Sell Like A Leader – Episode 42

David Kreiger sits down with Donald C. Kelly, founder of The Sales Evangelist, one of the longest-running B2B sales podcasts in the world with nearly 2,000 episodes, and Chief Creative Officer of Blue Mango Studios, to break down exactly how a struggling seller becomes a closer.

In this episode, they cover:

  • The role-play habit most reps avoid, and why it builds real muscle memory
  • Why leaders should be the ones earning market trust before an SDR ever picks up the phone
  • Why “the gift of gab” is the wrong explanation for who succeeds in sales, and what actually separates top performers
  • How Donald used AI to reverse-engineer a competitor’s client list into a hyper-targeted, FOMO-driven outreach campaign

If you’re building or coaching a sales team and still think talent is the differentiator, this conversation will change your mind.

About Donald C. Kelly

Donald is the founder of The Sales Evangelist, a sales training organization, and host of the podcast by the same name – one of the longest-running B2B sales shows in the world, with nearly 2,000 episodes.

He’s also the founder and Chief Creative Officer of Bluë Mango Studios, a South Florida podcast production studio that helps brands build thought leadership and generate leads through content, a business he’s run alongside TSE since 2019.

Podcast Key Takeaways

  • Talent isn’t the differentiator; process is. Donald was told he had “the personality” for sales, but his performance didn’t change until he learned a repeatable process.
  • Role play is about building muscle memory. The goal isn’t a clean, successful outcome in the role play; it’s rehearsing pauses, objections, and reactions enough times that they become automatic when a real prospect brings them up.
  • Taking rejection personally is a mindset problem. Early on, Donald saw prospects only as titles instead of humans having a bad day. Once he realized the prospect wasn’t rejecting him, rejection stopped being something he had to “survive.”
  • AI’s edge in sales is making outreach relevant. Donald’s team used AI to pull competitor testimonials and map them to lookalike prospects, building FOMO-driven lists in minutes; the AI didn’t write the pitch, it found the trigger that made the pitch worth sending.
  • Skipping one-on-ones is a bill that comes due later. Leaders who say they’re “too busy” for one-on-ones are trading a small recurring cost now for disengagement, tension, and drift that shows up three months down the line — by then it’s much more expensive to fix.

Connects

Connect with Donald C. Kelly: https://www.linkedin.com/in/donaldckelly/

Connect with David Kreiger: https://www.linkedin.com/in/davidkreiger

Subscribe to the podcast and follow our Podcast LinkedIn page so you don’t miss any episodes!

Transcript

David: Welcome back to another episode of the "Sell Like a Leader" podcast, the podcast for revenue leaders who are on a mission to cultivate a high-performing sales team within their organization. I'm your host, David Krieger, founder of SalesRoads, America's most trusted appointment-setting and lead-generation provider.

Today we are bringing you another great revenue leader, Donald Kelly. You might know him as the founder of The Sales Evangelist, a sales training organization, and the host of a podcast under the same name — amazingly, one of the longest-running B2B sales shows in the world, with nearly 2,000 episodes.

He's also the founder and chief creative officer of Blue Mango Studios, a South Florida podcast production studio that helps brands build thought leadership and generate leads through content. So, Donald, [00:01:00] it's great to have you on the podcast — a fellow South Florida guy. It's awesome to chat here.

Donald: David, thank you, I appreciate it. Yes, it's always good to connect with our South Florida friends here in paradise. We're coming into that beautiful season, right? Between December and April.

David: Yeah, we're getting there. Not quite.

Donald: Can only hope, right?

David: But we are getting there — almost out of the woods. Donald, I'm excited for this conversation. You've built your career around helping new and struggling salespeople, and I want to spend the time we have together talking about how you can take someone from a struggling or new salesperson all the way to closing.

So that's all we need to cover in 30 minutes here.

Donald: Let's go. No biggie.

David: Yeah, we can tackle it. I love your bio — you started, as you said, as a struggling seller yourself, and despite being told you had the personality for it, it wasn't until you [00:02:00] went through some proper sales training that you started seeing improvement in your performance.

Can you break that down for us? What changed for you in that training — what did that raw talent, or "sales personality" as people called it, not give you?

Donald: It was structure and process — a repeatable process. That's where I first fell in love with the idea of sequences working so well — not so much sequences in terms of how many emails or calls you send, but a sequence in a process.

Because once I got into it, I thought that if I had a discovery call with someone, I just needed to be convincing — and that led to me talking way more. It also meant I didn't have a structure for the information I needed to gather from them, or for making it a real conversation.

I didn't know what to do after that first meeting. I'd play the eternal follow-up game — "Let me just follow up with the prospect, they seemed to like the conversation, we were nice." But when I got training, it helped me understand that this is repeatable. [00:03:00]

Looking at some of the top-performing sellers I've known over the years, they weren't great because they had the gift of gab — it was because they had a process they followed. Often that wasn't visible to me, because they'd just go into a meeting and do a great job. I didn't see them doing MEDDIC, or following the Sandler process, or applying Challenger. I didn't see them building rapport or planning next steps. I didn't see any of that. But once I understood it, David, I thought, "This is liberating."

It was so exciting that I started teaching it to my then-girlfriend — now my wife — and sharing it with friends and family. I remember telling a friend at church about it, [00:04:00] about getting onboarded at this company and getting proper training, and how much I loved the process.

He's a Six Sigma black belt, so he loved processes too. It goes to show — if you give people guidance and a repeatable structure, they can thrive and really succeed. So I drank the Kool-Aid, and I've carried that same mentality ever since, teaching it to my clients as well.

David: A lot of times people feel like they can just wing it — that sales isn't something that needs a process, it's just something you do every day. That's where people go wrong on a few levels. Obviously, they're not following a process — they're all over the place. But sales is also a lot about time management and structuring your time, knowing what to do and when. Without that roadmap, you can be working really hard and still not making any progress. [00:05:00] Those frameworks not only make you better at things like discovery calls — they also help you know what to do next without having to think about it constantly, keeping you on track and making sure everything gets done without anything falling through the cracks.

Donald: Yeah, and that piece gives you a level of confidence — I don't have to stress about where a deal is, because I know it's in the proper stage and I've done everything I needed to. So the result comes as a natural byproduct. It gave me quiet confidence — maybe not so quiet.

David: Going to the fundamental skill-versus-personality question — a lot of people say they got into sales because they like talking to people. Do you think that's flawed thinking on its own, or does it need to be paired with training?

Donald: Paired with training, by far. There are people who go into sales because [00:06:00] they were told they have a great personality for it — "You're outgoing, you should do sales. You're good with people, you should do sales." That's all fine, but...

There are also a lot of people who simply fall into sales. One of our teammates, for example, was hired as a customer success person, evolved into a sales role, and then evolved out of it again — she never set out to be a salesperson, it just gradually happened. Another one of my best hires was someone I taught in an adjunct sales class. She was remarkable, so [00:07:00] she became my TA the next semester. I thought, "She's got the stuff." So I hired her.

What I meant by "the stuff" — she understood how to follow processes, communicate with people, ask effective questions, and listen. She was eager to learn and had personal goals she was working toward. So we trained her, and she became one of our top sellers, because she was a student of the process and committed to it, combined with her own passion and drive for herself and her family.

I feel like most of us fall into sales. There's a class of people who come into it because of the gift of gab, but for most of us, we fall into a sales career — and the ones who thrive are the ones who marry a desire with whatever process the company has. That's my theory, and I'm sticking to it.

David: I agree with that. [00:08:00] I really think that, from a personality standpoint, you can find great sellers who are extroverted, have the gift of gab, and know how to engage with anyone in any circumstance. But you can also find equally great sellers who are introverted, who are good listeners, and who sometimes have to push themselves into social situations.

I'm one of those. I think whatever personality you have — with a lot of gradation in between — you can find good sellers along those lines. But it comes down to the two things you mentioned. One, you need to be motivated to be in this position and enjoy the idea of helping people and figuring out ways to close — wherever that motivation comes from, you need some form of it, otherwise it's a hard profession. [00:09:00] You won't stay in it long if you can't find it. The other part, tied to what you're saying, is the will to learn. So it seems to me the personality piece can be a lot of different things, but those two things outside of it really drive whether you'll be good at this profession or not.

Donald: I think it was Daniel Pink who said it — the top performer, based on the data, isn't the introvert or the extrovert, it's the ambivert. Those in the middle. It's in his book, To Sell Is Human — the idea that these people are capable of being outgoing in situations where they need to talk to people, but naturally aren't seeking the center of attention. The beautiful thing about ambiverts is that, since they're not seeking attention, they put that on you — the prospect — so you share more, and you don't feel like you're competing with the salesperson for attention. It's a remarkable thing all the way [00:10:00] around.

David: Yeah. And as long as you're looking at it through the lens of training and learning, you figure out who you are and how to lean into your strengths while working on your weaknesses — that's where some of the magic really happens for people.

Developing sales skills was essential to turning things around for you. Looking at it from your own perspective, or from the people you train and coach, are there any learning strategies that really help it stick? A lot of people go through training, and a lot of companies invest in it, but what actually makes it stick — what makes it translate into success on the ground?

Donald: Some people may not like this, but I'll say it: role play. What I find is that the more you practice before you get into the game, the better you perform in the game. Some sellers say, "I don't like role play — it's too awkward, it's unrealistic, it's too rigid, so I don't do it." Because they skip it, they end up practicing on their actual prospects instead. But the goal of role-playing — this frustrated me at first, David. I went to school locally here — some of you may know, you're a South Florida guy — I went to Dreyfoos, an arts school, so there was an element of performance I was already comfortable with, and I enjoyed that. When I did role play, sometimes it felt like I wasn't getting a clean outcome — it was just practice, and I'd wonder, "When does the deal close?"

But what I learned is that, like with anything else, the goal isn't a wonderful, successful close in the role play — it's practicing a scenario until you build muscle memory for that situation. With an objection, for example, we may not necessarily resolve it [00:12:00] — we're practicing how to address someone's genuine concern empathetically, and practicing the questions we could ask. Once I started looking at it that way, as a practice scenario, I felt so much better in the real world, because when people brought those questions to me, it wasn't my first time hearing or practicing it.

I already knew what to do. I'd worked on my pauses, worked on when to be quiet, because I'd done that awkward practice with my teammates. That muscle memory took over, so it helped me be more effective and influential with prospects in real life.

Role play, by far, is the best thing I'd recommend — role play by yourself, in Monday morning meetings, and even in one-on-ones with sales leaders. If there's one thing I could say, that would be it, [00:13:00] because it's the closest you come to the real deal.

And with AI now, it's even more effective. You can role play with Claude or ChatGPT — tell it, "I want you to raise this objection, follow this basic model, our company's model, and be moderately challenging with me." You can do this anywhere, right now.

David: It's super important, and I agree 100%. Over the past 12 to 14 months, we've built role-play AI agents for every program, with different personas, because we agree. And it's always been frustrating when reps say, "I don't need to role play, I'm so much better in front of a live person."

Donald: I don't need to practice throwing a ball. I do it so much better in the game.

David: That's right. There are two huge analogies here — whether you're an athlete or a theater person. You don't go on the field or the stage until you've practiced enough. You practice [00:14:00] far more than you perform.

In sales, we actually spend a lot less time selling than we do on other things, which is unfortunate — but you've got to have that same mentality. World-class athletes don't just perform better on the field out of nowhere. They've worked thousands of hours kicking that ball or shooting that basket. It's the exact same thing. Like you said, it's muscle memory you need — objections can be similar, but the tone can be different, everything can shift slightly. You've got to know how to react to different scenarios, and the only way to do that is by practicing. It should be fun — you should make it fun. I agree 100%, Donald.

Donald: I want to emphasize — the people I've found who don't like role play either, one, don't like practicing in front of their peers because it's challenging and they don't want to be embarrassed, or two, feel like it's not real enough. [00:15:00] But it's not about being real — it's about mastering part of the process. Have an objective for your role play, and that helps you be more real. I just want to master how I react when you ask a question. That's what role play is for — not whether I overcame the objection. I don't care if you overcame the objection — did you follow the steps? Do you know what to do when you get thrown into battle? You'll figure that out when you're in there, but in the scenario, we can't practice everything that might come up — we practice the situations.

David: Building off that — even if it's not completely real, or it's a bit easier, you're still practicing, still building that muscle memory. One note to managers, though — I do think a lot of times managers go easy in role play. [00:16:00] Prospects are tough, and one thing I loved about AI role-playing early on is that it can be hard — it doesn't care. So one thing we coach our managers on is to be tough. It isn't going to be easy out there. You can't just roll over. You can't always have a successful outcome, because that's not how it works. So I think you can learn either way, but managers should be tough in role plays.

Donald: Be tough on them.

David: I know — come on, make sure they're prepared. It's amazing — you've talked to thousands of sales experts, and that doesn't even count all the coaching and consulting work you do. Looking back at your own early struggles, and with the perspective you have now from talking to and coaching sales leaders — what's something you wish someone had told you when you were just starting out?

Donald: There's so much. We already covered the sequence piece, which was helpful, but "don't take it personally" is probably one of the biggest ones. Especially when I first started, I went into it as Donald, and I saw these people as "prospects." I didn't see them as a man, a father, a mom, a son, or a daughter. I didn't see them as someone on their way to work who'd just spilled coffee. I didn't see any of that — I just saw an IT director, a director of nursing, or a doctor if I was selling an EHR solution.

That's who I saw. I wanted that person to be ready to buy — I didn't see the human side. So I took it personally when they didn't reply, didn't engage the way I wanted, rejected me, or said it wasn't the [00:18:00] right time, or that they weren't interested.

It made me so gun-shy that the next time at bat, I'd be all messed up — "This director of nursing rejected me." But in reality, they don't know me from Adam, and I don't know them. I didn't see them as human, and they didn't see me as human either. They saw me as a salesperson interrupting them — someone stopping by their office right after they battled traffic and got their kids to school, and now some sales guy is in the lobby wanting to talk.

I didn't see them as that, and because of it, it was all about me — they made me feel bad, they rejected me, they didn't want to listen to me. If someone had told me early on, "It's not about you, they're human too," I probably would have performed a bit better.

But I'm grateful I went through that process to get to where I [00:19:00] understand it now and can perform better. You can't assume the prospect is waking up ready and waiting for your call. We have to see them as human beings first, with their own challenges — and if we can address those challenges, it becomes easier for them to see us as human too, instead of just getting mad. They're turning down a salesperson, not turning down Donald.

Often, when you call that person again in two weeks, they don't even remember any of it. You can't take it personally or get caught up in your emotions.

David: That's one of the big reasons people don't make it in this career — there's a lot of rejection, and you need the right mindset around it, or there's no way to survive. But if you can learn that, like you said, it can become your superpower — especially [00:20:00] if you channel it into learning from each interaction.

Ask yourself, "Is there something I could have done better?" Sometimes there isn't — maybe they spilled coffee on themselves and are having a bad day, there's nothing you could do. But if you treat it like a puzzle and a way to learn every day, and remember it isn't about you — which is tough, even at our stage, it still stings a little — you've got to shift that mindset, and then it becomes a superpower. The people who accomplish the most in sales, business, or entrepreneurship are the ones who can take the rejection and the small failures and keep pushing on. That's great advice — I would have loved to hear it when I was young, Donald.

And lastly — it wouldn't be a B2B sales show if I didn't ask you about AI, or I don't think you'd get put on Spotify at this point. How would you advise young sellers trying to break in and develop their skills to use AI to learn faster? You already gave a great example with role play, but how would you coach them?

Donald: This is where I start getting excited — I love it. My view of AI used to be like everyone's — "ChatGPT can write emails for me" — and then everyone's emails started sounding exactly the same, and it got lame. But the way I look at AI now is as an assistant — an effective assistant.

Going back to what you said — most people probably missed it, but you mentioned what takes up most of salespeople's time these days. Selling isn't a huge chunk of it. Salesforce's data puts actual selling time at around 20%. [00:22:00] What I've found is that AI can help me sell more. My favorite word — I need to put it on a shirt — is relevant. If you're in sales, you've got to be relevant. AI helps you be relevant.

What I mean is, there are things called triggers that most of us are already aware of. The more we understand a trigger and the problem someone is having, the higher our chance of being relevant to that person at that moment.

Here's an example — for our production agency, we ran an outreach campaign. We looked at our top competitors, and like any good company, they have testimonials on their website. So we had Claude go through all of our [00:23:00] top competitors, find their testimonials, and categorize what each one said and what problem it solved. Then we took that client who gave the testimonial and asked Claude to find their competitors — so now we had our competitor's top client's competitors. We used that messaging to reach out to marketing directors at those other companies: "Joe at XYZ has been using podcasting and said it helped generate 10% more appointments — is that something you've explored?"

Marketers tend to agitate on each other anyway — they follow their competitors, so there's a FOMO effect. I gathered all of that information in a matter of minutes, [00:24:00] and when I reached out, it was highly relevant. We also looked at people who were new to their roles, or companies going through changes. My list wasn't huge — maybe 10 companies — but they were in-market, with competitors already using podcasts and seeing results. That made me far more effective.

If we can help sellers use AI to be more precise — to shoot with a spear instead of a shotgun — they'll be far more effective in outreach. At that point, it's not about AI writing the message for you — you already have enough relevant information, you've found the right triggers, and you're finding people willing to listen.

So when it comes to AI, it's making me more relevant, more effective at the pre-sale work — researching the person I'm having a discovery call with, [00:25:00] preparing for the call, looking at what's changed in their organization, how their organization makes money, how long someone's been in their role, and how this could impact them if they made the right choice with us as a vendor. AI helps with that prep work, and it also handles some of the busywork — like connecting Claude to Fathom to draft post-call emails and update the CRM. That takes away admin work so I can focus on meeting with more clients. I love AI for that purpose — not for blasting out 2,000 identical emails.

David: I love that use case, and I think it's a smart way to use AI. We've seen that one of the biggest lifts for us is in list building and targeting — figuring out the nuances of which companies might be relevant to our clients in ways [00:26:00] a basic industry filter never could. These AI tools can read every website, look at every LinkedIn profile, and help you prioritize your time toward the right people. I love that play you described — that's genuinely creative. We should start winding down, Donald. Before I let you go, we love to ask our guests a few rapid-fire questions. Ready?

Donald: I'm ready.

David: All right, let's do it. What's one thing people don't give enough value or attention to in leadership?

Donald: One-on-ones. I've had leaders tell me, "I just don't have enough time to meet with my team, I'm too busy." But spending one-on-one time with your team alleviates problems, builds culture, keeps people on track, and reduces tension. [00:27:00] Doing them consistently might feel ineffective, because it seems like you're just meeting — but stop doing them, and see what it's like in three months. You'll see everything trace back to that. So that's one thing leaders need to do — suck it up and spend time with the people you're leading.

David: Absolutely. Sometimes it's more meetings, not fewer — but they need to be the right kind of meetings. What's one skill you'd advise everyone in sales to master, leaders or not?

Donald: Listening. Practice it. It's easy for us to try to quickly solve a prospect's problem, but sometimes it's just about listening deeper. One of the best exercises is this — try it for a couple of hours after work today: go to a store, and with anyone you talk to, [00:28:00] just say, "Interesting — tell me more." Start doing that after everything someone says. I promise you'll have deeper conversations. Even your kid might say, "I want pizza today." "Interesting — tell me more about that." And you might find out, "I really like pizza because that was the first time we went out as a family together and had pizza — so every time I think about family getting together, I think about pizza." I wouldn't have learned that if I hadn't asked.

Just practice it, and you'll be amazed. If you really want to level up, do it five times — try the five whys, probing three to five times: "Tell me a little more about that. That seems like there's something else there." You'll see you have much richer conversations. So — listen more.

David: Love it. Favorite business, leadership, or sales book?

Donald: Oh, there are plenty on my desk, but the one I'm revisiting right now is Think and Grow Rich. One of my mentors and father figures gave me that one. It's not necessarily about the "millions of dollars" idea, but the fact that you can set a definitive goal and work toward it. [00:29:00] That's helped me in different areas — not just sales, but business and personal life too. Whatever you want to do, you can set a goal, work toward it, and have the mindset for it — I believe strongly in mindset. I don't believe in "put it out there and the universe brings it to you," but I do believe there's science and data behind visualizing, planning, setting a goal, and having a process behind it — that's how you achieve those goals.

David: When people hear "manifest," they think it's hokey, but it's really just setting your mind in the right direction and pushing yourself there. Favorite quote, mantra, or saying that inspires you as a sales leader?

Donald: "In order to be successful, do the opposite of what everyone else is doing." That's why my sales huddles aren't a measuring contest of "here's how many deals I have." Our sales meeting is a chance for us to sharpen each other, iron sharpening [00:30:00] iron. In my one-on-ones, I definitely want you to share all the details — but our team goals get discussed in our weekly sales meeting, and it's not about shaming anyone for having fewer deals than someone else. Let's handle that offline. Right now, where are we as a team? Are we hitting our team goal? If not, suck it up — we're a team, let's make it happen.

David: And lastly, what's the most important goal or project you're working on right now?

Donald: It's our baby, Blue Mango Studios — our youngest company. I've been doing content since 2013, David — as you mentioned, I've recorded around 2,029 episodes. What I've learned is that content done right is a business development tool.

The best salesperson in any company is usually the CEO, founder, or someone on the executive team — they just sell it better. But then we put the burden on inexperienced 19- and 20-year-olds to go talk to executives at other companies and sell to them. [00:31:00] That might blow up the current SDR/BDR model — not that we get rid of SDRs and BDRs, but what if leaders did the first "aerial drop" and shared content themselves?

Imagine your leaders sharing something on LinkedIn once a week, where their ICP is already hanging out. If they educate the market enough, they don't need to be Joe Rogan — they just need to be the known name in, say, the manufacturing space in Milwaukee, wherever the company focuses. If that's the case, share content once a week around the topics your SDRs and sales team are working on. So when my SDR calls into that small niche market, I'm already known as a bigger fish in that small pond — and that comes from content. My team sees it all the time — whenever they call a company and say, "We're with The Sales Evangelist," [00:32:00] the response is often, "Oh, I've heard of that podcast," or something similar. That gives them an opening to connect with me, the leader, before the SDR call even happens. So the most important thing many leaders can do is share content — that's one of our big projects right now. We help companies create content that helps them stand out before their salespeople ever enter the room. Content sells.

David: I think that's so true. Donald, if people are interested in learning how to build more content, how do they find you? How do they connect with you?

Donald: Two things — go to LinkedIn, search Donald C. Kelly, connect with me, and tell me you heard me on this podcast. Also, if you're in sales — we created a spreadsheet I used to [00:33:00] track my daily sales performance, to know how many calls I needed to make and how many proposals it took to close a sale. It helped me understand my ratios and plan better. You can download our free software at prospectpro.io — again, prospectpro.io. You can use it to log your daily activity, and over time it'll show you, for example, that if you need three appointments, you need a certain number of outreaches. Test it out — prospectpro.io.

David: That's awesome — we'll put it in the show notes as well. Donald, thank you so much for taking the time to be with us today and sharing your expertise. And listeners, thank you for tuning in to another episode. You can always reach out to me, David Krieger, on LinkedIn — I always love hearing from our listeners. Thanks again, Donald.