A recorded interview between Kevin "KD" Dorsey and Stephanie Herre about coaching managers to become better leaders. Stephanie emphasizes hiring for diversity (not clones), the need for leadership coaching, and that ego blocks manager development. Kevin focuses on role-fit for management, advising honest self-reflection and offering three pointed questions for aspiring managers: (1) Are you ready to have your paycheck in someone else’s hands? (2) Are you ready for your work ethic to no longer be tied to your results? (3) Are you willing to be accountable for your team’s outcomes (including negative consequences)? The transcript alternates between individual-focused decision guidance and company-level recommendations for developing first-time managers.
Chapters
What I see, especially in our industry, unfortunately, VPs want to hire perhaps people similar to them. I did a post recently about vps or C level need to stop hiring clones of themselves. Because here's where the issue comes with diversity and innovation and creativity bringing in another perspective. So first of all, hire the right people, hire with diversity in mind. Bring in other perspectives. Hire people different to you, smarter than you, that you can learn from. I see two things. I see a lack of leadership coaching. So there's nobody who's actually holding them accountable for these actions that are really destructive. But a second thing, unfortunately is the ego of the said manager. The ego is a huge barrier to any personal or self development in your career.
Right, okay, all right, we're going to unpack that in a little bit here because now as we start to go through it, I am a huge believer in role fit, right? Where there's certain roles that are better for people than for others. And I actually think there's a lot of people in management where management is not actually the right fit for them. Right. Like I believe I am, you know, relatively talented. I'm a very hard worker, I have somewhat okay levels of intelligence. But put me as an engineer, that's just not the right fit for me. Like I could probably do it, but it's not the right fit. So let's start from kind of the beginning here. How do I know if management is the right fit for me? What types of questions should I be asking myself if I'm considering to get into management? What sort of things should I be asking myself to make sure it's the right fit? Because if it's not the right fit, none of this matters.
Oh, couldn't agree more. And yeah, I actually wanted to say this to your audience. Not all of you listening would be a right fit for a leadership role. It's a skill just like any other skill. Just like learning how to do sales, anything at all. It's a skill that must be honed. And some of the things you must start off with, and I talk about this in my course, is honest self reflection. So get to know your personality type, get to know how introverted you are, how extroverted you are, what are your intrinsic motivators in life and what are your values? It must tie back to that. So for myself five years ago, when I jump started my leadership career straight after being an AE at SAP, I sat down, I was like, right, what is it that drives me? What is it that actually makes me tick? It's not just closing Deals I'm doing that, something is missing, something is not being fulfilled. So then I realized I am extremely driven to help others. And for me to share something that I learned and then to see someone else apply that and to see them improve, that is what is my biggest intrinsic motivator. So that's step one, be honest with yourself. A huge misconception I see especially in sales AES who want to be managers, they think that's, that's the ultimate goal and then you'll earn the most, you'll be comfortable. And that's not the case. As a sales leader, you typically earn less than your top performer. So that cannot be a motivator. Yeah, as soon as I hear that, I'm like, okay, that's not really the right fit for leadership.
No, it's so true. I asked three very pointed questions. In fact, I got a message on LinkedIn the other day, you know, should I get into leadership or not? I was like, I want you to go think about these questions and get back to me. Right. First question I always ask is, are you ready to have your paycheck in someone else's hands? First question. And that almost always catches a top performer off guard because they've never thought about it that way. As I are you ready to put your paycheck in someone else's hands? Second question, are you ready for your work ethic to no longer be tied to your results? When you're a sales rep, you can work your way to success more often than not. Like if you're just willing to put in more, you can't do that as a manager. Just because you're working harder doesn't mean your team is going to do better. And then the third is like, are you willing for me to be upset with you because of what your team is doing? Are you willing to fall on that sword? Are you willing to potentially lose your job because of other people? And that almost always catches some people off guard because to your point, a lot of first time managers, they're thinking about just the good side, coaching people and they do it. And success.
It's easy.
It's easy and it's just so fulfilling. Being a sales rep is way easier than being a sales leader. I miss those days.
Yeah, right? It's like, hey, I want to have control back. Yeah. When you're a leader, you give up all control.
Yes. So then what do I do about that, Stephanie? Right? So like, because that is, you nailed it.
Right?
As a rep, you're in control. And I think that is Why a lot of managers then try to control their team is because that's how they used to succeed, is they controlled what they did. So now I got control of my team. Let's talk about how teams should be developing their managers.
Right.
Because again, I want to be careful with. All right, here's all the things that you're doing, but at the end of the day what we're talking about is the companies are not developing their managers. So let's pivot to the company side, let's pivot to the VP side. What should leadership be doing to help their managers get better at these things?
Wow. I wish every organization would think from this perspective. What I see, especially in our industry, unfortunately VPs, VPs want to hire perhaps people similar to them. I did a post recently about vps or C level need to stop hiring clones of themselves. Because here's where the issue comes with diversity and innovation and creativity bringing in another perspective. So first of all, hire the right people, hire with diversity in mind. Bring in other perspectives, hire people different to you, smarter than you, that you can learn from that. Step one. I also think C level execs, they don't spend too much time actually maybe shadowing or just being present whenever there is a new leader and they are doing their thing, but there's just no one else in the room and they just, you know, you're trusted by default. And yeah, okay, the team gave not such a good feedback for that, but that's fine. I really like this guy. So we're going to keep him on and he'll learn and so on. So I think they need to take it a lot more seriously because the cost of attrition is way more detrimental than just keeping on somebody who you just get along with or you don't really have the time to mentor or coach. At the very least just hire a leadership coach for all of your first time managers who is a unbiased person in the room. Yeah.
And it's funny because this is a place where like ego comes back in. Where it's like, well, I don't want someone else training my managers because that's my job. But at the same time you're not doing it. So which, which would you prefer here, you know, to, to go around, around this. Because it's true, right? Like I told this story, many of mines, there were a couple hires that I made at my last role where they were hired specifically because they were different than me. Like that's quite like we had two, we had two amazing candidates. Ali And Jessica and they were both amazing, like phenomenal. In fact, sometimes I look back and go, man, like how rally have worked out, right? But I went with Jessica because she was different. She didn't think like me, she didn't talk like me, she wasn't like the rest of our managers. And that's exactly why I went that direction because like you have to diversify there because I, I don't want a team full of me's. That would be a nightmare, right? I'm a handful. Building a team of me is a really bad look, right? And so I love that idea of like, you know, getting them a leadership coach, like teaching them how to do this. Because I think is one of the biggest misses in SaaS that they've gotten away from. If you look back at, you know, kind of the history of business, right? The companies that did well, IBM, Oracle, when you became a manager, they sent you off like they sent you to management school. You went on site for like three to four weeks and got leadership development and then went back back two times a year, right? Like that's, that's how these companies build, right? Like was, you're going into leadership, you got to go to this academy, we're going to fly you out to it. You're going to stay in dorms for a week. Like that's what's happening then here in sas, like, hey, you hit your quota two years in a row, you're a manager.
