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#599 - How to Make a 10x Impact as a New Sales Leader | Sean Gentry

from 30 Minutes to President's Club | No-Nonsense Sales

34m 33s

#599 - How to Make a 10x Impact as a New Sales Leader | Sean Gentry

Sean Gentry, a sales leader, shares key insights on leading effectively in a new role. He emphasizes that culture is defined by team behavior when leaders are not present, and that leaders must set clear expectations early—such as valuing transparency, trust, and self-care—while being micro-aware but not micromanaging. A core strategy is identifying the "lead domino," a single high-leverage change (like initiating renewal conversations six to nine months ahead) that drives broader impacts. Sean uses AI to analyze team data, surface risks, and test strategies, enabling faster, data-informed decisions. He highlights the importance of measuring behavior change over results in early stages, as this reflects team alignment and engagement. Leadership effectiveness comes from proactive communication—weekly reports to executives and structured, consistent conversations—ensuring transparency and trust. Ultimately, Sean’s approach blends empathy, data, and strategic vision, showing that transformation starts with a clear, actionable plan rooted in observable, scalable behaviors.

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To me, culture is what happens when I'm not around. So when I'm not there, how is my team reacting? How are they behaving? What are they doing? I say like, hey, one of the things that you can expect out of me is that I don't micromanage, but I am micro-aware. I rarely ever get mad or upset, except when I find shit that I shouldn't find. Meaning that like, you've done something and kept it from me. I always want good news to travel fast and bad news to travel faster. So if we lose a big deal, or if we lose a big renewal, like you should tell me immediately so that we can try to triage or do something about it. (upbeat music) Good morning everybody and welcome to this leadership episode of 30 Minutes to President's Club. I'm your host, Mixagelski, with my co-host here, Mark Casaglow, and today was an interesting one. Today was a first for Mark, because Mark, we actually interviewed someone who is literally working for you right now. We've got on Sean Gentry, who's one of your sales leaders. So I'm gonna let you tell me, Mark, why should people listen to Sean? - So Sean came to me at outreach, cold. And he said, listen, I need to be your next AM leader. And I was like, okay, and at that point, I was getting dozens of those a week. Immediately after that email, I get a text from my boy, Katie, Kevin Dorsey. And he's like, yo, you're gonna hear from this dude named Sean Gentry. Most potential I've ever had in the manager, awesome dude. And you know, he interviewed great, we hired him. He crushed his role at outreach. He went the web flow, crushed his role there, worked for his current VP of mid-market of sales. And when our director of account management opened up here and no brainer brought him in, and he's had a humongous impact in his first few months. - All right, Sean, welcome back to the leadership show. I hope you remember we started every episode with your top three actionable takeaways. So let's get your three. - Yeah, awesome, thanks, Dick. So number one, I want you to build your people book before you start your new job. So most people wait until they get in and get settled, start throwing one of ones on the calendar. I think what actually served me best at starting off my new gig was reaching out to the managers and some of the reps before I actually started and having about 45 an hour long conversations, getting to know them before I ever took my first seat. - Beautiful. - What's number two? - Number two is when you get settled, you're gonna wanna look for everything that's fixable or you're gonna probably go for the lowest lever to pull and get your name recognized. I actually would say that you wanted to find and find the 10x change versus the 2x change. So not only determining what's the lowest effort, but looking at what's the highest impact change you can make that impacts all of your reps at once. So normally when a new manager steps in, they're looking for everything that's broken. Is it a call volume problem or is it a response to an hour-age sequence that are low? And they're gonna look to dig their hands and everything and try to fix out small problems that may impact one or two reps. More importantly, you wanna gather all information of what's broken across the team, find the biggest impact change. For us, it was having renewal conversations further out than we were having them now. Things that the top reps were doing, some of the things that the bottom reps weren't at that time. So you wanna document basically what was working and scale greatness down, knowing that it's gonna be a 10x change across the team. - Great. So I think the biggest change that I could make to make this episode better is ask you, what's takeaway number three? - Yeah, takeaway three is, it's hard to measure some of those results early on, especially as a leader, you could get in and get discouraged by not seeing the needle move. And so in the first quarter, you're gonna measure behavior change versus results. So you wanna actually see, are your reps, are your managers doing things differently? Day in and day out, some of the things that you've talked about is changes as a leader. And you're gonna measure that and reward that versus actually seeing the results happen because it's just gonna take too long to actually provide praise for some of those changes. - Because it's actually a first where in an interview on the leadership edition, I've talked to somebody that actually is currently working with me, so no pressure. - Great, this is like a one on one right now. - This is the big thing. And I think you can talk about it from your perspective, I could talk about it from my perspective since I'm still under a year. You come in in that laundry list of stuff that you want to change is really long. So you said you prioritize it. How, how do you look at a list of 20 or 25 things and pick the one or two that you know you need to start at? - Yeah, it's two things. So number one, I did use AI for a lot of this. And I'm sure that there's plenty of rats, plenty of leaders using it or what I even think would be scratching the surface. It all started when having these conversations with managers, with rats. I actually asked a series of the same four to five questions with every single person just to gather a baseline. So some of those questions were like, what's the good, bad ugly of the role in the company right now? How do they feel challenged and fulfilled at the end of the week? How do they like to be recognized, whether that's being shouted out in a slack message, whether that's having you mark, slack them directly and not being, you know, put up in front of the class. And then once you have all those things documented, I actually went to cloud and built a prompt as a director of sales at Dechebo and uploaded everything. And because of that, you're gonna get a lot of reps that say, oh, the sequences aren't working well. Or, you know, I'm not getting people to respond to voicemails and the way I always think about problems, I actually would attribute a lot of this to KD is that he's taught me whether it's a volume or a volume problem, right? You're gonna get a lot of reps who are going to say things that are loud in volume, like people don't respond to voicemails, but that might not be a volume problem that it's happening across the board. And so it is so KD, but I actually put that in the prompt for cloud to say, hey, I want you to measure, like, is this a volume, like, is it loud or is it actually happening across the organ going to make an impact? And what cloud and, you know, in Shazgbt were able to do was surface up basically the impact areas that I could make in the first 90 days. And so with the help of that, and like, I think having the same documentation, the same prompt, it was able to organize kind of my thoughts and put everything in, that it was able to give me a clear enough response to know which levers to pull. So one of those things is that we were doing a lot of forecast calls around expansions, right? And around, you know, net new acquisitions and dry-d revenue, which is fantastic. And it should be that way. But we were kind of mid in the side where we were talking about renewals that were coming up, especially ones that were happening quarters out. The thing that I noticed is that we were just getting to renewals too late, right? We were talking about them essentially in quarter for things that we could influence when realistically, CFOs and business, you know, DMs, they're making those decisions three, six, nine months out about what they're going to do with their feature contract. And so that was a simple change that we could make across the board, something our top reps were doing, are, you know, our middle of the path bottom of the path were missing at that point. But it was a lever that we could pull to institute, hey, you have to start this process, this behavior change of reaching out to these accounts much earlier. We implemented that from a manager perspective that they have to start doing this in forecast reviews and the deal reviews and measuring that behavior change, we were able to make essentially like that 10X impact versus fixing some of the things that were like a quote unquote, loud problem like, you know, the wording was bad in a sequence, which isn't going to impact the entire team at least to make a big change. - Sean, what this makes me think of is a concept that I learned from Tim Ferris actually and he calls it identify the lead domino. And what he means by the lead domino is, what is the one thing that you can knock down by which every other domino ends up getting knocks down? And if you can find the highest order domino, everything else gets solved as a result. And so I'm thinking about these, how do I save or win more renewals thing? It's like you could start by being like, all right, we got to help the reps get to power more easily or help them multi-thread better or run safe plans or identify the business impact. But if you're talking about a renewal that's in a week, you don't have the time or space to do all of those things. And when you start the renewal conversation, whatever, six months before the renewal happens, it actually gives you a little bit of space. And it sounds like for you, that was the lead domino that you identified. Mark, this is a question for you. When you started as the CRO at the table, I have to imagine that there were certain lead dominoes that you identified and I'm wondering for you which those were. Probably the biggest domino was the fact that there was a lot of good work being done and a lot of time being spent on it, but it was a random acts of well intention improvement. That weren't based around a centralized framework or strategy. So they, instead of, if you look at each one, they made sense, but if you added them all together, they became chaotic. And so the first thing I did is I sat and watched for about three months and started in July in October. I had my leadership team come to Toronto and I said, these are the two frameworks that govern all of our decision making. If it's inside these frameworks, we do it and we do it great. If it's outside this, I don't care how cool it is, we ignore it. And that just brought a lot of real definition to how we want to operate. And whenever I do decision and Sean does this, whenever I do decision or talk about stuff, I usually do it in the frame of the R-ROM, of our recurring revenue operating model. I do it in the frame of moments of impact which we haven't quite released yet, but we're getting close to that. So everything is, for me, the lead domino was, if you don't have those kind of North Star frameworks and strategies in place, everything else after that will kind of sprawl looking for the edges versus if you define it, you're infinitely creative inside the boundaries you set. - Well, one of the reasons that I joined the Chevo and thrilled to work with Mark again is because I know, like working with him long enough, I worked with him for years at outreach, obviously carrying over, is that Mark is so driven by process And like, operating within those frameworks that truly is like our love language, I feel the same way that coming in, it's like I think and implement a process and track the behavior and see how things are working. And I will say like one of the things that I love working about Mark that's taught me to be a better leader as well is that you never want to go into a meeting and say how great everything is point things out as a leader, anybody can find that stuff and in a CRM. But more importantly, it's like, how do you come in call out what's not working in the plan to save it? Right? And so early on, I knew that if I could come out in a line with him and our other leaders to say, Hey, this is the issue that we want to focus on raising the bar, whether it's renewals or, you know, expansions, whatever that is that we laying on together as a team, what's the plan towards that? And then keep them updated? We're going to be successful. We'll lead with the bad news. And leading with bad news, you have to do it the right way in the right frame. And you can't just be negative Nellie and in there like, this is bad, this is bad, this is bad, this is bad. The way that you do that is one is, most people lead with good news. And what it does is over time, you know, the meeting runs lay or the meeting needs it finish or something. And you don't really quite get into the bad news. So most of the bad news feels unresolved while the good news feels resolved. After that happening over and over again, what ends up happening is you start to develop mistrust because it can't be this good. And they don't feel like we'd get the good, the bad stuff resolved when you flip the script and you say, Hey, there's some good things that I want to cover at the end of we have time. But let me make sure we talk about some stuff that we need to work on first. And then you have time to really flesh out and resolve, okay, here's the action I'm going to take. Yeah, thanks for your input and stuff like that. Then you move to the good stuff. That's a right way to frame and order the conversations where now like when Sean and I talk like I'll put something in slack, Sean will DM me and be like, Hey, you're right, this is an issue, this is another issue related to that. Here's what I'm doing for this. Here's the sheet I just gave my managers, this is all this. Do you know what I think? Sean's got it. Yeah, I might check in a couple of weeks later and be like, Hey, how's it going Sean? But other than that, like I'm like, Sean's got it. Sean does that half a dozen times in his first few months here. And all of a sudden, Sean is not on my mind now. Listen, that's that could be bad. It can be good. The reason is good, though, is because it shows a sign of trust that must be earned. And secondly, it allows me to work on other stuff that the leader doesn't have as much control over as I feel like Sean has control over his area. And that's when as a CEO and as a leader, you really can start to make a difference because you don't have a bunch of balls in the air that you're trying to make sure don't drop. You got like some that are just set over there on the counter, they're in their display cases, they look beautiful, they're shining, when everything's something's wrong, it whispers to you and tells you what's wrong. And then those back to those awesome little case, and then I can deal with the much fewer balls, which is makes me way more effective. Today, Sean was brought to you by pipe drives easy to use and customizable CRM with built in meeting intelligence. My favorite discovery question is the multiple choice question, which sounds like typically when I'm talking with folks like you, they're focused on a, b or c, which is it for you? Now, a, b and c have to be problems that you can solve, because that's how you steer the conversation in the direction of places you can help them. Now, pipe drives built in meeting intelligence helps you focus on your follow up question, not on scrambling to take live notes. And we will take full discovery toolkit with them free in the 30 NPC Closers hub. There's a link in the show notes. Today shows brought to you by a line, b a ideal workspace that helps sales teams close complex deals. So here's a tip about multi threading. There are stakeholders in your deals that you don't even know exists like the VP of finance, who's viewed your champions recap twice this week, but no one actually introduced you. That is the type person who's beacon around your deal and might sneak up to kill the deal at the finish line and aligns AI surfaces it before it's too late so you can multi thread to them. We built a full multi threading playbook powered by a line. It's free in the show notes. Today's show was brought to you by outreach, the agentic AI platform for driving execution across every stage of your deal. Great sellers drive velocity at every stage of their sale. And one thing that's worked well for me is assigning redline deadlines to my prospects when we kick off vendor review, even artificial micro deadlines for things like first cut of red lines and security review helps my prospects get their internal team moving. We built a guide on how to help you drive six and seven figure deals with our friends at outreach, get it free in the show notes. Okay, so just to go back to what you shared earlier, so step one is you're going and you're having these conversations with all of these managers, all of these reps, you are taking the recordings from those calls, you're putting them into cloud. And then what you were doing is you are saying, hey, help me identify some of the common patterns and themes while also keeping in mind volume versus volume. And then what you shared with me actually on the pre call is you're sharing your plan to try to start to solve this stuff, but you are asking cloud to pressure test that plan and call out where you might be thinking about things wrong. You go from someone who's just like, yes, yes, yes, yes, yes, sounds great to someone that is a thought partner. So at this point, now you have a plan of attack. I want to ask you in your first 30 days about we started to touch on this with the bad news first versus the good news first, I want to ask about how you communicated that plan downward to your team, and also upward to the folks that you report to. I'm curious about what that first like those first couple team meetings that you led looked like, and then also what your first couple one on ones with your boss might have looked like where you shared that plan. It's not the first time that I stepped into an org and been quote unquote, the new guy, right, both the managers that I started working with have been into the table for years, like my top senior manager has been here for over four years now. And so stepping into the roles is kind of the new guy, I don't have true like industry experience for the table as well. Right. So it's it's I've done this role before, but I'm not in the same space. And so stepping in, I feel like you have to kind of call out the elephant of the room. And that was I think one thing that was helpful on these initial calls to say like, Hey, I understand that you probably wanted my job. I am not from this space. I am new. But here's why I believe I'm the best fit. And here's why I'm excited to work with you, right? And kind of you as a team. So I think when I was communicating things with my managers, you have to lead with some empathy to call out that, Hey, I'm new, I am coming in. There are going to be things that we are likely going to change. But I also want your input because there were certain things that I would ask my managers about and they could either say, Hey, yeah, we tried this before, and it didn't work out. Or that's just a stupid idea. Or, you know, yes, let's go ahead and try it. And so I wanted to make sure that I had their buy in. So it comes with empathy and really the why. So if also I came to them with some like unbiased or undata driven approach of why I wanted to fix what I wanted to fix, it would get thrown out the door. So that's where I feel like some of this data and talking to the entire team and coming with that support was helpful and communicated down and then communicated up. I think it's similar. Like I understood what the data showed, I understood what the voice of the team was, some of the biggest things they were running into. And I was able to identify, I believed a big enough problem to pull on that lever to help the business. And so working with, you know, Cory RVP working with Mark and saying, Hey, this is where I want to focus and make the biggest change. They were able to align on that as well, because the numbers were what the numbers were, right? And say, like I believe that if we move, you know, this percentage up here in terms of renewal rates, this is going to be a huge impact to the business. This is basically the flag that I want to plan in the ground over over the next couple of quarters, right? And then I think more importantly, because we work in a remote environment, like my boss is on the east coast, I'm in Seattle Washington, you know, Mark is Eastern Standard Time, I can't be in the room with them at all times in communication. So I do my best to proactively communicate with them as much as possible, right? So one thing that I've actually started to do even way back to my outreach days is that every single week, I send my boss a full report on what I've done that week. So essentially how I'm pacing to my number, what our renewal percentage is, what my expansion and pipeline numbers are, I send him any trends that I'm noticing in the business. So what's working well, what's maybe not working well? And then I also send him my focus for the next week, what are the things that I'm looking to tackle, whether that's like, you know, filling open headcount or, you know, winning this huge rule that's coming up. So when we get into our one-on-ones, that's usually the first thing we cover is the top two or three topics. So we can keep on pace. But also, he rarely ever slacks me and says, like, hey, what the heck are you working on? Right? Because I'm always trying to do my best to let him know. Sean, I think another aspect that you nail in the beginning is measuring behavior change versus results. And we know results are so lagging, but behavior change can be instant. And that also lets you know, like, do you have the hearts and minds of your people? And, you know, we both understand how important that is is, give me an example or two of a behavior change that you did here. And then how do you track it? Like, how do you see that it's happening? One of the things that I noticed very early on is especially talking about renewals. So I noticed two things from the leadership side and then the individual like contributor or rep side. So from the rep side, I noticed that we were starting to talk to renewals, you know, one quarter in, right, which especially in our segment is too late. People have already made their decisions. If they were going dark, they had already decided something, you know, four to six months, maybe even prior to that. So the first behavior change I wanted to do is start out forecasting two or three quarters, right? That we were looking in Q one, we were looking to Q three and even Q four and starting to forecast those deals. So each rep had roughly, you know, say 20 to 25 open renewals for the fiscal year. Have they communicated and started talking to those ones that are going to renew in September, October and November, because I know Mark, you and I have talked about this like a renewals essentially start once that first contract is signed, right? Once they sign on the dotted line, like that is the start essentially of a renewal process, right? The customer journey. So that was the first thing I wanted to notice is that are the reps able to actively communicate with the quarters out deals that are going to renew? So the second thing is from a leadership perspective is that the managers had to be expecting this and then inspecting it. So when they were going through their weekly deal reviews, they weren't just talking about the open expansion deals in pipeline. They were starting to pull up their Q3 and Q4 renewals to say, hey, is there the activity? Are there conversations happening? Is there engagement? Do we have a champion at the site, right? And part of the way that I use ClawD and ChatGbT to help is that I started essentially exporting all of our annual renewals in GONG. I would get an email sent with every single open renewal. I would throw that into ClawD and it would basically surface the opportunities or the renewals coming up that didn't have any activity for this year. So rather than looking through a lens of GONG and pulling everything, you can just export all of the open renewals. Send them to ClawD. I cross-reference that with some of our internal usage data. So I could essentially see, are the reps contacting them? And then is the customer actually utilizing the platform? And then if neither of those things were true, these are the red flags that we need to start at home on and on. And that's what I would have my managers go after. So ClawD was essentially also helping me surface like where is the biggest risk that's coming up? And then can the managers manage to that on a weekly basis? And then are the reps actually doing their execution of it? Did this live in an application? Or were you just like putting it in a spreadsheet? Because as I understand it, the process for this renewals dashboard exports all open renewals from GONG to see the engagement with the account. To look in the CRM, are we actively trying to contact them? And then three internal usage data. Are they actually using our product? One, was there any other data that you pulled into that? And then two, did this live in an application? Was it a spreadsheet? Did you just send out a memo to the team? I'm curious what you did. You basically used ClawD co-work to build a prompt. Essentially, this is what you're looking for, right? So if I go in and say, hey, I'm the director of sales, I'm looking for open renewals that are coming up in Q3 and Q4 and beyond. So let's say in the next 12 months, I'm looking for deals that basically are flagged as risk. So having low activity in the last 90 days, let's say we have not engaged with a single person there, like meaning the same person consistently. Therefore, a champion, are we having utilization or usage issues that are coming up? And so plugging in all of the export data from GONG from Salesforce that you can pull as well. You can download a CSV, you can drop that in there. I was downloading a CSV from a company called Totango that we have that measures all of our usage and utilization. And then we actually built a glean agent that surfaces any risk through these three things. And we're pulling in the glean agent to ClawD as well. ClawD was able to essentially build out a full web browser for us that we could click through and cycle through and dig into the data where it shows us what the AM or the account manager is actually tracking and how they forecasted it. And if there's discrepancies in what the AI is calling. So an AM may call out and say, hey, you know, I've got super biz that it's coming up in December and it all looks good, it's likely, right? It's going to renew, but the AI is telling us you actually haven't talked to anybody there in the last four months. Their usage is down from 70% to 40%. Maybe they had a couple of leadership changes and you no longer have a champion there. This actually shouldn't be likely. And so from a leader's perspective, we're able to dig in and say, hey, where are the discrepancies here? And these are the ones that we're starting talking forecast calls now in May for a renewal that's coming up in Q4 versus the way we're doing it before. - We were talking about the concept of the lead domino or the highest leverage change. I have to imagine that there were things that you knew were problems, but they weren't the highest leverage problems to solve. And I'm curious what were some of the problems that you intentionally let and maybe have still left burn that you're able to share with listeners? - You know, some of the small changes that you can always go through, especially when this comes to prospecting is built in my blood. I mean, starting off so early at outreach. Like, you should always, always, always be creating pipeline, like pipeline over everything. This is how I've always thought. And I think that's where most managers come in and they say, hey, I want to tweak how we're doing our phone call blocks and I want to tweak how we're sending our emails and some of the verbiage in our emails or our voice mail. And it's easy to change call scripts and things like that to see if there's going to be an impact. I had reps come to me and say, hey, like some of the sequences I'm sending out aren't worded the way that I would word them, right? And I could go through and probably make that rapper too happy by saying, hey, I'm going to reword this for you and send it out. But essentially the change wouldn't be enough to impact whether the entire team or see the needle move enough that I could go back realistically to Mark and say, hey, like, I changed wording in this sequence and we saw response rates go from 20 to 22% for one rap, right? But essentially for the lift, it was not going to see the result that we needed to see versus are we starting to contact people six to nine to 12 months out? Are our managers running through this in our forecast calls? And now I can go back to Mark a quarter or two out and say, hey, we got our renewal percentage on these major deals from X to Y. And that was like the goal that I'd set out to achieve. Because that's going to impact, yeah, millions of dollars a revenue. Today's show was brought to you by Pipe Drives easy to use and customizable CRM with built-in meeting intelligence. My favorite discovery question is the multiple choice question, which sounds like typically, when I'm talking with folks like you, they're focused on A, B, or C, which is it for you. Now, A, B, and C have to be problems that you can solve because that's how you steer the conversation in the direction of places you can help them. Now, Pipe Drives built-in meeting intelligence helps you focus on your follow-up question, not on scrambling to take live notes. And we built a full discovery toolkit with them free in the 30 MPC Closers hub. Today's show is brought to you by Align, the AI deal workspace that helps sales teams close complex deals. So here's a tip about multi-threading. There are stakeholders in your deals that you don't even know exist, like the VP of Finance, who's viewed your champions recap twice this week, but no one actually introduced you. That is the type of person who's beakin' around your deal and might sneak up to kill the deal at the finish line and Align's AI surfaces it before it's too late so you can multi-thread to them. We built a full multi-threading playbook powered by Align. And one thing that's worked well for me is assigning red line deadlines to my prospects when we kick off vendor review. Even artificial micro-deadlines for things like first cut of red lines and security review helps my prospects get their internal team moving. I guess I have one more question for both of you and this is around cultural change. So one thing that you guys might not be aware of is Armand and I recently switched jobs at 30MPC. Literally for the last five years. I was leading our sales team and Armand was leading our content team. And part of the reason that we made the switch was we both had taken the business really far in our original roles, but we felt like and in order to get to the next level and scale, we were both like, I think you'd be better at my job and I think you'd be better at my job. And so we switched. So I am now leading our content team, Armand is leading sales. And one of the things that I found that I observed when I took over our content team was that there were some cultural changes that I wanted to make. And I imagine for both of you when you took over your new sales leadership job, there were cultural changes that you all wanted to make. And I think a lot of times people talk about culture in this very like nebulous, fluffy space and they don't actually get into like practical actionable things that they did to change the culture for the better. Sean, I'm wondering if there were any concrete steps that you took on the cultural front and then Mark, I'm going to ping that question over to you. - It's always helped me to understand what culture truly means, right? And how I define it, because it's like you said, it's nebulous, it's different for every person, like culture used to mean like kegs in the office and ping pong tables and things. - Yeah. - To me, culture is what happens when I'm not around, right? So when I'm not there, how is my team reacting, how are they behaving, what are they doing, right? And so very early on when I came in, the first thing I did is sat down with the managers and set expectations. Like this is how I run my team, this is how you can expect, like what you can expect from me and this is therefore what I expect from you. Then I did the same-- - Can you give me some specifics in terms of like what you said in that conversation, Sean? - Yeah, so one of the things is I basically walk through a whole deck that I've created about working with Sean, working with SG. Like I say like, hey, one of the things that you can expect out of me is that I don't micromanage but I am microman aware. Like part of my strength and skillset, I always want to know what's going on, what's happening and like I tell them like I rarely ever get matter upset except when I find shit that I shouldn't find, right? Meaning that like you've done something and kept it from me, I always want good news to travel fast and bad news to travel faster. So if we lose a big deal or if we lose a big renewal, like you should tell me immediately so that we can try to triage or do something about it. And so part of it is like this is what you can expect out of working for me. I also tell them one of the huge things that I try to pride myself on is that I've got two young children, I am family first, right? If you've got both of my managers have kids, if you need something for your family, your partner, like your kids, like I will never ask anything about that. Like take care of your family, take care of your kids. And similarly like I also really cherish like time outside to exercise to work on my fitness work on my mental health like and so I want my reps and my managers also to put themselves first I believe that if they are not taking care of themselves whether that's physically mentally emotionally that it's very difficult to give their best at work so if they need that time to like go for a walk do yoga go for a swim go for a run like what I want them to do that and I give them that flexibility and freedom upfront so that they should never feel bad about that because like if they can't do that I don't think that they're going to give their best to me so part of that is all the expectation setting up front and I truly believe like if you know somebody and you trust that person like Mark and I work together for a long time I would say that we trust one another like we are going to work hard for one another because we have that trust right like if you don't trust your boss you're not going to work hard for that person and so part of that is the expectation setting up front and then I think the second thing around culture is that I believe like you know a lot of managers say oh never get too high never get too low like there should be a floor of how upset but there should be no ceiling like you can get super excited you know raise the roof off everything and so I always try my hardest I'm a perfect but I try my hardest to shout people out the way they want to be recognized around behavior so if you know if we had one of the reps on our team that did had an awesome you know renewals call and that could share like I want to celebrate that person I want to celebrate people for their for their actions and their behaviors also for the results right but I believe there should be no ceiling in how high the team gets I love it well so on this has been a phenomenal episode the clock is ticking we got to move to the final question so we've talked about a lot of best practices for leaders to follow when they're starting in a new job now I get to flip that question on its head and ask you about a worst practice so my question for you is what is one bad habit that you think all sales leaders need to break when they're starting in a new job so that every sales team out there can get better yeah if we bring it back to AI it's just the avoidance or reluctance due to fear right like there I think I I've talked to leaders and I work with leaders outside of this that just say like hey I just don't know where to start right just don't know what to do with AI yeah and so they just use it for recipes or you know or like gym workouts and it's like hey get into it play around with it spend the time and I think the biggest hack that's held me is like I'll use the prompt like this is what I'm thinking I want you to pressure test this or I want you to like see areas that I'm not thinking about or tell me where I'm wrong and using it as kind of a devil's advocate that's been the best way that I've been able to like go back and forth and learn how to actually like use it or prompt it so I would say for any new manager like just don't avoid it it's it's here whether you like it or not so dive in and use it spend the time I love it Sean thank you for joining us everybody stick around for a 60 second recap coming up soon already market is time for your two by two recap what do you have for your two two by two one is from a man kd via my man sg which is volume versus volume is it loud or is it a lot and loud could matter maybe not volume like a lot that always matters and then second don't micromanage be micro aware that I'm stealing that I thought that was brilliant I thought it was so dope so uh those are my two takeaways for today all right my first is actually one that I got from you mark which is when we were talking about cultural change the first piece is you have to define what kind of energy do I want in this organization and then you have to know that you're the energy engine for that and you have to start to attach to the energy that you want the things that you're going to do for you mark those were things like anytime we closed a deal over $10,000 the AE was getting a personal message it's anytime Sean sends a plan for hey here's a problem here's how I want to solve it you're giving it a big let's go for Sean the way that he's extending that is he has a floor for how low hello allow himself to get but from a ceiling perspective there is no ceiling you can raise the roof infinitely and so when you're making cultural change you have to understand that you are the energy engine that gtm is the energy engine and that starts with you as a sales leader and then number four Sean talked about the proactive updates that he sends to his leadership at the end of every single week which are things that he worked on that week problems they're running into what his focus is for the next week and he is giving proactive visibility into these things so that leadership never has to wonder what is Sean working on right now all right mark that's the episode I guess how can people help us out yeah listen they can always help us out one way is in the comments below put some stuff you want us to talk about or questions you want to ask or if you have a great sales leader put their name in there and let's get them on the show and then secondly you can always help us out by hitting that like and subscribe button right I love it thank you to me now you are a youtube layer this mark obstacle of the youtuber folks thanks for listening we'll see you next week on 30 mpc today sure was brought to you by pipe drives easy to use and customizable CRM with built in meeting intelligence my favorite discovery question is the multiple choice question which sounds like typically when I'm talking with folks like you they're focused on a b or c which is it for you now a b and c have to be problems that you can solve because that's how you steer the conversation in the direction of places you can help them now pipe drives built in meeting intelligence helps you focus on your follow-up question not on scrambling to take live notes and we built a full discovery toolkit with them free in the 30 mpc closer sub there's a link in the show notes today shows brought to you by a line b a ideal workspace that helps sales teams close complex deals so here's a tip about multi-threading there are stakeholders in your deals that you don't even know exist like the VP of finance who's viewed your champions recap twice this week but no one actually introduced you that type of person who's beacon around your deal and might sneak up to kill the deal at the finish line and aligns AI surfaces it before it's too late so you can multi-thread to them we built a full multi-threading playbook powered by a line it's free in the show notes today show was brought to you by outreach the agentic AI platform for driving execution across every stage of your deal 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Podcast Summary

Key Points:

  1. Culture is defined by team behavior when leadership is absent, not by surface-level perks like ping pong tables.
  2. New leaders should establish clear expectations early, including transparency on bad news, no micromanaging, and mutual trust.
  3. Prioritize high-leverage, scalable behavior changes—like starting renewal conversations six months in advance—over small, isolated fixes.
  4. Use AI as a strategic tool to analyze team data, identify patterns, and pressure-test plans to uncover blind spots.
  5. Measure behavior change (e.g., reps initiating early renewal talks) rather than lagging results in early leadership stages.
  6. The "lead domino" concept—identifying one high-impact change that triggers broader improvements—is essential for cultural and operational transformation.
  7. Proactive weekly reporting and alignment with leadership build trust and ensure consistent progress visibility.
  8. Avoid AI avoidance; embrace it as a collaborative tool to challenge assumptions and accelerate decision-making.

Summary:

Sean Gentry, a sales leader, shares key insights on leading effectively in a new role. He emphasizes that culture is defined by team behavior when leaders are not present, and that leaders must set clear expectations early—such as valuing transparency, trust, and self-care—while being micro-aware but not micromanaging. A core strategy is identifying the "lead domino," a single high-leverage change (like initiating renewal conversations six to nine months ahead) that drives broader impacts.

Sean uses AI to analyze team data, surface risks, and test strategies, enabling faster, data-informed decisions. He highlights the importance of measuring behavior change over results in early stages, as this reflects team alignment and engagement. Leadership effectiveness comes from proactive communication—weekly reports to executives and structured, consistent conversations—ensuring transparency and trust.

Ultimately, Sean’s approach blends empathy, data, and strategic vision, showing that transformation starts with a clear, actionable plan rooted in observable, scalable behaviors.

FAQs

To a sales leader, culture is what happens when they're not present—how the team behaves, reacts, and operates in their absence. It's not just about office amenities, but about daily actions and accountability.

New leaders should clearly communicate their expectations, such as not micromanaging but being micro-aware, and emphasize transparency—especially around good news traveling fast and bad news traveling faster.

The 'lead domino' is the single, highest-leverage change that triggers a chain reaction of improvements. Identifying it allows leaders to solve multiple problems efficiently by focusing on the most impactful change.

Behavior change can be measured quickly and reflects team alignment and engagement. In the first quarter, leaders should track whether reps and managers are acting differently, not just whether results are improving.

AI can be used to analyze team feedback, identify patterns, and pressure-test proposed changes by asking 'what if' scenarios. This helps leaders find high-impact, low-effort changes that affect the entire team.

Leaders should model self-care by prioritizing personal time for fitness, mental health, and family. This sets a tone of trust and encourages team members to do the same, leading to better performance and morale.

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