Can you really work with friends? Stranger things have happened.
Okay, I absolutely love Stranger Things! I mean who doesn’t, right? Don’t worry... There are no spoilers here, I promise! I have waited with bated breath for season 4 for a whole year. And so far its been worth the wait. The first couple episodes sent me through so many emotions because the kids on the show have entered an entirely new world… the world of high school (oh the horror). The show has always been about their friendships, but in this latest season, everyone’s friendships are changing. They are changing.
We, too, are trying to navigate changing friendships. In case you don't already know, I hired my besties to join me in creating Herself Media. I have known Stephanie since I was 13ish. I have known Brooke since I was 14, and I met Jenny my freshman year of college at the age of 18. I've known them forever! So I thought Id share about how we navigate being long time friends and co-workers.
My number one guideline when working with friends is the importance of having a really vulnerable conversations about what it means to be working together. For me and Stephanie (who I've called Nini since we were kids) it was like being reintroduced as adults. Let me tell you, we had to put on our big girl panties for these conversations.
Nini always had a rule to never work with friends. And who can blame her, there are lots of people who recommend that you never mix business and friendship. So when I asked her to work with me, she was curious but hesitant. So, how did I convince her to come aboard? I didn’t. And that was also important. My friendship with NiNi and her friendship with me could handle the answer “no.” I didn't convince her, I just answered her questions as best I could… and let her decide for herself.
Nini and I had to talk about our past friendship as kids- the ways we have changed, the triggers we may still have. We talked about our hopes for this company, how our roles would be defined, and how to preserve our friendship. We talked MONEY (hello, somebody!) but we also talked about our desires, our disappointments, our dreams. We put it all on the table so that we're super clear with one another.
Our conversation couldn't be about convincing her because the temptation to just tell her what she wanted to hear would be too strong. I had to tell her the truth and hope that the truth was compelling. Because frankly, we're not sixteen anymore. At that age, you are in the midst of growing and figuring out who you are. It's easy to adapt to what you think people expect. We arent so adaptable anymore- lol. And while we can extend one another grace, we know a lot more about who we are as individuals- and who we are not.
NiNi said recently that our conversations felt like the opposite of a job interview. In a job interview you put on your best and share all the reasons why you’re great for the position. But this required something different. This required that we strip down and say “here are all the reasons you may not want me”. It was a vulnerable conversation about flaws and expectations, about our shared history with different perspectives.
We both were on the same page - friendship comes first. In fact, we already have our contingency plan laid out if the business ever starts to come between us. We are clear that our friendship will always be more important than the business or the money.. you know, if we make any (lol).
The second thing that I have learned is that even though I know all of my team members really well, they still have the ability to surprise me. I'll use Brooke as an example. Generally, she is very go-with-the-flow. She’s opinionated but never uses those opinions to clobber those around her. She is generally very easy going. But I have noticed she has a perfection streak that I didn't know existed. It really surprised me, but now I'm glad I know because it means she has another perspective that will only make our team better. I do know my team well because of our shared history, but I can never assume I “have them figured out”. They're individuals who are growing and changing and I am learning more about them in this new landscape.
Brooke has realized that in many of her friendships, she worries about making people uncomfortable. I mean, she always makes us uncomfortable because her sense of humor often leans toward things that are disgusting. But thats not the kind of discomfort we’re talking about here. Brooke often worries that speaking up will be something of a strain on the people she loves. But in this environment, we need Brooke's voice. So she is learning how to trust us with her voice. She has to take a leap of faith with us- that she can trust that her voice will be heard, and will be held graciously. And in turn, we have to remember that it takes a lot for Brooke to speak up. So we are cognizant of not being mean (even playfully), ignoring her, or her worst fear- telling her to hit the rails with her stick and handkerchief with her bonnet and retainer inside.
I also needed something really important from my team. I needed the freedom to fail. Of their own accord, each of my team members expressed that even though we were going to try this, they all understood it just might not come together! I needed to know that if it all fails, that they wont hate me, or leave me, or never speak to me. I needed to know that each of them believed that trying was worth it. Jenny told me, “you're never getting rid of me, Austin. I don't care what our LLC name is.”
Jenny said an important moment for her in the very beginning of becoming friends and coworkers was having a conversation about what we experienced at other toxic workplaces. Naming those things was important for two reasons. One, it was actually incredibly bonding. It was helpful to know what wounds we were all bringing to the table and it helped create a unifying vision of not just what we were going to make but how we were going to make it. Two, if we start seeing toxicity surface we could address the cause. The shared vision of a healthy work environment became the goal as opposed to just making it work with your friends.
The prize jewel of working with friends is the knowing that you’re cared for, knowing that we are all rooting for each other. Every person knows we want them- the real them- at the table. But don’t get it twisted. I didn't choose them because I like them. I mean, we could always hang out on Saturdays! I chose them because I saw their gifts, their skills… and I saw how their previous workplaces dulled their shine instead of enhancing it. As opposed to expecting them to be grateful to be here, I am the one who is grateful.
Are there any work relationships where you need to have a risky, vulnerable conversation?
Are there people that you need to allow room for change, growth or surprise?
Do you feel like you have permission to fail?
Does it feel possible that your current endeavors could be successful simply because you are trying?
This week’s spotlight is on two friends, Aminatou Sow and Ann Friedman. Aminatou is a digital strategist, writer, influencer, and co-founder of Tech LadyMafia. While Ann is a journalist and contributor to New York magazine, The Los Angeles Times, and The Gentlewoman. They co-hosted the hit podcast for long-distance besties everywhere, Call Your Girlfriend. They have also co-written the book, Big Friendship: How We Keep Each Other Close.