Work With Your Best Friends
Tutti and Irene; FloMo roommates, Stanford; 1994
For many of the busy professionals I work with, it’s easy to fall into the trap of transactional leadership. We focus on the work that needs to be done—the performance reviews to be written this week, the decisions that need to be made in this meeting, or the deadlines that must be hit to meet our quarterly goals. The days are split into 30 or 60 minute meeting chunks, leaving little space for connection in between all the tasks that must be done.
One secret to mitigating this transactional leadership is to work with your best friends. You may not always have this luxury. And there’s also several possibilities to start exploring. You could work on side projects with your friends. If you’re starting a company, make sure that you like your co-founders and are friends with them. If you’re currently working, consider who among your coworkers you‘d like to be better friends with.
Lead for Connection
Many solopreneurs I connect with, especially those that used to work with large teams, talk about the loneliness of not having coworkers. That completely resonates for me. I mostly work alone supporting clients one-on-one as well as speaking, teaching, and writing. How I choose connection is by teaching workshops and retreats with people I love.
Irene Salter is one of my best friends. I’ve known her for almost 30 years. The picture above shows us as happy-go-lucky college roommates. We each had a first career, hers in neuroscience & education and mine in design & technology. We found our way to working together when we both became coaches in our latest career swerve.
For as long as I can remember, Irene and I have taken a weekend away together every six months. Last fall, in the midst of the pandemic, we were socially distanced in Mendocino, California as we camped and hiked side-by-side. In the midst of missing travel and adventure, we hatched a dream to run a women’s leadership retreat together. Now it’s come to fruition, and I finally get to work with one of my best friends. Irene and I are running a 4-day women’s leadership retreat in Mendocino over Labor Day to help women discover their own Heroine’s Journey.
It’s our first experiment in working together. Above all else, we’re already connecting and having fun in as we co-create the program.
Make space for connecting with other humans in your workday. It could simply be taking the time to pause and listen to what really matters to them. It could be sharing a joke or an anecdote about the past weekend before diving into work. Embrace connection over transactional leadership.
Seek out the differences
A newer friend, Jim Herman, and I are teaching our third series of leadership workshops together. We met during our coaching certification program, and instantly felt intrigued by each other. While we resonated over living in different cities around the world, he could not be more different than me. On top of the obvious demographics—he’s a retired white man—our styles are as different as night and day. I am more planned, no-nonsense, and serious. He is outrageous and light-hearted. Together, we make a wonderfully diverse co-teaching pair and have learned how we adapt and improvise together. I’m grateful that Jim makes me a funnier person.
When you work with friends, there’s pre-existing relationships and a camaraderie that exists. You might know the person socially or have worked together in another job. You know more of their story. This depth of personal relationship makes it easier to celebrate how different they are from you. Because of this shared trust, it’s easier to learn from the differences rather than become defensive or resistant.
Trust and Agreements
The benefit of working with friends is that you have pre-existing trust and relationships. However, it’s important to intentionally transition the friendship to a working partnership by setting clear agreements and expectations.
I support many co-founders and have heard consistent themes over what could go wrong. It gets even more complicated when you add more cofounders—4 is the max I’ve worked with. Tensions can arise from these situations:
Two co-founders have quit their jobs to work full-time on the startup but the third is still working at her day job. There’s a perception of inequity of effort.
The details of the cap table aren’t transparent to everyone. Each person believes that they deserve more, and there hasn’t been a clear discussion of what division is most fair.
Roles and responsibilities which continually evolve in a fast growing startup become murky when not made explicit
The solution to all of these is to have closer communication and an ongoing discussion on how much each person can contribute and what the financial compensation should be. These agreements need frequent revisiting as startups evolve quickly.
It’s especially crucial to set agreements and boundaries when transitioning from one set of relationship norms as friends to a new set of norms as co-workers. You don’t want to ruin the friendship by working together.
Bottom Line
To build more meaning into our professional lives, work with your best friends. There’s many forms this can take—working on side-projects with friends, picking friends to be co-founders, or looking for new friends in an existing workplace. This mentality helps us move away from purely transactional leadership to building more connections at work.