Paul invites sales leader and best-selling author Carson V. Heady to share his perspective on common challenges facing the sales community and provide powerful solutions to apply in any marketplace.
SHOW NOTES
“One small win doesn’t mean all that much, but when you combine all of those small wins, it leads to big change.” -Carson
Engaging key stakeholders as part of the process is instrumental in the success of a relationship or deal.
“You can’t feast until you set the table.” – Carson
Success in sales means sometimes learning to live with uncomfortable or ambiguous situations.
“There is no seller more confident than the seller that walks into a deal that they don’t need.” – Paul
Don’t become a prisoner of hope; take control of the controllable elements of a deal.
Connect with Carson at carsonvheady.wordpress.com
Purchase Salesman on Fire and Birth of a Salesman on Amazon or at your local bookseller.
ALSO MENTIONED
The Q and A Sales Podcast: What is a Go-Giver? with Bob Burg
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How do I even get started? with Carson V. Heady, Salesman on Fire
(Transcribed from podcast interview)
It’s difficult. It’s challenging to make that decision because unfortunately, sometimes you’ll ruffle feathers because, unfortunately also, sometimes there’s politics and there’s other things at play and you can step on some landmines. I’ve stepped on plenty in my day, but I’ve made that conscious decision to sometimes be, as I like to say, the hero that can be the villain. – Carson Heady
Paul: Hey friends, Paul Reilly here welcoming you to another episode of the Q and A Sales Podcast. Today, we are going to have a special guest on the show. Carson is a friend of mine. He is a native St. Louisan, but he’s a sales guy at heart. And that’s what we’re going to be doing on a few more of these interviews. We want to have salespeople that are out there, you know, carrying the bag, that are taking meetings, that are leading sales teams. We want to keep that perspective fresh. And so, we’re going to have Carson on today’s show.
Now a little bit of background about Carson. Carson is not only a sales leader, but he’s also a bestselling author of the four-book series, Birth of a Salesman. He’s an eight-time CEO President’s Club winner across six sales and leadership roles at AT&T and Microsoft. So, he’s successful, right? He’s been there. He’s been through the challenges you face, and he’s going to bring us some unique perspective. He’s also been recognized as the #1 social seller globally at Microsoft. And he currently serves as the sales director for Microsoft Health and Life Sciences division. Again, he lives here in St. Louis with his wife, Amy, and he’s got three daughters as well. Just like me. It’s a great conversation. Thanks for tuning in.
Paul: So, hey, Carson. How are you doing today?
Carson: Paul, I’m well, yourself?
Paul: Doing great, man. As a native St. Louisan, it’s good to get together to connect like this. You know, if you would, tell the audience a little bit about yourself and really what your sales career has looked like up to this point.
Carson: Yeah, thanks so much for having me, Paul. Been a fan of yours for a long time. I’ve been a student of sales for, I guess, the majority of my life now. It’s been a fascinating run. I never really intended to get into sales either. It started roughly 20 years ago when I started at AT&T, which was, at the time, Southwestern Bell here in St. Louis. And I thought I was walking into a service type role. Turned out, it was a pretty aggressive phone sales and I developed a knack for it. I enjoyed it. Started having strong results. Was promoted numerous times at AT&T. Wound up running my own division that had placement in multiple states. The most serendipitous thing happened though, it’s when I decided to write a book about. And I didn’t want to write a book that was just a regular sales book, because it’s been done many, many times by, uh, folks on this call better than I could ever do.
And so, I decided to write a fictional story: a protagonist that I created that actually writes his own book within the book. So I took kind of a unique approach there. That book actually got me noticed by my next role. And I worked for a few smaller organizations and large
organizations throughout the years, but it was relationships after writing that book that led me to Microsoft, where I’ve been for the last 7 ½ years.
Been in multiple roles here as well—both leadership and individual contributor. I’m currently a sales director in our Microsoft Health and Life Sciences division. It’s been an insane ride. Paul, I could never have fathomed walking into it. I’ve been recognized as the #1 social seller in all of Microsoft. Which, I have to pinch myself as I say that.
So, it’s been an insane run, but I also always tell sellers and leaders that I’ve not done anything that others can’t replicate with hard work, resilience, dedication, and passion for their craft. So, proud to be a student of the selling game and happy to be here as well.
Paul: Awesome, Carson. Thanks for the intro there. And, you know, you mentioned something that stood out to me. You know, 20 years ago when you started, really it wasn’t with the intention of becoming a salesperson. I hear that quite a bit. You know, sales is sometimes a profession that we stumble upon or fall into. You know, me, I spent a lot of time in detention in high school and grade school, so I figured sales would be a logical spot for me, right? But what a great career path, and the fact that you’ve written a book along the way. I’d love to hear more about that. It’s interesting because there are so many sales books out there, but, written through the form of story—that makes it powerful. It’s easier to read. It reminds me of one of my favorite books. It’s in the form of a parable, The Go-Giver by a guy named Bob Burg, who, actually, we had on the podcast several episodes ago. But, you know, for the listeners— wanted to share with you guys what we’re going to be doing.
We wanted to bring salespeople on here, sales leaders, people that are in it every single day, so that we can have a conversation about what are the challenges salespeople are facing. And, Carson, having you on here brings a lot of perspective. And before today’s show, I asked you to email me a couple of common questions that you’re hearing from your sales team or things that you’ve experienced as a salesperson. And I’d like to talk through these, if we could.
The first question you mentioned was, you know, let’s say a salesperson gets a new account assignment. They get a new prospect coming in. The question is, “Where do I begin?” “How do I even get started?” And what a great question, because it reminds me of, you know, being a salesperson, still, to this day, but also in my previous life, selling, going after big opportunities. Sometimes you have an opportunity so big you don’t even know where to get started. You don’t know how to start. When I think about that, I thought ‘What a great question,’ because there is one thing that we can do, and that is focus on small wins.
Small wins are those concrete outcomes of moderate importance. By itself, you know, one small win doesn’t mean all that much, but when you combine all of those small wins, that leads to big change. And so for new salespeople going after a new opportunity, they need to focus on those small wins. One exercise that I share with sales groups is to basically reverse engineer your success. You know, think about the three or four biggest successes you’ve had in the past year or so, and ask yourself, “Okay. From initial contact to contract, what were the series of small wins that led to the culmination of that sale?” Is it, you know, getting in front of the right decision maker? Is it getting that first meeting? Whatever it is, just identify those small wins. And then that’s where you focus your time, your energy and effort.
These small wins also keep you focused. They keep you motivated. They keep you engaged because it can be frustrating going after a large opportunity. You’re going to face multiple setbacks, but those small wins will help you stay focused. So, I’m curious Carson, as a sales leader, when you see this question, when you hear this question rather from your team, what are some of the things you will do to, to help them out, to get them started on the right path.
Carson: Yeah, Paul, I think you brilliantly articulated many of the ways that you have to look at this from a perspective standpoint. You can’t feast until you set the table. And I think the critical element is to—. I’ve managed hundreds of accounts in my career, you know, had a lot that have come and gone or that I’ve been tasked with—you know, a new book of business, a new territory—whatever it is, you’ve got to set the foundation.
You’ve got to understand the playing field. Who are the players? Who are the key influencers and also, the influencers of those influencers? What is your process going to be to go to market? How are you going to create those relationships? What resources do you have to bring to bear? What industry alignment exists? You know, how are you going to tap into that intelligence? Here at Microsoft, we just started a new fiscal year, and, uh, I shifted into a new territory, new role, working with a team that is new to me. And the first part of that is, you’ve got to get to know each other. You’ve got to understand the players. You’ve got to understand who’s on the team.
As you start to look at some of these accounts, you know, there’s ways to set up email alerts. There’s ways to look at their existing investment if they have one. And understand what’s there and start to look at what opportunities may exist. And Paul, I love what you said about finding those small wins, because a win isn’t just creation of, or solidification of the deal. A win could be, I set up two or three meetings this week with senior executives at this organization, and I had conversations, and I was then able to introduce them to other resources that are part of my team. So, you know, when I look at a new account, a new territory, whatever that is, I’ve got to understand what exists. Are there relationships? Are there plays that I should be thinking about? Are there resources that I should be bringing to bear? Are there things that they’re investing in today that they’re not using? Try to find that angle or that industry intel, or maybe even that personal knowledge that you find out about this executive or influencer on social media and leverage that to get that meeting. But set the table first and make sure you’ve got those pieces in place before you go to market.
Paul: I love it. And the analogy you used there, “You can’t feast until you set the table.” What a glorious analogy. I’m going to have to use that from now on. I’ll give you credit. And I’m hungry, by the way. I’m fasting. Do you ever do that intermittent fasting?
Carson: Every once in a while. Yes, and I probably should do it more. Yes, and I have not had breakfast yet today, so that’ll be next on my list.
Paul: We got to set the table before we feast, right? But, there you go. Anyway, love that analogy. Great examples of just being prepared to go out there and to sell after those new opportunities, right? I remember hearing one time, “There’s no greater burden than having a new opportunity.” With that comes expectation; with that comes new effort. But with that comes excitement and being able to go out there and make things happen. That’s one of the best parts about sales, I think, is that challenge of just getting started. And, you know, you’ve probably noticed this too, working on the size deals that you’ll work on. They take time. They take time, but you’re going to generate momentum along the way. And you get to that point within a deal where the deal almost continuously moves forward on its own momentum. You have enough people buying in. You have enough people on board. Everything is working. They have budgets in place. They’re ready to sign. It’s like you generate that momentum towards the end. So anyway, good stuff.
Let’s get into one of my next favorite topics. And that is, “Man, I’m stuck in procurement. How do I strategically engage an opportunity?” This is a common challenge I hear from salespeople on just how to get out of procurement. And my question is, why do we even start with procurement if you’re, if you’re stuck there. But let’s talk about this a little bit.
So Carson, why don’t you get us started and just share your thoughts. When you’ve got a sales team that is getting stuck in procurement, what advice do you have for them?
Carson: Yeah, you know, Paul, this is a common one. And I think it all begins when you have to ask yourself, ‘What kind of seller am I going to be?’ You know, because there are order takers and then there’s the hunters and farmers among us. And I think it’s critical that we are a hybrid of the hunter and farmer. You go out, you find relationships, you engage with key stakeholders. You’re not going to understand truly the need of an organization until you find the folks that are kept up at night by these issues.
So, I loved how you said, “Why would we start in procurement?” Now, granted, naturally, this is always going to be a relationship that begins immediately. And don’t get me wrong, I have some phenomenal relationships with procurement. I wouldn’t say to discriminate against them or not talk to them or stay away from them. They are a key part of the relationship. However, it is going to be instrumental in success of a relationship or a deal to engage key stakeholders as part of the process. I will tell you this, I spend a lot of time doing what I think a lot of people call social or digital selling. I leveraged LinkedIn and other tools and insights to create relationships across a business. In fact, one of the organizations that I worked with most prominently around a very strategic pursuit or deal, I reached out to over 500 people in this organization connecting on LinkedIn with well over 250 of them. And so, had a very good alignment. And I will tell you that sometimes there will come some discomfort. If you want to be very successful in sales, you’re going to have to live sometimes with uncomfortable or ambiguous situations. And you’re absolutely going to have stakeholders or people as part of their organization that tell you, “Hey, the relationship stays here.” You have to make the conscious decision to own the all-up relationship with that organization, as opposed to allowing yourself to be siloed.
And it’s difficult. It’s challenging to make that decision because, unfortunately, sometimes you’ll ruffle feathers because, unfortunately also, sometimes there’s politics and there’s other things at play and you can step on some landmines. I’ve stepped on plenty in my day, but I’ve made that conscious decision to sometimes be, as I like to say, the hero that can be the villain.
I know that by owning the all-up relationship sometimes, my working with key stakeholders within the organization to make sure that I plug into their business needs, make sure that I avail them of the resources that are at their disposal, to make sure that I go along with the journey with them. That’s what ultimately leads to great relationships and deals.
But along the way, sometimes you have to be the hero that can be the villain. Not everybody’s going to like you. And I hate to borrow from Gordon Gecko, but, uh, you know, he did say, “If you want a friend buy a dog.” It’s a very callous way of basically saying that sometimes we have to be Batman, we’ve got to go out there and do for the greater good what’s right for that organization. And that isn’t necessarily making friends along the way. It’s making the tough decisions, creating relationships with meaningful stakeholders, than owning the all-up relationship with that business.
Paul: Man, Carson, I love it. There’s so many things there that you mentioned that are important: owning that all up relationship, being willing to step outside your comfort zone, you know, being the hero that is also the villain. What a great way to explain it. And I think about that hero piece as well. You know, oftentimes, it’s about making that procurement person feel like a hero along the way as well. The procurement dynamic—it’s an interesting one. It’s an interesting one because, as a salesperson, you are led to the procurement department. That is the path of least resistance into any deal whatsoever. And companies do this on purpose. There’s a reason why it’s easy to find the procurement person’s contact information. There’s a reason it’s easier to meet with them, because once you are led to the procurement path, you’re going to get stuck there. That’s part of it.
So, you’ve got to take that road less traveled. Finding out, you know, who the other key stakeholders are. Identifying what’s important to them, how it’s going to impact their business. But, you know, when you do get stuck in that procurement path, one thing that I would urge salespeople to do, first of all, find a way to make them look like a hero to the rest of the organization, but connect procurement to the other departments impacted by this decision. You know, procurement is not only buying a, you know, a multimillion dollar software package, they’re also securing the contract for their uniforms the next year. They’re buying office supplies. They’re buying any number of products. They live in a transactional way. And so, in this transactional world, they’re not often made aware of the impact that their decisions can have on the rest of the organization. And so, they take a narrow view of the overall—let’s call it the overall buying path. And then they’d look at the mere transaction versus the actual impact that it’s going to have. So helping them look beyond procurement, look beyond just that mindset. That’s going to be critical.
Another piece that we talked about, you know, taking the path of least resistance. Sometimes it makes sense to start at the very top. Sometimes it makes sense to start in the very middle, you know, when you’re going to be tapping those influencers, other decision makers, those people that have the information, start in the middle or the top. All right. Starting at the bottom, it’s harder to work your way up. But with procurement, it’s a challenge.
The other challenge is you’re trying to sell a solution, a value-added solution, to the one type of decision maker that’s the least likely to buy on value. Price is going to be their primary concern. That’s going to be one of the factors. So, you know, getting out of procurement is key. The tips you mentioned, those are perfect.
So let’s get into this last topic. And this is one I hear quite a bit. What happens when a deal gets stuck and the customer goes completely silent on you? How do you manage that? When I think about that, I’m thinking of something my dad mentioned quite a bit when he was in the sales training and speaking world. He would say, “Don’t become a prisoner of hope.” Prisoner of hope. And that’s when we just believe out of sheer will and hope that we’re going to win that opportunity eventually. It’s almost cliché. Hope is not a strategy. Right? We’ve heard that so often. But hope is an important part of sales, we just don’t want to become a prisoner of it. So, from your perspective, when you get a deal that is stuck, when you got a customer that’s gone silent, how do you navigate that?
Carson: Yeah, I mean, this is a common one for sure. And, I think the challenge is that some of this starts before the deal gets stuck, obviously. You, as a seller or as a leader, you have to control the controllables. Don’t get me wrong, sales is a probability game. It’s about relationships and resources, but people and process. And so, you’ve got to make sure that you understand—and it’s very similar to when you break ground in a new account or new territory—got to understand the playing field. Who are the players? Who’s going to sign off on this? Does the board have to look at the deal? Does it have to go through a legal process? Also, you know, what thresholds are going to trigger additional actions on their part? Do they have the budget? Are you working with the right shareholders that have the power to sign off on this ultimately? And then, have you mapped out together the key milestones and why those milestones are important?
Because there’s an element of mutual accountability here, Paul. We’ve got to make sure that we’ve identified that need as a seller in the organization that we’re working with, but we also have to understand any implications or ramifications if they don’t execute. So, sometimes, it’s fear that inhibits change. And so, as sellers, we often have to face the reality that if the fear of change is not outweighed by the fear of standing pat, then the likelihood of them making that change is very minimal. So we have to make sure that there is an understanding of, and that they see the return on investment that we’re working with the right folks, that we understand their processes, and that they understand ours.
I believe—. I’m a big believer in deal transparencies. So I make sure to help other organizations understand all of the resources that I can bring to bear, as I am an evangelist and an advocate for them within my organization, and what discounts, what pricing, anything that’s set, anything that’s part of this deal. But when the deal gets stuck, there can be a variety of reasons for this. I often find that it’s because we’re not working with the right people, because we don’t have all of the right people in the boat with us. And when this happens, the challenge is you’re relying on whomever you’ve been working with to sell this concept to someone else—to the real buyer, to the real influencer. And why would you put the power into—, of doing your job into the hands of the wrong person? And that’s why I think a lot of these start before the deal even goes out onto the track. You’ve got to make sure that you have those right relationships.
Now when the deals get stuck and let’s say, for all practical purposes, it’s something that everybody at the table agrees that this is something we want to do, but for whatever reasons that it gets stuck, typically you want to go back to these folks. And I always make it about them. I always make sure that I say, “Look, this is Carson. I’m calling because I want to make sure we’re still aligned to the timelines that you identified as important. I know that this project needs to be signed off on, or moving by XYZ date, because of some of the critical milestones that you’ve indicated to our organization. In order to line up our resources appropriately, or in order to make sure that this process is on time to capture some of the resources we’ve provided or incentives we’ve provided, we need to move. And we need to do it by X date.”
Anything that you can do to underscore the priorities that they have outlined to you makes it personal. But I can tell you that sometimes these things work. They don’t always, but they will give you a higher probability of at least getting some kind of response or return.
Lastly, I would say that sometimes to your point earlier, Paul, deals sometimes get stuck just simply because there may be a lack of interest. And so it comes back to the risk factor. If there is no significant progress, if they have not responded to multiple overtures, then you’re not risking much by going out there and saying, “I’m going to have to pull attention or resources off of this project if we don’t move by X date, because these resources are in demand.” Or “I may have to shift my attention because I’m being called elsewhere, and I haven’t seen the momentum that we need to see to continue to invest.” You’re not risking anything by doing that. And I think that’s a hard Bandaid for some to pull off, but you have to look at it dispassionately. To your point, hope isn’t the strategy here. The strategy needs to be calling them back to the table based on priorities that they’ve outlined, but making it as personal as you can. But it doesn’t work every time, it just gives you a better chance of doing so.
Paul: Yep. And, you know, to build on that, especially, you know, ripping off that Bandaid and having that tough conversation, it’s easier to have that conversation when you have a pipeline bursting—that is filled with opportunity. At this point, when you are following up with a customer, you know, obviously reiterating all the things you mentioned, “Hey, this is the timeline that we set forth based on the priorities you set.” All that’s critical. Restating your value proposition, focusing on what they stand to gain, while minimizing what they need to sacrifice. All of that’s going to be important. But following up with confidence is also going to be key. There is no seller more confident than the seller that walks into a deal that they don’t need.
Think about how you felt in your career when, let’s say, you’re 120% of quota, and you’re following up on a few deals that will just be cherries on top. You go in there with so much confidence seen by the customer, they see it, they experience it. And people want to do business with people that instill confidence in them, that they see them and they’re saying, “Okay, yeah. He really must know something,” or “She really has an understanding of what we need. We need to move forward on this.” So that confidence piece is going to be key as well.
One other thought. You know, customers that go completely silent. You know, I’ve seen this with salespeople where they’ve called, they’ve emailed, they’ve followed up, they’ve sent a telegram, singing telegram in some cases (chuckling), you know, where they just give you no response whatsoever. You know, it’s important to send a message. And this is typically when you’ve reached the walking point, when you’re like, “We’re probably not going to get this deal. Something that’s going on here.” Just send them a note and say, “Look, I feel like we’re a strong fit, that we can help, that we’re aligned and we’re going to make a difference in your business, but I’ve not heard from you whatsoever. If you are still interested, let me know. But if you’re not, let me know that as well and I’ll quit bothering you.” I’ve found sending a transparent message like that, where you’re just leveling with them and saying, “Look, what’s going on?” that’s going to give you a response. Now, maybe it’s not the response you want, but at least you will know.
Think about how often salespeople get strung out on a maybe, where they just don’t hear anything. And a lot of times salespeople, you know, they want to keep those deals in their pipeline because it gives them that sense of security, where they feel like they’ll be able to resurrect that deal at some point. It looks like a clip out of Weekend at Bernie’s, when they’re trying to keep Bernie alive. They’re trying to keep these deals alive. It’s just not going to happen. Admit it. Move on. The easiest way to move on is to have three or four other deals in the hopper that you’re working through right then.
Great questions today, Carson. These are things that we hear constantly. Now, I would love to hear more about your book. I know you’ve got a few books, but the one that started it all Tell me a little bit more about this guy, the protagonist, the sales guy in the book.
Carson: Yeah. You know, I wanted to write all my life, and I started writing these newsletter columns when I was AT&T, and they were all about sales. I wanted to write a sales book, but as I mentioned, you know, it’s been done so many times so well that I didn’t want to replicate that. So I created this fictional protagonist, and his name’s Vincent Scott
Paul: Is he related to Michael Scott from The Office?
Carson: That’s to be determined. He has a meteoric rise, and he has some trials and tribulations. He pays his dues like all sellers must do. But, basically, he writes a book inside the book and it’s some of the lessons that he’s learned along the way, but it shows how he learned those lessons.
So, Birth of a Salesman came out in 2010. My latest was Salesman on Fire this past year, which was actually, I personally interview this Vincent Scott character and it’s kind of a day in the life. I try to take each one as an individual one-off and just kind of a unique approach. And now, I mean, the character has aged a little bit and he looks back on his career a little bit differently, has a different perspective. So, I’d like to think that the perspectives change over time. I grew up in a cold-calling environment—one-call close—and have spent the last decade in enterprise sales. So, uh, definitely have a different vantage point than I once did.
Paul: Nice. That’s great. And where can people pick up the book?
Carson: Yeah, they’re available Amazon, Barnes & noble Walmart. Any of those outlets, you can find the full series.
Paul: Awesome. Great, Carson. Well, everyone, we’ll have links to all that on this episode’s webpage, so you can check it out.
Carson, wanted to thank you for coming on the show today. Truly appreciate it. And thanks for helping out the sales community with your thoughts and your advice.
Carson: Paul, always a pleasure to talk with you, and it’s the least I can do. The sales ecosystem and community has given so much to me, and I love giving back to it.
Paul: All right everyone. Thanks again for tuning in. Make it a big day.
