The Secrets of Manager Development with PatientPop VP of Inside Sales Kevin Dorsey

All right, we are now live on our livestream, and Kevin, I am going to start counting you down so that we head off the hour and we start allowing attendees in. And 5, 4, 3, 2, 1.

Alright, hello, what's up everybody? I see everybody jumping in, so I'm gonna give people a couple seconds here, a couple minutes to dive in because they gave me a hard 20-minute cap, which is a rarity for me to go for, and I want to make sure everyone can hear everything I'm saying. So we'll give everyone a minute or so here to get in. As my old coach used to say in high school, if you're early, you're on time. If you're on time, you're late. And if you're late, don't even show up because you're running laps. So I'm not allowed to make y'all run laps, so I'm not, I'm not given that sort of power. But we'll give it a minute here and then we'll kick this off. And so for those of you that have not sat through one of my presentations before, I want to give a couple, I guess, heads up, or I don't know if I can give ground rules or not, but I'm going to move fast. I want to cover as much as I possibly can and give really tactical, tangible advice, like things you can actually go do. There are screenshots in here. Pictures of my exact playbooks or structures that I use for my managers and for my reps. But if you have questions, throw them into the Q&A. Tammy is on here, she's gonna throw questions at me as you go. This isn't one of those save your questions for the end type thing. If it hits you, if it's top of mind, throw it into the chat or into the Q&A so that Tammy can send it to me and I'll try to answer it as I go. So I'm keeping an eye on any messages coming from Tammy, but I wanna make sure everyone gets their questions answered so that all of this makes sense. So with that, it is 12:31 my time. I'm gonna dive into this so that I can cover everything I possibly can, as long as that's okay. Tammy, can you chat me real quick, make sure that I'm good to go now, or should I wait like an extra minute or so? Tammy says I'm good. All right, y'all, let's rock. So my name is Kevin Dorsey. I'm the VP of Inside Sales at PatientPop. We are a medical software company in Santa Monica. I head up the inside sales squad there. So I have a team of about 35 inside closers, another team of 35 SDRs. There's a channel org as well, a field org. And all in right now, I have about 7 managers and 2 directors. And so talking about manager development is really near and dear to my heart because I think it's something that isn't really talked about enough, right? If you look at most companies and most orgs, manager development and coaching is almost nonexistent. But your frontline managers are your biggest asset or also can be your biggest detriment if you're not treating it the right way, right? Because the number one job of a manager is to improve their reps. If you were to spot check any of my managers and ask them what their job is, they should be able to respond back and tell you it's to make my reps better. It's not to hit a number. It's not to achieve quota. It's to make my reps better, to improve my reps. But then who's improving the managers? Who's making the managers better so they can actually make their reps better? Not enough people actually do this intentionally and do it the right way because this is something I want you to think about, especially if you're scaling, if you're trying to grow. You can only be as good as your worst manager. That might sound harsh. That might be sounding like a really hard call-out, but it's the truth. If you are trying to grow, you can only be as good as your worst manager, not your worst rep, your worst manager. And if you're not making your managers better, you're always gonna be in this sticking point of not being able to grow as fast or as big as you want to. So I believe that manager development is really the missing sauce for a lot of companies. And it's a shame. It really is a shame because of this right here. One rep versus one manager, who has a bigger impact, right? If you have a great manager, that great manager impacts the 10 people that are under them, but also impacts the entire org because it's an example to look at. They have great reps that spreads around what they're teaching can go to everybody else. But all of our coaching and development, it seems like, is focused on the reps. And let's be honest, that's a different session. Most companies don't invest enough in their rep development either. But if they're not investing in the reps, they're sure as hell not investing in the managers. And that's a problem, all right? Because if your managers are not strong, you can't scale. You can't, right? You also— you're gonna lose people. I think people underestimate how important a manager is, but also the impact that they can have. Right. A manager has the livelihoods of their team in their hands because if they are a bad manager, they actually impact the ability of their people to make the money that they want to make, to have the careers that they're looking to have. Right. That's not okay. Your results will be inconsistent if you don't have manager development. It's on you as the leader to develop them. I want to make this very, very clear. It's on you. You can't outsource manager development once a year. You can't just sign them up for a course and say, okay, I done did it. I developed my managers. I bought them this course one time and they went through it, or we had an expert come on site for 2 days to work with our managers. That's not how development works. You can't outsource this. You need to take this on as the leader to say, I am here to make my managers better. You need to create a budget and a plan. Now, if I just ended right here and all of you walked away and actually created a budget and a plan to develop your managers, you'd already be in a better spot. Most leaders that I talk to in most companies, they never plan how they're going to develop their managers, and that's why it never happens. And by the way, most of what I'm going to cover requires no budget. It just requires Mind spend, not time spend, not money spend. It's actually thinking about doing these things. So what should manager development look like? Okay, well, let's ask this question. How do you expect your managers to develop their reps? What do you expect your managers to do to make your reps better? Well, you have to do the exact same thing for them. And I'm not sure why people get this so confused or twisted, especially for first-time managers. They were a salesperson, not a manager. They figured out how to be a great salesperson, not a manager. They have experience as a salesperson, not a manager. But then we promote people to management and we wonder why they struggle, right? You have to do the same things you'd expect your managers to do for your reps. And by the way, this never ends. Just because you hire someone who has management experience doesn't mean that they actually know how to be a great manager because again, very few people are ever actually taught this stuff, right? So almost to the letter, you wanna follow it. If you expect your managers to shadow their reps, you should shadow your managers. If they're supposed to do role plays with their reps, you need to role play with your managers. Scorecard for the reps, you need scorecards for the managers. Goals, developments, reviewing, All of that you need to be doing for your managers. It needs to be consistent, scheduled, and intentional. There's a huge divide in the industry around the coaching people think they're doing versus the coaching that people think they're getting. I can't remember who did the study. I think it was CEB Insights did a study. They asked how many managers spend time coaching their reps. And of course, like 73% of managers say, yeah, I coach my reps on a regular basis. And then they ask the reps, how many of you are getting consistent and impactful coaching from your manager? And it's like 37% say they actually are. So there's this huge guy, this huge, you know, gap between the two. What do you think it is if we asked managers how much coaching they are getting? As leaders, we tend to think feedback is coaching or giving them direction is coaching. That's not what coaching is. We're going to define it a little bit later. Now, before we get into development, one thing I did want to touch on very quickly is making sure you have the right managers in place, because if you don't have the right managers in place, it's going to be very hard to develop them into who they need to be. So real quick on who should be a manager, because as a heads up, it's not always your top rep. And in fact, oftentimes it shouldn't be. To be the top rep, almost inherently, you have to be selfish. You have to take care of yourself to be that number one rep. Being selfish is not a good characteristic of a great leader. So it's not always going to be your top rep, and oftentimes it shouldn't be unless they're displaying the characteristics that you're looking for. So these are questions that I ask any of my reps or any of the people that reach out to me for mentorship when they say they want to get into management. I ask them these questions. First question, I said, are you ready to give up control of your paycheck? Are you ready to put your paycheck in someone else's hands? Are you ready to potentially make less money working harder? Are you ready to have me be mad at you because of what your team is doing? Are you ready for that? Are you ready to fall on the sword for your team? Are you ready to never place blame? Because once you're a manager, you can't blame your team. Now, the team loves to blame their manager. But once you're a manager, you can't blame the team because that's your team to develop and grow. Are you ready to put your ego to the side? And lastly, are you ready for your work ethic to no longer be directly tied to your results? So many of us got into sales because work ethic was applied to results. The harder I work, the better my results will be. It doesn't work that way in management. You can't work your team to being better. That's not how it works. Oftentimes those questions catch people off guard, and then I have to walk them through— there's a difference between being a leader and a manager. You can be a leader and not be a manager, but to be a manager, you also have to be a leader because the manager is responsible for their team. Leaders are just developing. So what you want to look for here is, one, are they already doing it? Who on your team right now is already displaying the characteristics of management? Who on your team is already helping people even though they don't have to? Who on your team is volunteering for projects, right? Who is already respected on your team? When you promote someone on your team to management, it should almost always be pretty boring. Like, people should be like, yep, saw that coming, makes sense, they're already doing it. It should never be a surprise to your team because they're already respected and already doing what you'd expect a manager to do. So then we're gonna move into role plays. So I actually was just on vacation a couple of weeks ago, and this was part of the message I left with my managers. I said, WWKDA, what would KD ask? This is what I want my managers thinking about, not what would KD do? What would I ask if you were to bring me a problem or an issue or an idea? What are the questions I would ask you going through this? And I made them go through this exercise. Right, of like, okay, what are those questions, right? Because this exercise gets them to start to think. This is how you start to make your managers better. Oftentimes managers can rely on their director or rely on their VP to solve problems or to make sure they're doing the right things. But guiding them through and asking them the questions that you would ask is where you want to do it. And when I came back from vacation, I had them send me an example of where they went through this process. What were the questions they asked themselves along the way to make a decision? You want to role-play this with your managers. Give them a situation. Say, okay, you have a rep, they've missed quota for 2 months. Here are their metrics. Where would you focus? And you have them walk through where they would focus and why. What questions are they asking themselves to make sure that they are behaving and thinking the way that you want them to. When they bring situations to you, roleplay them out. Don't just solve them for your reps, or sorry, for your managers. They say, hey, I'm really struggling with Bob. Okay, walk me through what's happening, but then walk me through your decisions. Walk me through how you're thinking it. Okay, what if Bob says this? What are you gonna say? What if Bob says that? What are you gonna say? What are you gonna do next? What's your follow-up email going to look like? What are you going to do if Bob doesn't follow through with what Bob is supposed to follow through on? You actually role-play situations with your managers. Then you get agreement and you move on and you follow up. And this was a mistake I made very early on when I was starting to manage managers was I didn't follow up. We do some of these exercises, we do these conversations, but then I wasn't following up to make sure it got executed on. You have to follow up with them the same way you'd expect them to follow up with their reps, but you want to roleplay. What are the situations? What are the things that you've learned as a leader? Because if you're managing managers, my assumption is you've worked your way up through that. You have more experience. You've seen things they haven't seen before. Roleplay those situations as you go through it. The next big area that I see a lot of companies go wrong with is their managers aren't spending their time in the right areas. So I actually work with my managers on where their time should go. So I love the 80/20 rule. It applies to a lot of places in life, but I really love it in management. And one of the things with the 80/20 rule is 80% of your results come from 20% of your activities. 80% of your results come from 20% of your activities. And so if the end goal of being a manager is improving your reps' performance, what are the 20% activities that they should be focusing their time on. And then again, you as the leader are making sure that they are, and you're also removing obstacles from them if they're not, right? We just had this example come up this week. Like I asked, you know, the manager team, like, hey, could someone look into this for me? And someone responds back, yes, like I'll have it to you today. And I'm the one that says, wait, hold up, no, no, no, timeout. This isn't an urgent thing. This could be end of the week. I don't want to disrupt you from the things you should be doing today. Right. And we know what those things are. Most managers are not spending their time in the right ways. And I want you to think about it. What are the 4 biggest activities that lead to rep improvement that a manager can do? What are the 4 biggest activities a manager can do to improve their reps' results? You've got one-on-ones, you've got call reviews, because if you're not reviewing your reps' calls and the managers aren't, there's a massive gap in your entire process. Practicing and coaching, and then company-dependent number 4. Maybe you're growing a lot, so you have to do a lot of hiring. Maybe you're rolling out new systems, so they got to write out all the cadences, right? That number 4 is dependent on you and your company, but one-on-ones, call reviews, and practicing coaching sessions is where they should be spending most of your time. Now, we might have people watching right now going, well, wait, wait, wait, KD, we Where's the closing? Where's the closing of the deals? I don't believe that is the primary job of a manager. I believe the manager's job is to make their reps capable of closing those deals. Yes, a manager should step in on a call. Yes, they should help with deals. That's where those one-on-ones come in. But I don't want my managers carrying a bag because now you have conflicting goals. One needs to be selfish, one needs to be selfless. That doesn't work. Are your managers spending their time in the right places to make their reps better? So the next part is you need to document everything. So this is actually a page right out of my Manager's Playbook of documenting what does good management look like. Have you ever actually defined it? Have you ever actually written down like, here's what good management at your company looks like. Here's what good management looks like working for me versus other places that you've worked, you need to document it. Cheat sheets, checklists, things to remind them. They have 100 things that they have to work through, right? How do they know if they're doing a good job? And not just from results, because also too, you can have a so-so manager that has a good team, and so they hit their results and you're like, good job, manager. But if they're not doing the things that they're supposed to do, they're not a good manager, right? So manager tribal training— how have your managers help train each other, teaching each other what they are learning, what to look for and where? I'm gonna give you a guide here in a few more slides about issue diagnosis, but like, what should they look for? Where should they spend their time? How do they solve these problems? Every training you do— and if you're not doing regular management training, that's part of the problem— record it. I'm going to show you towards the end of here, I've got over like 9 recorded modules on manager training. Those live forever so they can come back and watch them again, record it and share it. But this is another aspect. If you have managers reporting to you, do you ever give one manager some good advice? I mean, I hope so. Take that advice and share it with the rest of the team, or even better, Even better, have that manager share it with the rest of the team. Hey, I had my one-on-one with KD. I was struggling with this. This is the thought process we went through. This is what we decided to do. And here was the impact of it. Have them lead that training. But this is something that just— we miss it. We give one manager some great advice or great feedback or solve a problem, but then we never share that with all the other managers. Well, now that training just disappeared. Share the feedback and the advice, all of it, right? So, um, Trek asked a question, can you share examples documentation? I got more examples coming up for you, man. So things like one-on-ones need to be documented. There needs to be a framework for your rep one-on-ones, right? If you've got 3 different managers running one-on-ones differently, you're gonna get in trouble. So the one-on-ones are documented. Here is how the rep one-on-one should look. It starts with the metrics. Now, this is something I think I do differently than other leaders, is the reps report their metrics to the manager, not the manager reporting the metrics to the rep. The manager should already know the metrics. The reps need to know the metrics. So the reps report their metrics to the manager. They're filling this out on a weekly basis of the most important metrics they need to be paying attention to. The reps are filling out how they're pacing to goal. The reps are filling out all these different things here. Brag time, what's going well, where are you struggling with, call feedback, right? This is structured so the managers know how to run a great one-on-one. We actually now use a tool called Potari.io, phenomenal tool, right? Got this out of Google Docs and into a tool where I can actually track it, but it needs to be structured so they know how to run a great one-on-one. So this is an example of documenting it. But then so does the manager one-on-one. The manager one-on-one needs to be documented either to your director or to the VP. So this is also the beauty. Now I have directors in place, so I don't have managers reporting to me directly, but I can still go in and see what's happening in these one-on-ones. Now with the manager one-on-ones, it's different. The managers are responsible for explaining the why and how they're doing things, not the what. I know what the metrics are. I know what the results are. I have a dashboard. I don't care about the what. I care about the why. Why is it? Why is it that way, right? Metric identification. Are they calling out the right metrics? Are they paying attention to the big metrics? They report to me the coaching plans for their reps and their team plans. How are they this month making their reps better? And the reps are individual. This is how I'm making Kimmy better. This is how I'm making Marcy better. This is how I'm making Robert better. What's their number one metric and what's the coaching plan to improve it? And it's all documented. Next part, defining good. Do you know what a good call looks like? This is another one, a call scorecard, right? Again, if you've got 5 managers giving call feedback all differently, That's not okay. It allows you, the managers and the reps, to have a quantitative measurement of what is good. So having this in place helps develop your managers to make sure they're listening for things in the calls that you would listen for. So if you took one second, you took one afternoon and sat down and said, what are the 10 things that I know have the biggest impact on our demos? That if a rep does, not if the prospect does, if the rep does, you have a better chance of success. You document this so that your managers can now be giving the right feedback, the same feedback you would. All of you, what do we have on here? We have almost 200 people on here right now. You guys could probably come and score my reps' demos and calls because it's defined. You could know nothing about my industry, but you could come in and tell me whether or not it was a good call or not. That's how you document things. The team should help build it. And then you practice it and you chunk it, right? So, oh, the tool that I mentioned for my one-on-ones, it's called pittari.io, P-I-T-T-A-R-I-O, right? So that's what you want. It just, it helps structure it so that all this isn't just living in Google Docs, right? So this is a big one: issue diagnosis. Do your managers know what to look for if this than this. So if you can see right here on the side here, this is an example of an issue diagnosis. So if someone is struggling with revenue, first you need to look at total sales, right? Is it their conversion rate or their pipeline volume? If it's conversion rate, look at their pitch, their follow-up, and their qualifying. If it's their pitch, look at the needs analysis, recommended, and looping. It walks them through, right? It walks them through what to look for when problems occur. This is what allows them to do it without having to lean on you. It's giving them a cheat sheet. What would you look for? What would you look for? Right? And that way they can go through this process. So when they give you a problem, you can check and say, did you go through this? Okay, Jenny's struggling with revenue. Did you check her conversion rate, her pipeline volume? Well, no, not— go do it and come back, right? This is the issue diagnosis that you want to have here, right? Is saying, okay, am I helping my managers do the things that they need to do? What questions do they ask themselves first? I love to ask this: what questions did you ask yourself before coming to me? What things did you try? What things did you think about before you came to me? So the coaching framework, I just want to take you through real quick because it applies to reps and managers. You observe, describe, prescribe, absorb, and apply. This is where a lot of people don't help their managers. They never observe them. When's the last time you sat in a manager one-on-one with a rep? When's the last time you reviewed the notes from those one-on-ones to know if they're doing it the right way? When's the last time you reviewed the feedback your managers are giving your reps on their calls? The coaching framework applies. You need to observe your managers. Then you describe what they did, not what they didn't do. That's not great coaching. You said, you You said this, not you forgot to do this. You left out versus you didn't do this, right? Implication, here's the result of what you did. Here's what you should do, or what do you think you can do? The difference between directive and indirect. Absorb, do they understand it? Have them tell you back and ask them, how are you going to apply it? And you follow up, right? This is how they should be coaching the reps. This is how you need to be coaching your managers. Observe, describe, describe the implication of what you saw, prescribe, absorb, and apply. Okay. So behavior-based leadership. This is something my managers, they get so tired of this, I promise you. I rarely talk about results with my team. I almost always talk about behaviors because you cannot change results. You can only change behaviors and skills. I'll say that again. You can't change results. If it were that easy, you could just go get more revenue. But to get more revenue, you have to have a skill or process improve. A behavior has to change in order for the result to change. So I talk to my teams and my managers about behaviors. What are they doing? How are they doing it to get to the results? That's how you need to talk to your managers. What behaviors are leading to these results? So this was actually a calculator I built that mapped out the different behaviors that the rep should be doing to get to their goal. It's behavioral. That's the key. Well, shoot, if I can improve this skill or this behavior, that's how I can actually achieve the goals that I'm looking for. But behaviors are what matters. So if all you're ever talking to your managers about is results, you're gonna miss out because they need the high-volume coaching. It's ongoing, but coaching to behaviors, not results. It doesn't work that way, okay? So I just love this real quick, pre-demo or follow-up, this is when I love to do high-volume coaching. You got a big follow-up call, okay, what are you gonna say if they do this? What are you gonna say if they do this? Okay, I'm the prospect, okay, I said this, now what? You do the same thing with your managers. Okay, you got a big one-on-one or a challenging conversation coming up? Okay, what are you gonna do if they say this? What are you gonna do if they say that? What if I, what if I storm out of the room? What will you do? Right, you help them prepare before they step into the situation. So last few things here, ongoing development, record everything, record every training. This is from one of my manager development folders, right? Tribal training, how to be a coach, how to actually coach, how to spend your time, how to prescribe, how to issue diagnose, your first 30, 60, 90 days, the call scorecard and pipeline reviews. Teach it once and record it. And if you've never taught your managers how to do these things, how are they supposed to learn? So if you look at the foundational trainings, you need to teach them how to run a good one-on-one, how to work with morale, what metrics to look for and how to change them, time management, call storing, and how to give feedback and how to be a coach. You need to teach them this, but when you do, record it so they can come back to it. I have had my managers watch these probably 5 or 6 times. So quick recap, I know I covered a lot, y'all. I really wanted to give you as much as I can, but managers are your biggest leverage but also potentially biggest weakness point. You need to make sure you have the right people in the seats. Coach your coaches. That is on you. It's not something you can outsource. Help them prioritize their time, organize the trainings, and invest in your managers. One manager can positively impact 10 people or more. That's how you need to start thinking about it. So it wouldn't be me if I didn't give some management books. These are must-reads for all of my managers. We actually just went through Cracking the Sales Management Code again as a group, chapter by chapter, to reinforce some of the things we'd gotten away from. So Sales Manager Survival Guide, Cracking the Sales Management Code, Leaders Eat Last, and Radical Candor. And with that, I'll leave you with Peter Drucker: Management's doing things right, leadership is doing the right things. And as a leader, it is your job to make sure your managers are doing the right things and getting better at those things. So with that, thank you. You can follow me on LinkedIn. Um, I have a Patreon group you can subscribe to, Inside Sales Excellence, but I appreciate your time, your attention. If you have follow-up questions that I didn't get to address, hit me up on LinkedIn. I'm happy to answer them. But thanks, y'all. This was fun.