Sell Like A Leader – Episode 39

David Kreiger sits down with Lynn Hidy, Founder of Up Your Telesales, to explore the most common mistakes inside sales leaders make and what it actually takes to build a team that performs consistently over time. 

Lynn spent over two decades on the inside sales floor and made the unconventional choice to step back from management and stay a seller. That decision gave her a rare, ground-level view of what leadership gets wrong and what it takes to get it right.

In this episode, they cover:

  • Why the skills that make a great individual contributor rarely transfer to leadership
  • How redefining success inside a sales org keeps your best sellers doing what they’re actually good at
  • The bell curve reality that most leaders are ignoring
  • The shift from product talk to problem talk, and how it makes your team less transactional almost overnight

If you’re a sales leader trying to build a durable inside sales team without burning out your best people, this conversation will challenge how you think about promotions, performance, and coaching in 2026.

About Lynn Hidy

Lynn has spent over two decades in inside sales, starting out as a top performer herself, earning a Golden Circle Award and two consecutive President’s Club recognitions.

From there, she moved into sales leadership, then made an unusual decision: she stepped back onto the sales floor. That experience ultimately led her to found UpYourTeleSales, where she has spent years coaching inside sales teams to move from good to what she calls fantastic.

And most recently, she published her book, Mastering Inside Sales Leadership.

Podcast Key Takeaways

  • The best seller is rarely the best leader. The skills that drive high individual performance are fundamentally different from what it takes to coach and develop other people.
  • Your biggest leverage is in the middle of the bell curve. Most leaders split their time between managing top performers and documenting out the bottom, and the middle 68% gets ignored entirely.
  • When inside sales teams anchor conversations on features and offerings, they become transactional. When they anchor on customer gaps and desired outcomes, they become consultative
  • AI should make coaching better; not replace it. Lynn is seeing a troubling pattern: leaders offloading coaching to AI tools entirely, rather than using AI to sharpen their own coaching conversations.

Connects

Connect with Lynn Hidy: https://www.linkedin.com/in/lynnhidy/

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. I'm your host, David Kreiger, founder of SalesRoads, America's most trusted sales outsourcing and appointment setting firm.

And today, we are bringing you another great revenue leader, Lynn Hidy. Lynn has spent over two decades in inside sales and started out as a top performer, earning a Golden Circle Award and two consecutive President's Club recognitions. From there, as many do, she moved into sales leadership. But then she made the unusual decision, and she stepped back and decided that she wanted to stay on the sales floor.

And we're going to dive into that a bit with Lynn today. But that led her on her journey to found her current company, Up Your Telesales, [00:01:00] where she has spent years coaching inside sales teams to move from good to what she calls fantastic. Lynn, so great to have you on the show today.

Lynn: Thank you very much for having me. It's great to be here.

David: Well, let's dive in, and I'd love to start with what I alluded to in the intro. Because most organizations reward their best sellers by promoting them, and you have seen that go sideways. And starting really with your own journey, why did you make the unusual decision once you got promoted to say, "No. No, thank you. I'm good where I was"?

Lynn: As a human, I am childless by choice, and probably immediately I should have noticed that organizations sometimes tend to treat frontline managers as the parents of the people that are on the team. So [00:02:00] I picked not to do that in my real life. So it shouldn't have been a shock that I didn't want to do that in my work life.

But I will say that I've always thought I could be responsible to you. You have to be responsible for yourself. And in my personal experience, sales organizations seem to want the leader to be responsible for the performance of the people on their team. And although I was a successful, from the outside, sales leader, right? My team made goal for the year, right? It looked great. I really was not the person that they really wanted in that seat.

David: And so do you feel like that is a trend among sales promotions? And what have you seen also through your consulting and what you've seen where people get promoted? Is that the right move for companies? When is it the right move, and where has that [00:03:00] gone sideways, in your opinion?

Lynn: So speaking for sales in general, yes, someone's a great sales performer, let's move them up the corporate food chain. Happens all the time. So what people... I don't know if they don't know, because it seems crazy to me that they don't know, but they forget that the skills that make someone a really high-performing individual contributor are not the same skills that people use to manage and lead people.

And I do talk about that managing and leading are two different things, right? So managing tasks and things, right? You're managing activity. You're leading the person. So how many companies do you know that have a formal leadership training for people they promote internally? I mean, I don't know very many. Especially outside the Fortune 500, right? There's not this leadership development machine inside most [00:04:00] corporations. And that's a disservice to the company, the people you're promoting, and to the people that are on their teams because it's missing, right? There's no playbook for how to be a good inside sales leader.

David: Yeah. So I think there's a few things in there I want to unpack. The first relating back to the way that you approached it is I think that both organizations think that they're supposed to promote the top salesperson, but I also think salespeople feel like that's supposed to be what they want and is supposed to be the goal. And I think that's true in society, right? We have these conceptions of success and what success is, and success is getting a promotion and getting the title.

Lynn: I had that, right? That was, that's why I said yes, right? Because sure. I will say that in sales, I feel like we have the—I'll call it a luxury—of changing the definition of success and really having people understand that sales [00:05:00] success is a different kind of success rather than a promotion.

And I will say that in a lot of organizations that I work with, I recommend that they give the opportunity for someone to have a different job title, right? So inside a sales team, you may have multiple job titles based on performance, expertise, right? Like that I can move inside the sales organization at least from that corporate hierarchy feel. And there are perks that can come with it as well. I will tell you that I consulted with a company that decided that the top three salespeople could have any job title they wanted. That was a perk of being in the top three. That for the year that you are in the top three, you wrote your own job title, and I got to tell you, people got super creative.

David: That's awesome. Yeah, I hadn't thought about it that way. I think there are ways to mitigate and give people that feeling of success without changing [00:06:00] the job that they're already good at, and that they really, even if they don't realize it, that's what they really want and they really enjoy.

Because sales leadership is a different set of skills. It's a different set of stresses. It is managing people instead of managing pipeline. And some people can cross over but some people can't. And some people really find themselves like, "Why am I doing this?" And in some ways, my second VP of sales that I worked for, he said at his last company when he was the top salesperson and was promoted to VP, it was the biggest pay cut he ever took.

Lynn: And oh, I will tell you that if compensation plans are written well, the top salespeople absolutely should be making more than a leader.

David: So you have got to understand those trade-offs, and I think sometimes that can make for these mistakes to happen less frequently.

Lynn: And I think that if, as a leader, [00:07:00] you are really having conversations about the goals of the people on your team, it will help you as well, right? So I mean, I talk about the fact that having a coaching conversation is about what they want for their career. You're not coaching to pipeline, right? That's a whole different conversation, right? But if you're digging into what makes somebody tick, then you can help them orchestrate the career that they want instead of allowing them to think that, "Oh..." And especially if they're young, right? Because you're right, societal expectation is you get promoted.

David: Yeah, and I like that. I'm a big believer in that as well. I think that it does two things. One, it does help you to coach them better because you understand what their real goals are or help them to understand what their real goals are. And I think that's super important because they're generating pipeline or closing deals to really achieve their life goals, right? [00:08:00] And it can be powerful when you can connect the two.

The other thing is you're creating a level of trust and a relationship that is really special between that person, that rep, and that manager. And we've all been there. I know the sales people who are listening have been there. When you have that special manager who you know really has got your back, there's just something special about it, and there's an innate trust, and you'll sometimes just do anything for that person because you know how important they are in your life.

Lynn: You're doing better work, and if the salesperson, you're doing better work, and that becomes the success. I really like when you said as an individual contributor, you're managing pipeline, not people, right? So I believe that salespeople need to look at what do you want to be responsible for [00:09:00] before they think about what the next career thing is.

David: Absolutely. Yeah. And what gives them energy? What are they excited about? And before you want to be, you can take on a new hire and help mentor them without being their manager. You can test leadership and see whether it's what you like, and are you looking forward to those mentorship meetings or are you being like, "Ugh, I could have had another discovery call instead of this meeting," and then you're starting to get your answer, right?

Lynn: And I found that the coaching and training of salespeople and leaders was the part of being the manager that I liked, right? So I've created a universe where that's what I do, so you can figure out where you want to go.

David: So I'd love to take a step back, and this could be part of your answer, what we're talking about right now. But you work with a lot of sales leaders across many different organizations, and so I'd love to hear your perspective on what some of the most common breakdowns are in inside sales leadership today.

Lynn: So my number one pet [00:10:00] peeve is that people think everyone can be their next rock star. They want a team of rock stars. If your team is rock stars, there's no rock. That's not really how the world works, right? And so that would be the first thing that I would say is, okay, look at your team realistically.

The bell curve is there for a reason. It's math, right? You're going to have some people that are top performers, some people who are at the bottom, and the chunk of people in the middle. And if instead we start to think about raising up what the baseline of that curve looks like,

David: Yeah.

Lynn: Then that is a real—that is realistic. You're still going to have the people distributed, but you can raise the whole. But to raise the whole, you have to work with the people in the middle.

David: I like that perspective. And it does create meaningful changes into how you address problems throughout the [00:11:00] organization versus just cutting the bottom and trying to find more of the top when really a lot of it is going to be finding that beautiful middle too and making sure everybody within the organization can be raised up through some of the processes, coaching, and training that you introduce.

You also believe that inside sales teams are too product-focused. And so you train on what you call the shift from product talk to problem talk. So can you maybe walk us through that and how you help leaders break that pattern?

Lynn: So it's... In inside sales, a lot of times people start to think of it as consultative selling, but I think that sometimes complicates things more than it fixes them. But if you shift conversationally from talking about you, right? Product, services, what you sell, what you do, [00:12:00] and start to talk about what is the result that your customers get, and really have that drive the conversations that your team is having, then all of a sudden you are less transactional because you're looking for people who have problems that you can solve and people who have gaps in what they're doing today.

And it changes how prospects and customers view having a conversation with you because you're bringing value to their conversations. You're not pushing product. And I like to use warranty as my example of that. Warranty is just a feature of somebody's product. What do I get if you have a warranty is a whole different thing to talk about.

David: Yeah. Yeah, I think it's important and it's important how it is framed in the [00:13:00] training, because I think people—we do talk about how we're solving problems, but time and time again, people revert back to the product. And I think it's two things.

One, sometimes it's a little bit harder because you got to diagnose the problem and things like that. But if you look at any training, sales training when you start at a company, it always starts with the product, right? Starts with, "Here are the different services. Here's all the brands," all that type of stuff. In many ways, you can make an argument that don't even talk about the product in the first day or so. Just talk about the personas, talk about the clients, about the problems you've solved, and really get intimate with that, and then you introduce the product. And so I think sometimes it's just in training it's where it's just always been done that way, and if you can reverse it, you can reverse the mindset too.

Lynn: And almost every organization that I work with sells more than one thing, right? They're not [00:14:00] selling a pink pen, right? They're selling a suite of offerings. And if we start with the problem, what ends up happening is you end up with choices. There's multiple things that your organization does that could fill that gap or fix that problem or help that customer. And it's funny, but you will sell more product if you are more problem and gap conversation focused.

David: 100%. I'd like to go back a little bit to our conversation about the bell curve, because I think I'd like to unpack that a little bit more, and I think it's a really interesting concept and a way of thinking about things. And so maybe if you could... You've introduced the concept a bit, but can you talk about how you coach leaders to rebalance their focus between top performers, middle performers, and underperformers? And is there something structural that needs to change within an organization to do that?

Lynn: [00:15:00] So I don't know that something needs to structurally change, but I believe in this enough that I have a manifesto about it, right? So I think the biggest thing that ends up happening is top performers demand your attention and time, and HR demands you spend time and documentation on the bottom of the bell curve, right? Those two edges end up sucking an inordinate amount of time away from a sales leader's day.

And that's the biggest thing that has to shift: how you view where you're spending your time. Because in the middle, right? So we're not gonna do the math, but in the bell curve there's the line down the middle. The people on that thirty-four percent positive to the line, those are the people that are chugging along, making goal most of the time. So they're doing good enough, so you leave them alone. And the people that are right below that [00:16:00] thirty-four percent that are on the negative side of the line are inconsistent, but again, probably doing enough.

And those are the people, when I talk to salespeople, that are flying under the radar, right? That's their preferred methodology is to fly under the radar. And in sales, if you become a rock star, there's no under the radar. Like it's spotlight time, right? You're on stage as the rock star.

So not only are they not currently performing at the level of your rock stars, they don't want to be them. Which doesn't mean they don't want to be better at what they do. But there's a chunk of people in any sales organization that are comfortable in their space, which doesn't mean they don't want to produce more. And we started talking about you need to know what makes them tick in order to know whether that's [00:17:00] financial stability, right? They want to pay off a loan. They want more money in their retirement, their kids going to college, right? What that looks like in their world, or are they somebody that is looking for a boat to win the President's Club trip or the, what I would call the 1950s view of why salespeople sell.

But if we give those people in the middle a little bit more time and focused attention, they are going to do better. Because right now they get ignored because they can, right? They're doing okay without somebody spending time and attention. So if we give them a little time and attention, all of a sudden their performance improves.

David: Yeah, that's an interesting concept. I'll have to think a little bit more about it, that those middle folks want to fly under the radar. If they want to fly under the radar, what happens when the manager is now all of a sudden spending a lot of time with them? Is there a little bit of friction upfront?

Lynn: So I will tell you, I don't think you need to spend a lot of time with them. That's [00:18:00] the other thing, right? We are not trying to make these people rock stars. We are trying to get them incrementally better. I talk about what if a salesperson—like, what if your middle performers hit goal one more quarter a year? That's a significant lift for the organization.

David: Yeah.

Lynn: In a world where I haven't looked at 2025 numbers because the percentage of salespeople making goal seems to go down every year in current memory, right? Like that idea. So it's one of those things where I feel like just, again, move the baseline up

David: Interesting.

Lynn: One more... Hit—have everybody on your team hit goal one more time this year, and all of a sudden, you've got people outperforming goal, you have people underperforming goal. But if everybody makes it one more time, we're shifting the whole organization up.

David: Nice. So I'd like to move on to your diagnostic framework: can't, won't, don't know how.

Lynn: So first, we need to give Dr. Hannah Rudstrom of Cornell University fame—I will call it fame because I think she should be famous. So Dr. Hannah Rudstrom is the one who created this model. I leverage it in inside sales with her permission because sales is complicated enough. Let's not make the diagnostic complicated. So I loved her model.

So "can't" is either organizational or person. And the easiest way to look at that, like which one is it, is: Is most of your team running up against a roadblock? Now, salespeople are going to find a way around the roadblock, so I'm not saying that they're not getting to where they need to go, but it's a heavy lift, and some of them aren't able, right? There's an organizational [00:20:00] something in there that's stopping your team from being successful.

I'll give you an example. I was working with an organization, and they were losing deals because they couldn't turn the proposals around fast enough. It turned out they had two pre-sale engineers and twenty-five salespeople. Those engineers were incapable. They didn't have more time, right? And it turned out that the engineers, the way the structure was, every single proposal ended up going through those two engineers.

Step one was, okay, they had some tenured salespeople that on non-complicated deals from a technical perspective could put it together themselves. So one of the things that they did is they said to a group of salespeople, they did not have to go through engineers until something hit certain criteria. They could put the proposals together [00:21:00] themselves without any engineering help at all.

They had another group of salespeople that they were pretty confident about. That group of salespeople could put the proposal together and have it validated by the engineers. And then everybody else had to put everything through that, right? But right away, all of a sudden we're turning stuff around differently, right? They were fixing the organizational "can't." They did also end up adding another engineer. But just there were structural changes, and as the leader, you need to identify what are the structural changes that are roadblocks for your team, and it's your job to get rid of them.

David: Yeah.

Lynn: Then there are people that can't do something. So you got to figure out, okay, is that person incapable of what you're asking them to do? And then, okay, is it a bad organizational fit? Like they're not a good fit for your inside sales team, in my case, right? Or are they a bad fit for that job? Or can they [00:22:00] be successful with some kind of workaround? Because again, salespeople are great at figuring out a workaround, but the question is, is that good for your organization, right? So that's the "can't" piece of the puzzle.

The "won't" is: I know how to do something. I am capable of doing it. I don't want to. I choose not to. That, you got to look at the coachability of the person. Because coaching's the only thing that's going to fix that. Like, why aren't they doing it? Why are they unwilling even though they're capable and know how?

And then "don't know how," training fixes, right? They have a, there's a missing skill set. Unfortunately, almost all sales organizations that I run across don't do the diagnosis, and they throw training at it. And training is only going to fix something if I don't know how to do it.

David: All right. Interesting. Thanks for walking us through the framework. I'll definitely look it up too. [00:23:00] So obviously in every podcast we have to have the AI question come up. And so curious from your perspective how AI is changing the way leaders coach today, and are you seeing that it's improving or is it just increasing the noise?

Lynn: So I'm going to say my disappointment is I feel like people are offloading coaching to AI rather than leveraging AI as a tool to make their coaching better. So I think it is a fabulous tool to run calls through and to get call plans. Are people following the call plan that they said they were going to follow? Are they asking open-ended questions? Are they listening, right? Like doing that kind of diagnosis of a call.

I don't know about you, but if I'm doing call reviews for somebody, I have to listen to the call multiple times. And if it's a 20-minute discovery call or an hour-long meeting, that's a significant amount of [00:24:00] time. Using AI as a tool to help you coach people, I think is important. I keep seeing people, though, just saying, "Oh yeah, we have them run through this coaching AI tool, and they can do their own thing." And I'm like, okay, but...

David: Yeah, I think that it is a tool, and I think that the most ambitious reps should be using AI to self-coach on things, but it shouldn't be a replacement for your weekly meeting with your manager or your quarterly review by any means, or any of those types of things. So yeah, I think like with all AI, we are leaning on it too much, and I think it will also degrade those skills if we lean on it in that way.

So last question before we get to our rapid fire questions portion. In your book, "Mastering Inside Sales Leadership," you used a metaphor of a puzzle. Could you break that down for us and [00:25:00] what that looks like in practice for a high-performing sales team?

Lynn: So the reason I like the metaphor of a puzzle is twofold. Number one, you need to know what the edges are, right? So what is inside and what is outside your purview and control, right? And everybody's puzzle butts up against somebody else's inside an organization. Inside sales is a small piece of the overall company. What are the edges?

And then also, how do you fit in? Like, where do people fit? Where do tools fit? How can we put everything together? And the only way to put it all together is if you have a vision of what you want it to look like. So I don't know about you, I couldn't put a puzzle together if I didn't have the picture on the outside of the box, and that's what the vision of your team is. You need to have a vision of what you want the team to be or else you're never going to be able to put [00:26:00] all the pieces together that you need for your puzzle, right?

To my example from earlier: two engineers, 25 salespeople. Okay, that's not gonna get me to the puzzle picture that I have on the outside of my box. I need another piece. I need the pieces to fit together differently.

David: Nice. That is an interesting way to look at the literal puzzle of inside sales and putting it together. So what I'd love to do, Lynn, as we wrap up here, is we love to do a rapid fire question section with our guests. And so I'm gonna ask you a few different questions, and if you just let me know what your perspective is.

Lynn: I'll give you my quick response. Yes.

David: Awesome. So what is one thing people don't give enough value or attention to in leadership?

Lynn: Listening.

David: Yeah. What's one skill you advise everyone in sales to master, leaders or non-leaders?

Lynn: So it goes to listening, but [00:27:00] being curious and really building that as a way you think.

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

Lynn: So I'm gonna cheat because I'm gonna use Colleen Stanley's "Emotional Intelligence," but there's a sales success one and a sales leadership success one, so that's really two.

David: All right. Fair enough. We'll let you cheat here. Favorite quote, mantra, or saying that inspires you as a sales leader?

Lynn: "The harder I work, the luckier I get," Stirling Moss, a 1960s Formula One driver.

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

Lynn: I am turning the book "Mastering Inside Sales Leadership" into a mastermind platform, so to have an inside sales leader mastermind.

David: Love it. That sounds great. We will look out for that. Lynn, thank you so much for coming on the podcast, sharing your experience, your knowledge. If people want to [00:28:00] reach out to you, connect with you, how can they find you?

Lynn: David, it's easiest to find me on LinkedIn, and because I'm in inside sales, my phone number's actually available there, so call me.

David: Okay. That's awesome. Well, thank you all for listening to another episode of the "Sell Like a Leader" podcast. Don't forget to subscribe on Spotify, Apple, wherever you get your podcasts. Also always feel free to reach out to me. I'm on LinkedIn. Hit me up with any questions, comments, or guests you'd love to see. Until next time, thanks so much. Appreciate it. Thanks, Lynn.