Finish-line coaching during crunch time with Mark McWatters, VP of Sales, Ambition

Devin Reed: Welcome to the show. You are now part of Reveal, the revenue intelligence podcast powered by Gong. We're your hosts, Devin Reed.

Sheena Badani: And, I'm Sheena Badani. Revenue intelligence is a new way of operating, based on customer reality instead of opinions. It's an unfiltered view of your customer reality. In other words, making data driven decisions based on facts instead of opinions or guesswork.

Devin Reed: And, it's made up of three success pillars. People success, deal success and strategy success. You know, the things all revenue teams need and care about. Every week, we interview senior revenue professionals, and they share their stories and insights on how they leverage revenue intelligence to drive success and win their market.

Sheena Badani: You'll hear how modern go- to- market teams win as a team, close revenue with critical deal insight and execute their strategic initiatives. Plus, all the challenges that come along with it.

Devin Reed: Sheena, by the time this episode goes live, we are in the thick of holiday selling season. People are closing out their quarters, people are trying to close out their year. They're booking road trips, plane rides. It's a hectic time for salespeople.

Sheena Badani: It is, it is. You have a lot going on personally, too, with the holidays, and planning and family. You're getting pulled in so many different directions. It's a crazy time.

Devin Reed: As a human being, it is stressful. In a good way, sometimes, but like you said, there's a lot of plans, a lot of people, a lot to do. And then, also professionally, there's a lot to do, all at the same time and it can be very challenging. Holidays are supposed to be about cozying up by the fire, but often times, for sales leaders, it's putting out fires.

Sheena Badani: Yeah, that's so true. I like that.

Devin Reed: That's why we wanted to hang out with Mark today, he's the VP of sales over at Ambition. And, what's cool is it sounds like a coined term, like a marketing phrase, but it just came up in our call when we were talking about what should we cover, given the time and where people's brains are going to be at. He was like, " Why don't we talk about finish line coaching?" I was like, " I don't know what finish line coaching is, but I also know exactly what finish line coaching is, based on the context." What we chatted with him about was, essentially, how does coaching change when you get into crunch time or end of year. And also, specifically he talks through how you're one- on- ones should shift. What you should focus on, what you should not be worrying about and it was really interesting, because as a sales rep, you feel these things, your priorities shift and your mindset changes. But, it was really cool hearing from Mark, he embraces it, he acknowledges that and he has a game plan for it.

Sheena Badani: Exactly. It's like what's the role of a leader during that crunch time, at the finish line. How can you be supporting your team, across the various capabilities that they have. You're looking at your A players, how can you be supporting them versus folks that may need a little bit more support. I thought it was a really, really great conversation. And actually, a lot of, also, tactical tips that you could take out for your one- on- ones. Specific questions to ask in those coaching sessions and things like that.

Devin Reed: Yeah, nice and tactical on this one, and I enjoyed that. Gong, we're all about sales coaching. Ambition, also about sales coaching. We're official partners. This was a match made in heaven. So, really looking forward to the conversation, hope you listeners are, too. Let's go hang out with Mark. Mark, I am thrilled to have you on the show. It had been years since we last connected, before the show so I'm glad that we've reunited.

Mark: Same here. Good to see you. And, a very different place than our original meeting.

Devin Reed: Which leads me to the unscripted question I'm actually going to open with, is do you remember when and where we first met a few years back?

Mark: I do. We were really big deals, working a really tiny conference in the basement of a terrible hotel in San Francisco. I remember Gong and Ambition having little fold out tables next to each other. There wasn't a whole lot of activity at that conference, so what do you do? You just wander over to the table next to you and hope that that guy or girl is working a similar deal that you ares so you can trade notes and try to figure out if you're the priority or he is. So yeah, wandered over to the Gong table and there you were.

Devin Reed: Yeah. We were just hanging out. And, funny because it was one of those dark, dingy rooms that you're excited to get to the conference, and you open the doors and you see what you're working with. And you're like, " This is not going to be a super fun day, is it?" But you know, you've got to earn your stripes and work your way up. Sure enough, Gong and Ambition has done that. And yeah, I remember it fondly. I'm like, " Hey, I don't know if Mark's buying from me, but I got a cool guy I can talk to."

Mark: I remember when I first saw that you got your current role, or maybe the role before. It wasn't an AE role and I was like, " Wait a second. That was the dude that I met at the conference and we were spitting deals. I didn't know he had left sales." It's funny how things change over the years. But, pretty cool that we're here now.

Devin Reed: Absolutely. And, we are here today to talk about how to close out the year with finish line coaching. To break the ice some more, even though I think it's melted, I like this quote that's on your LinkedIn. It says, " I lead a high performing, straight shooting sales team, full of A + people." I love the word choice there, by the way. Which made me wonder, what have you learned about coaching teams of A players over the years?

Mark: Well, the first thing about coaching a team of A players is you have to get out the way. If you hire good people, especially in a stage like Gong or Ambition where it's growing really quickly and sure, you're giving them some guidelines on what right looks like, but every time you hire, you're trying to level up who you bring in. When you bring in A players, you have to trust that they're bringing something to the table that you, as the leader, may not. So, how do you give them the tools to be successful, but at the same time step aside and let them run a little bit? The first thing about coaching an A player is learning how to humble yourself and allow them to figure out what right looks like, inside of what is your ever evolving process. The second thing on an A player that I've certainly learned is they very much value their development. I think there's a misconception that, " Oh, the A player just wants to run free and never talk to their boss and hero sell every deal." My experience is your A player, if they're going to consider leaving, they're not going to consider leaving for more money. They're going to consider leaving because they can get developed further. They're the continuous learner who is trying to break your system to improve your system. If they feel like they can go somewhere else and learn from someone else, that is a threat. So as a leader, you have to be self aware enough to know, " Okay, can I continue to develop this person in said area? Or, can I find outside ways to get them development, continue to pour into them and keep them at the top of their game?"

Sheena Badani: Clearly, coaching is a big part of your day. You specifically talk about finish line coaching. Can you tell us what exactly is that? And, what is the role of finish line coaching, particularly at the end of the year?

Mark: This is the time, our fiscal ends with the calendar. Be it mid- November, week before Thanksgiving, this is crunch time for your forecast and is the contract out, is there enough time. The one- on- ones here at Ambition are very focused on helping reps get unstuck. I think end of year coaching really has to be focused on the deals in flight and where the rep feels like they may be potentially stuck. The way that looks here is, " Give me an example of where you're stuck. What have you already tried, to get unstuck? What would you suggest I do to help you get unstuck now?" It's just, " Hey, I'm stuck with Gong. I've already tried to go to Devin, but he's not responding to my calls, emails. You might help me because I saw you're connected to Sheena, from your days working at X company. Do you mind sending Sheena a note on my behalf, or calling her?" And again, this goes back to A players, is even A players are going to get stuck. They're also going to try something, before they get to you, or they should. And then, you as a leader have to think, " Okay, how can I use, even if it's just my title... " As lame as that sounds, it works. My connections. We had one the other day, for a quick story. We have a rep who's really late stage with a ride sharing company you've all heard about. He was stuck with IT. I messaged another sales leader, that is in the sales marketing space and just like, " Hey, do you guys by chance work with this ride sharing company?" He's like, " Yeah. This is the rep who closed the deal." So 48 hours later, the reps are both talking to each other. And our rep is able to ask him, " Hey, did you see a similar hurdle? How long did that take? What might you recommend?" And then, the reciprocating of, " Hey, who are you trying to get right now? Is there anybody that I've been working or closed in the past that I can help provide guidance?" I think a misconception is leaders think, at the end of the year, they have to have all the answers. The reality is part of the job as a leader is to leverage your network to help unstick parts of the deal. And you may not have the lever in each area where someone is stuck, but someone else on the leadership team might, someone in your professional network, like the example I just gave, might. And again, being able to take a little bit of your ego as the sales leader who knows all, and you definitely don't, but being able to take a step back and say, " Okay, if it's not me, who is it? And, how do I help connect the dots?"

Devin Reed: Well, that's a big difference. There's a different between coaching or knowing the answer and getting a rep there, versus connecting. Which is putting them on the right path or guiding them to, like you said, the right resource. It sounds like, maybe it's just most recent or one of the more common ones, is that path. How can I help you source the right information, to get a deal unstuck and guide you. Are there other scenarios that you run into commonly, of helping reps get unstuck at the finish line or maybe even specifically for end of year?

Mark: So end of year right now, what you see a lot is that, to use you all as the example, Devin wants to buy Ambition. But Devin knows, in order to get Ambition purchased, he needs Sheena in IT to approve the timeline. Well, maybe Sheena approves it, maybe she doesn't, but procurement is involved and procurement says, " Hey, Devin, it's November 18th. We need to wait until mid- December to have this conversation because we work in software. We know software, buying end of year is the time. So I know you have this great relationship with Mark, but let's just let this coast for a minute and let's see if we can position this later in order to find a better deal." So sometimes, getting unstuck is having been there enough to know that, " Hey, Devin has told us that he's going to buy Ambition. He's told us how this process works. He's also told us that procurement, he doesn't have a whole lot of control over and that, ultimately, his job is just to get us to that point." So as a sales leader, there are times... This sounds counterintuitive to what maybe most sales leaders' advice would be. But, where you're having to tell the rep actually to chill, we're okay, " I've seen this play before. That conversation is coming, time won't kill this deal and let's just sit tight for a minute because Devin is a great champion, he's told us everything. He's trying his hard as we are to get this thing done so let's wait for the next step. It's okay."

Devin Reed: It almost sounds like recognizing you're actually not stuck.

Mark: I think every rep... We're trained, be the biggest critic of every deal, find every hold in your deal. And, that paranoia, I like to push back on that. Okay, the best salespeople I know aren't the ones who protect every ounce of risk in the deal, the best salespeople I know are the ones who think, " How do I get this done?" Not, " How will it not happen?" So yes, have that healthy amount of risk, but to your point, Devin, sometimes you're not stuck. Sometimes, this is just enterprise software sales. And, the fact that 10 days went by between steps isn't the most uncommon thing, this late in the year, when a buyer's trying to create leverage.

Devin Reed: We both know that end of month, end of quarter, end of year are all a big deal, no pun intended. The Harvard Business Review shared a study affirming our focus on not just finishing, but finishing strong. HBR said that salespeople close three times as many deals at the end of the month as they do during the rest of the month. The big surprise, they also lose 11 times as many deals. Why does this happen? It's pretty straightforward. The volume of deals increases but the overall win rate plummets. As a sales leader, this data matters because it means your team might need more support to close deals during crunch time. Let's get back to Mark, as he shares ideas on how to help your team finish the month, quarter and year strong.

Sheena Badani: I wanted to connect the dots a little bit, between how we started the conversation, which was about coaching A players, which sounded like it was much more around learning and development and getting those opportunities versus the finish line coaching, which in some ways, maybe it's a little bit more hands- on or tactical. It's problem solving, in the moment. Do you see those as two different things? Should some of that developmental coaching be happening in the beginning of the year? Is there a better time for it? Just walk us through that a bit.

Mark: Let's just use a finish line coaching session with an A player. My first question is always what have you already done, and then actually, what do you think we should do. " You've thought about this a lot more than I have. What suggestion do you have?" What I find, often times, is they're typically right. If they're not right on what we should do, they're really close. They're saying I should email that person versus you should call that person. With an A player and that finish line coaching, there's the ability to let them lead themselves to their own outcome and there's a trust there that you may not have a B or a C player in late stage. I am definitely guilty, with a B or C player, of when they ask me what to do, I just tell them exactly what to do. It's shortsighted, to be honest. It's more like, " I don't have time to go through the 20 minutes of self discovery to get you where you need to be. Go call Sheena right now and this is what you should ask her." This time of year, I justify it because every minute matters. Whereas if this is in February of next year, I'm going to approach it with the 20 minutes and trying to develop the person in way where they get their own answer next time, without having to come to me. One of the biggest signs of a weak leader, in my opinion, is the leader who has to approve and have every conversation about every day with their rep. If you're hiring good people, you have to trust them to run in these deals. Give them, again, the guidelines of how they can work. But, if you're ultimately have to approve each next step, how that next step is set or communicated, that means you haven't enabled your team in a way that they can operate on their own. What happens when you go on vacation? Or, what happens when you're suddenly out of the office? You need to build a team that can run itself. The only way to do that, really, is to create the self discovery. But, Sheena, Q4 finish line coaching, B or C player, I'll definitely jump on the fact that I directly tell them what to do very quickly.

Devin Reed: So, Mark, everyone has their one- on- one outline plan, maybe it varies from like you said, A players or rep to rep based on what folks need. But, I'm curious if your one- on- ones change as holiday season, holiday selling, crunch time. If it does change, how? How do your one- on- ones change during that time?

Mark: I'll tell you about my standard one- on- one, if you will, and then I'll tell you what it looks like in mid- December. The standard one- on- one here, on my team, it's usually five to seven questions. I have all my one- on- ones on Mondays and Tuesdays, I try to stack them at the beginning of the week. They're 45 minutes, on purpose, so I have 15 minutes to create whatever action plan or deliverable that needs to happen afterwards. But, in those five to seven questions, it usually starts with last week's highlights and low lights. I want to know what happened last week that you really felt like was a success and what was really disappointing. Then, I have them call out a deal in what we call is a champion's choice stage. What that means is that someone internally is trying to buy Ambition at said company. In that deal, I'm asking them what they like and what concerns them, and how I can help them in the deal. So really, there's four questions around one deal in that one- on- one. So you've got the highlights, low lights, your calling out the deal, the four questions. And then, at the end I'm asking, " What else?" My standard coaching session really revolves around highlights, low lights, picking apart a deal and how I can help them. Making sure they're seeing it through the right lens. And then, at the end, letting them bring whatever else they would like to talk about. The reason I think this works is it is mostly rep led. While I'm providing the questions, they're the ones who have written the answers. When we come to the one- on- one, I've already seen it, I've had a chance to think about it. We get right to it. But, the way that changes when you get into late December, as I've already alluded to a little bit around getting unstuck, is that in late December, all you need to talk about is the deals that are going to convert in December. You don't need to talk about last week's highlights and low lights. All that rep is thinking about is the three deals that he or she has dated December 31st. Which, by the way, don't date them December 31st, date them December 17th, that's the Friday before Christmas. But, they're focused on those deals and you need to ask them why those deals might not close. If it's that late in the year, you do need to have the approach of what risk still exists. Now, earlier I said be about how you get the deal closed, that's how I feel through, call it 80% of the deal. But, when you're there at the end, you need to be thinking about what possible risk still exists. So in the one- on- one in mid- December it's what do you still forecast here, at the end of the year. List each deal, what potential risk you see. How can I help you minimize that risk? Or, anyone else in the company. Because also, mid- December, I hope that anyone will help you get that deal across the line. I'm talking from a medium size company. But, is it your head of product? Is it your VP of CS? Our CEO is like, " Sign me up, put me in whatever conversation you need," and I imagine Gong's is, too. So when you talk about what's left, what risks still exist and who can be involved in that, you're de- risking the deal for the rep, in a way, because you're telling them, " Hey, do not lose by yourself if you're going to lose. Get me, get the CEO, get head of product, whoever it is, so we are throwing every possible touchpoint to make sure this future customer knows how important their business is to us." So we sell to salespeople, predominantly. The last thing I'll add in on this late December deal that kind of gone cold, it's making you nervous, the first thing you're thinking about when you wake up in the morning. What I find myself constantly coaching sales reps on is just humanizing the last ask. We sell to sales leaders. If Devin's the CRO and he's the one signing this, ask Devin if you can forecast this deal in December. Tell Devin that your CRO, which is not me but my boss, asked if we could count on said customer to execute in December. Mention that you just got out of your one- on- one with your boss and your boss asked. Everyone has a boss, every salesperson has a quota. Since we are selling to salespeople, you need to use those powerful questions that they fully understand as a weapon, frankly, to get honesty and know if you can or cannot forecast in December.

Devin Reed: I think you can just tweak the question, if you're listening to this and you don't sell to salespeople. It could be, " Hey, I was just talking to my VP, Mark, and we were talking about your account, Sheena. He wanted to know if there's anything missing that would prevent you from moving forward this month. Or, do you have everything that you're looking for? Are you fully taken care of?" You can make it about them while also mentioning, " We do have this forecasted for you to become a client this month. Mark wanted to make sure you have everything you need. Is there anything missing?" And then, you also start to unravel if there's any hidden objections in there.

Mark: We do a lot of business in enterprise, just call it 1000 plus employee accounts. In those types of deals, where the obstacles are seemingly 10 X the mid- market or SMB deals, we'll talk about board level deals. " Hey, this partnership is being discussed at board level." That carries a gravity to it that is very real, let me tell you, as the VP of sales. But, it also carries to the gravity who's considering the investment. Nobody is trying to make you look bad in front of your board. No one is actually attempting to do that. So if you can use that kind of language in a larger opportunity, it can also be really helpful for, again, humanizing the ask. Because then they're thinking, " Oh man, Mark's got to talk to the board about this and I know this deal is going to happen or isn't going to happen. Let me pick up the phone and give him some more clarity."

Sheena Badani: So, Mark, you've probably seen a variety of a quality of coaching, from amazing coaching to folks who maybe could be doing a better job. What do you see that sales leaders often get wrong, when it comes to coaching?

Mark: Their one-on- one is a manager talking at an employee. The manager is the know- it- all who has every answer. I have made this mistake. I started my career at AT& T and led retail teams. And, was working with a lot of people in their first sales job. I was very much, " Okay, you've got 30 minutes with me. How much knowledge and wisdom can I give you in 30 minutes about how to be a better salesperson?" And then, they would walk away and probably think, " Man, who is this kid?" So I've made that mistake, and now as a sales leader, especially working with a higher quality salesperson, if you will, there's so much value in the rep led conversation. And, that's how people remember what they took from the coaching session, right? People remember what they say. So how do you get them talking about the most important priorities? How do you make the next move their idea? That's how you begin to scale a team who knows what they're doing, whether you're around or not.

Sheena Badani: How did you realize that you were maybe doing it wrong yourself, in those AT& T days?

Mark: I had a boss who had been around the block a few times. What's funny about that is I wanted to show her how great I was at one- on- ones. And so, she came and did a skip level, but it wasn't really a skip level because I was there and I'm having these conversations. Y'all, I thought I was God's gift to AT& T retail when I was 22, which is so not true. And at the end, she pulls me aside and she's like, " Mark... " She gave me the old S sandwich, if you will. Of, " I really like your coaching. Do you realize they don't talk at all? The story's performing, but imagine if you led them this way." That was an eye opener for me. I had always been the type A person who made their own plan and had the answer. And, that was how I had gotten to where I was, I guess. And, learning that man, it's so much more powerful if you let them bring the idea and most of the time, they bring the right idea. Especially as you continue to do it, because they start to put themselves through the thought process before you even get there. That was a big moment for me. And, it allowed me to free up time because now, I didn't need to answer every question.

Devin Reed: Well, the other thing too, is when you let them provide that answer, even if you think you do or if you do have the right or the best answer, by letting them provide it you can scale where they are, in terms of how educated they are. If it's, "Oh, I was way off," I know where you are and how to coach you to get to where I need. Or if you're 5% off, you basically got it exactly right. I think that's a good way, also, to evaluate where folks are at and where those skills gaps or critical thinking gaps could be.

Mark: We do quick call debriefs here. So if we're in a demo and we hop off, there's 100% chance myself and the rep are going to do a quick debrief. It's really two questions. What went well? And, what do you think you could do better? And then, I will give some feedback on if they didn't present what they think they could do better. What happens every time is they talk about what went well, and then they basically tell you, " I know what you're about to say. That one part where I talked about pricing and just kept talking, I should have just stopped." You're like, " Yeah, Devin, you're getting it." Here we go, we're starting to stack some of these development conversations. When they're coaching themselves, that's a huge sign that things are moving in the right direction.

Devin Reed: Because the next step is they just do it. It's being told, then telling you, " I know I should have done that," and the next one is just doing it. It definitely levels.

Sheena Badani: Mark, we're going to ask you one final question, which we ask all of your guests. Which is how would you describe sales in one word?

Mark: My one word is people. At the end of the day, I love process. When we're scaling companies, we all obsess over process. But, the reality is sales is still very much a people game. It is solving a problem. It is taking care of a pain for a person or persons. And, while I know there are a lot of people out there who think, " Oh, sales, eventually it'll all be automated and then I won't have to talk to that person." Get out of here. It is a people game. And, I think it'll continue to be the way sales teams differentiate themselves, is through really good people who tell them how it is, whether they're a great fit or not a great fit. Trusted advisor is so overused, but it is a good description of the best salespeople are able to make suggestions that improve upon what they're already trying to buy. For better or worse, I will die on that hill, that it is a people game.

Devin Reed: Every week, we bring you a micro action, something to think about or an action you can put into play today. As we approach the end of the year, it's especially important to minimize deal risk. And with the busyness that comes in the season, you need to make every second count. If you only do one thing after hearing this conversation, do this. Try using Mark's end of year questions in your final round of one- on- ones. As Mark shared, you can one, make a list of deals you're forecasting for the end of this year. Two, add potential risks that you see for each deal. And three, brainstorm how you, manager, can help minimize that risk. These questions will narrow your focus to what matters most at the end of the year. It'll also help your people learn to coach themselves so they can continually improve. Did you like today's episode? Subscribe now so next week's episode will be waiting for you on Monday.

Sheena Badani: And if you really liked the podcast, please leave a review. Five star reviews go a long way to help get the word out there.

Devin Reed: And if you're not ready to give a five, check out another episode and see if we've won you over by then.