals. People commit to those, or they don't join the company; anyone can give input, but there is someone who decides. Mainstream companies have to negotiate contracts where not everyone may get what they want. They need to define hierarchy (we tried Holacracy and everything else you can imagine, but every "more fair" model actually caused everyone in the company more work, strife, and feelings of being out of control). They take risks, and set intentions that they may not be able to meet, because that gives them incentive to grow.


Full-Frontal Leadership

While I was contemplating these questions, my company was at a decision point. Should we hire a CEO? Should we hire anyone new, or keep on with business as usual?

After weeks of soul-searching, good coaching, and an MDMA trip, I decided. 

It was time to become a CEO.

Since that decision, I've discovered a couple of things that, to me, distinguish the type of leader I want to be from the one I have been. I strive to be a leader who doesn't lean only towards the feminine, and doesn't polarize towards the masculine; includes and collaborates, but also directs and decides; one who identifies (like I do in gender) with both sides. I'll call this the "Path of the Paradoxical Leader".

Largely as a result of discovering and following this path, my company has: 

  • Raised $70,000
  • Hired 4 new team members (likely soon a 5th) to double the size of our order
  • Created an accurate org chart and inspiring set of company norms and values
  • Created a thriving social media presence (entirely Jason and Ankati's doing; I can't take credit for that)
  • Started internal classes for team members, taught by team members, called "Authentic University"
  • Did NOT launch any new products this month, but began planning and pursuing a cohesive marketing and student leading strategy
  • Went from no meetings at all to a monthly vision, monthly culture, and weekly stand-up which people have started voluntarily staying an hour late at to discuss new projects. 
  • Also, we're using Slack and OKRs and IT'S WORKING. 

So, without further ado:


The Path of the Paradoxical Leader

  • I am absolutely responsible for the financial well-being of my company. However, I am transparent with my team members about our finances, and ask them for the help I need.
  • I make the final decisions on vision, partnerships, norms, and overall structure for my company. However, I never transcend the authority team members have within their own roles, and I use advice process to gather feedback before making important decisions that affect my team.
  • I can hire and fire people. However, I do this through discussion rather than mandate, and only after adequate feedback and chances to improve. Most of the time we both agree that leaving is the right choice.
  • I hire the best possible people for the jobs - aligned in both skill and culture - and figure out how to pay them what they're worth, instead of asking them to take more than slight pay cuts. If they do need to take pay cuts to make the job work, they agree to that willingly, and we have regular check-ins to see how that is feeling, and a timeline for when we may be able to pay them more.
  • I honor deadlines and proactively work as much or more as I ask others to. However, I am also proactively honest about when moods, monthly cycles, trips, and personal needs require me to re-allocate my time for a while. If I do this, I always check in on whether anyone has needs of me before I change my availability.
  • I make no more than the highest-paid member of my company. However, I may make more profit from equity if we are successful, to honor the work I have put in without pay in the past.
  • I have options for any financial need. However, the base cost for my programs is the amount they're worth. I never stop revising those programs to be the best they can be, but I don't let the knowledge that they can be better stop me from running them at all.
  • I am competitive in my company's offerings. However, I never undercut the competition.
  • I am caring and relational. I am also boundaried and clear. I will make decisions people don't like, but I will be communicative on my reasons, available for impact, and willing to make changes as necessary. Just because my door is always open doesn't mean I can't close it when I need the space.
  • I play the role of power without becoming it. 

I see myself as a card dealer in a blind game. Without the dealer, nobody can see each others' cards. The most confident people, or the loudest, shout that they have the highest numbers. Nobody can check, so loudness becomes the power to win. 

The dealer is not there to mandate who wins. The dealer is there to wear the suit and hold the power. They deal the cards equally. They pass the winnings to the people who have the best cards for that game. They create and hold the morality to halt cheating, resolve conflict, and pay out for the chips. 

The dealer is, ultimately, responsible to the players and to his/her/their institution. They know the limits of their power; they hold it in trust. They know who they are and what they are here to do.

They wear the suit and play the role. Parts of it, they can never take off. They have all the power and none of it. They are paradoxical. 

And yet, they create a beautiful game.


With love and (un)certainty,


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