Being Authentically You as a CEO with Mark Josephson

INTRODUCTION: Welcome to The Daily Bolster. Each day, we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here today with my friend, Mark Josephson. Mark is the CEO of Castiron. He is former CEO of Bitly and Outside. in and former general manager of about. com. Mark, welcome to The Daily Bolster.

Mark Josephson: Thanks for having me.

Matt Blumberg: So one of the things that I truly appreciate about you, Mark, as you and I have gotten to know each other better and better over the years of being in a lot of the same VC portfolios, is just how completely and totally authentic you are at all times with all people.

Mark Josephson: To a fault sometimes.

Matt Blumberg: Well, that may be true, but I know you have a good framework that you've organized for yourself over the years about how to bring that authenticity and honesty and the true you to work as CEO every day. So, would love to have you share that.

Mark Josephson: Thanks, Matt, and thanks for doing the Daily Bolsters. They're awesome. I love getting little bits of information to help me be better at my job and a better person every day. So I do think it's one of the highest order things that a leader can do and a human can do in any interaction is to bring their authentic self, be honest and open about who you are, what you need, and how to be successful. So I do have a three point framework for that. And they sometimes seem obvious, but the first one is actually starting with the truth. What is the truth about the interaction that you're having and the problem that you're trying to solve? And sometimes it can be direct. Sometimes it can be crisp. There's a difference between radical candor and brutal honesty that I think is really important to tease out. But in the interactions that you're having with your team, you have to start with the very first principle of truth. The truth is we're not growing fast enough. The truth is these leads cost too much. The truth is the page takes too long to load. The actual granular truth-

Matt Blumberg: The facts.

Mark Josephson: The facts.

Matt Blumberg: Facts on the ground, right? So set aside spin. Maybe you get to that later. You start with the facts on the ground.

Mark Josephson: Yeah. That's right. The second is a concept called the meta message. The meta message is a thing that you may be thinking or feeling but aren't communicating well because you're afraid you might hurt somebody's feelings, or you're afraid to actually speak the truth. So this shows up in personal relationships all the time, and it definitely shows up for me as a leader sometimes in my interactions with my team. So for example, instead of saying, " Matt, I think you're working on the wrong thing," or" I think this isn't good enough," which can be a hard thing to actually say to somebody. Instead, I would find myself almost passive aggressively asking 30 questions, knowing how that interaction would end up. So making people feel uncomfortable by saying, " Well, how did you think about that? What are the leads? Where are they coming from? What's the conversion rate? Did you think about this? Did you think that?" Passive aggressively proving they're wrong instead of actually saying what I think needs to be said. And that meta message is one of the things that we do at Castiron in past places, is in moments where you feel like maybe there's some tension or maybe things aren't being said, is the permission to say, " Hey Matt, what's the meta message here? What are you really trying to say?"

Matt Blumberg: I love that you've brought that language into the company, so that's great.

Mark Josephson: Yeah. What's the meta message? The meta message here is, " Okay, I'm really uncomfortable with our growth rate." And the third piece here is something called mentalizing. Mentalizing, which can often be confused with or overlap with empathy, but mentalizing is the act of putting yourself in the other person's shoes to understand what they're bringing to the interaction. Their needs, their fears, their goals, and what they're hoping to get out of this. And I find this is really helpful to me, particularly in skip levels when I'm talking to people who... I get into a habit of talking big picture, strategy, lean back, " Wouldn't it be great if..." When really that person might be coming to this interaction thinking, " Oh my God, I'm going to get 50 things given to me today. I don't have the resources to do all the stuff I need. I wish Mark would just tell me what I need to do versus brainstorm with me things I'll never get done." So I picture myself in those moments leaving my body and sitting across from me, trying to anticipate and understand what their needs are. So that ability, it's not always easy, but really helpful in getting authentic, honest, true interactions with your team.

Matt Blumberg: I love the concept of putting yourself in the other person's shoes. I've never heard the phrase mentalizing, but I'm going to try to onboard that one. Mark Josephson, thank you so much for being here.

Mark Josephson: Thanks, Matt.