On a new episode of The Sales Hunter Podcast, Mark sits down with bestselling author and sales leader Jill Konrath to talk about hitting the wall in sales and what it really takes to turn setbacks into pivotal growth.
Hitting the Wall Is Inevitable
Every seller will face moments where nothing’s working. Prospects ghost meetings. Deals stall or vanish. Even the best-trained reps hit these walls. As Jill Konrath puts it, “A lot of people really perceive it as a big problem… It really makes salespeople scared. And when we’re scared, we do some things that aren’t really positive and don’t really help.”
But setbacks aren’t just part of the job, they’re a chance to rethink your approach and evolve as a pro.
Make It About the Customer, Not the Product
The biggest breakthrough comes by shifting from a self-focused to a customer-focused mentality. Jill Konrath shares a personal story: She used to approach meetings with a strict agenda: moving prospects toward demos and closing steps. The epiphany? “Everything is about the customer… what matters to them, what issues they’re facing, what they’re trying to achieve.”
The most common trap for salespeople is to fall back on pushing product or racking up activity just to hit KPIs. Focusing instead on truly understanding customers changes the game.
Learn Deeply, Prepare Intentionally
Forget the idea that success is just about hitting more activity targets. Top sellers stand out by investing serious time learning about their buyers. Jill Konrath describes how she would interview existing or beta customers, digging into challenges, before-and-after scenarios, and real impact. This immersion let her speak the customer’s language and deliver relevant value.
Preparation is the differentiator. That means going beyond LinkedIn research, really understanding “what’s important to these buyers.” It also means bringing a long list of thoughtful, open-ended questions to every conversation knowing not all will be needed on day one.
Embrace Experimentation and Stay Curious
Growth in sales comes from being a constant learner. It’s okay to try new techniques and mess up. Jill Konrath advises reframing failures as experiments: “If you treat it like an experiment, you’re never a failure, you’re learning.”
She recommends:
- Interviewing top-performing colleagues
- Listening to their calls and decoding their discovery process
- Trying their approaches, then tweaking and improving
Above all, curiosity and self-evaluation will move a seller further than memorizing sales scripts.
Teams Win Together
The best sales organizations don’t just reward lone wolves, they turn individual strengths into team learning. Jill Konrath suggests:
- Highlighting what different team members excel at and making space for them to teach others
- Running monthly challenges focused on one sales skill (like demos or first meetings)
- Role-playing in groups and sharing feedback
This team-centered approach lifts everyone’s performance and turns sales into the ultimate team sport.
The Art and Preparation of Great Questions
High performers don’t walk into meetings hoping to wing it. They arrive ready, with layered questions that invite real conversation, not just a yes or no. Jill Konrath says, “Questions became an art form in working with customers… How could I change this question to get it to be a better question that would give me more information?”
Great questions aren’t about fishing for the answer you want. They’re about understanding the person behind the title, their real pains, and how you can help.
Don’t Shy Away from Tough Conversations
Many sellers fear asking tough or deeply personal questions, like probing into a prospect’s key performance indicators (KPIs). The advice: try it, and don’t be afraid to follow up with secondary or supporting questions. As Jill Konrath teaches, “You can ask a tough question if…the prelude to it is good.” Set the stage, show empathy, and people will often open up.
Grow by Reframing Setbacks
Setbacks are inevitable, but they don’t have to be permanent. Jill Konrath wrote her latest book, Pivotal Moments, because every seller, and person, faces being kicked out of their comfort zone. The difference comes in how you respond.
“A pivotal moment can be a real problem… But change is terrifying, you know, to me that there’s a lot that can be learned that can be so helpful in dealing with these times of life.”
Sales pros should find inspiration in the walls they hit. Every challenge becomes the raw material for reinventing your approach, becoming more customer-centric, and reaching the next level of performance.
As Jill Konrath reminds us, these moments of discomfort? They’re where the biggest leaps in growth get made.
Mark Hunter :
You’re in sales and you hit the wall. We’ve all been there. Come on. Don’t tell me otherwise. And in order to get past it, you have to make a pivotal change.
Jill Konrath :
Hey.
Mark Hunter :
With me today is the legendary Jill Konrath. Why am I talking? Let’s get the show going.
Jill Konrath :
Right now, you’re listening to the Sales Hunter Podcast with Mark Hunter, where the focus is to help you as a salesman, sell with confidence and integrity. And now, here’s your host.
Mark Hunter :
If we’re going to talk about how you get through the wall, there’s only one person you can talk to, and that’s Jill Conrath. Welcome to the show, Jill. Let me get you up here on the screen. There you are. Thank you so much for joining us today.
Jill Konrath :
I’m delighted to be here.
Mark Hunter :
And I’ll tell you what, you have written your first book, Selling to Big Companies. I remember this is how I was introduced to you, and it made a huge change in the way I sell. You’ve written so many other books. Snap selling. I’m holding up here, too. And you’ve written your most recent book, Pivotal Moments. Wow. Talk to the audience.
Mark Hunter :
Let’s cut right to the chase. The wall. Every salesperson has hit the wall, and right now, more than ever, salespeople are hitting the wall because customers are just. They’re just locking up. They’re just plain locking up. How do we get through it? Talk to us.
Jill Konrath :
Well, that’s a good question. And a lot of people really perceive it as a big problem. You know that it’s hard to get through to customers. They’re prospective customers. They don’t show up for meetings. They stop their decision process in the beginning. And it really makes salespeople scared. And when we’re scared, we do some things that aren’t really positive and don’t really help.
Jill Konrath :
But mostly it’s a time when we have to think about how can we do things differently to prevent these kind of things from happening. And it really requires us to rethink what we’re doing and do it in a positive way that allows us to grow in our own capabilities, I guess, is really important.
Mark Hunter :
Yeah, I like what you said. And before we hit the record button, you were sharing a story. Early on in sales. You said you were having a problem, and then you went through a pivotal change.
Jill Konrath :
I did, and it was really fascinating to me to go through that change because I had been well trained. I, you know, was doing what I thought I was supposed to do and, you know, as it was directed. But what happened is I’m sitting with the customer and I am trying to achieve my agenda. I mean, close the meeting to get to the next step of the sale. And all of a sudden I had an epiphany. It really was an epiphany that it’s not about me, you know, going through these next steps and getting to the demo. Everything is about the customer, the prospective customer and what matters to them, what issues they’re facing, what they’re trying to achieve, the bottlene in the place, how their people are working together, whatever it is, it’s all about the customer, not me selling. Even though I thought it was at first, I spent many years, many months pursuing that path.
Mark Hunter :
We’ve all been, we’ve all been on that path. Yeah. So how do we get out of this product focused mentality? How do we get out of it and get focused on the customer?
Jill Konrath :
Well, really, we need to learn about the customer. If I would say, what can we do? A couple things. I spent a lot of years working on new product launches and I had to learn about customers really quickly. And I interviewed existing customers. I would go back and interview customers or companies existing customers or beta customers, if it was a new product or service they were bringing out and I would really find out what difference it was making. What were you doing before you bought this product? What issues and challenges were you facing? How has it made a difference? What issues did you run into? And I really, the immersion into the customer was probably the biggest, best thing I could have done for me to help my clients and to be more, more, you know, intelligent and helpful to my clients. And I don’t think people spend enough time really understanding their customers because they’re focused on selling. It’s like it’s back ass words as my mother used to say.
Mark Hunter :
It’s so true. And seems like, okay, we got to sell, we got to go out and push the product. Push the product.
Jill Konrath :
Yeah.
Mark Hunter :
Okay. I kind of unpack this more because again, how do we as salespeople, we’re time constrained, we’re pressured to make quota, we’re pressured to make sales calls, yada, yada, yada. How do we make the time to dive in and do it right?
Jill Konrath :
Well, first of all, I guess it starts with a decision, doesn’t it, that you’re going to try to figure something out. Let me just give you an experience that I had when I was new, fairly new in sales, and actually I was doing quite well. I was the number one person in the branch at that particular time. And my boss called Me in for my one on one. And we sat down and he said, jill, your numbers aren’t, you know, you’re just not doing the numbers. And I said, but Maurice, I’m. I’m number one in the branch. And he said, yeah, but you’re not making enough calls and you’re not giving enough proposals and you’re not giving enough demonstrations.
Jill Konrath :
And I said, but Maurice, I’m the number one, you know, person in the branch. And. And he, and he ultimately said, well, Jill, I’m a chart. You know, my numbers roll up and you’re. I’m looking bad because your numbers are bad. Which I thought was a really strange thing to say. But the point is, at that point, what is, what was I doing that was different? And what are the top performers doing that. That are different than what is the prescribed way of selling? To me, that’s a fascinating question to take a look at in any organization if you’re a sales leader, to look at it and say, what are they doing differently? They’re making fewer calls, they’re having fewer proposals.
Jill Konrath :
What are they doing differently? Because there is a fundamental difference between how people are doing things. And then I think it becomes. If you’re a single salesperson, I would be interviewing people who are doing well in the company. I would listen to their phone calls, I would follow what they’re doing. I would literally interview the salespeople that are doing well to find out how they’re tackling X subject or this subject, or, you know, initial calls and what they’re doing during discovery. And how are they, what questions are they asking? How do they ask the questions? If you get curious about it, you can go down a long path and learn so much. And then you have to move into another mode which was, you know, to try to incorporate those skills, that knowledge base, into your own behaviors. And that’s hard too, because when you start anything, you don’t do it really well, if you know what I mean.
Jill Konrath :
You screw up, you forget. And I think you need to give yourself some grace during that period of time and look at it as a period of experimentation. Not can I, but how can I, what else do I need to do? How can I make it better? And then experiment and evaluate yourself. I mean, if you treat it like an experiment, you’re never a failure, you’re learning. If you treat it as a challenge, it’s not a problem. It’s an opportunity to grow. And so I think part of it is redefining things in your own brain that you’re A learner. And you’ll always be a learner.
Jill Konrath :
And you can do better if you’re willing to take a look at what you’re currently doing and, you know, interview people, experiment, get deep into it and figure things out.
Mark Hunter :
Wow. There’s a lot there that you said. And as you were sharing that, I kept thinking about your new book, Pivotal Moments.
Jill Konrath :
Yeah.
Mark Hunter :
And it’s amazing because you share a number of stories from different people who really hit the wall and they had to rethink things. And that’s exactly what you’re telling salespeople here to do.
Jill Konrath :
Yeah.
Mark Hunter :
Now, let me pose this question, because I’m a. I’m a sales leader. I’m managing a sales team, and. And I’ve got this. This. This whole thing that I gotta create. X number of meetings, X number of proposals, X number. And I’ve got a high performer like you who’s doing it right.
Mark Hunter :
It’s not quantity, it’s the quality. And that’s what you were getting.
Jill Konrath :
Yes, exactly.
Mark Hunter :
How does a sales manager get his whole organization to shift their thinking to be like what you were?
Jill Konrath :
Well, if I was that sales leader, I would really start looking at all my people and see what they excelled at, you know, and different people excel at different things. And so if you realize that you have a team with people with different strengths, how can you bring this person’s strength to the team? And how can you get people to spend time working on it? I mean, to me, it’s like, why can’t we have a challenge on our team and just say, okay, we’re going to spend this month focusing on how to, you know, fill in the blank, And Mark is really good at that. So I’ve asked Mark if he would, you know, if he would share with us what he’s doing now, by the way, that makes Mark look good and he feels really well. And then have people submit questions and then have Mark do role plays on different things, you know, so people could see, you know, I mean, this can be done with your team as it meets in person or is, you know, zooming on it, but, you know, to actually do things together and give people examples, and we could talk about a demonstration, and somebody could play the role of a typical customer in what they do, and then we could see what this salesperson is doing differently. And then we could have a month of experimentation. Let’s all try to improve our demos. Let’s all try to improve our initial conversations. I mean, that’s the way you spread it and you lift everybody up.
Jill Konrath :
At the same time, I like what
Mark Hunter :
you said there because it’s not about you, the manager, doing it all, it’s getting your team involved. Because again, it is a, you know, sales is a team sport and you get, and like I said, it lifts everybody up because it’s amazing how we do a better job of learning from other people than we do from the manager themselves. It just always is. So here’s the challenge. What does a good level of preparation look like? Because you were a top performer, clearly knocking on fewer doors but doing better? What was the level of preparation that you went through and what’s some advice you could share with salespeople today?
Jill Konrath :
Well, I spent a lot of time talking to buyers, prospective buyers, about their jobs if I was out with them in an actual meeting or to find out what they were doing. So I was compiling a deep knowledge base of what was important to these buyers. Now, when I was selling, we didn’t have LinkedIn where I could do things, nor do we have AI where I could find out all this information by myself. But I think what I did probably more than most people did, is I really prepared for every customer contact, you know, whether it was, you know, in person again or, you know, it could be via phone or whatever. And I was especially focused, and you probably were too, on the initial conversations. Because if your first couple interactions with a customer are all about me, me, me, let me tell you about me. It’s not going to go anywhere, but if you can have a meaningful conversation, literally conversation, not just you finding out the information you want to find out, you will move things along. And let me just say, from my own preparation standpoint, when I was moving into something new and hadn’t figured it out yet, I actually went into meetings with and I didn’t just have typical discovery questions.
Jill Konrath :
What I had were that some of the questions that I wanted to ask and then, you know, some personal things in there. But I had major category and then sub level questions. So I wouldn’t just say to you, you know, what are your biggest challenges? I would have under that, you know, have you had problems with this and how did you deal with it? And I would ask second and tertiary questions. So we had a true conversation.
Mark Hunter :
I love where you’re going with this. And you said something and you may not have realized that you said it, you were focused on the person and you didn’t think company, you were focused on the person.
Jill Konrath :
Yes.
Mark Hunter :
And so critical because again, I’m finding the more we focus on the person because if I can’t establish a level of trust.
Jill Konrath :
Right. You’re not going anywhere.
Mark Hunter :
Yeah, yeah, yeah. You know, again, were there little insights? Because, again, and I love your focus on questions because I think it is. We have to go in with more questions than we can ever begin to ask. But, you know, I. I never want to run out of questions, and I want to run out of re. I want to have great questions that create a conversation.
Jill Konrath :
Yes. And it takes. Let me just say, Mark, it takes work to figure that out, because. Yes, you have to figure how to ask the question, get the maximum response from your customer. I mean, to me, questions became an art form in working with customers in terms of what if I. How could I change this question to get it to be a better question that would give me more information and what sub levels can I go to, you know, that would be important in the process of how they make the decision or what they’re choosing to do or how they manage their finances or whatever. But to me, the art of questions is crucial early on in the state, you know, in working with clients or prospective clients.
Mark Hunter :
Okay, you just said something. It’s how you ask the questions. Can you share some advice as to how you ask those questions? How do you do the how?
Jill Konrath :
How do you do that? That’s funny. How do you do the how? You don’t have yes, no questions at the beginning. It’s truly an art form in terms of finding out what is their situation, the challenges that they face, and knowing that there’s a sequence and that you can’t jump the gun and go right to someplace. What would it take for you guys to justify this? No, you got to find out the issue it is or what they’re trying to achieve and how you can work with them on that and go slowly enough that you’re building a relationship with them, a true relationship with them, that they understand that you’re. You’re rooting for them and what you’re doing. You have some ideas on how to help them. And it’s not about you making your quota. It’s about them achieving their goals all the way through.
Mark Hunter :
Yeah. Because if you help them achieve their goals, you’ll make your quota.
Jill Konrath :
Bingo.
Mark Hunter :
And it comes back to this whole thing that you have to be dialed in on them. Too many people ask questions because they just want to revert to their product. Let me, Let me tell you about my product.
Jill Konrath :
Yeah, exactly.
Mark Hunter :
What you’re saying is. No, no, stay with the person. Stay with the person.
Jill Konrath :
Yeah.
Mark Hunter :
That is powerful. This may be a random question. How Many. How long was your list of questions that you would take in on a sales?
Jill Konrath :
It depends on what I was selling. But yeah, when I was selling services, it was kind of long. But it didn’t all have to be done in the first meeting either.
Mark Hunter :
Thank you for saying that.
Jill Konrath :
Yeah, I mean, there is a second meeting. You want to come back. And, you know, part of coming back is this is a good start. You’re making me think, Mark, of some things that, you know, might be important for you, us to talk about. Can we get back together next week and I’ll. I can even send you some questions ahead of time so, you know, you know, what might be important for us to talk about? I mean, there’s nothing wrong with sending that. And the other thing I always did is, you know, that was really helpful in moving things along is rather than going right to a proposal, here’s the price. I would put together a discussion document that, you know, here’s what I think, you know, would work and, you know, here’s why, and here’s how we’d move it along.
Jill Konrath :
But it wasn’t an official proposal. It was a discussion document. And we talked about it and I would get there a, you know, concurrence on this, and then I could come back with a proposal, a real proposal. But it was that step in between that made the proposal the acceptance of the proposal significantly higher, like they had bought into the process, as opposed to me coming in and saying my, here’s my proposal may. I would give them options and stuff too, and we would talk about the options before they got the proposal.
Mark Hunter :
Oh, I love what you’re saying there, but you clearly said something that. You clearly are connecting all the calls together. I mean, something that comes up on one sales call, you’re linking it to the next one, you’re linking it to the next one, and it’s keeping the conversation going. I, I’m going to throw something out, though, that so many salespeople are afraid to ask questions that are maybe tough for the customer to answer. They just lack the confidence. Any suggestions there?
Jill Konrath :
Try it. Practice. Seriously. Nobody’s gonna punch you, you know, if you do it. And again, have secondary or tertiary questions to go along with it and how you set up a question. You know, you can ask a tough question if you. The prelude to it is good. You know, I can say, you know, Mark, a lot of the customer, A lot of the, our customers are really struggling with some of these, this particular challenge right now, and they’re worried about this kind of thing.
Jill Konrath :
And so you’re letting that person know that they’re not alone and that, you know, they wouldn’t be bearing their soul if they would say, yeah, we’re. We’re having those problems too. So how you tee up a question is so vital, too.
Mark Hunter :
I love it. One thing that I’m finding right, right now is, is finding out from the customer what their KPIs are. You know, that’s getting really personal. That’s getting really personal.
Jill Konrath :
It is.
Mark Hunter :
And. And because again, they got to achieve their KPIs if they want to keep their job. Right.
Jill Konrath :
So how do you set a question up like that up, Mark?
Mark Hunter :
Well, you know what’s funny is, is I asked this of a VP of sales the other day, and I was very. What, what are your specific KPIs? So I know where to focus my attention.
Jill Konrath :
Oh, I like that.
Mark Hunter :
Yeah. Yeah. And the VP of sales was taken back by it. But then, because we’ve met three, four times, was very forthcoming in sharing them, and, wow, it took our relationship to the next level.
Jill Konrath :
What I really like is you weren’t going to waste your time, his time, if you couldn’t affect his cap, his crucial KPIs. You were working with him on what mattered.
Mark Hunter :
Right, Right. Because so many times. Because so many salesmen can walk in with a solution, who cares? It’s. It’s. I mean, it may be a great solution, but if it doesn’t address the problems at hand, that’s. Hey, I want to talk about your book, Pivotal Moments.
Jill Konrath :
Yes.
Mark Hunter :
Tell the audience a little bit about it and why you wrote it.
Jill Konrath :
I wrote it because so many of us are facing tough times and challenges in our life. We hit the wall. We’re kicked out of our comfort Z. We get an idea that we want to pursue, and we really get scared. You know, we. We don’t know what to do when those situations happen. And everybody has them. Everybody has them.
Jill Konrath :
It’s just, when are they going to happen? That you hit your own pivotal moment. And I realized that there wasn’t a lot out there dealing with those different situations. And, you know, like I already mentioned, you know, some pivotal moments can be a real problem. And you lose your job. That’s a real problem. You, you know, you’re not meeting your numbers. That could be a real problem. And.
Jill Konrath :
And I realized that I had so much. I’d use so much different, so many different techniques over the years, and I had so many ideas on how to deal with, you know, getting kicked out of your comfort zone or you get an idea. And then you go, oh, God, I don’t. I can’t possibly do that. The question is, no, you, how can you. And it, you know, and it’s just. I wanted to share with people what they could do when they. Moments in life where they were scared or they had something, but they didn’t have the confidence to go forward and, and they wanted to make a change.
Jill Konrath :
But change is terrifying, you know, to me that there’s a lot that can be learned that can be so helpful in dealing with these times of life. And believe me, pivotal moments can make your life so much better. I mean, I was in a job, I hated. I hated it. I was a high school teacher. I hated it. I was miserable. I had a pivotal moment that changed my life.
Jill Konrath :
So I became a salesperson because I had to do something else I wanted to do and discovered, wow, this is really interesting. I’m getting a chance to learn this and this and this and this. I hit the wall. I had to invent my own future. And it led to something that was even better than I could have ever, ever, ever have at that point in my life.
Mark Hunter :
Wow. The book is Pivotal Moments. You go out to Amazon and of course type in Jill Conrath. You see all of her other books here. We’ve been talking.
Jill Konrath :
Yeah, but you gotta tell them. Mark Conrath with the K. Conrath.
Mark Hunter :
You’re right. Conrath with a K. Right. K, O, N, R, a T, H. And she’s written so many great sales books selling to big companies. Your first book, it’s still selling just as well as it. It always has been great. Anyway, want to thank you for being on the show.
Mark Hunter :
You’ve been listening to the Sales Hunter podcast, two episodes a week, one like this, where we do a deep dive with a subject matter expert. Jill certainly matches that qualification. Second one is just where I do a one single topic in a 15 minute episode. Do me a favor, leave a review on your favorite podcast app and hey, share a friend with the show. And hey, if you haven’t picked up pivotal moments, when you’re buying that, pick that one up. And then pick up my new book, Integrity First Selling. I’m Mark.
Jill Konrath :
Let me just say, Mark, it’s really it to everybody. I have read Mark’s book and it’s wonderful. And nobody’s written a book like that before. It’s absolutely worth a read.
Mark Hunter :
Well, thank you so much. We won’t edit that part out. We’ll actually. Thanks so much.
