Well-Rounded Leadership: Mark Kosoglow’s Guide to Micromanagement and Work-Life Balance

Welcome to the Leader Pulse podcast, the podcast with actionable insights for leaders revolutionizing the world of work. I'm Holly Tate, your chief marketing officer and co-host of the Leader Pulse podcast. If you've enjoyed the last three episodes with Matt and Mark, you're going to love listening to the entire conversation here on our bonus episode, where it is the unedited conversation with Matt and Mark. As you've heard over the last couple of episodes, they talk about what it looks like to be an effective manager. Do you micromanage? Do you macromanage? What's the right balance of that? Then they talk about the idea of work-life harmony versus balance, and then the quantity versus quality debate. Is it more is better or better is better? So tune in as you hear Matt and Mark talk about what being an effective leader looks like in a high growth environment. And if you haven't already, make sure you follow Mark on LinkedIn, where he posts regular hot takes on leadership and company growth. Okay, well, hey, Mark. So nice to meet you today. Get some time together. I had a motto for a long time. It was called refuse to be the bottleneck. And I recently got some feedback from someone that said that that was a silly motto. And especially as an executive, they said, you should choose when to be the bottleneck. So instead of saying you're always going to slow down, you're never going to let anything slow down. They said choose when to slow other people down. In other words, choose when to be the bottleneck for excellence. Don't let everything just go through and let it be fast. Choose when to be the bottleneck. However, I've learned that as I start to be the bottleneck, in other words, go down in details, people have described me as a micromanager. And I've heard you have kind of a hot take around this potentially that being a micromanager or being interpreted as a micromanager is not always a bad thing. So I want to hear your thoughts. Tell me more about this. Yeah, I think that there's just some functions inside of a job that warrant micromanagement. And for me, I'm going to use my area of expertise, which is sales. And there are probably 1% to 5% of sellers that will prospect without micromanagement. The other 99% to 95% will not. And it doesn't matter how you incentivize them. It doesn't matter how you compensate them. It doesn't matter what resources you give them. It doesn't matter what training you give them. It doesn't matter how automated you make it. They just don't think that that's their job anymore, or they don't like it so much, or they use excuses not to do it, whatever. And at Outreach, we went for a long time. All of our pipeline was sourced outbound. Then we brought in marketing. Marketing caused us to explode. Then we reached another part where we needed to explode. So we reintroduced AE prospecting. And my AEs at this point hadn't prospect for probably five years at Outreach. And when we did that, our first attempt failed. Our second attempt failed. Another third attempt. We became micromanaging assholes, and it blew up. Got it. And so I have one of my right-hand guys at Outreach. His name is Nate Broom, and he was a former SDR leader turned into a sales leader. And he brought the rigor that we needed in prospecting. And we started to say, listen, there's a spectrum for everything that we ask people to do. There's micromanagement, and then there's complete freedom and autonomy. In every project that we release, we have to determine where we're going to put it on the spectrum in order to get the right level of execution. And some things have to be all on micromanagement side. Micromanagement assholes feels like a great book. I feel like you've got to write that. Yeah, yeah. Got to be right. Okay. So tell me when you know it needs to fall on that spectrum of micromanagement. Is it the level of suck of the job, of the role and responsibility? Is that when you're like, okay, prospecting sucks. That requires micromanagement. What's your level? How do you measure it? I think that that's one axis. Another one might be like how important it is. For example, let's say that we're putting in $250,000 into Dreamforce. We have a booth. We're sending people. We're doing lead stuff. And I've asked my reps, I need you to invite 20 people from your territory to this event. Now, I can just tell them everything we've done and hope that they do it. But we know less than a quarter of your reps are going to respond to that email. What it takes is I will send you a list on Monday. On Monday, I need every rep to say they got the list. On Tuesday, I expect at least five people to be on the list. If you don't get on the list, they'll send you a personal Slack and talk to you about what you need to do to get started. By Wednesday, I need 10. By Friday, I need 20. And this is how we're going to do it. It's how everybody's going to do it. If you don't do it, your manager is going to call you and do it with you. But that's an imperfect example, like boring. It's important, not urgent. I don't really need to do this, but I know that it's going to help me in the long run. This is more important. And so you just have to... Micro-management can relieve some of the decision-making stress on someone. If I'm being told exactly what to do, how to do it, when to do it, then that's a lot of stuff I don't have to figure out on my own. But would the response to that be, if you're the direct report being on the receiving end of that, would they say, you don't trust me, you don't value me, I don't have a voice here, I don't get the responsibility to step up and make decisions, and that's okay? My response is, the last three times I've asked you to do this, you haven't done it for me, so therefore we have switched into micro-management mode. We have to remember, most salespeople's comp is two components, a base salary and commissions. Commissions are based on your skill, your expertise, and all that stuff, and how well you perform, and the base salary buys me an amount of your time to do whatever I ask you to do in that amount of time that's within the scope of the job. Interesting. We've lost this. I'm paying a mid-market rep $80,000 to $100,000. Guess what I've bought? I've bought the right for them to do prospecting. I've bought them to get me back an event list in a week. I've bought them to do cold calls every day. I'm buying that with your base salary. Now, if you don't want to do that stuff, then we need to renegotiate your base salary, because that's what I'm paying for. Then everything that that does and sets up, now that on your own, your commissions take care, and the better rep you are, the more money you make, but I get to dictate some stuff because I'm giving you a base salary. Makes sense. Two follow-up questions. One, you said, hey, this is the third time, so now we're micro-managing. Does that mean they can earn the macro-managing back after they've proven functioning under micro-managing for a season, maybe? I think that there's some things that need to have an org-wide energy or vibe to them, like prospecting in general. There's no opting out of it. You need to do it this way. Everybody does it. We're all going to suffer together. Now, if you have a better way, you can do your better way, but you still need to do some of our way. Everybody's got an org, so everybody's got a row. Just because you have a motorboat doesn't mean you get to jump out of the ship and jump in your motorboat. Right, right, right, right. But some other stuff isn't quite as demanding, and so yeah, you could earn the right back. Okay. And then the second question, you said, I think you said you get freedom for a lot of other things. Is that the word you use? So it's micro-management on one end, and then you get the freedom to choose on the other side. Complete freedom on the other side. Do whatever you want. And so I think the message behind the message is you can't just have a culture of micro-management. You have to have the seesaw. You've got to even Okay. It's a very powerful tool when used correctly, a powerful tool for good. It's a powerful tool for evil when used incorrectly. I see if you talk to the hundreds of reps that have worked with me, that they would say, in general, Mark's culture is fun. It's very safe to talk about risk. You're going to be expected to be hard and held accountable, but you're going to learn a ton, and it's going to be really positive, and you're never going to... I just had somebody the other day was like, Mark, every time I came to you, I never had to worry what Mark I was going to get. I was going to get end of the quarter stressed Mark, beginning of the quarter happy Mark, middle of the quarter worried Mark. Just consistent Mark. I'm the same person every day. And so that allows me, then that gives me room then to be sometimes super free, and then sometimes super micro-managing, because we'd always explain why we're doing what we're doing, because we made a conscious decision on that spectrum of how micro-managing or how free we got it. We have a lot of first-time manager listeners, and I can hear some of them thinking in their heads, micro-management was always taught to me as a bad word. How do I maybe make the jump to be a little bit more in that direction? Do you have any practical advice for them? Yeah, so you definitely can't tell your reps you're going to micro-manage them. That's got too much... That word is laced with too much meaning, right? What I would say is, we have a structured process we need you to follow, right? And so sometimes that structured process might include one or two steps. Sometimes it might include 20 steps. And the more steps, and the more direction, the more micro-managing I would consider it, right? I love that. Okay, let's change gears for our last few minutes. One thing I've heard you post about in the last six months or so is you're a CFO on the weekend and a CRO Monday through Friday. Can you talk to us a little bit about this? So my journey, after I went through a sprint season at a startup, I needed six months off between gigs. And I'm glad I got to take six months off, but I don't think that's the right way to do it. I don't think I should have had to have had to take six months off, if that makes sense. So I really appreciate your idea of being a CFO on the weekend. Can you touch on what that means for everybody? Yeah, so I'm the chief fun officer of my family. I like to be responsible for us having fun and everybody being happy. And I wouldn't say it's like the weekends. I'd say what happens is, I learned early in my career that there's a real fallacy. And it's a word that's talked about a lot, which is work-life balance. And work-life balance creates a quantitative situation where you're always being like, well, I spent nine hours at work, seven hours with family, and eight hours sleeping. That means tomorrow I need to do nine hours of family. You know what I mean? There is no balance. There's times when your job needs you more. There's time when your family needs you more. What you want is work-life harmony. You want that qualitative aspect where you feel like one is helping the other. And when one needs you, you have the freedom to go do it. And if the other one needs you, you have the freedom to go do that. But ultimately, you just want them to work in harmony with each other. At eight years almost at Outreach, I started there. My day started at 7 a.m. I do demos from basically 7 a.m. to 5 or 6 p.m. Then I would go to soccer practice, basketball practice, dinner, put my kids and wife to bed. And then from 10 p.m. to 2 a.m., I just worked on operational stuff. And most people are like, Mark, you're crazy. You're going to burn yourself out. Never burnt myself out because I had harmony. My kids knew what I was doing. They realized the sacrifice I was making. They were supportive of me. They were harmonizing my personal life with my professional life. And then there were times, you know, when my daughter was a senior and playing in AAU basketball and she needed to travel over the country, she needed me there. Like she wanted me there. And you know what? So I took that time and did that. And Outreach had to deal with it just because they take another time, right? And so I believe in this, especially if you're a young manager, don't chase balance. It doesn't exist. Harmony can exist, but you have to be a very good communicator with both sets of people so everybody knows what you're doing and why. And you're not trying to like slink around like I'm taking off on Friday. Yeah, then you feel guilty for it, right? You're like, now I feel like I'm withdrawing from that area of my life when you shouldn't feel that way. That makes total sense. Well, hey, last question for you. What do you want to say to just encourage the leader out there that's trying to do better at leading people, that's trying to do a better job of turning up and having a culture like the one you just described in your team? What do you have to say to them? Well, listen, I think in order to have a great culture of coaching, you have to be the coachable one. And one way to do that is I have a silly little saying that says, a lazy man's better is more. And the worst way that you can show that you are a coachable learning person and want to have an entire sales team and a culture built around that is by constantly reverting back to lazy, boring, bad ideas and just being like, this isn't working, so crank it up to X. Oh, 50 cold calls isn't working, do 75. 75 isn't working, do 100. All that shows is that you don't really understand what's going on. So I would just encourage young managers, more is actually the enemy. Better is your friend. Better is hard. Better takes thought. Better takes more than just your brain. Sometimes it takes people outside your company. But always striving to do things better rather than more is the best way to create this amazing culture inside your company where your sales team actually wants you involved and stuff, seeks out your stuff because they know they're going to get better. Yes, I love that. Love it, Mark. Thanks so much for joining today, man. Appreciate it. If you enjoyed today's episode with Mark, then you've got to follow him on LinkedIn. So check out today's show notes wherever you're listening to this, where we'll post Mark's so you can connect and follow him, where he posts regularly his own hot takes on company growth and leadership. We'll see you next time on the Leader Pulse podcast.