Why Sales Feels Icky (And How to Fix It) | Jonny Holsten

In this episode of Imperfect Marketing, I sit down with Jonny Holsten of BridgeSelling to unpack why sales gets such a bad reputation—and how to fix it. We dive into what actually works in modern sales conversations (hint: it’s not scripts or pressure).

Jonny shares his journey from marketing into sales strategy and how that shift led to his book Fix Your Broken Sales Calls. Together, we explore how to move from chasing leads to building meaningful, problem-solving conversations.

Here’s what we cover:

From Leads to “Best Fit” Clients

•  Why all leads are not worth your time 
•  The 4-part framework for identifying a true “best fit” customer 
•  How narrowing your focus actually increases conversions 

Why Sales Feels “Icky” (and How to Fix It)

•  The real reason selling feels uncomfortable for so many people 
•  Why belief in what you’re selling changes everything 
•  The difference between pushing a sale and solving a problem 

The Power of Better Questions

•  How great sales conversations start with curiosity, not pitching 
•  Why most salespeople skip identifying the real problem 
•  A simple technique to get prospects to open up more 

Handling Inbound Leads the Right Way

•  Why inbound leads aren’t always qualified (and that’s okay) 
•  How to guide conversations like a consultant, not a salesperson 
•  The importance of setting expectations and taking control early 

Knowing When to Walk Away

•  How to gracefully exit conversations with poor-fit prospects 
•  Why referring someone elsewhere can actually grow your business 
•  The mindset shift: serving first, selling second 

Improving Sales Without More Leads

•  Why most teams lack a clear plan for sales calls 
•  How small tweaks to discovery calls can drive massive revenue growth 
•  The importance of reviewing and learning from your own calls 

Key Takeaways

•  Selling should feel like helping—not convincing 
•  Clarity in your message makes everything easier 
•  The better your questions, the better your results 

Connect with Jonny:
LinkedIn: https://www.linkedin.com/in/jonnyholsten/

If sales has ever felt uncomfortable, awkward, or forced—this episode will change how you think about it.

Ready to make sales feel natural (and actually work)? Tune in.

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Transcript

Welcome And Why Sales Matters

SPEAKER_01 0:27

Hi, I'm Kendra Corman. If you're a coach, consultant, or marketer, you know marketing is far from a perfect science. And that's why this show is called Imperfect Marketing. Join me and my guests as we explore how to grow your business with marketing tips and, of course, lessons learned along the way. Welcome back to another episode of Imperfect Marketing. I'm your host, Kendra Corman, and today I am joined by Johnny, and we are going to be talking about sales. It is a four-letter word, sell, right? That people hate to talk about and hate to deal with. But for us to grow our businesses and do what we want to do and achieve what we want to do, um, even if you're not in business, I think all of us have to sell at some point, right? So I think it's really important um to talk about selling overall. So welcome, Johnny. Thanks so much for joining me.

SPEAKER_00 1:27

Thank you for having me, Kendra. I'm excited for this chat. And um, yeah, let's let's talk sales.

SPEAKER_01 1:32

All right. So talk to me. So how did you get into sales? Because you started in marketing, right? Is what you said. Or you have a background in marketing.

SPEAKER_00 1:38

I do. Yep. I I started in marketing. And if you anyone in who's in sales is gonna rub shoulders with marketing and vice versa. So starting in marketing, my work started helping marketing teams figure out what their messaging is. So figuring out what are we gonna say to drive the right, drive a qualified best fit client in the door. And after I did that long enough, I just sort of organically kept getting passed along to the sales team. After I'd worked with the marketing team, I was a I had my own practice. And after working with the marketing team, oftentimes the CEO or the CRO would say, Hey, let's do a similar exercise with the sales team. And so I think I got pretty good at figuring out how are we gonna have a one-to-one message that brings the great, a great fit lead in the door. But then how do we take that lead and have a even more unique one-to-one conversation with it, with our sales team? So did that for a while and then eventually just I think had so much fun and hit a lot of traction on the sales side that I I said goodbye to the marketing piece of the company and and have been focused on sales exclusively for a while now. So that's the backstory. It it happened kind of on its own.

SPEAKER_01 2:43

And then you wrote a book recently, right?

Bridge Fit Criteria For Best Clients

SPEAKER_00 2:45

That's correct. Yep. After after a couple of years of doing that, wrote a book called Fix Your Broken Sales Calls. And that came out uh at the time of this recording a couple weeks back. So um, yeah, that's that's fresh and new, and it's it's doing well. So I'm really excited to be excited to be done with it because a book launches a lot of little, a lot, a lot of work.

SPEAKER_01 3:03

Very cool. Well, we definitely have the link to it in the show notes. So be sure to check it out if you want to learn more. Um, okay, so one of the things that I love that you said repeatedly in your introduction is and your background is best fit. I think that too many people look at leads and not best fit um when they're doing it. So when you're talking to marketing or sales teams, how are you defining that? How are you helping them define it? How do you get people off of lead and onto best fit?

SPEAKER_00 3:35

Well, the what at our company we call that a bridge fit. So a best fit, our company called is called bridge selling. So we call it a bridge fit. Best fit, we look at four things. Does the customer have the pain point you solve? Do they have the authority and budget to make a buying decision at full price? We like to make that clear too. The third thing is a timeline that aligns with your capacity. And the fourth thing is a high chance of success. So depending on what you do and what your service or product is, you need to define those four categories. That's what we look at for best fit. And so that's where an example, I guess, sort of it to go to the marketing world where one company may say, Hey, we sell to we sell to CMOs or we sell to um, we we sell web design to CMOs. Well, a bridge fit would be a CMO with a$25,000 budget and X amount dedicated for maintenance that wants a site in 90 days, right? So we're we're really tightening that that definition. And that's where you go from just a lead to a right fit or qualified lead.

SPEAKER_01 4:35

Well, I think that that's so important because time is so valuable nowadays, right? And so getting those best fit or those right fit or the bridge fit people to be where you're investing your time is important, right? I mean, I think I think that's a that's a mistake people are doing by wasting time with the ones that are not the right fit, right? Having conversations with everybody. How do you rule those people out?

SPEAKER_00 5:02

What we'll train a team to do or try to design a sales process to do is if if your marketing is bringing somebody in, ideally you're bringing in someone who's at least intentional enough that they're they're hoping to move forward sometime soon. And we don't always look at timing as whether or not someone is disqualified or not disqualified as much as we do figuring out what's the timeline of this for forecasting and for next steps. And so if someone is wanting to go, wanting to start now, right? They might be just as much of a right fit lead as someone who's ready to start in several months. But where you get into weirdness in a sales process is when that's never defined and the salesperson never gets really clear on the timing and the timeline. And so then you get stuck in a weird game of follow-up or we're not ready yet, check in in a couple of weeks, and you do that for months when everybody's time would have been saved, getting really clear on that early on and changing your approach after that first conversation. So um, yeah, you're right. Time can get wasted by everybody when we're not clear on a best fit and an urgency.

Consultative Selling Without The Ick

SPEAKER_01 6:09

Okay, very cool. So let's talk about um selling, right? People view it as not a good thing, usually, right? And they think of like pushy, overbearing salespeople, right? I mean, there's the stereotype of the used car salesperson. Um, how how are you working with people so that they're they're not sounding pushy?

SPEAKER_00 6:33

Well, there's a few things I like to say with this when it comes to stereotypes like this. You're probably always gonna feel icky if you're selling something that you don't want to sell. Like even if you do it in the right way, because there have been companies that um have come our way, and it's just like even us, we're sales strategists and we work in in helping other companies sell their stuff. If it's not a product that we're excited about helping others sell, it's the same effect. You can feel icky. So the first thing I would say is if you're in sales or if you're a small business owner, you should be asking yourself, one, yeah, I experienced this early on in my business too. Maybe my offer didn't really fall in line with what I really wanted to be doing. And that made selling feel way worse than when I had a perfectly dialed-in offer. So that's the first thing is make sure you're selling something you really want to sell, or ask yourself, could I enhance this or tweak it to make it more enjoyable to sell? I think that's the first, the first step to getting rid of some of that sleaziness that can can creep in sometime.

SPEAKER_01 7:34

Oh, I like that. And I like being, I think if you're proud or excited about something, right? It makes it a lot easier because you know you're adding value. Right. I think one of the first things that you said about a best fit lead or bridge fit lead was that do you solve the pain point that they have, right? You're fixing something for someone. I think that's just so much overlooked in these conversations. They have a problem, you can solve it, right? You're not actually selling, you're adding value. And I think people forget that all the time.

SPEAKER_00 8:06

The main point of a sale is to solve a problem. And most salespeople never try to find out that problem. So when we think of the times we've been ripped off, and to use your example of the cliche used car salesman, right? Typically that's an uncomfortable experience, whether it's cars or any other product, because the first thing they ask you about is what's the most you absolutely would be willing to spend rather than what's wrong with your current car? Like what do you dislike about your current car, right? Those are different conversations. One is focused on solving a problem, the other is focused on, you know, squeezing every juice of or a drop of juice out of a lemon. So there are two different approaches. And I think even being sold to by someone who's more focused on the pain points, that feels good. That that's a almost like a project of solving a problem with another person.

SPEAKER_01 8:52

You feel like listened to, right? I mean, if you someone's asking you about your problem and and getting you to explain it and even maybe narrow it down even a little bit more in your own mind. You feel like they did something to help you in a way. And it builds some trust.

Inbound Lead Discovery Questions That Work

SPEAKER_00 9:09

And if you can get really good at digging that out as a salesperson, you can do two things. One, you can actually help people solve their problem, but um, you can also send people where they need to go if you can't solve that problem too, which I think is is um it feels just as good at the end of the day helping someone solve a problem, even if you're pointing them somewhere else.

SPEAKER_01 9:27

I find that when I point people other places, I get a ton of business, a ton of referrals and inquiries from them. So there's a lot of value to that too, especially when you handle somebody with care and um take the time to really exactly understand that someone else can do it better, right? Or offer that different service. There's so much there. So let's talk about inbound leads because inbound leads are the ultimate goal of what we do here at imperfect marketing, right? We're we're out there, we're marketing imperfectly. Really, the goal is to get people to say, Hey, I think I want what you have. What's the key to getting that to become closed business?

SPEAKER_00 10:08

You've got to be a really good consultant. You've got to be great at steering a conversation, and you've got to be good at asking good questions. So I think the downside, you've got like in sales, you've got two worlds. You've got your outbound engine and your inbound flow. Inbound is the gold standard because you don't it saves you a lot of time and effort on the outreach and outbound side. The one downfall of that is sometimes it's hard. You will get people who aren't qualified coming in the door just because that's the name of the game. And it, I don't care how good of a marketing engine a company has, you will always have the occasional bad fit, either because of timing or budget or something else going on. So I feel like one of the best skill sets a seller who's fielding inbound leads can have is the ability to really sense whether someone is the right fit or not. And typically that is having four or five really good go-to discovery questions about what caused you to fill out this form or what caused you to book this call or what caused you to reach out today and getting really clear on, like you said, some people don't actually know the real problem. Maybe they feel like there's a surface level problem they're trying to solve, but they need someone to draw out more of the real pain. And so the secret sauce to that is asking great questions and then repeating it back with some form of sentence like, um, you know, you're telling me this. Um, what else have I missed? Is there anything else that I missed there? And I find that language alone is really helpful because a buyer will oftentimes open up with all sorts of information you never would have thought to ask about.

SPEAKER_01 11:39

So, what do you find people's biggest issue is when they're trying to be better question askers? Because I think that that's, again, that's the key, right? And I mean, my experience is that we're processing so much in our heads that we're not always listening as well. Um, and it's hard to ask questions, right? Especially when people can't explain accurately what it is that they're trying to do. How do you help teams become better question askers? Or what do you recommend that they do to do that?

How To End Bad Fit Calls

SPEAKER_00 12:10

The first step is you need to be able to take control of that conversation so that you have permission to ask those questions. It doesn't matter if you're a professional salesperson or or if you're founder led selling at a small business. If you start off a call with question, answer, question, answer, and it goes back and forth, that can feel really weird. And I found probably the best way to make everybody feel at ease is to have, we call them magic pivots. How can you go into a conversation or move out of a part of a conversation? What's your language to guide, guide that conversation back and forth? And it all starts with saying, hey, thank you, you know, thank you so much for finding a time for reaching out. What I'd like to do next here for the next however minutes, many minutes, is ask you a series of questions. And if that's okay with you, I'd like to, I might ask some weird questions that maybe somebody else hasn't, or I might go a little bit deeper than others have with you. And that's because I want to make sure that this is a good fit for for both of us. And um, if that sounds good to you, I can go ahead and dive dive into some questions. Then you've got the permission to act, you know, actually do five or 10 questions, where if it feels like a game of ping pong back and forth, then it can be hard to know who's actually in control of that conversation. So taking control so you can ask questions, I think is the first step.

SPEAKER_01 13:25

Okay. So let's just say you take control, you ask the questions, the person is not the right fit. Um, what's the best way to get rid of them?

SPEAKER_00 13:34

Well, this is where you could end up on a 30-minute or hour-long call with someone that you know five minutes in is not going to be a good fit. So one thing that I would practice.

SPEAKER_01 13:42

Like I need that 30 minutes or an hour.

SPEAKER_00 13:45

Oh, don't we all?

SPEAKER_01 13:46

Or then I need that call.

SPEAKER_00 13:47

Exactly. Well, I think there's there's two things here. Speaking of pivots, everyone should practice the phrase, we're not for everybody, or it doesn't sound like we're the right fit for you. Every call should end with like clarity leaving. So I think it makes a lot of sense to say, hey, I don't think we're the right fit for you. But, you know, let me connect you with ABC so they can actually help you and still think if we're trying to solve a problem for someone, we can help them solve the problem, even if it's not with our our business or with selling our product. So I would keep thinking that way and then phrase the way you wind down that call with that same level of serving the other person. So, hey, it doesn't sound like we're the right fit. I would hate to take up 45 more minutes of your time over something that is not gonna help you. So let me, you know, hand you off to my partner at uh Impervict Marketing or wherever you're sending them next is um the way to do it, but it really comes with practice. You have to say that phrase. I don't think this is a good fit. I'm not sure this is a good fit. What I'd like to do is introduce you to or send you to this. That's really the only way to do it. It doesn't feel fun at the start, but after a while, um, it it doesn't feel as bad as it does in the beginning.

SPEAKER_01 14:55

Okay. So how long do you let the call go on for? You've identified in the first five minutes that they're not the right fit, but then it sort of feels like a major brush off, right? So, like, where would you say that they do that?

SPEAKER_00 15:07

It depends on how many leads you have in coming in the door, right? So, like I'm thinking of one project I was on where it was call center, national television advertisements going around the clock. As soon as you pick up on the fact that someone is not able to move forward in that environment, you have to shut it down and you have to be really good at shutting it down. If you can afford a few extra minutes to make an appropriate introduction or help somebody a little bit, I would say it's mostly about how are you making the other person feel on the other side of that conversation. So let's say by five minutes you want to have clarity, or if you're gonna wind it down at five minutes, just give that person a little more time just to be generous, just to treat them well. Wherever the cutoff is, go a minute or two more to make sure they feel taken care of. But in my eyes, I think the sooner the better. And um, I do know some people though, where the other way you can look at it is, hey, you've got this, and I've done this at times. If it's someone that's not a great fit to work with me, but we have the time reserved, I'll say that early and I'll say, hey, here's the deal. It's not a good fit, maybe for budget or product market fit. But I'll say, we have this time set aside. What else can I do to help you while we're still here? And sometimes the buyer in that case will end it and they'll just say, Thank you, no, thank you so much. You've been kind, and then you know, wind it down there. So there's a couple of approaches. It does depend, though, how much time you have available and how many leads you have in your face every day. You can't spend time all day with people who aren't a good fit.

Build A Call Game Plan

SPEAKER_01 16:33

I love that. So let me ask you this question. So, working with teams, working with other companies, what would you say? Could you give me an example of a success story that you had? And of course, not blaming this successful or innocent or anything like that. I don't have to name names, but what's a situation where you made a big difference?

SPEAKER_00 16:53

Most of our work is based around how can we give sales teams a very, very clear outline for their calls, whether that's a consult or a demo discovery call. And it's true that almost 70% of salespeople have zero plan going into their conversations. 50% of businesses don't have a planned structure for their sales calls. So the first thing we try to do is say, all right, what is our game plan? What is our strategy? What plays are we going to run? And how can everybody follow that same game plan? In one case, if as long as the lead flow is high enough, just figuring out a game plan for your calls will see major, major results. It can be as simple as creating new discovery questions or helping a sales team learn how to end the call successfully. But one of our biggest projects went from$3 million a month to$8 million a month in 30 days, just by changing the strategy and the setup of that call. So you've got to have, that's not a guarantee for everyone. You've got to have the leads to get that done. But that's our focus, and that's one of our success stories that we're very proud of is okay, if we were to treat this call like it were a football game or a basketball game and make a real game plan for it, what type of impact could we see? We like to think of it as revenue hiding in plain sight, which is without increasing your lead flow, without growing your sales team, and without changing your product, how much more could you grow just by dialing in and tidying up your discovery calls? So that's that's the pool that we try to swim in.

SPEAKER_01 18:19

Do you recommend that people have discovery calls or um as part of their sales process? Or is there is there a process that that you've identified that helps people that have those higher ticket items?

SPEAKER_00 18:32

I think a discovery call is never a bad idea if you're selling higher ticket. It it really depends on your marketing. The goal is the better your marketing, the sh the fewer conversations you should have in the sales process. So without uh committing malpractice by giving some, I guess, a blanket answer. My the way that I always look at this is how good is the marketing? Are we doing spray and pray? You're probably going to need to have a few conversations before someone really understands what you do. If you've got a great presence online, your website's really clear, you have great nurture, and maybe you maybe you don't make it super, super easy to book a time till someone's really ready to go. Those are all things that can shrink your sales process. So I've seen people do six-figure deals in one call closes because their marketing is that good. And then on the flip side, if you're not if you're not dialed in, you can see projects a fraction of that size stretch on forever. So the to answer your question, I would say a discovery call is never a bad idea if your marketing is still improving. So if you're working with for your clients, I'd say one call close all day, right? Yeah, if it's yeah, exactly right.

SPEAKER_01 19:38

Okay, no, I think that that's that's awesome. Um all right. So someone who feels that the sales part of their process is what's costing them business. What's the first place to start?

Call Reviews And Clear Messaging

SPEAKER_00 19:54

The first place you're gonna want to start is it's hard work, but sit down and listen to a whole bunch of sales calls. Sit down and listen to five or five or 10 to 20 per uh people on your team who sell and get a really, really clear idea. What I would say is sit down and score those calls. Uh, say, are we are we batting 100 or are we lacking? And what trends can you find? Because with sales, you want to be looking for a trend that has gone wrong in nine of your last 10 calls because you fix that trend. Now you are you are fixing a lot of leakage. And so the first place you're gonna start is sit back and just listen to a bunch of calls. You'll be surprised at how many aha moments you have. And depending on the size of your team, you may have someone who's really good at selling and someone who's nowhere near as good. What you're gonna learn from the one who's really good, you can teach to the one who's struggling. And it makes it a lot easier when you can point back to some proof. So that's where I would start.

SPEAKER_01 20:51

I love all the things that you've said because I do think, you know, best fit, um, asking questions, right? That's important in marketing and in sales. Um, and then sales should not feel icky if you are proud of the problem that you solve and how you do it, right? So you shouldn't feel that way if you're selling, whether it's your company or you're in a sales role. I think that that's that's all really good stuff. So thank you so much, Johnny. I really appreciate your time. Um, but before I let you go, I do need to ask you the question that I ask all of my guests. And that is that this show is called Imperfect Marketing, because marketing is anything but a perfect science. What has been your biggest marketing lesson learned along the way?

SPEAKER_00 21:33

Have a clear message. Really know who you're selling to and what problem they have. Uh, a clear message will make up for all kinds of marketing mistakes. Um, and a foggy or murky or muddy message will slow down a lot of marketing dollars. So get clear on what you want to say to your buyer and things get a lot easier.

SPEAKER_01 21:55

That's great. And again, going back to what you said about listening and asking questions, that is the best way to make sure that your marketing is clear, right? Listen to your customers, listen to your best customers and what problem you solve for them. Understand that, find out what resonates with them, ask them questions and let that show up in your marketing, right? Whether it's marketing or sales, the questions and working with the best fit leads is always going to be the best place to start. So thank you so much again for all your. time today. I hope that you guys all learned something today. I know that I did. I really enjoyed our conversation. If you're looking to connect with Johnny and Bridge Selling or check out his book, we'll have links for that in the show notes. So be sure to check it out. And until next time, have a great rest of your day.