EPISODE 653: Gretchen Gordon’s Advice for Becoming the Happy Sales Manager

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Today’s show featured an interview with Gretchen Gordon, the author of “The Happy Sales Manager” and one of her clients, Mike Dorrington, VP of Sales and Marketing for AMAROK Security.

Find Gretchen on LinkedIn. Find Mike on LinkedIn.

GRETCHEN’S ADVICE:  “Adopt the mindset of adapt or die. Our world is changing and it’s not going to slow down anytime soon. It’s for salespeople, it’s for sales managers, it’s for leaders of managers, it’s for leaders of companies. It’s not a, “I did it and I’ve got it figured out.” You have to have that mindset of adapt or die, which is from the movie, Moneyball, but is also an adaptation of Darwin’s theory. You have to have that mindset that it’s going to be constant change and you’ve got to adapt.”

MIKE’S ADVICE:  “Embrace change technology, being a student of sales is my passion. That is part of what makes a difference between a good sales manager and a great one, or sales leader, is really that love of the game of sales. That really resonates. If you do that, you’ll see a difference in your results.”


Fred Diamond: Gretchen, I’m excited. You have a new book out. It’s called The Happy Sales Manager and we’re going to be talking about that book. We also have one of your clients who’s read the book, Mike Dorrington. He’s the Sales VP at AMAROK, which is one of Selling Power’s Best Places to Work in Sales. Your company’s called Braveheart Sales Performance. Get us caught up, Gretchen, tell us about this new book. Tell us why you wrote it and let’s get deep into some of the ways that Mike is utilizing some of the things that you talk about.

Gretchen Gordon: Thanks, Fred. I wrote the book because I at one time was an unhappy sales manager. I had been a successful salesperson, got promoted into sales management, which is the typical path, let’s say, and found that I didn’t really know what to do. It didn’t come naturally to me. I’d been trained in sales. I started at Procter & Gamble very regimented sales program. Several years later through a couple different jobs had been promoted, and I was miserable. I was stressed out, I was frustrated. I didn’t know what to do, and I didn’t want to ask my boss like, “What should I do?” Because they apparently had given me the confidence to do it.

The book has been in my head for about seven or eight years. I’ve had the table of contents for seven or eight years, went back to it and changed it, decided finally to get it out onto paper and in Kindle version so that we could help as many other frustrated or questioning overwhelmed people who have been thrust into a sales management role and don’t really know what they’re supposed to do. I wrote it in a very basic fashion to make it super easy to consume.

Fred Diamond: One thing we talk a lot about on the Sales Game Changers Podcast is that first time sales manager is probably the hardest job in the company. Of course, we’re doing today’s recording in November of 2023, and it’s three years after the pandemic. A lot of people were promoted to sales manager in early 2020 and never got a lot of the stuff that you would typically get in the office with your leadership to learn. They had to learn on Zoom and it’s really interesting.

Mike, when I told somebody I was interviewing the author of The Happy Sales Manager, they said that’s an oxymoron. I even went to your Amazon page, I think it might have even been on the Amazon page as well. Give us some of your insights, Mike. Again, you’re the Senior Sales Leader at AMAROK. Tell us a little bit about what AMAROK does and give us some of your thoughts on the book and what you got from it. You’ve been working with Gretchen for a number of years. I’m interested in now that you saw her thoughts out of her brain on paper, how you accepted what she had put out there.

Mike Dorrington: Thank you so much for having me. It is a pleasure to be on with industry experts and someone who is a true mentor of mine and Gretchen. I couldn’t be more excited to talk about her, her book, and anything sales related. It’s my favorite thing to talk about. I have a very similar story to Gretchen’s, maybe a little bit different. I was a top performer at a company called Cintas years ago. My manager, who I wasn’t really happy with, but he was the person who hired me, he left the company. I remember having a conversation with my dad, who was the CEO of another organization, and I said, “I’m thinking about leaving Cintas. They fired my boss. He left there.” My dad looked at me, he goes, “Wait, you’re going to leave because your manager’s gone?” I go, “Yeah, I mean, he hired me. There’s nobody in that role.” He goes, “Do it yourself.” He gave me a book at the time called Be Your Own Sales Manager and it gave me good foundational principles of a better mindset as an individual contributor of how to lead myself through metrics.

But I will tell you, the reason I was excited about Gretchen’s book when she was telling me about it, was I really don’t think there is another book like it that talks about the basic foundational principles of what it takes to be a happy sales manager, but also a very effective sales manager. I was telling her in a conversation recently where someone had said to me before, as I was into sales management, like, “Hey, listen, you know the basic principles of sales management,” and I fumbled through a bunch of stuff. He’s like, “Hey, no, you run effective one-on-ones, you run inspirational sales meetings.” As I was reading Gretchen’s book, I’m like, “Oh man, she nailed it.” I would love to have given this book to the 12 people I promoted out of the pandemic and who did not get probably the leadership that they needed in training. I think it’s a great foundational book. I appreciate being here. I appreciate Gretchen as a mentor and friend. Also, I think she’s created something that is very useful in sales management, because it is a miserable time taking over that role.

Fred Diamond: I want to ask you a specific question. I haven’t asked this before. Again, you mentioned the word mentor. You’ve been a client of Gretchen’s. Give some advice, Mike, if you could, on how you utilize Gretchen as a mentor, how you utilize her as a resource. I’m presuming you pay for her company services to provide some consulting and guidance and training. We have tons of sales leaders who listen to the Sales Game Changers Podcast, give some of your advice on how to best utilize the expertise of someone like Gretchen. Then Gretchen, I’m going to ask you the reverse question, which is, how do you like to specifically work with leaders like Mike to ensure that they optimize their performance?

Mike Dorrington: I will say this, probably the best mentors are the ones who enjoy the mutual communication between both parties, and they’re not always looking to get something out of it. Listen, at the end of the day, I’m a salesperson, Gretchen’s a salesperson, so obviously, hey, listen, we want to sell stuff. I will tell you that mentorship starts from a pure love of the sales game, for both of us. Well, I was lucky enough at the time that I met Gretchen that I didn’t know anything about the industry I was going into, which was the security industry. Instead of trying to sell me on all services of consulting and security industry, she really just listened to me as a seller and what I needed to do to find the right people for me. That’s really where we started our relationship. As we continued to grow and develop, she listened to ways that she could help me. I know that comes with the sales part of it, but it was also, it went beyond that. I would refer her to people that I knew because it was a pure ability to help versus sell.

Fred Diamond: Gretchen, same question. Give some advice to the Mike Dorringtons of the world, the sales VPs that your company services, that you’ve tutored, mentored, consultant to, trained over the years about how they can best accept your expertise and guidance.

Gretchen Gordon: If I think back to the relationship like we have with Mike and his company and other clients that we enjoy working with and see the biggest impact, is that the leader does have to be totally engaged in wanting to grow, change, adapt, and not just be like, “Here, go fix my people, or just fix this one thing,” but be totally immersed. We always start with a deep dive analysis from a very data-based perspective, science-based, not just like, “Okay, this person’s selling, that person’s not selling very well. I don’t think that person’s going to make it. I think I’m just going to get rid of them.” We don’t rely on gut instinct.

I would recommend that leaders of the organization not just rely on their instincts and their gut, but you can get the best out of an outside third-party perspective by also not relying just on the third party’s gut instinct, but using science and data. Mike does that really, really well in all aspects of his leadership of the sales team, so that you can make changes. I’m not saying changes as in we’re going to get rid of people necessarily, I’m saying so that you know how to optimize the effectiveness of all the people on the team.

Fred Diamond: Mike, Gretchen mentioned the science and the data. Talk about some of the critical metrics that you spend a lot of time thinking about as you ascertain the performance of your team. Obviously, reaching quota, but get a little more specific into what you look at, what’s most important to you. Then Gretchen, I’m interested in your thoughts on what Mike says.

Mike Dorrington: From a pure sales standpoint, the thing that we try to get away from is just a pure measurement of activity. I’m a believer that an active person is a successful person. But if you just stick with that, I do think you’re really selling yourself and your organization short. We really look at, yes, the hustle statistics to understand the buy-in, but also then we start to look at the skill-based stuff, really looking at what it takes to convert something properly to an opportunity. Then can you apply a sales process with effectiveness to bring those things to close. Win rate is always really important. Conversion rates are really important. But we use a business case on every single prospect that we use, and we use those to make sure that the person can justify mathematically that there’s a proper return on investment, or that what we’re selling is actually valuable.

That is something that Gretchen’s team helps me with, because you’ll find a lot of salespeople who are not comfortable even talking about money in their own lives. That’s one of the key metrics we look at in the beginning of when we’re hiring people to make sure they have that comfort level and we do tests for it, but we also test them in interviews to make sure that what we’re getting is they will translate into success when they’re here. That’s one of the biggest ones.

Fred Diamond: I agree with that. Gretchen, what do you think?

Gretchen Gordon: One of the things that’s made Mike so successful, and therefore the culture of his company so successful, is that he focuses on the accountability factors. The quantifying of factors, following a process, that type of thing. But also, the quality factors. Coaching, it’s not just about activity. It’s also about how well do they do the job, how well are they doing it when they’re having those conversations? I would say that that’s maybe one of the things that really sets Mike and his organization apart, is that focusing on accountability and coaching. Focusing on what the person has to do to be successful because they have the data associated. They know you can’t make one phone call or you can’t do one thing a week and have success, but also how well are you doing it? Then stepping in and coaching and helping individuals know what good looks like, et cetera.

Fred Diamond: We talked at the beginning of the show about how many people were promoted into sales leadership at the beginning of the pandemic, and some of the challenges that that led to. Most sales managers of course come from the sales ranks. Gretchen, give us your thoughts, and then Mike, I want some of your real-world experience too, how can you tell if someone will be a good sales manager? Conversely, how long do you give them? That comes up all the time. We promote somebody obviously because they’re a high performer, and then either they succeed or they don’t, for reasons. But give us some insights, Gretchen, into how you could tell if a person will be a good sales manager or not.

Gretchen Gordon: Because they were a good, strong salesperson doesn’t necessarily make them well qualified to be a sales manager. Now, being highly motivated, and I know Michael talked about this, is helpful, but probably the biggest distinguishing factor is that they have to be team focused instead of me focused. It’s not too different than selling. It’s like, “Okay, what do I need to do to help the whole organization, the whole team thrive?” That means understanding the individuals on the team, not just being focused on me, me, me. That’s probably the biggest distinguishing factor. It doesn’t mean that people can’t grow that. That’s really a mindset thing, less so than a skillset.

Fred Diamond: Mike, what are your thoughts on that? How long will you give someone? Obviously, it’s a big decision on who you’re going to promote to leadership and you hope that that person’s going to have a nice, long, successful career. Give us some of your insights into that and how long do you give someone to reach the level that you expect them to?

Mike Dorrington: I wish I could tell you like, it’s six months, or something like that. I would say the time specific part of it is probably a little more feel, and here’s what I mean by that. If you’re looking at someone who can do the fundamentals of the job, they can actually perform and show up and run a sales meeting, they can do a coaching field ride, but their team just isn’t taking to their coaching and developing, I’ll give those people a little bit longer than their peers who have a harder time even doing that stuff.

What I find is the top performers that come in and are mostly successful based on feel, gut instinct and things like that, like, “Oh man, if this person can’t perform like me, they’re out of here.” Those people, I will pull the trigger on faster because they are going to disrupt a larger part of the organization than the people who can do the fundamentals and they’re just not able to get there. Which sounds like the opposite, because you think that those people who can come in and by feel you can make quick changes and then people’s success jumps through the roof. To me, I think getting the fundamentals of sales management is actually harder than being, you’ll understand the feel instincts of either selling or of sales leadership. I really look for the people who understand a balance of that science and the art, and if they can do that, I can work with them and help them be a better leader, a better coach, things like that.

There’s one other thing I wanted to say about this topic overall. If a seller was a highly active person, and that is how they define success, I have a harder time feeling that they’re going to be successful at the next level than someone who had a good mixture of both art and science and understanding how they became successful. Because the sales leader that goes to the person who says, “Hey, just do five more calls, you’ll be successful.” I got to think that the failure rate is probably 80% or higher.

Fred Diamond: I’m going to ask you a question in a second, Mike, about how you’re using the book and how you think that sales managers can use the book. Gretchen, I’ve got to ask you a question. I do this differently. Usually, I would ask this question of Mike, but I’m going to ask it of you. How would you describe Mike as a sales leader? This isn’t to build his ego or anything, which would be nice, of course, but no. I usually ask the question, “Mike, describe yourself as a sales leader.” But I’m going to flip it, since you have such a nice relationship. Gretchen, how would you describe Mike as a sales leader? And tell us some of his strengths. Again, you work with the hundreds of sales leaders, obviously, as do I, and I’m curious about how you view him.

Gretchen Gordon: Mike is high energy, so he is charismatic, so that’s just a personality, that’s just him. He attracts activity. He’s always active, but that’s not necessarily what makes him a great sales leader. What makes him a great sales leader is he is diligent about the analytics. He’s diligent about the accountability of what does somebody need to do, but he is got this massive human side that he wants his team to be successful, and it comes across. He’s not just a, I’m a high energy, just do what I do and crack the whip and all that kind of stuff. He is living in the trenches, so to speak, with his managers. He’s got several managers underneath him, and he knows what they need to do to be successful, and he is not just telling people, “Go do this.” It oozes from him that he wants everybody on the team to be successful. I would say that that is not necessarily always a trait that we see. Sure, sales leaders want the business to be successful, they want to grow more sales, but he’s very much interested in what motivates all the individuals on the team and helping them achieve their goals.

Fred Diamond: Mike what are your thoughts on what she just said and how have you taken some of the things that Gretchen just said to create, let’s just say, a great culture at AMAROK for salespeople?

Mike Dorrington: First of all, thank you, Gretchen. That’s very nice of you to say. I appreciate that and thank you for setting that question up. That’s so awesome. Here’s what I think. I have a four-word mantra that I use to define my leadership, which is inspire, coach, care, win. To me, my purpose for being is to create the most successful leaders that I can create. I always remember a story early in my career. One of my favorite stories was there was a senior vice president in a company I worked with and they were retiring. To celebrate their retirement, they brought up every single person on stage who they had either managed or that person had managed, and their whole coaching tree. I just thought it was the coolest thing I’d ever seen. To me, that was it. In life, when I get to retire sometime never, hopefully they’ll put up the people I worked with at every organization who I hopefully have tried to inspire them, coach them, care about their success, and help them win. That’s, to me, the ultimate success. I appreciate that. I work hard at it, so I appreciate that.

Fred Diamond: One thing that the Institute for Excellence in Sales does is we have an award event every spring, and we’re going to have our 14th annual award event on May 17th in Northern Virginia. We give out an award, it’s called the Jay Nussbaum Rising Sales Star Award. Essentially, the main criteria is someone under the age of 40 who we expect will have an amazing year. Jay used to run the public sector divisions of Oracle, and Xerox, and Accenture. A lot of times we’ll refer to him as having that Bill Parcells type of down chain, if you will, where the guys and ladies who’ve led teams that so many technology companies around the DC beltway all have reported up to Jay at one point.

I’m curious, Mike, before I ask you one more question about the book, what does your management expect of you, the people you report to? What do you wake up every morning thinking about? What do I have to do, or what does my team have to do to achieve what the people I report to want me to achieve?

Mike Dorrington: The first thing is we are in a unique business in that, well, security has a lot of competition, but for what we do, there isn’t a lot. We are really running to set records. That is really what I’m tasked with every day, is that every hour, every day, every month, every year, I’m trying to set a new record and build. We want to be the ultimate perimeter security company in North America. I don’t mean to just pull our vision onto that, but they expect me to be doing the little things and the high-level things to make that happen for not only the organization, but for everybody inside of sales, outside of sales. To me, it all starts with sales. I set the tone for the entire organization to make sure that everybody has a successful call, hour, minute, day, everything. That’s what they expect.

Fred Diamond: I like that concept of setting records. Before I ask you both for your final action steps, your final thoughts, Gretchen, what else do you want us to know about the book? I love what Mike was saying about it. How do you want people to use it? What are you hoping to achieve from it? What can our listeners understand? I know it’s up on Amazon. Is that the easiest way to get it also? Or how do you recommend people find it?

Gretchen Gordon: It’s the easiest way to get it. Or they can go to thehappysalesmanager.com and you can order it then on Amazon, and there’s other resources available on that website. How I want people to use it is to recognize that sales management, sales leadership, to be successful, drive sales, and also still have a life and enjoy what you’re doing, you might have to adapt and learn some new skills, but you also have to have the right mindset. The book is really a short read. It’s designed for people who have limited attention spans, and there’s a workbook that goes along with it too. The book will give you the place to download that so you can actually apply some of the principles immediately. That would be my recommendation. It’s designed mostly for someone who is either new to sales management or has been struggling. It might even be a founder of a small company who is trying to build a sales team and doesn’t know exactly what to do. It’s pretty foundational and designed to be a roadmap to make it easier to do your job.

Fred Diamond: Well, congratulations again on publishing the book. I published two books last year, and publishing a book, for people who listen, I tell them all the time, it’ll change your life, so definitely do that. Congratulations again. Have you written a book before this? I forget.

Gretchen Gordon: No, this is my first book. I’ve done some eBooks and things like that, but this is my first book. You’re right, it does change your life, and it also helps you really cement the way you see the world. The goal is, it’s not completely altruistic, but it is to get the message out to a wider audience, beyond maybe the client companies that we work with, which are B2B middle market companies.

Fred Diamond: Having published a book and knowing that someone read your book, I like to say, if one person reads my book, then one person reads my book. Hopefully we’re looking for thousands and hopefully companies are going to buy a couple dozen, a couple hundred. The funnest thing about writing the book is signing the book. Mike, I don’t know if you had Gretchen down to your location, if you guys meet anywhere, but do that. Have her come down, sign the books, talk about it. It’s always a lot of fun. I want to acknowledge you again, Mike, I want to thank you for all the great insights. Again, the sales leader at AMAROK, one of Selling Power’s top places to work for salespeople. Thank you both for the great content. This hour really flew by.

I want to ask you for your final action step, something specific. You both have given us a lot of great ideas for sales managers to be happier, to have success, give us something specific people should do right now after listening to today’s show or reading the transcript. Mike, why don’t you go first, something specific they should do right now?

Mike Dorrington: I’m going to do two things. I’m sorry, I’m a rule breaker in that way. The first one is, life’s too short to be unhappy, so be a happy sales manager. I’ll say that. Not just to plug the book, but I would say, hey, the reason I like this is it is a good foundational principle and something that my team uses and will continue to use as we put more people into sales. Overall, I do think embracing change technology, being a student of sales, maybe one of the more important unsung things about being a sales leader, it is my passion, it’s my favorite thing to do. I think that that is part of what makes a difference between a good sales manager and a great one, or sales leader, is really that love of the game of sales. That really resonates. If you do that, you’ll see a difference in your results.

Fred Diamond: Gretchen, why don’t you bring us home, give us a final action step people should do right now to take their sales career to the next level.

Gretchen Gordon: They need to adopt the mindset, and I’m going to dovetail off of what Mike said, they need to adopt the mindset of adapt or die. Our world is changing and it’s not going to slow down anytime soon. It’s for salespeople, it’s for sales managers, it’s for leaders of managers, it’s for leaders of companies. It’s not a, “I did it and I’ve got it figured out.” You have to have that mindset of adapt or die, which is from the movie, Moneyball, but is also an adaptation of Darwin’s theory. You have to have that mindset that it’s going to be constant change and you’ve got to adapt.

Fred Diamond: We’ve all gone through so much over the last three years. Again, the show is being published in 2024. It’s a fresh new year for everybody. There’s a lot of optimism. We work with a lot of companies, well-known companies around the globe. Everyone’s doing their best to stay optimistic and adapt. Once again, I want to thank Gretchen Gordon. I want to thank Mike Dorrington. My name is Fred Diamond. This is the Sales Game Changers Podcast.

Transcribed by Mariana Badillo

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