34 min read
Sales Coaching Done Right: Game Footage, Role Plays, and the Mindset of a Great Coach With Chris Duprey
George B. Thomas
Sep 13, 2025 4:59:51 PM
Let me ask you a simple but powerful question. Do you spend enough time coaching inside your organization? Not just telling your sales team to “sell more,” but actually rolling up your sleeves to guide them, develop them, and help them flourish?
If the answer feels like a shaky “maybe,” you’re not alone. Most leaders underestimate the importance of coaching. They assume performance problems mean their team just needs to “work harder” or “make more calls.” But the real issue usually lives somewhere deeper, hidden in the way we listen, observe, and coach.
That’s where game footage, role plays, and true sales coaching come in. And to unpack this the right way, we’re drawing insights from Chris Duprey, a U.S. Army veteran, leader, and sales coach with two decades of experience inspiring people to grow.
So let’s get into it.
What Is Sales Coaching and Why Does It Matter?
Here’s the reality. Too many organizations confuse leadership with pressure. They push sales teams to perform but never pause to actually look at what’s happening on the front lines.
Sales coaching is about shifting from assumption to observation. It’s not just about telling your reps to sell more. It’s about:
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Watching sales calls like game footage.
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Identifying real challenges.
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Providing training and guidance that address the root problem.
Without this, leaders end up shouting instructions from the sidelines without ever seeing the play. Coaching makes sure you know what’s actually happening before you try to fix it.
Why Game Footage Is a Sales Leader’s Secret Weapon
Think about sports for a second. Can you imagine a football team refusing to watch film from their last game? Of course not. Yet in sales, so many companies skip this step entirely.
Recording and reviewing sales calls — your team’s game footage — unlocks three big wins:
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You see the difference between what you think is happening and what’s actually happening.
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You can provide specific, actionable feedback instead of vague “good job” or “that was bad” comments.
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You create a shared library of real-world moments your whole team can learn from.
Tools like Gong, Chorus, or even HubSpot Playbooks make this easy. And if budget is tight? A spreadsheet and a Zoom recording button still get the job done. The important thing is to start watching.
Role Plays: Turning Cringe Into Confidence
Let’s be honest. The word “role play” makes most salespeople break out in hives. We’ve all seen it go sideways — awkward, unrealistic, even downright goofy.
But when done right, role plays can transform your sales culture. Here’s how to make them work:
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Use real scenarios. Don’t make things up just for fun. Practice real upcoming calls or replay a tough one from last week.
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Prep the “buyer.” Give the role player the same background info a real buyer would have.
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Pause for learning moments. Stop in the middle, give feedback, and keep going.
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Define good feedback. “That stunk” isn’t helpful. Specific and actionable comments are the goal.
When role plays follow these rules, they stop being dreaded exercises and become training sessions your team actually looks forward to.
Reviewing Calls Without Falling Into the “That Sucked” Trap
Most of us watch a sports game and sum it up in two sentences: “That was great” or “That was terrible.” But a coach doesn’t stop there. They break it down play by play.
The same is true in sales. Reviewing a call means looking for specifics:
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Did the rep pitch before understanding the buyer?
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Did they ask follow-up questions that dug deeper?
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Did they uncover a real problem worth solving?
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Did they earn a clear next step?
Whether you use a formal scorecard or a simple checklist, the goal is to move past surface-level reactions. Good feedback isn’t about judgment. It’s about growth.
What Makes Someone an Effective Sales Coach?
Not everyone is built to be a coach. A true sales coach needs curiosity, empathy, and the ability to communicate with clarity. They aren’t dictators barking orders. They’re guides helping others sharpen their skills.
The best coaches:
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Stay curious about buyers, the business, and their team.
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Blend different sales methods into what works for the organization.
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Lead with empathy, building trust before pushing for improvement.
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Inspire confidence, reminding the team they’re already good and capable of becoming even better.
Think Top Gun. The pilots were already the best of the best, but they showed up to flight school to become even sharper. That’s the energy a great coach brings to sales.
Strategies and Tactics You Can Use Right Away
If you’re ready to put sales coaching into practice, here are a few immediate steps:
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Redesign your sales process to be buyer-centric, not just internal box-checking.
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End every call with the next meeting booked, not just “I’ll send you an email.”
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Train reps to ask second smart questions that go deeper than surface-level answers.
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Build role play sessions into your regular schedule, using real-world scenarios.
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Record and review calls every week. Even an hour of footage makes a big difference.
These aren’t theory. They’re practical habits that create lasting results.
The Common Pitfalls to Avoid
Here’s what derails sales coaching faster than anything else:
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Believing top performers don’t need coaching. They do. Even Tiger Woods has a swing coach.
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Avoiding recording because “buyers won’t like it.” They will, especially if you explain why.
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Giving generic feedback instead of actionable coaching. Vague comments don’t move the needle.
If you can avoid these traps, your coaching will make a lasting impact.
The Role of AI in Sales Coaching
One of the biggest excuses leaders give is, “I don’t have time.” That’s where AI comes in.
With tools like ChatGPT, you can:
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Generate role play scenarios tailored to your team.
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Create buyer personas instantly for practice.
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Analyze calls for patterns and missed opportunities.
AI won’t replace the human element of coaching, but it can save you hours of prep and give you sharper insights faster.
One Big Takeaway
Sales coaching isn’t about shouting “sell more” from the sidelines. It’s about watching the game, breaking down the plays, and guiding your team to grow as world-class communicators.
If you don’t know what the real problem is, you can’t fix it. Coaching reveals the truth, builds trust, and equips your team to flourish.
So here’s the question for you: are you ready to stop assuming and start coaching?
Sidekick Strategies Expert Interviews
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Show Transcription
George B. Thomas (00:01.128)
All right, I have a question for you. Do you spend enough time in your organization pertaining to coaching? This could be sales, service, marketing, heck, it could be coaching yourself or any team in your organization. But let's get real specific. How are you coaching your sales team? Hey, you know what time it is. Welcome back Hub Heroes. Today we're talking about
game footage, role playing, and being an effective sales coach with Chris Dupree. Chris, how the heck are you doing today, brother?
Chris Duprey (00:35.774)
I am awesome, man. I'm so happy to see you, so happy to talk about this.
George B. Thomas (00:40.144)
Yeah, it's going to be a fun conversation for sure. Now, Hub Heroes, just so you know, Chris Dupree brings over two decades of multifaceted leadership experience from both the military, let's go, and the business world. Driven by a desire to inspire and develop others, Chris is a high energy, you'll find that out through this entire interview, high energy leader, always working to better his team.
and their clients. An Operation Iraq Freedom and Operation Enduring Freedom veteran, Chris has held numerous leadership and staff positions while serving as an infantry officer in the US Army. Let's go! The highlights of Chris's military career was serving as the commander of D Company. See where we're pointing here. By the way, if you're listening to this and you can't see the background, you should go to the community and watch the video. Anyway...
D Company, 1st Battalion, 504th Parachute Infantry Regiment, 1st Brigade Combat Team, 82nd Airborne Division. The pedigree is large. The pedigree is dope. Chris has a BA in Liberal Studies from Thomas Edison State College and an MS in Organizational Leadership from... Chris, how the heck do I say that university?
Chris Duprey (01:54.51)
Quinnipiac University.
George B. Thomas (01:56.272)
I'm glad I didn't even try. While working to inspire and develop his team, you catch him writing music and jamming with his band. Now ladies and gentlemen, let's get into the good stuff. Chris, one of the things I love to do on the Sidekick Strategy Show is really level set. So people that this might be their day one can kind of understand, okay, moving forward, the conversation that George and Chris is having today, it's based on this foundation.
Chris Duprey (02:13.774)
Mm.
George B. Thomas (02:23.836)
So Chris, can you explain in your mind what sales coaching is and why it's crucial in driving better results for sales reps and organizational success?
Chris Duprey (02:35.554)
Yeah. So George, I think that a lot of organizations feel, especially today, but they feel this pressure of sales needs to perform better. And a lot of the time it comes back to sales, even if it may be a marketing issue, maybe whatever, like we go to our revenue producers, our revenue generators. Right. And so the problem that we keep hearing is
Sales leaders or leaders of the companies say things like, we just have to sell more, but they don't know how to get their folks to go do it. Right? And so when I hear people saying that, the first thing that I talk about is, well, have you watched any sales calls recently? And most people give me that look like they don't know what I'm talking about. And so what ends up,
Becoming the problem is we feel like we have a sales problem. We aren't leading the sales team correctly, not because we're negligent, just because we haven't thought to. And so when we talk sales coaching, it's helping the overarching business leaders, you know, if we're talking to SMB, that could be the owner, the CEO, understanding that
You may not even know what the actual problem in your sales organization is today, or it's that VP of sales and just helping them by uncovering problems, looking at what's happening, and developing training to fix those problems.
George B. Thomas (04:18.78)
Yeah, I love this so much. The idea of spending time on what's important and understanding what your team is saying and being able to actually coach them through saying it better or thinking about it differently. And the amount of companies out there that don't have a tool that gives them the ability to actually record game footage and then watch said game footage is absolutely mind blowing. Now, Hub Heroes, I brought my set of questions. But as your watch.
this. If you do have questions on anything that Chris brings up, make sure you put it in the chat pane. I'm keeping an eye on that. I'll ask questions along the way. Also again, if you're listening to the podcast version of this and you wish you could interact, yes we do it live and yes you could be watching the video at community.hubheroes.com. But Chris, let's continue down our journey. We try to do things, right?
Literally on what I said, somebody might go get a tool, they might start creating game footage, they might start watching the game footage. But Chris, what are some common challenges that sales teams face regarding this whole sales coaching? And the more important question is, how the heck can they overcome those challenges that you're actually gonna talk about?
Chris Duprey (05:34.154)
Yeah, so it's a great question. So how do they overcome them? What are those challenges? The biggest piece is they've likely been taught to sell from a pitch-first mentality. So think about every SaaS organization you've ever dealt with. And SaaS folks, I love y'all. And at the same time, a sales interaction with a SaaS platform.
is one of the worst buying experiences ever, right? And if you're saying, well, Chris, why are you saying that? Think about it. You show up as the prospect and they might ask you a little bit about your business and then dive into a pitch, right? And now they're pitching, and things aren't going that great. So the first thing as we get into this training is like looking at sales process from a, what are we trying to do on?
call one through whatever. Right? And so as we start, there's this.
What is the purpose of discovery and how, like what are the things that a buyer needs to, quite frankly, self discover or have to actually make a purchase, right? And so that's the first thing, because George, as we think about, especially as I think about sales, you lose on the first call.
So you might lose, you might actually get told no three calls down the road. But if you have an amazing first call.
Chris Duprey (07:17.214)
you're likely gonna get there. And an amazing first call is, you've asked more questions than they have. You've probably only talked for about 40% of the time. And they have a legitimate problem, right? And so the hardest thing to get sales folks to understand is, if your buyer doesn't have a legitimate problem that's worth solving,
You could have the coolest thing in the world. Nobody's gonna buy it.
George B. Thomas (07:52.116)
I love this so much. Chris, you're talking about the pitch first.
And it's funny because my brand, I like to kind of simplify things as we're on this podcast. You know, you'd be far better served if it was people first. Right. Like getting to know them, actually being able to sell yourself before you even try to sell the product. You might even be better off if it's a problem first approach. Now, imagine a people and a problem first approach versus that pitch approach. But here's the thing, Chris, because we're talking about game footage.
about hurdles that they might face. This brings in, if you have that game footage, if you understand the hurdles, why didn't we make the touchdown? Well, this is something that teams do. They go out and they practice.
They actually go out in the field, they throw the dang ball around. So I wanna get into probably what will make people break out in hives when they hear the word, but I wanna talk about role plays. And so I'm gonna ask you the question, could you share some of the best practices for what sometimes feels like, I don't wanna do that, or why do we have to do it? What are some of the best practices for conducting effective, very key word there, sales role plays and how sales teams can utilize this technique
Chris Duprey (08:53.122)
Yes.
George B. Thomas (09:11.762)
sales team's performance over time.
Chris Duprey (09:15.306)
Yeah, so to start, you have to get everybody in the same head space. So we've got to address all the reasons that people don't like doing role plays. And so one of my favorite things to actually do is to show that clip from the office when Michael makes Dwight role play with Jim. The thing is, is it's not far from
a lot of people's experiences with role playing, right? Where everybody just goes off the hook and is just plays the fool because it's fun. So we gotta show that and talk about what makes role plays not effective. Then we gotta talk about what makes them effective, right? And common things come up. People will say that they're not realistic. Okay, so how do we mitigate that George? We use real life scenarios, right? We can either use
game footage from the week, the month before of a client issue and highlight something and go practice that. Or what do you got coming up? Let's practice that discovery call that you've got two days from now with ABC Corp. Right, so we make it real. So that's the first step. The second thing is you have to tell the person role playing the buyer.
what you want them to do as the leader, right? So as a sales leader, you've got, you can't just say, okay, be the prospect. You have to give them, hey, if it's a real person, here's the actual activity they've done on the website. Here's all the info that Sales Rep has or you make up a background because you're trying to test something, not simply throwing your sales team into the wind, right? So there's some structure to it.
And then you execute it, right? And as we execute it, we stop it when there's learning moments. We get everybody's feedback, the good and the bad, and we specify what, what good feedback is, right? So we say that everybody will, everybody would be willing to take constructive feedback, like if you're not willing to take constructive feedback, you've probably got bigger issues, but we define that.
Chris Duprey (11:42.786)
as it is specific and it's actionable. So saying that stunk, neither of those things, right? Just like saying, Hey, that was great. Isn't specific or actionable. Specific or actionable is, Hey, when you started the call, you gave the prospect the opening to take control of the call. Next time.
get into it by asking them a focused question that actually leads us down the path we wanna go.
That's, so for role plays, if you just do those things, right, use real scenarios, prep the role player and give constructive feedback, role plays don't suck then, George. They actually become the lifeblood of your organization. So I've got a company that I've been working with in all places in New Zealand, two of them. I actually have two sales, training and coaching clients in New Zealand.
We role play every other week and they get into it and their team brings up things that didn't work to go fix. So we're not like playing nice. They're going, I just had the worst sales call in the world. Here's what happened. Can we role play it so it doesn't happen again?
George B. Thomas (13:11.54)
I think this is so interesting, first of all, just because this idea of bringing what didn't work to light
instead of what I feel like many organizations do is they try to sweep it under the rug. Like, hey, let's forget that we had that call. It was a catastrophe. The other piece is I'm actually kind of amazed how much that question and the last part of your answer feeds into the next question that I wanna ask you. But let me put a caveat to that. When you were talking about, well, that sucked, like just a general statement, I feel like many of us can watch, we'll just say a soccer game, football game, whatever,
Chris Duprey (13:22.626)
Mm-hmm.
George B. Thomas (13:48.734)
Whatever sports you love, you're watching the game. And typically we have two outcomes. Man, that was a great game. Or that game sucked. But if you were to ask somebody, why was it great?
or why did it suck, them actually understanding or watching the game in a way that they could break it down is something that we don't naturally do. And so Chris, my question is, how can the sales team or the sales leader effectively review the game footage or the sales calls in return instead of saying, great call, Jimmy, or Bobby, you suck, bro.
instead of giving one of those two actions, be able to provide constructive feedback to the sales reps. Like how is that reviewing or looking at process, what does that look like for us?
Chris Duprey (14:40.398)
So the very typical to ask you answer response of, it depends, right? But so let's break down what can make it depend. So first and foremost, it's what is their actual sales process and hopefully we've switched it to a buyer-centric buying journey, all that stuff. But there's key things that you need to know before you move people forward, right? So I like to talk to sales leaders about
what decisions does the buyer need to make to buy from you? And so then it's like, what decisions does a buyer need to make to even move forward into the next stages of the process, right? So when we know those, we can sort of, depending on if we have a tool, right? So if you use something like Chorus AI, you can set up scorecards in Chorus. I think same thing with Gong, you can set up these scorecards, right? So if you're using tools, they're simple, they can be there.
you put what you were, you know, what you were looking for. So at Impact, we use chorus. I have a scorecard. My biggest thing that I'm always looking for is what is their compelling reason to actually take action? Right? Because without that, you got nothing. But I also have things in there like, are we asking great questions that lead to
aha moments or discovery. Are we going deep enough and getting past surface level issues, getting to root causes, right? So if you don't have those tools, Google Sheets team, go fill out a basic scorecard to go look at. And if you're really just starting, listen for, did we pitch before we understood?
Did we actually seek to like, was my rep curious about why this person gave us their time to meet with us? Do we understand more about their business than we did when we first got there? Do they have a reason to actually work with us? Like just thinking about those questions and any others that you want to listen for. And so now I'm not listening.
Chris Duprey (17:05.046)
just for like the holistic thing, I'm going, did we ask deeper questions? Because George, you've ever been, so you bought tons of stuff in your life, right? Just like all of us, just a little bit. And it's clear as day, right? When a salesperson asks you a question, but they don't ask you a follow-up, they just go on to the next question, what's the first thing that comes to mind for you?
George B. Thomas (17:15.24)
Just a little, just a little.
George B. Thomas (17:28.732)
Well, I actually get lost in the process because I'm thinking about the question I want him to ask me so I can give him the answer, but maybe I'm weird.
Chris Duprey (17:34.434)
Right. So listen, so that's definitely one of the outcomes. The other one for me, I think that they're just trying to scope. And you all know when you have that person, like, so how many computers do you have? And how many phones and how many this and how many that? Like, not asking any follow ups shows us that you've just checked out and you just found a checklist. That is also really key in the beginning. Because for too long,
And this is, this is now some dupe right thought, but for too long, we've said salespeople need scripts and they need questions in a checklist because we're trying to drive them to simply get to some outcome, to meet some efficiency number or some activity number, I want to challenge, especially small business leaders to develop your salespeople to be world-class communicators and give them
outcomes you're going to, not just boxes to check.
George B. Thomas (18:37.736)
Chris, it's so interesting. First of all, I think we reached the first rewind point. Just rewind and start to jot down all those questions that Chris started to list out that would be a matrix of things that you might not be asking in your organization. But second of all, when I hear you talk about that, I hear this almost movement of turning your sales team into players who are advisor mentality, thought leader-ish, like folks, instead of just order takers.
Chris Duprey (18:49.364)
music.
Chris Duprey (19:07.074)
They have to be, George. They have to be.
George B. Thomas (19:07.109)
Right.
Yeah. The other thing, by the way, is because we are in the Hub Heroes community, and you're talking about tools. First of all, if you don't have a tool, get a tool. If you can't afford a tool, Chris, I'd love you to death that you brought up, you know, Google or a spreadsheet or something. But hey, you might go check out Playbooks in HubSpot to do something with that as well.
Chris Duprey (19:32.686)
Good. We, so, so the funny thing is we use playbooks for after said meeting to record those answers. So as a sales leader, I look at game tape, playbook, call log in HubSpot and make sure that they match, make sure that things are there. So that is definitely a tool that we, we coach people to use as well.
George B. Thomas (19:58.undefined)
Yeah, so what I want to do is I feel like we've been kind of drilling in thus far. I want to step back out, kind of bring it at 50,000 foot level. Because I can imagine people watching this and going great, get game footage. Look at game footage and come up with constructive criticism. Who's going to do it?
Chris Duprey (20:06.164)
Mm-hmm.
George B. Thomas (20:22.98)
Like, and what I mean by that is I don't think everybody on the planet is built to be a coach. Just my personal opinion. But what essential qualities and skills make someone effective sales coach? And how can the sales team develop these qualities or identify them in potential folks that already might be in the sales team? Like, how do we get, how do we know this is going to be an effective sales coach?
Chris Duprey (20:28.718)
They're true.
Chris Duprey (20:51.082)
Yeah. So they gotta be curious. So let me take a step further. I would argue anybody that thinks that their way is the only way is likely wrong because you got to be open. Right. So there's several sales methods out, several sales coaching methods out there. You've got, you know, you could think of gap selling with Keenan and you think of Sandler sales and all this stuff.
For me, it's smash everything together and see what works for your organization, right? So that's the thing. So I would start with, is, whether it's your sales leader or you hire an outside coach, are they open to understanding your business? Are they open to understanding your buyer? And are they curious? Right? So that's the first thing. If you're gonna be a good coach, you gotta be curious. Because if all you're gonna do is come in and preach at people,
or tell them exactly what to do. You're actually not really a coach. You're, you know, you sort of fall into this, you know, for lack of a better term, like a dictator. Like dude, the beatings will continue until morale increases, right? Like, and what we want in a sales coach is somebody that's going to challenge, provide insights, and help our leaders. So this is the funny thing is they should be helping your sales leader.
And if you don't have a sales leader, small business owner, you're the sales leader. And I think a lot of small business owners don't like they sold at the beginning, then they hired a sales guy or gal and then went, cool, I'm done with sales. No, no, no. So your sales coach got to coach your sales leader to lead your sales team while at the same time guiding.
your sales team on what looks like over a period of time so that you can keep going.
George B. Thomas (22:51.184)
Yeah, so good, so good. Chris, keep going if you got more.
Chris Duprey (22:54.358)
Yeah, well, I was just gonna say, so when it comes down to like, who watches the game footage? Lottie dotty everybody, George. Right? Like, holy smokes, man. So leaders, you need to be watching it. Sales folks, they should be watching each others and giving each other feedback. Marketers, and I know there's a ton of you out there. Holy smokes. If you aren't watching your sales teams,
How do you know what the buyers are actually talking about? Right? It's a team sport. Today we're talking about sales and sales coaching, but holy smokes. Watching game tape should be something that everybody in the organization does. It's just at what iteration, how often, right? So you talk about impact. If I don't take the sales call, I watch it. Right?
in some of my other organizations that I'm working with, the leaders watch two to three calls a week, the teams each watch one of everybody else's a week. So it's like an hour a week if you're a rep, you're watching somebody else's stuff or your own, which by the way, gets you to understand the vocal tics that you have. The way, like, I used to push my glasses up all the time. Guess what?
I'm not wearing my glasses today, am I? Because I watched myself and said, boy is that distracting. These are all the different things that we've got to be able to uncover.
George B. Thomas (24:30.548)
I love it. Yeah, you don't realize, you know, you twist your ring, you push your glasses up, you say, if, um, like, right, like too many times when you're talking, right? No, I'm kidding. That was a joke. But, but watching that footage, it really does help you become a greater communicator, a better communicator. You mentioned that early and I hope people heard when you said that. The other thing that I don't, I want to double click on here because we kind of, you, you mentioned it, but we skirt skirted right past it.
Chris Duprey (24:43.217)
Hahaha!
George B. Thomas (25:00.942)
If you're a marketer in the room listening to this, first of all, God bless you because it's literally a sales-focused, sales-coaching piece of content, and you're a marketer watching this, thank you. But here's the thing, many marketers will look at the technology, the tool, and say, oh, those are just sales conversations.
Chris Duprey (25:14.274)
Mm.
George B. Thomas (25:21.572)
And the fact that we're not tying it back to that, that is the hidden gem, the holy grail. The like, you mean I don't have to schedule calls with current customers, I can just watch the sales tapes and probably get 27,000 ideas for our next marketing campaigns? Anyway. Anyway, I digress. Marketers start paying attention.
Chris Duprey (25:39.894)
Yeah.
George B. Thomas (25:46.184)
to the sales and what they're saying and what is happening there. So here's the thing, I'm gonna ask Chris at first what might feel very much like the same question.
but it's not, because I feel like I'm trying to drill in one layer deeper, and it's not what is in a sales coach, but it's kind of what comes out of a sales coach. And I mean, in your experience, what mindsets, and dare I even use the word soft skills towards this, but it might be mindsets, it might be soft skills. In your experience, what mindset or soft skills should sales coaches have when actually working with
that independent sales rep in having those conversations.
Chris Duprey (26:27.786)
Yeah. So it's totally all about communication. Right. So I would even argue that I'm not a sales coach. I'm a communications coach, right? Because at the core of sales is communication. And so, so that's what we need to be focused on. Now there's the, there's the tactical hard skills, but if somebody doesn't know how to ask great questions, they will never be able to sell anything unless.
unless you work for Apple and everybody just loves Apple. So you go buy all the new stuff, right? Like, you know, for me, it's guitar salesmen don't need to be any good because I'm gonna go buy the next thing when I just feel like it, right? Nobody's gonna sell me on it. But when we're talking about most others, it's about communication. So sales coach has to come in and know that is the root thing.
And oftentimes, George, organizations don't put any attention on teaching anybody in their organization, how to be effective communicators. We focus all of our sales training on the tools. We spend it all on activity based things. I'm going to tell you, having watched probably 50 or so companies struggle on the sales front.
It all comes down to how effectively are they communicating? How effectively are they asking questions? How are they digging into being curious? And that's the key. So if a sales coach isn't doing those things, if a sales coach isn't willing to watch the game footage and then give feedback and then lead role plays and then teach the sales leader how to do that. You've just got somebody to go in and teach you something.
Right?
George B. Thomas (28:25.456)
I love this so much because we're talking about like we're not talking, you know sales preacher We're not talking sales teacher. We're talking sales coach and Chris I love that you brought this down to communication, but I would be remissed We would be remissed if they're listening this or watching this in the community and we didn't state that Communication is a team sport
And so if you are the coach, you also have to be really good at getting the team wanting to play. And where my mind goes with that is they're going to listen to you if they trust you. They're probably going to trust you if there's some level of, and I'll say strong empathy. I don't mean weak empathy, but strong empathy and understanding of the process that they're actually trying to go through. And so.
Chris Duprey (29:10.414)
Mm-hmm.
George B. Thomas (29:16.964)
the soft skills of empathy and building trust and understanding the GPS of the sales process is gonna get you into a place where you can do exactly what Chris said and have that fundamental great communication happening internally with the teams. So great, great stuff.
Chris Duprey (29:37.834)
Yeah, well, so George, it's funny. Most of us will know this scene in a movie, right? So Top Gun, they get there. I think it's Viper. I think Viper's standing up in front of everybody. They're in the hangar, all sitting there. People are footing with their pens. And Viper says like, you're the best of the best, the top Navy aviators in your squadrons. We're here to make you better. That's the mindset of a great sales coach.
George B. Thomas (29:46.03)
Love that movie.
Chris Duprey (30:07.014)
and for sales leaders. So if you're a new sales leader going into a sales team, whether or not it's fully true, let's be real about something. While salespeople should have really thick skin because success means that you still fail more, right? You're almost like a baseball player, right? But the reality is, we also are a little egotistical at times. We also are rough around the edges. And so,
When somebody new comes in and just says, y'all are bad at X, Y, and Z, we've gotta get better, you're gonna start from a position of friction. So you go in and you bolster up what's good, and then you talk about, well, we're here to make you better. We're here to sharpen that saw. And then you get, you know, whether it's somebody that's been selling for 30 years or somebody that's been selling for 30 minutes, they get fired up because, you mean you're gonna teach me how to be Iceman and Mav?
Like, let's do this, right? And that's how you have successful coaching engagements. That's how, quite frankly, as a sales leader, if you lead that way, your sales team's likely gonna be better in general.
George B. Thomas (31:20.764)
So good. I love that section just because I want to grow up to be Maverick, by the way. I'm just gonna throw that out to everybody. I got the need. I got the need for speed, ladies and gentlemen. Such a good reference. I love Chris how that actually, it's fun to talk about, but it's like a good visual reference of like, oh, oh yeah. We are the best, but we always can become better. It's such a good piece. So that leads me into wondering like,
Chris Duprey (31:30.852)
Oh yeah.
George B. Thomas (31:49.52)
Well, getting better, well, better or bad ass maybe, but better. It does sometimes come to a happy mix of two things, strategy and tactics. So are there any specific strategies and tactics that sales teams can implement immediately after listening or watching this episode, Chris, to improve their sales coaching efforts like that, immediate things that you would tell people to do.
Chris Duprey (32:15.106)
So depends who I'm talking to. So I'm talking to a leader, sales leader, business owner. Go take a look at your sales process. Who is the hero of that process? A lot of us in HubSpot, we have things like explore call booked, explore call complete, qualification call. But like we have all of these internal things as our sales process. And I would challenge everybody to go.
change that to be more about the buyer. So at impact, we use a tool, like we use baseline selling. It's if you're into baseball, it's real simple. But instead of the old days of explore, call books, for completed, I've got first base is discovery phase. There's a playbook that has questions that once those are answered, the buyer is actually now into the qualification phase.
because they're qualifying us, we're qualifying them. Then we go into what we're calling prescribing. That's when we know they're bought in, they've got all that stuff. Now we're telling them, here's what we're gonna do. And then you go into, like you score. But ours is based on how a buyer would actually make those decisions and do all that stuff. So that's where I would start and say, is your sales process a box check?
that is pushing people to decisions before they're ready or slowing people down because you've got to go through all these hoops, even though they might be ready after the first call, right? Cause in a buyer centric process, George, I might do one call and then move all the way to prescribing because I was able to get through a whole bunch of stuff in one call, right? So I would look at that. If I'm talking to reps.
Curiosity, are you asking follow-up questions that progress the conversation forward? Right? That's, that's the initial thing. And then if you want the next step is are you ensuring you have a compelling reason for them to take action and are you leaving the call with the next meeting booked, not tentatively, but booked like the days of I'm going to send you an email with next steps and then we'll lock something in.
Chris Duprey (34:43.298)
You're never talking to that person again. Book the call on the call. It's the simplest thing in the world.
George B. Thomas (34:51.54)
So many good pieces in that section, Chris. First of all, I love this idea and I talk about this idea of second smart questions and being equipped with what's the second smart question based on the answer that I just got. And...
If you're listening this or watching this and you haven't actually researched the seven levels of why That philosophy or books that talk about the seven levels of why some it might be five levels of why it might be six But you get the idea being able to ask those questions to get to a true deep or more important piece of information
game-changing in what you might be doing. The other thing though that was interesting and I know some people have emailed me and they can tell on these episodes when somebody says something that my brain like leaves the interview and I start to I do this tilt of the head thing.
But when you talked about baseline selling and you brought up the baseball analogy, I kind of giggled and I let my brain journey for a little bit, because it's very interesting to me that would be the model. Because in baseball, you have a first base coach and you have a third base coach. And they're literally there to let people know when they should run or when they should hold up. And we're talking about sales coaching.
We're talking about watching game footage and your coaches are the first and third base coach has been like, hold up, hold up, hold up. Make them stay there a little bit more. Ask them a few more questions. Wait, wait, hold up, hold up. Stay at first. We gotta qualify them a little bit better. We gotta like, and I just hope that people are understanding in what you were creating of the framework of what the customer runs through that the coaches are on the outskirts watching the entire system.
Chris Duprey (36:41.226)
And George loved the analogy. And here's where most salespeople actually make the mistake. Somebody gets to first, right? So they're, we're in the discovery phase and we learn some stuff. George, we just love X, Y, and Z. We're really excited. And salesperson goes, great. And they run across the infield right to starting to prescribe. Well, if you follow baseball, you know, if you don't touch second base.
then you're going to be out if you try to, like you can't score unless you touch second base. And so that's why when I look at sales processes, when you build that and then layer in the coaching analogy there, it's perfect. Because too often we get happy ears and we rush when the reality is you've got to set, like you got to let people sit in their problem to actually understand they.
George B. Thomas (37:26.045)
Yeah.
George B. Thomas (37:41.492)
The problem has to marinate. Oh my goodness. It's funny, I never really thought of a sales issue being happy ears, but that makes me kind of happy just even thinking about that. What's funny is we're already kind of going into what I wanna ask, because if we're trying to reach success and we're trying to run those bases, we're trying to have effective coaching, there's gonna be some pitfalls along the way. There's gonna be mistakes that we've made. And I know you and what you do at Impact, you have seen
many companies, seen many people trying to get people to run the basis. So are there any common mistakes or pitfalls that sales teams should avoid regarding sales coaching, like any lessons learned or particular tips that you would want to share around those?
Chris Duprey (38:25.538)
Well, just the best of the best need coaches. Right. So, so, and I am not saying that I'm the best of the best, but here's what I will say. I get people like, I am a sales coach that works with businesses and I have a sales coach. Right. So, so I've got a guy like impact has a sales coach that helps me refine what I'm doing. And so the idea is.
your top dog that sits there and always hits his number or hits her number, that thinks I don't need coaching. No, no, no. You need it. Just like Tiger's got a swing coach, right? Just like, you know, Steph Curry's got all the different coaches. The best, the goats in sports all have coaches. Everybody does. And so to think that, cause this is the biggest hurdle, George, is
People don't think that it's worth it. People don't understand that having an outsider to come in and help you see what you can't see, to hold the mirror, all those things is worth it. I'm gonna tell you, if we're in the same company, and I tell you something, you're gonna go, yeah, okay, cool, I'll write that down. If you're paying me as an outside coach, and I go, read this book, you're gonna be like, great, the whole company's gonna read this book right now. Right, like.
It's the funniest thing and hopefully some folks are chuckling right now because you've watched your team do this. Like I've literally watched this happen at Impact over and over again and it's the companies that we coach. You've got to bring in that other set of eyes. That's that number one hurdle. And then the second one, George, is you've got to get people over the idea that people aren't going to want to be recorded.
That's just flat out wrong, brother. Right, and so the worst thing that can happen is that they say something and you turn it off. But I'm gonna tell you, act like the horrible internet providers that just start with it recording and say, your call is gonna be recorded for quality assurance purposes, right? Zoom does that, Teams does that. Just set up the record right away. And when you listen to sales folks say, well, people aren't gonna tell me the truth, like that's hogwash.
Chris Duprey (40:52.474)
understand and teach them how to talk to somebody about why it's being recorded. But there's 10 X more reasons to record sales calls than there are against. And so, so that's the other hurdle.
George B. Thomas (41:11.348)
I love that so much. By the way, I have literally had calls where, and I do the same thing. It just says, hey, it's recorded. This meeting will be recorded. And I actually love when somebody goes to me, will be like 20 minutes in 30 minutes. And they'll be like, can we turn off the recording?
And I'll be like, yes. And I'll grab my notepad that I usually don't have to use because AI is transcribing the notes for me, which we might talk about that in a minute too, as far as this conversation that might lead into a future conversation, AKA episode. But I love when they say that because I grabbed my notepad because I know I'm about to get the real tea.
Chris Duprey (41:43.438)
Ready to go.
George B. Thomas (41:50.5)
I know that we finally got to the point where we're going to talk about the real issue that it's Jimmy and HR who keeps walking by and doing whatever it is, right? And so don't be afraid of that. And that can only happen if it starts with what Chris said where, hey, this meeting is being recorded. But it's how there's so much good stuff in this episode. My fear.
Chris Duprey (41:58.454)
Yeah.
George B. Thomas (42:14.596)
Not a big fear. I'm not actually a big believer in fear, but my fear is people will watch this and they'll be like, what's the next actionable step that I can take? Meaning, Chris, what I'd love to know is if there's like recommended resources, books, tools that sales teams can explore further to enhance their understanding and skills of sales coaching and kind of the conversation that we may have started for many today.
Chris Duprey (42:39.522)
Hmm. So when I'm talking to, to sales teams, there's a couple of books I was recommending, you know, got to give it up for my brother from another mother, Marcus, uh, Sheridan with ask you answer. Right. So that's usually the beginnings because while the sales section isn't super deep, it still resonates and talks about all of the principles that we talked about today in terms of great questions and getting ahead of things, educating, right.
Then I'm a huge fan of Orin Clough. So Orin's written two books that I think are really phenomenal, Pitch Anything. And I know that I said, don't start with a pitch, but what the big takeaway from Pitch Anything is this idea of frame collisions. And so he talks about in any interaction, people are trying to be in charge.
And so how do you set the frame? How do you get the frame back? How do you have a give and take? And I think in sales, you have to be able to own the frame at the beginning, relinquish it to the buyer for a bit and then pull it right back. And so that book really talks a lot about that. His other book, flip the script talks about some other techniques that are really solid from a communication standpoint, right? So those are, those are the couple of books.
that I always go to that radical camp, you know, Kim Scott's radical candor, right?
Chris Duprey (44:14.282)
The last one, it's tough for read, but everybody's read it as challenger sale. Right? Like there's just so much data in those guys' books. But the idea is if you're not willing to use radical candor and challenge a buyer, you're going to struggle. So that's more tactical stuff. Right? But if you're sitting there going, how do I get started? Start recording sales calls. Leaders start watching them.
make other people watch them. That is truly, if you do nothing else other than that, you're going to get better, right? So those are my initial takes.
George B. Thomas (44:56.02)
I love that. And there's some additional resources, some stuff that you can take.
It's funny that you bring up, They Ask, You Answer, because here's the thing that's typically looked at as a marketing book, right? For marketers and a content strategy and that kind of thing. I love that you brought in that section that is really not talked about a lot, but assignment selling. And Chris, I gotta be honest with you, I've always wondered when the companion book to They Ask, You Answer, that is simply titled assignment selling,
I don't know if it'll ever happen, but I've always felt like that section of the book would have legs to live and breathe on its own in so many organizations because it's just a fundamental way of doing things different which Dramatically piggybacks onto what we're actually talking about today
Chris Duprey (45:49.762)
So I'm not gonna give anything away, George, but I will say there is work coming from us that will have enhanced things in the next, hopefully early 2024 that will cover some of that stuff, that will go into it a bit more. Because listen, you wanna talk about how you accelerate selling. Like we were talking about sales coaching game film today.
George B. Thomas (45:52.188)
Uh oh! Uh oh!
George B. Thomas (46:09.005)
Oh.
Chris Duprey (46:18.794)
But Holy smokes set the conditions for the sales calls you're going to have. That's how you, that's how you win. Right. And, and so, you know, I say that they ask you answers, a team sport, sales is a team sport, business is a team sport. And so if the sales folks, you don't know what marketers are thinking about and doing, you're going to struggle in the selling as well.
George B. Thomas (46:26.214)
Yeah.
George B. Thomas (46:43.484)
Yeah, I'm going to ask one. I have a couple of questions just that you didn't know about to kind of end this, but I am going to ask one question that's probably going to tease us into an entire another episode in the future because all of this is great. It's a beautiful conversation. It's a way that people can go forward and do better than they probably ever done around sales coaching and their sales teams. We haven't talked about the mindset of people like, whoo, that sounds like a lot.
I don't know if I have time for all of this. Chris, talk to me about how you're leveraging AI in the sales coaching process. Just a little nugget to kind of wet their appetite and tease them a little bit and get rid of this, I don't have the time mentality.
Chris Duprey (47:29.226)
Yeah. So the first thing is if you don't have the time to work on sales, you're going to go out of business. So just, so that's, that's step one. Step two is if you have not started to embrace just the basics, like GPT-4 as something that you bring into your daily activity, you're already, I would say behind the ball a little bit. And how does this apply? So if you go in without being tech savvy, like, listen, I used to fall out of airplanes, right?
Like I am not this, I am not the tool wizard like George. I am like, how do I do this? And I've been able to use chat GPT to, you know, I've got the paid version. So I've got some plugins so I can go scrape a website or I can just pull up. You know, the service offering copy and paste it teach my little robot pal about the product or service. And then I can start asking it.
Hey, what questions would you have as a buyer? And then it starts giving me questions. I can then even go as far as if I wanted to just role play through text, say, be a buyer for this, and we're going to go into a sales role play go. And it'll just interact with you. Or as a sales leader, you can type in, hey, I'm having this issue, this issue, this issue that I've seen in sales call reviews. Can you set up three scenarios for us to role play? And the tool builds you.
what you need to give to the other person. It gives you the scenario, and you just have to go in and execute the role-plays. I did this yesterday. I won't tell you the company, but I'm working with the sales leaders. So they're a large organization, and we're doing communications training to help them from a leadership standpoint. We've identified some scenarios. I didn't do any work. GPT-4, I gave them the scenario, like some information.
generated five scenarios. Me and the EVP of sales were like, yup, go with one, then three, then four. And we role played for an hour off of stuff that ChatGPT pulled in for us. And it was a great session, right? And I could go on for, we could talk for another two hours about this, but it's as simple as that.
George B. Thomas (49:51.636)
Yeah. Yeah, it's definitely going to have to be another episode. But moral of the story, if you don't have yourself a little AI assistant yet, you might want to get that happening. Chris, you didn't know this was coming. But what is one thing you hope people take away from today's episode? If nothing else.
Chris Duprey (50:09.962)
You can't fix your sales problem if you don't know what the problem is. And so telling salespeople do better, isn't leadership. Watch what's happening, coach them, and you will get the progress. And if you need help, there are people like me and George and others that are out there to help guide you down this path.
George B. Thomas (50:37.22)
Yes. Chris, if people have questions for you, where do you want to send them? Where do you want to point and where can they connect and have conversations with you?
Chris Duprey (50:43.062)
Yeah. So listen, the best, if you want to have a conversation, the best way is to simply go to impactplus.com, click book a meeting with an, like, I don't know exactly what it says right now, probably says book a meeting with a coach. You're going to talk to me. If you go to Impact's website, the big orange button on the top right says talk to us. That gets to me. Okay, so that's number one, you want to have a good call. Number two, I'm all over LinkedIn. It's Chris Dupre. You can find me there.
And, um, you know, just if you are a sales leader, a business owner that is inspired to actually fix your sales problem, I want to talk to you.
George B. Thomas (51:23.972)
Love it so much. You can feel the passion. You can feel the passion. Ladies and gentlemen, time flies when you're having fun. What a great episode. Hey, if you listen to the audio, make sure you head over to the community, community.hubheroes.com. We love to service you over there and help you with all the things dealing with HubSpot. Until we meet in the next episode of the Hub Heroes Sidekick Strategies show, remember to be a happy, helpful, humble human. Of course, we'll see you on the flip side. Enjoy. Thanks, everybody. Thanks, Chris.
Chris Duprey (51:52.63)
Thanks, George.