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sales coaching journey
January 14, 2022

Sales Leader Interview: Embarking On Your Sales Coaching Journey

sales coaching journey

I sat down with Brian Geery, Managing Partner at CEO of SalesNV, where he and his colleagues support sales professionals to deliver better sales demos. If you don’t deliver software demos don’t fret. The main focus of our conversation was about delivering great sales coaching.

In this conversation you’ll learn:

  • Lessons Brian gleaned from his first sales coach and mentor.
  • What differentiates an average and awesome product demo.
  • What does really good sales coaching look like?
  • The importance of coachability and accountability among sales teams.
  • How do you manage a rep who doesn’t respond to coaching?
  • The importance of storytelling and catching people doing something right when sales coaching.

Embarking On Your Sales Coaching Journey

To learn more, read the complete transcript.

Rich: Brian Geery, welcome.

Brian: Thank you. Glad to be here.

Rich: Why don’t you kick us off with a bit of an introduction to you and your background, and we can get into some of the details of what you’re going to share with us.

Brian: Sure. My career has been in software sales, and I was fortunate over the years. I’ve always had great mentors, great sales managers, great coaches if you will, and after a successful career in software sales, I quit, so I could in essence teach what I had learned. I started as a consultant, and that’s 20 plus years ago.

Brian: Recently, I’ve focused my practice on coaching software sales professionals to do better software demonstrations, but to your point, much of what I do is sales coaching in general. Whether you’re selling boats or software or houses, you need a good coach. That’s why I was looking forward to talking to you about it.

Rich: Excellent. So you have a book out on Amazon, How To Demonstrate Software So People Buy It. I don’t know about you, but I do like to go on to Amazon and check out the reviews of products. It’s funny, your reviews are universally positive on the book, but there was something that stood out in one of the reviews that I wanted to share because I think it speaks to maybe some of the content we’re going to go through. I’m going to paraphrase it, but effectively the person reviewing your book enjoyed it thoroughly, and they described it a little bit like when somebody gives you a Rubik’s cube, and then somebody else comes along and shows you exactly how to unlock the Rubik’s cube and solve the puzzle. Why the focus on software demos for you personally? What was it about? I know your background is clearly in software sales, so that is a logical next step, but why focus on that nowadays? What is it about software demos that you find particularly compelling?

Brian: You know, it goes back to early in my career. One of my first mentors, Tom Modine, was a top-flight sales professional for a competitor. I was working at SoftPoint data systems. We sold the software to manage pharmacies. This was in the days before the big chain pharmacies.

Brian: Basically, I couldn’t beat Tom Modine. He worked at Script Systems, and everywhere I went people said, “We’re buying from Tom Modine.” So I convinced management to hire him. Can’t beat them, hire them. So there’s a little trick for you, by the way, but I got to observe how Tom demonstrated software, and ultimately how he was so successful and why so many pharmacists said, “We’re buying from Tom.”

Brian: When I would demonstrate software, I would show people, “Hey, here’s where you enter the prescription information. Look how easy it is. There’s this drop-down menu to select from. Now you enter the patient’s name. Look, you can enter Manuel Rodriguez and spell Rodriguez three ways, but still find the right one.”

Brian: Quite honestly, it was a yawn. I was teaching people how to use the software, and when I observed Tom selling software, and demonstrating software, it was a very different experience, and he coached me. He taught me his approach, his Rubik’s cube, to use your analogy there.

Brian: What Tom would do, he wouldn’t teach people how the software works. He demonstrated how the software solved the prospect’s business challenges, how the pharmacy could fill more prescriptions faster, avoid inaccuracies, collect receivables, increase net revenue, improve customer satisfaction, That learning experience, having a mentor, having someone who knew what they were doing, say, “Hey Brian, let me give you some guidance. Let me provide you some feedback in your approach,” and then having a chance. I mean, from there I never looked back. I mean, I was a top producer in software sales for years, because I applied the skills that I learned from a great coach and literally friend and mentor. So I think that that was kind of my catalyst, were just wanting to focus on software sales.

Rich: So let’s deconstruct that a little bit and let’s unpack some of that. What is it that differentiates the average software demo? I’ve certainly been on the receiving end of some of those. From your perspective then, what is it that’s the differentiator between the average and the really great demos?

Brian: Sure. Well, the bottom line is the ability to show how the software solves business challenges, not teach people how the software works. One is training. Training is supposed to take place after the sale. The other is persuading people to purchase. That’s the demonstration. Your demonstration needs to be compelling and persuasive.

Brian: So there are several other components to that. One is making sure that pre-demonstration, with having the conversation to truly understand the why behind the prospect’s interest in software. What causes the prospect to have an interest? In fact, that’s like the opening question, I think when any software person or software salesperson is talking to a prospect.

Brian: After, “Hi Rich, how are you? Rich, What causes you to have an interest in our software at this point in time?” So then why now, and then several other things that are often missed. One is competitive positioning? I mean, prospects want to know why is your software better than any other options. So it’s up to the software sales professional to explain, “Hey, here’s what makes our software uniquely better.” Prospects want to know, “Can I afford it? Is the cost justified?” It’s up to the software salesperson to have the business case conversation, “Here’s why it’s worth it.”

Brian: Prospects want to know, how can I get here, not having software, to there, being up, running, trained, implemented on the software. Prospects need to have an implementation plan, and then finally the software demonstration itself has to be memorable because prospects don’t necessarily make a decision at the point of demonstration. They want to see other demonstrations with other competitors, whatever, time goes by. So when they all meet in the room to say, “Hey, which company should we select?” The sales professional whose software demonstration was most memorable is often the one who’s going to win the sale. So those are really some of the key elements that I look at.

Rich: Let’s move away from the software demo for a second and think about coaching more broadly then. What does coaching look like? Not necessarily in relation to software demos, although I think it’s a good starting point. What does really good coaching look like from your perspective?

Brian: First, the coach needs to understand that position, the sales position, not the person, but the position that they’re in. What are the key skills required to succeed in the position? What are the behavioral characteristics? The coach can learn that often by observing the A players. We call it the 20%, which seems to always meet or exceed their quota, monthly and quarterly. So first understand the position and its demands. Then looking at, I call it the coachee, the salesperson, and assessing, “Hey, how does that salesperson match in terms of their skills and their behaviors, and where are the gaps? So what are their strengths and where do they need to improve?”

Brian: So that’s, let’s say, in essence, the starting point for any good sales coach. Understand the sales position and its demands, and then assess the salesperson and their match against those position attributes.

Rich: We’ve recently put out some content, which I wanted to get your thoughts on around coachability as well. I mean, how pivotal do you think coachability is, as well, on the part of the rep, and trying to ascertain their coachability, their openness, or their willingness to be coached?

Brian: Boy, that is a good question, and, man, it can be a challenge in my opinion. I mean, the coachable people, well they just, it just works. You provide good coaching. You catch them doing things right, reward the behavior, let them know what works, so they keep doing it, and you provide guidance for areas where they could improve, and then they accept it.

Brian: They maybe ask questions. They look for more feedback. They go try it. They come back and say, “Hey coach, how did I do?” Those are the easy ones, but that’s really not typically what always happens. You often have people who, as a coach, you do what you’re thinking is all the right stuff, and then you anxiously await to observe the behavior change on the next sales call and nothing.

Brian: Now sometimes you’ll coach someone. They seem to get it. They’ll say, “Yeah, Rich. Now, that makes sense. Absolutely. I want to try that.” Nothing. Now what? What do you do at that point? And my answer is, first, look in the mirror. You’re a professional coach. Your job is to change human behavior and if you’re doing what you think is your job, but the behavior of the sales professional is not changing, first, double-check that you’re doing all the right things.

Brian: When that happens here at my firm, we talk to each other. We’ll run the scenario by each other because sometimes you get caught up in the coaching moment if you will, and maybe you missed something. Maybe you didn’t really learn the person’s personal goals or what they want to spend their commission check on. Maybe you communicated in a manner that wasn’t right for that particular person. Maybe you need to have some more conversation that gets around the emotion of the job.

Brian: Then, you know what, Rich? Sometimes even that doesn’t happen. It’s not working. So there’s a point … And this is the art of coaching. At what point do you say, “Huh? This person really just isn’t right for the position, or the position isn’t right for the person.” Whichever way you want to look at it. It’s hard to do, but what I would say is, to do it reasonably, expeditiously. It’s not a conversation you want to keep having. Another month goes by, another month goes by, another month goes by and you’re like, “Man, Joe over there, he got a little better, but he’s still making the same mistakes he was three months ago.” So it’s a big dilemma, and it is a common challenge in coaching.

Rich: Yeah, I don’t think there’s a simple answer to it at all. I think it’s nuanced, just like the people involved. One of the things that I’d be interested to get your thoughts on, which is sort of slightly tangential to that point though, is the perception perhaps that some people think that a coaching approach or a mentor approach is somehow sort of a soft approach or there’s perhaps not really accountability there. Some people might think that this is a numbers game. We just make the deals. Others might see coaching as an easy way out or lack of accountability. Have you any thoughts around that, in terms of coaching and its role in accountability?

Brian: That’s an interesting one. A good coach holds the salesperson accountable for what the salesperson agreed they were going to try to do. I don’t consider that soft. Maybe it’s hard to measure sometimes. I mean, in the end, sales is easier because it is a measurable outcome. You are either achieving or exceeding your quota or you’re not, but the behaviors, the sales activity that you perform, and the quality of those activities are what produce the results.

Brian: So you need a coach, and there’s so much research now, that’s really surfaced in the last few years, but it’s kind of always been there, but it seems to be more prevalent, correlating those top producers have good coaches, period. Like, that’s the facts.

Rich: I think if we think about some of the specifics about the delivery of good coaching, speak to this idea around criticizing behavior or holding people accountable for their behavior and not necessarily the person. Really keen to get your thoughts on some of the mechanics of how good coaching takes place and some of its features of it.

Brian: If say to you, “Rich, you’re not a good listener,” what’s your reaction?

Rich: Tell me more.

Brian: Are those little feathers going up in the back of your neck a little bit? I just basically put you, as a person, down. But if I said, “Rich, sometimes during your conversations, I observed you speaking before the prospect finishes their sentence. What are your thoughts?” You know, the subtle difference, in the first case I said “You’re not a good listener.” That’s criticizing the person. In the second instance, I was criticizing the behavior.

Brian: Think about how you want the salesperson to feel when they leave a coaching session. To me, a good coaching session means the sales professional left feeling, A, motivated, and B, that they have new ideas that they can apply immediately. That’s a good coaching session. A lot of coaching is about pre-planning your conversations and thinking about what you’re going to say and ask kind of leads to another topic. I think a big portion of coaching is asking, not telling.

Brian: Here’s how I look at it. When I have a coaching session, and I reflect on my own session, I think back, and say it’s a 20-minute meeting. I think, what questions did they ask? How many questions did they ask? Was there a nice balance of me asking the coachee questions? “What’s working? Where are you having challenges? Tell me a little about the last call you were on. How did you apply that?” And tell, “Hey, here are some ideas that I’ve seen work, and I think they can work for you.”

Brian: So the short answer is a good coach definitely asks questions and they’re insightful and thoughtful questions, but they also communicate. They relay new information, provide ideas, and by the way often in the form of storytelling, kind of yet another topic within all this, but if I’m coaching you and I can tell you, Rich, a story or two stories about other people who have been where you are and have changed and tried and done new things and then achieved larger commission checks, it’s easier for you to hear. People like to hear stories. It goes back to our childhood, and it’s not me, the coach, saying, “Hey, do this.” It’s me saying, “Hey, here’s a cool story about how someone else, who had the same challenges you, in sales, managed to overcome it and sell more in the end.”

Rich: Have you got a story? Have you got an example of a time when somebody that you were coaching was up against a real problem or where coaching has helped somebody, and maybe a little bit about what it was specifically that you did as a coach to help facilitate that change?

Brian: Yeah, so I had a salesperson that seemed to do everything right in terms of they were, well, they were just likable and they were enthusiastic and knowledgeable, but they interrupted people. Their enthusiasm would overcome them. If you were the prospect, and I was that particular salesperson, and maybe you started to tell me about your business challenge, and I was there with you. The salesperson just can help themselves. They’d jump in and interrupt. “Yeah, no man, I know what you’re saying.” Like, “But Rich, you didn’t finish what you were saying.”

Brian: This was pretty easy to fix by recording the coaching session, and I’ll give Allego a plug now, because Allego, with your coaching software, we had in our best practice library an example before and after of another salesperson on the team, who had the same challenge, where they were often interrupting the prospect, and we just had little clips in the library. One was before and one was after when they learned how to be a better listener and just zip it up, be quiet, just let pregnant pauses happen. That’s okay. Silence is golden.

Brian: By letting this salesperson have the interruption challenge here, appear, who had the same challenge and then tab the challenge, like to two different clips, and it just crystallized for them. Like, “Oh my gosh, that is me. I do the same thing.” It was just like that defining moment. I mean after that, that person rarely if ever interrupted a prospect. So that would be one approach. Ideally, if you have awesome coaching software like Allego, great, but even if you don’t, the ability to have a person who’s got a challenge, see and hear about a peer who used to have that challenge receive some good coaching, and now doesn’t have that challenge.

Rich: I think it’s a really good example, Brian. Of course, always grateful for a plug of Allego. We’re just touching on the end of the allotted time that we’ve got together. So I’m curious, have you’ve got any other final thoughts, any parting words of wisdom for the audience?

Brian: Sure. Catch them doing it right. What I mean by that is, as a coach, it’s so important to let the people you’re coaching know what’s working. Whatever they’re doing that works, just reward that behavior with simple recognition. I mean, it’s human nature. We like compliments, and everyone you’re coaching is doing something right. So, I think if there’s a big takeaway from all this conversation if someone wants to be a really good coach, just remember, catch people doing things right and reward the behavior with simple verbal recognition.

Rich: Excellent advice. Brian, just before we go, how can people find out a little bit more about you and the work that you do?

Brian: Sales, the letter N, the letter V, for envy, dot com.

Rich: Thanks for taking time to speak to us today.

Brian: Take care.

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