#563 - How to Build Reps Who Don’t Need You on Every Deal | Jason Miller ft. Unify
36m 38s
In this leadership episode, guest Jason, VP of Sales at Unify, shares three actionable tactics for sales leaders. First, he emphasizes creating focus through a "post-it note" approach: identify the single most critical objective for the entire team (like unifying messaging) and then distill it down to one specific, repeatable action for each rep—even as simple as "smile." Second, he advises coaching the issue, not the outcome. Rather than telling reps to "book more meetings," break down the cold call process into stages (connect rate, opener success, pitch engagement, meeting conversion) and coach the specific weak point. Third, he stresses forcing critical thinking by having reps manually complete prep documents and type in their own KPIs, resisting the temptation to let AI do all the thinking. Jason warns against over-indexing on AI for tasks that require deep understanding—for example, never use AI to summarize a call you didn't attend; listen to the full recording to catch nuance. The conversation also covers how new leaders should prioritize: focus on key metrics, start with the lowest-hanging fruit, and build trust by working on areas the rep wants to improve. Hosts Nick and Mark relate these ideas to their own experiences, emphasizing the need to solve one big problem at a time rather than spreading efforts thin.
You've got to let them start drowning a little bit, let their head kind of bob under the water. Back up before you kind of save them. Once they sit in that pain a bit, I think it resonates a lot more. So it's a tricky balance. For I think sometimes we fear, again, letting somebody fail a little bit and making sure that, okay, drawing that kind of hard line. Good morning everybody and welcome to this leadership episode of 30 minutes to president's club. I'm your host Nick Sagelski joined with my wonderful co-host Mark Casaglow. And today we have a man who went from sales manager all the way up to our VP at Monday.com. And he is currently the VP of sales over at Unify and Man. Mark, we were about to kick this episode off and you were like, Nick, we don't even need a game plan for this interview. This guy knows his shit. But tell me Mark, why should people listen? I think he nailed it. Like there's some people that when they talk about stuff, you can tell us the first time they've ever kind of verbalized what's in their head. And then you can tell people who have, they're almost bored talking about it because they have it so dialed in. There's two or three things that Jason talks about that are super powerful but rarely used. And he explains them like he's told the story 10,000 times. That's the type of person you want to listen to. And a three, two, one. Don't bore your guests. Alrighty, Jason, welcome to the show. We start every single episode with your top three action. It will take away. So let's get your three. So first, what about creating focus? I call this first one the poster verse, the post it note is leaders in the organization. There can probably be 19 different things we want to improve. We can't possibly throw 19 different things at our management layer or our reps and think that any of them are going to get done well. So for me, this is what helps me to still all of those things down into what is most critically important or what is most critically important for my people to be focused on. So the poster thing of it is the thing that I want to put on the wall. And I want everybody in a team, a department and organization to work towards in a herd type of mentality. So an example of that for me is I'm still fairly new to unify is first and foremost, the messaging. So when we are speaking with a prospect or if we just meet somebody on the street, right, the elevator pitch. How is somebody articulating who unify is why we exist in the problems that we solve. If I asked five different people, I don't want to hear five different things. I don't even want to hear three different things. Maybe I can hear like one and a half different things, right? And it's really important to me. And so that's like my one to many right now. Then you distill that down to like the post it note aspect. So the post it note is now, okay, I've got my whole team operating towards this one thing. If I'm working one on one with a rep, there's probably again 10 different things that they can prove on in in their sales cycle. So how do I get them to just really get good at one, maybe two of them. So I want to know what is the most important thing that you can do is just get a lot of reps. And then I want to know what is the most important thing that you can do is just get a lot of reps. So I'm going to bed and letting their head hit the pillow, knowing that they've got a plan of attack for tomorrow, first waking up tomorrow on a panic and then trying to reorganize my day or reshuffle my day or reschedule something. I've had a post it note for a rep be as simple as I smile, right? People want to buy from people that they enjoy talking to. And so I've had some as just as simple as is that for us. Amazing. Well, I have a post it note on my desk here that says, ask about tip number two. So coach the issue, not the outcome. So I think that you can actually even relate this to the post it note and how do we make sure that we're coaching to something that is meaningful for the rep. Coaching can be hard, right? And it's very difficult to sometimes coach large scale like metrics change, right? So I think that's the example like increase your conversion rate or telling a rep you need to book more meetings on the phone like, yeah, I know I said, I know like more meetings on the phone. How do I do it? So as cliche as it is relating sales to sports. It's like a sports team I need to score more touchdowns, right? I'm not going to just be airing the ball out on a hot route all day long. I'm going to actually watch the game film and figure out where are things going wrong. And so we need to make sure that we're doing the same thing in sales and then coaching to the piece that's going wrong. So if I'm relating that to my current role, we've got big outbound initiatives this year. A lot of people that know about unifying are coming to us, but there's a lot of companies out there that have no idea who we are and what we can help with and we need to find a way to get in front of them. And maybe it's just the way I started in sales of a huge proponent of the phone. So for us in the phone, it was actually uncovering the data and figuring out, okay, what does the rep need to get better at in four different steps of the cold call process. So we've broken it down into connect rate, which can be partially them, but partially the data. Secondarily, it's what percentage of calls get past the opener. So right kind of that breaking of the ice and what, how do we get permission to actually pitch. The third one is then how often do we get past the pitch into an engaged conversation with the prospect and then finally, how many of those engaged conversations actually turn into meetings. Because I can have two different style of reps. I can have a rep that's actually booking meetings, but there's still an area of kind of those that four step process that they can improve upon to book more meetings or I have a rep that's maybe not hardly booking anything on the phone. And where do you start? And if they can't get people on the phone or get past that first 15 seconds, that's where we focus. And then you can do the downstream stuff as you get better and better. Round us out Jason, what's number three? Probably my favorite day in and day out. And it's really about forcing critical thinking. And it's kind of in the face of AI a little bit because AI is so powerful, but it should be powerful at being an assistant is I see some people over indexing in AI is doing like all of the thinking for them. Or sometimes if you're a manager, we can have a tendency to think telling a rep exactly what to do is going to yield the best result. And it might in that specific instance when you're not around for the other 99% of the time. How is the rep going to handle that situation when you're not whispering something in their ear. So for me, I really think about or go about this in two different ways. First is anytime I get asked, how do you think we should handle or like what do you think we should do or I'm being presented with a problem. I will always reframe it first and how do you think we should handle it or how do you want to approach the situation. And that will create the baseline for where that manager or where that rep is today. And then you can start talking to them about different ways about approaching the situation or different ways to think about it. The second thing I like to do is more of like if you are a frontline manager or your director VP and you're getting engaged in the bigger deals is have your rep in your manager. Sometimes one sometimes both take the time to complete a fairly intensive prep document. So for me, I will always make sure that a rep is circling the two to three most important calls on their calendar for the given week. And then they will generally fill out a prep doc for one or two of them. And my pretty hard and fast rule is you can't use AI to fill out the doc. So it's actually got to be you thinking through what do you know and what do you what do you not know and it will go all the way through what is the desired outcome of this meeting and how are you going to set that in the upfront contract to who's attending the meeting who have you spoken to before and who is new and what can we do between now in the meeting to actually find out a new piece of information or drive a relationship or the deal cycle forward. All the way down to what is the pain that we're trying to solve and how well do we know it and then any questions like the information you want to find out is one thing, but I take it all the way down to what are the exact questions that you're going to want to ask. So even an example from earlier in this week, I had a rep that understood that there's a pipeline gap right it's one of the most common problems that people come to us with, but we did not understand how big the pipeline gap was and or the impact to the business. And so then you're actually speaking to that rep of okay, how are you going to get this information you're getting into conversations on some very touchy subjects with with a prospect and you can't just generally ask how does that impact the the business right this kind of like a gross way of asking that question and people kind of put a wall up. So it was working with them and kind of adding context to a question right which is another one of my favorite things where if you want to understand the size of the pipeline gap instead of just asking what's the pipeline gap we're going to catch somebody kind of falling back under their heels. I like to say hey I I speak with clients that are missing their pipeline gap by 5% I talk to others that are missing it by 70% which ended that spectrum do you fall closer to and now they realize you talk to people that have 70% pipeline gap. I don't feel so bad telling you I'm missing by 45% now. And so again, if you get them down into the level of exactly how you're going to do something they're starting to develop the thinking of how does that apply to all of my other conversations when that person's not around. What is a specific example of something that you absolutely don't want somebody using AI for and why. Yeah, yeah, don't get me wrong. I love AI and I think AI needs to be a critical part of many facets in the in the sales profession. I just think again, you can see people over indexing for example this prop doc that I was talking about. I have had reps fill it out and it is filled out so in depth that it's like there's a lot of things that I can do.
There's no way you did all of this, right? Or you've got to get away. There's an M-dash every other sentence, right? And it's just like, okay, you didn't do this. And that's then what concerns me, right? They can use it to analyze a transcript or whatever, but I don't want them copying and pasting it into the document. I want them looking through it and actually keying in the information to the product docs. Same thing, I've got like a one on one doc that tracks some core KPIs. In a rep we'll always ask, like I can see that in the dashboard. I'm like, I know you can see that in the dashboard, but there's a different psychological approach. When you have to key in that you scheduled no meetings last week, then a dashboard telling you that you scheduled no meetings last week. And so I think that's kind of the give and take of like where you consume data or where you use AI. Verse, yes, if you're thinking about research and you're going to go into a call and you want to get an executive brief on a company, understand how they make money, what types of trends are happening in their industry. I think like that's a beautiful case for AI in terms of ingesting it, but then you got to think about how to apply it. I read multiple seven to 12 page memos per day every single day. And I feel more on top of my game right now than I've ever felt my entire career. If I had summarizing guarantee you wouldn't feel like that. The only real hard and fast what I have is really around the prep doc that I talked about because it's very easy for me just to say, like you could use it and you might summarize something, but it's like you have to be the person that's typing things in because one, it's making you think too. Also, it's just like when you write something down or when you type something in, it's going to be, it's going to be set in your mind and your memory a little bit better. Right. So it will actually come out, I think, more naturally when you're on the phone call. I think summarization can go in one of two ways. If you were present, I think summarization you will miscontext in verse, if you were the rep that was in the conversation, then summarization is okay. I could give you another example. We've had an onsite next week for a very big opportunity. I will not use summarization because I wasn't in the calls. I will go back and actually listen to all the conversations to understand what that CRO cares about because I promise you, there's two things to three things I will pick up on that the summary will not, that will make that meeting much more effective. That's a dope ass rule. Like, hey, if you're in the meeting, summarize away. Because that's just going to jog your memory of all the context from the meeting. But if you are in the meeting, you better listen to the call. You're going to lose the nuance. I love that. Deal Velocity is a huge driver of win rates, which is why Armand and I partnered with the easy and effective CRM pipe drive to film a 60 minute video masterclass that covers all of the different ways that you can drive velocity in each individual stage of your sales process. Literally from opening call all the way to contract review, we documented our favorite tactics in this pipe drive and 30 NPC masterclass, which you can get for free in the show notes. Today's tactic is brought to you by attention, which uses AI to capture all of your sales interactions, automate sales, busy work like CRM updates, and flag hidden deal risks. So if you want to avoid ghosted deals and every discovery call with these three questions, number one, do you want to buy a K validate if the deal is real? 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One of the big things themes that you were talking about in your upfront takeaways, Jason, were there's the concept of like diagnosing what actually needs to be solved and then creating focus so that you are only solving that one thing. Because if you try to solve that and 12 other things, well, you're not really solving anything in full. Armand calls this, he coaches me, he says, you need to nuke the problem, pick the one big problem, and go like obliterate that problem, and then find the next biggest problem to solve. Jason, your three to four months in is a VP of sales over at Unify. Mark, you're eight, nine months in to the CR role at the Chebo. I guess I'm curious for both of you, like when you both started at the company, how did you figure out what needed to be fixed? Because I imagine there was like a million learning exercises and briefings and like one-on-ones, and like it's really easy to have your head spinning, and now you're just trying to like hustle, hustle, hustle and work seven days a week, which is kind of the trap that I feel like I've gotten into, where I'm like, oh my gosh, I feel like everything needs fixing. And as a result, I'm not fixing anything. I can at least tell you how I approached it, as I looked at for me, what are the primary metrics that I'm looking at moving that I'm going to measure myself off of? At least for me this year, there's like three key ones, right? There's outbound pipeline built. There is increasing conversion rate from meeting schedule to qualified pipeline, and then there's wind rate. And so I will look with those three buckets and figure out where do I think the lowest hanging fruit is. So when I talk about like the messaging component, to me, that is directly correlated to the pipeline conversion. Are we setting the right tone in the discovery call on what we do and the problems we solve? That's going to get someone to write along with us in the right perspective of what we can then solve and increase the wind rate. And I actually found that we were pitching too much of like a consolidation plate, which immediately gets us into a tit for tat on certain technologies in their tech stack. And so I wanted to reframe the problem around, okay, you have X problem. Here's how we can solve that problem. If there's some other software is along the way that we can consolidate, amazing, but we did not exist to consolidate software. We existed to create a pipeline to solve a pipeline in a revenue problem. The last thing I'll say is if I'm at the more rep or that that post it note level, I think an easy area to start is an area that that person wants to improve in. So that's the somewhere I will always start and build trust there while figuring out the areas that I think they need to improve. And then you kind of weave that in once you've built up that trust. Yeah, for me, every tree grows from a seed and I have to make sure the right seeds have been planted or I'm going to go clear cut the whole fucking forest. And the seed for me is around a few things. One is do you have a framework and a methodology from which all decision-making can be tracked? If you don't have that, then you're going to be super randomized in all over the place. The second is do you have a clear and easy way to understand for people to understand what is the the thread that connects us and makes our customer journey super powerful, an awesome experience and something that generates revenue as a machine. Not just like one off. Oh yeah, well, onboarding. Well, guess what? onboarding has to redo the discovery because the AE doesn't pass the notes along in the right way. And it wasn't scope correctly. And then we end up with a nightmare and now onboarding, which then becomes a nightmare and success. And like for two years, we're just trying to keep this person along. We spend hours and hours and they just turn anyway. So I would say like Jason's levels on the sales level. Mine is on the full CRO level since I have everything from basically where marketing ends all the way through the rest of the customer journey. But like for me, I got to start with my master framework that all decision-making comes from. And then the second is what is that golden thread that I pull through the customer journey. So it feels like we're one company. My motto one team one journey. We're all one team. We're all one one journey. It's one customer going through it. Let's make it seem like it's like we love each other. So Jason, I've done quite a few episodes. Posted versus posters stealing it. That is unbelievably awesome. Now here's what my brain goes. I told you to name it that. That was good. That was a brief, that was a brief little glimpse of Nick's genius. I can have a couple posters around the hall. And yeah, those are big and for everybody. You know what happens is the creep happens. And all of a sudden a couple posters turn into a hundred. And instead of like a few sticky notes, it's a wall of sticky notes. Because your CFO wants something. Your CEO wants something. Your CRO wants something. Your VP of success wants something. Like how do you keep it focused? Because a C of post that's around my computer doesn't have the same impact as one post it on my computer. It's tricky for sure. To your point, everybody wants something. And all of those some things take up mind share at the end of the day. And it's not to say that we don't have multiple posters on the wall or potentially multiple post it notes kind of creeping in. But I think it's for me, if anybody is feeling overwhelmed at the end of the day, it's just like how do you shed some of that weight and come back to what we said was critically important. So the idea is that you actually can't put too many posters on the wall. You can have a stack of posters that people want on the wall. But as a sales leader or a leader of any department, it's up to you in terms of what you put on the wall and what you put up when. So I think there's a lot of accountability on our behalf where if there are too many things up, that's kind of our fault that we didn't protect our people's time and or push back on some of those initiatives because maybe they don't align to the top line goals or align to where we are at this exact moment in that journey. This is where your enablement partners can help a ton too. If you have a central place that understands everything that the field is needs to be doing based on all of the requests coming in.
like you have to have like one person that's kind of like the traffic cop who's like, "Okay, wait, you're holding up. You can't cross the sidewalk yet because we got a couple cars coming through." Okay, now you can come in because you're right. Like, I often ask people, "How do you eat an elephant?" And everybody says, "One bite at a time." And I respond, "Actually, it's the illegal to eat elephants. You shouldn't do it." But if you were to do it, one bite at a time is a way to do it. And that's right. And we, a lot of times as sales leaders, we shove the whole elephant down everybody's throat and then wonder why they can't digest it. It's impossible to get down our throats. One bite at a time is a right way. You were talking in the pre-show about, "You've got a manager on your team who's like feeling overwhelmed with all of the different things on their plate." And when you were talking about creating focus, there were two sides to it. There's the piece that you have people zoom in on and that's what's on the post it. But then there's also the concept of all of the other things that they discard and choose to say no to. And you speak no to one thing, you're really saying yes to something else. And so I'm wondering if you can give some examples of things that you have encouraged managers or reps to discard and shed and purposely neglect so that they can focus on more important things. There is for sure. I mean, I think there's a couple of things like take that manager, for example, like in protecting their time and making sure that they've got their day scheduled like the next day. They're, we've all been guilty of this. Like we put like a do not block time on our calendar or it's supposed to be like deep work time. But then we don't protect that time. So that's like a simple example. If you're going to put it on your calendar, protect it. Don't actually allow people to book over that meeting. So if someone wants to book time with you, they need to find time either later in that day. They need to rearrange their calendar or they need to put it like a day or two later. Because if you're not going to protect your time, no one's going to protect your time for you. So I think that's like one more like thematic example. I think for us like another one that we were discussing, that won't go into like great, great detail about it. But it's kind of what Mark was talking about at the CRO level and like how are you connecting all of the departments, right? And we've been doing a lot of conversation and planning in terms of how do we move somebody from sales into customer success and account management and making sure that we're onboarding that client effectively, that we're getting kickoff calls scheduled efficiently and effectively that we've got the right sponsors on the client side, etc. And so we're ideating on some ideas on how to make that more fluid and get stronger commitments from the client upfront. And it was a conversation happening probably between four or five people into what I mentioned earlier of like if I allow it to become too noisy, that's my fault. Although I wholeheartedly believe the conversation that we are having is the right one and if the right thing to do, if I let that happen now, it's going to have a cascade effect and knock down like two to three other things that I want the theme and the reps focused on. So I said, Hey, we can talk about it and plan on it in this group, but I can't do anything on this until minimally Q2, which for us is may, right? We run like February through through April. And so they kind of know where that timeline is. And then I'm kind of writing that in as like one of my one to many, or maybe what is going to be a poster for call it like a month's period and in time. Today's show is brought to you by Titan X, which helps you connect with prospects instead of dialing into the void. So if you can make a hundred cold calls a day, but if nobody picks up, you are burning time. So Titan X literally guarantees you will triple your cold call, connect rate, or they will pay you $10,000. So the link in the show notes down below will show you that they match literally 5,000 credits for every 5,000 you buy. So check it out. I use it personally and it's a phenomenal way to get more conversations on the phone. Today's show is brought to you by Unify, which helps you prioritize the right accounts at the right time. Try this. Stack your tier one highest intent leads at the front of your morning dial block. So if someone signs up for a trial, visits your pricing page, dial them first before any other accounts before you open your Slack, your email before anything. Unify makes it stupidly simple to surface those tier one accounts automatically. Be built to guide with Unify on how to get 100% of BDR's to quota in 2026. Go check it out in the show notes. Today's show is brought to you by AirCall, the AI-powered communication platform built for sales teams. If you want reps to adopt AI, you have to be intentional about building AI skills. On my team, we wrap our weekly sales meeting with a five minute builder, where each week one person shares one learning that's helping them be a more effective seller. AirCall helps you by bringing AI into real customer conversations that reps are already having. So you can't help but realize the benefits. And we partnered with AirCall on a resource for building AI confidence in sales teams, which you can get free in the show notes. I think you have several really powerful yet not widely used techniques that you talked about like Postes versus Poster being a great example. But the another one that you do is this whole, I'm not going to tell you what to do. I'm going to ask you to tell me what you would do. And then I'm going to tell you why it's great or why it needs a little work. So how do you, like, and as a VP of sales, you're not always having that conversation. That conversation's happening between the manager and the rep. How do you get your managers to overcome that desire to just tell them what to do? I mean, I think you can sometimes clearly see where the manager is probably like overstepping to a degree in deals and or where they might be super wrapping things. Super wrapping. So it's trying to understand, again, to the point of like take the prep document, right? Like, are they all doing that or are they not doing it? So are they creating that that forced critical thinking? And then I didn't get into this in the takeaway, but the prep document isn't just for the rep. The idea is that the prep document gets shared at least 24 hours before the call and then you can asynchronously review it. So what I will do or manager will do is leave a bunch of notes in terms of a different way to free frame a question or to think about a problem. And then that rep can actually ingest whatever recommendations they like and embed it into their plan or they can disregard the things that they don't like. And so I think when you, for me, if I can start to review some of those and see how the manager is either challenging the rep or getting the rep to think, that's very helpful for me. So having that process allows me to kind of see some of those things. So you're kind of looking for reps that are going past being a manager and that's a sign for you that they're probably also telling reps what to do, not actually coaching, right? Correct. Yeah. I mean, you can look at a couple of other things, the calls that they support on how much are they talking versus how much is their rep talking. If I am being the executive sponsor on the deal, yes, there's a time and a place in which I need to speak. But my number one goal is actually really to not talk at all. I'm there as a layer of support. I'm generally not there to be the one leading the call unless we planned on that going in. So I think as long as you've got some infrastructure in place where you can semi review how your managers are interacting with the reps and the pipeline reviews and the one on ones through like documentation. And then secondarily, you have call, like we use attention, right? And I can go in there and actually digest some of the calls and they've got a great agent that can help me scrape what a manager is doing in the conversations that can help me figure out where to then coach that manager as well. What coaching or guidance do you give managers about how and when to get involved in deals? Because as a first time sales manager right now, I'm like, I really want to do risk our pipeline. And so I'm trying to like, I'm getting involved in deals and I probably am speaking up more than I should. I guess what coaching or guidance would you give me? The biggest guidance I would give you and I actually did that with one of the managers here and it helped them tremendously is much like we've got the prep doc for the calls that are happening. Something similar should happen for any call that you attend and you tweak the question, one of the early side questions and or you can just ask it to the rep is what is my role in this call? And it's up to them to tell you what that role is and again, it helps with the critical thinking and potentially where they need help. Risks might need to be talked about or or hedged against it during the conversation. And so I want that wrap or even for me, if it's the manager or director that's pulling me into a call, why am I coming? What do you need air coverage on? What do you want me to talk to? And then we we riff from there. A big theme I hear in how you lead Jason is preparation. Like don't show up to a call without the questions you should ask. Don't show up to a deal without a perspective. Show up to a deal review with a manager. If you don't have an idea about what you want to ask about, like how do you drive that behavior into your apps? Because you know, what do they say? If Abraham Lincoln, you gave him two hours of cut down at your ease, been 90 minutes sharpened in his acts or however it goes. At least for me, it's a process over the course of sometimes a couple of weeks to a couple of months of helping people understand the level of seriousness. I take around those things to the point of if we've had enough interactions that you know what my expectation is and you come to a pipeline review and you're telling me you need to update dates and next steps will cancel the pipeline review. Like this is not a good use of either one of our times. And so you set the expectation that you expect someone to come prepared, right? And you can only expect the types of behaviors that you tolerate. And again, but it's also an ownership level to make sure that you're putting the right processes in place for people to actually execute on your expectation or no your expectation. Yeah, I heard from one of my first VPs gave me this book and he said, "People, I'm sorry,
there's only three reasons people don't do their job. They don't know what to do. They don't know how to do it or there's something in their way. And as a leader, that's your job. This is how you do the job. This is what you do in this job. And is there something in your way I can get out of the way? And like, I think once you deal with that, then as we were talking about earlier, it was a lot easier than to say, well, how would you do that? 'Cause you're testing that the how you've already taught them aligns with the how that they're actually doing it. And you're always trying to find those, like misalignments. Well, listen, I know you have your way doing discovery, but do you see how it's different than Sarah's? Sarah's gets so much deeper. She follows our process. Like, let's get on the process. Try it a few times and see how it feels, right? - I like that. You're gonna steal the posters for me. I'm gonna steal that for me. Or for a mentor, whoever it was, but I think, and I like the simplicity behind it. Like, that's kind of the idea is you try to create these complex things and be able to articulate it in hopefully somewhat of a simple way that it can resonate or get people to repeat through the process. If you relate it to some of the post-it note stuff that we were talking about earlier and mark what you just referenced, I like to think of skill set development and coaching as a skyscraper, right? Like, you can't actually replace that post-it note on your computer until it's become embedded in the way that you work. Because the minute you take it off and put something bells on, you can't let that thing we just worked on actually disappear, right? So everything about building that skyscraper and all those different levels, are you building it on quicksand? And you're either giving them too much to focus on or you're making them change focuses too fast until they're actually really good at something. Or is it foundationally solid where now you can put something on top of it? - Jason, the clock is ticking. So we got to move to our final question here. So you've talked about a bunch of themes here, but I think one of the big ones that has stuck out to me is like the critical thinking, the diagnosis, the helping people help themselves, as opposed to you doing everything. And so my last question for you is, is what is the biggest mistake that you see sales leaders make when it comes to coaching or extending their impact around critical thinking that you think if they broke, they would be far more effective? - It's a difficult one 'cause it's something you talked about earlier. Nick is like, it's when and where do I get involved in a deal, right? Every deal is critical to the business, every deal is critical to you, to the rep, but there's gotta be a point where you are okay with somebody failing. Or you've gotta let them start drowning a little bit, let their head kind of bob under the water and back up before you kind of save them a little bit because once they sit in that pain a bit, I think it resonates a lot more. And so it's a tricky balance, but I think sometimes we fear, again, letting somebody fail a little bit, or we fear coming down on somebody if they're taking the easy way out. Again, I'll go back to the prep doc and yes, it'd be really easy to fill that prep doc out with some sort of combination of chat or clog, tied into attention, and it just like fill out for them, right? Even like that defeats the whole purpose. And so it's like, no, you can't do that and making sure that you're okay drawing that kind of hard line with folks. - Killer, Jason, thank you for joining us. Everybody stick around for a 60 second recap coming up soon. All right, folks, it's time for your two by two recap, Mark, what do you got? - Well, you don't gonna take posters versus post it. So I mean, that was, I know that's your phrase, and that's his idea, but I'm telling you, that was really, really good. And it's funny because a lot of times I'll tell somebody, listen, put the stick you know on the side of your screen right now, like otherwise you're going to forget. And so I think the idea that there's big things for lots of people that need to be broadcast widely, and then there's narrow, tiny things that need to get broadcast to just a specific person, and having that frame is a really good frame. That's number one. Number two, probably the most powerful management technique I know, don't tell people what to do, ask them what they would do, and then respond with the reinforcement of the process that they should be doing. Even if the answer's genius, if it's not aligned to the process, you're outside the consistency of methodology, you're creating inconsistent bad data, you will not be able to make decisions off of that data because it doesn't make sense because it's all different. So don't tell people, just take a second, ask them, see what they say, get curious, ask them what they figure, like take a second, what would they say? And then is it aligned or not? If it's aligned, let them run. If it's not aligned, you got a chance to correct. So my first one was the forward looking prep doc, whereas a leader, when you're working with your reps, you ask them to circle the three most important calls that they have that week. And on the prep doc, there is one rule. They are not allowed to use AI in putting this prep document together because, with your point, Mark, you want them critically thinking about how they're going to run that call. Jason goes down to the level of getting them to write out the specific questions they are going to ask based on what they know they need to get on the call. And this is where as a leader, you have an opportunity to annotate on that document to help coach them for the call that hasn't even happened yet, as opposed to retroactively being like, oh gosh, this one went off the rails. Now I need to go save it. So that was the first one. The other one that I had, this was like a really niche thing when it was around sizing the impact of something. And Jason talked about Unify, what he explained to us is like it's helping teams with pipeline building. And if a customer or prospective customer has a pipeline gap, you wanna understand how big that gap is. But Jason described it as gross to be like, oh, how's that impacting the business? How big is your gap? Instead, he recommended giving them a massive range from, hey, is the gap 5% to, is that gap 70%, which is ridiculous. If they have a 70% gap, they are in trouble. But by almost overshooting and giving this ridiculously bad scenario, it makes them feel more comfortable sharing if they have a 40% gap. So when you're sharing the sizing of impact, if you give a big range and give something that would be just like, hellacious, it primes them to be a little bit more comfortable sharing like the truth of how bad things actually are, which obviously helps you sell against. Party Mark, how can people help us out? - You know, 30 NPC got your back along with Unify. We've put together a little playbook. It's actually not a little, it's comprehensive. And it's how to get to 100% of your BDRs to 100% of quota in 2026. Come on, y'all, y'all want that. It's down in the show notes. - Thanks for listening, folks, and we'll see you next week. - Deal Velocity is a huge driver of win rates, which is why Armand and I partnered with the easy and effective CRM pipe drive to film a 60-minute video masterclass that covers all of the different ways that you can drive Velocity in each individual stage of your sales process. Literally from opening call, all the way to contract review, we documented our favorite tactics in this pipe drive and 30 NPC masterclass, which you can get for free in the show notes. - Today's show is brought to you by Consensus, which helps you demo keep selling even when you're not in the room. Before I show a demo, I set it up like it might have to work without me. I include these three slides before I drop in. Number one, the biggest problems I learn in Discovery. Number two, how we solve those problems. And number three, what does success look like today slide? You can steal that exact 30 NPC Demodeck template powered by Consensus, go check it out in the show notes. - Today's show is brought to you by Insightly. The CRM helps you spot deal risk early, so pipe reviews actually drive your number. One question I ask in nearly every deal review is, what do we need to get in our next interaction with the customer? If my rep can't answer that question, the deal has risk and I have something I can coach to. Now we built a guide with our friends at Insightly CRM on how to run pipe reviews that surface real risk and get deals moving again. and you can get it for free at the link in the show notes.
Podcast Summary
Key Points:
Focus on One Priority
Coach the Issue, Not the Outcome
Force Critical Thinking
Use AI Wisely
Start with Low-Hanging Fruit
Summary:
In this leadership episode, guest Jason, VP of Sales at Unify, shares three actionable tactics for sales leaders. " Second, he advises coaching the issue, not the outcome. Rather than telling reps to "book more meetings," break down the cold call process into stages (connect rate, opener success, pitch engagement, meeting conversion) and coach the specific weak point.
Third, he stresses forcing critical thinking by having reps manually complete prep documents and type in their own KPIs, resisting the temptation to let AI do all the thinking. Jason warns against over-indexing on AI for tasks that require deep understanding—for example, never use AI to summarize a call you didn't attend; listen to the full recording to catch nuance. The conversation also covers how new leaders should prioritize: focus on key metrics, start with the lowest-hanging fruit, and build trust by working on areas the rep wants to improve.
Hosts Nick and Mark relate these ideas to their own experiences, emphasizing the need to solve one big problem at a time rather than spreading efforts thin.
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