Jessica McKellar discusses managing disagreements in long-term business partnerships. She and her co-founder used executive coaching and built mutual trust to resolve conflicts and improve their leadership skills.
You've been together for 15 years as this incredible team. What happens when you disagree? Do you have a sort of ritual, sort of a way of making decisions or like what happens?
Oh yeah, and I should clarify it like, and Jeff, he would be fine with me saying this because I've said it in front of him before. Jeff and I didn't get along for like the first seven years of our relationship together as like kind of business owners together. And you know, I think what that speaks to is that, I mean a lot of what, what running a company is about is about just interpersonal stuff and, and that's something that you get better at over time. Like you, this is like a muscle that you practice. One of the most transformative experiences that I had as an adult was actually at Dropbox in an executive coaching program that they, they kind of deployed with various departments, including the engineering leadership team. And you know, they run you, they, you sit in the fire with, with, with that type of executive coaching program like that. You get a bunch of like very detailed, you know, like they send questionnaires to everybody who works with you, like your manager, your peers, the people who report to you. Like, everybody gets like a 200 question questionnaire where they're rating you on a five point scale on like every possible attribute of your leadership style. And, and then an executive coach distills that into themes like where are your strengths, what are behaviors that are not serving you well or not serving you well anymore. And you like process that together and then you decide how you want to come out the other side of it. But you know those types of reflections, they make you a, they made sorry I. Statements. At least for me. It made me a better leader, but it also made me like a better partner in my personal life because it really forces you to reflect on how you engage with difficult situations, how you engage with conflict. So yeah, I mean it's like, it's like a pro, It's a, it's a, it's a continuous investment in oneself and the team to be better and better as a, as a people manager and as a leader that happened, that was a really transformative experience for me and I think I benefited from it, you know, coming into, coming into pilot because I, you know, that that's an experience I hadn't had in the previous two companies.
I'm just really touched you share that because I personally went through something very similar and it was super eye opening just having that feedback come back and then eventually working through. For me, I am incredibly conflict avoidant. If I could, I would just hide in a cave. And then I realized over time and through a lot of coaching and continuous development, like you spoke about, like, conflict is not always bad.
Right.
I think sometimes we have this perception, you know, as I was growing up, it was like, oh, conflict is not a good thing. Or like, culturally it's not a good thing. And yet it's kind of where the good stuff happens. It's like when people are able to be so compassionate and respectful and laid out on table, you may find better solutions and better outcomes from it. And yeah, I talk about this because I think especially for students, sometimes there's this desire to go solo because then you'll have less conflict. But actually, we're missing out on some great interactions and great opportunities to develop.
Yeah, absolutely. And then to go back to your kind of direct previous question, I was like, how do we resolve conflict? Well, first, we've gotten a lot better at it because I think we've mostly kind of sorted out our issues over the past 15 years. And so if you're, if you're coming at it from a place of, there is sincere mutual trust and respect. And for me, it's like I had hang ups about feeling like I had earned my place at the table, right? And so, like, challenge things that felt like they were challenging that made me react in a counterproductive way. When I have it, once I work through those things, it's like, oh, okay, we're having a disagreement. Like, we're both reasonable people. We both trust each other. Let's make sure that we're working off of the same fact base here. Like, maybe that's, maybe that's the issue. So, like, let's make, let's check if we're, if we have the same information and if we do, great, we probably have two reasonable opinions that just happen to be different. And we just need to make a decision about, you know, whose lane. Whose call is this? Because some things are my call. They're in my kind of sphere. Some things are, you know, Jeff's call, some things are Waseem's call. And, you know, you can really, you can like, pull the card if you need to say, like, hey, this is a deal breaker for me, but otherwise we're making a hundred decisions every day. Like, I, I'm not gonna micromanage. I don't have time nor the interest to micromanage everything that these folks are doing. They're highly capable. They're better than me at their. The stuff that they're doing. So let them do what they're doing. Let me do what I'm doing. We'll make sure that we're aligned on the big ticket items for sure. And then you just let it go. You, like, disagree and commit. Let's move on. We've got a million other things to do.
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