Sep 18, 2025
Joshua Long
#1 Reason Salespeople Fail (and how to prevent it) | Ep 7
The Bottleneck Breakthrough Podcast
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In this session, I go over the #1 reason salespeople fail and how to get the most out of them. The answer isn’t a new CRM or innovative new offer that demolishes the competition. And it’s definitely not just to work harder.
Transcript
Speaker A
00:00:00.800 - 00:24:58.440
This is episode seven, and I'm going to reveal the number one reason salespeople fail and how to get the most out of them. This is the Bottleneck Breakthrough podcast.
I'm Josh Long, and this is all about helping you find and fix the biggest challenges in your business to unlock growth and profits that last. Hey. Hey. Welcome to the podcast.
Today we're going to dig into a hot topic, one I think a lot of business owners struggle with, and that's how to get more out of salespeople. And really the number one reason salespeople fail.
And I think the reason that we see a lot of business owners struggle with managing salespeople, getting the most out of them, figuring out what to do, how to build a sales team, is because the typical business owner is the best salesperson. And so they do it naturally.
And as the company grows, they realize, gosh, I could get some better leverage on this company in this organization by having sales staff, by having people taking care of sales responsibilities, taking care of things that are going on on the front end of the business so that the owner can set more vision and grow the company and move on from there. So the number one reason salespeople fail is due to a lack of coaching. I recently saw a post by a guy I know named Alex Charfen.
He said it best and it was, every manager should be a mentor or they are doing it wrong. And so sales management is no different than any other management.
And in the world of sales, I think I view, really do view the sales activity like any kind of athletic ability or professional skill, that it takes lots and lots of practice, it takes refinement. And just like Roger Federer practicing on the courts with his backhand or his serve, if he's not doing it every day, he gets rusty.
And just like professional speakers that aren't speaking regularly, they. They get rusty.
And I think sales is the same thing that if you're not working on your craft of sales, that you get rusty and you fall into ruts or routines. And without effective coaching, your salesmanship is not improving.
And so you tend to build things that work, habits, tricks, shortcuts, whatever, that work for a while, but the market changes, your business changes, the competitors change, and so you have to stay relevant and stay current. So what does coaching look like? Well, it's no different than any other kind of management. You start by establishing a baseline.
And if you're dealing with an existing sales team, I sit down and I go through their funnel, their status of how many leads are they talking to, how, how Many have they gotten, how many proposals are out, how many have been approved, how many have been declined, how many have ghosted them, and then what's their revenue off of that? Get a baseline. Once you establish a baseline, then you have some idea of what to work from.
If you're getting started with your first salesperson, the first thing you want to do is break out the sales process that you go through. Is it a one call close? Does it take six months of nurturing to get somebody to close?
Is there a 35 step proposal process that has to go through so many committees and so many approvals and so many decision makers to finally get to the point where they can get started?
Just outline the basics of what your process is so that the new salesperson can get up to speed on it and can start going through their own process with prospects.
I find that for the typical business owner that's hiring their first salesperson, that they need to break off small chunks of the process and start delegating that to them, coaching them through it, looking over their shoulder, reviewing the process with them so that they get better and better at each stage, and then eventually you can hand it all off.
The kiss of death that I see in so many spots and companies, when companies are growing and, and owners are trying to get things off their plate, is they just wholesale abdicate something to them to the new hire.
And that ends up being a horrible situation because that person hasn't been given the outlines, hasn't been given the structure of what's working, what's not. They're left to figure it out on the fly. They tend to make bad decisions that the owner wouldn't approve of because they're not the owner.
They don't know all the parts of this baby. And so then the owner gets frustrated, usually overreacts, fires them or belittles them, berates them, and it creates a bad situation.
So when I am coaching salespeople, I try to find where their bad habits are. So number one bad habit of all salespeople is discounting.
They tend to negotiate against themselves when a prospect isn't moving forward and they start throwing out discounts. They start throwing out something that they figured out is acceptable by the owner. It's the bare minimum that we need to make to make this deal.
So I'm happy to keep going to that point and discounting.
But the problem is, you know, as an owner, the problem with discounting is you may discount, they may discount 10%, but let's say you have a 15% net profit margin at the end of the day? Well, they just cut two thirds of your profit right out of the deal.
So it may only seem like 10% to the salesperson or to the prospect, but they just cut your net profit at the end of the day. So to make up for that net profit loss, they have to sell essentially three times as much, if not more to offset that discount.
So a 10% discount, depending on your business model, depending on your margins, could be a huge, huge cut hit to the bottom line. And that's we're talking with them about the net profit and or business model.
I know it may feel like you're revealing too much to them or showing them too much how the watch is made, but the reality is that if they don't know the implications of their bad habits, they're going to continue them.
And that's just part of communicating as a leader, is not expecting them to have the common sense that, gosh, if they discount this, that it's cutting into our bottom line. Most salespeople don't think about that because nobody teaches them about it.
The other thing that I work on coaching is helping them handle objections better. And this isn't to become an objection jockey or wrestling with the prospect.
In my book, I talk about the typical sleazy Sam car salesman or the objection jockey that is able to handle every objection quickly and deftly to keep the prospect from feeling like they're getting any, any upper hand in the negotiation. So when I'm talking about handling objections, it's not that. It's not people stupid things like the prospect saying, well, this is expensive.
And you say, well, compared to what? And use some red herring example that doesn't make sense or compared to the inaction you won't take today.
Like, those kind of objection responses are stupid and belittling. So when I'm talking about objection handling, it's stuff like, let's say that you sell something that has some kind of marketing tracking, right?
You have the ability to show that your agency gets more leads for your clients. Well, in analytics, in data tracking, there's no such thing as perfect data. There's attribution.
Today is really, really hard to figure out exactly what caused the person to come in to become a client, to inquire.
And so you might end up in a situation with your clients where the clients are like, hey, that was a referral, I know where that came from, or oh, that. How do you know for certain that that came from your ad campaign for us? Well, instead of trying to arm wrestle and say, well let me see.
And the sales rep has to go back and try to pull some huge report or the account manager that's maintaining the account can't find that data so they feel paralyzed. Instead of trying to argue over the data, it's give them the answer that there is no such thing as perfect data.
We track broad trends for you and that's why we want to know how your business is growing on a month to month basis so that we can show a trend of our activities for marketing, for advertising produce results for you. And this is really important for agencies that are serving non e commerce businesses because the sales transaction isn't clean and easy.
It doesn't follow from a click on an ad to a landing page to an order to a credit card processing that feeds back to the the ad system. So being able to handle that objection of look, we don't have perfect data and we never will, there's no such thing.
So we look at trends, we look at overall growth trends for you. And if you're doing something else significant outside of our services, we'd like to know it so that we don't take credit for that.
Or we can figure out what share of value that that activity has.
But giving your salespeople or your account managers more language, more empowerment to handle the frustrating questions from prospects or customers, those are the types of objection handling scripts that I like using. The other thing that I like coaching on is improving the sales process. So a lot of salespeople nowadays, I talk about it in my book.
I find the most common sales profile today is what I would call a golden retriever.
It's somebody that just like a golden retriever dog, one of the most popular dogs in America, I don't know, maybe worldwide, but at least in America they're popular because their personalities are reliable, they're very friendly, they're rarely aggressive and they're fun and easy to be around.
But when you're dealing with a salesperson that acts like a golden retriever, that salesperson's fun, easy to be around, very friendly, but they are willing to just chase whatever ball the prospect throws. They never take charge. And so that prospect shows up and has a default buying process. I want to see some of your client testimonials.
I want to get referrals, I want to see your price sheet, the basics, right? That's what most people are looking at when they come to buy a service. But they don't know what they don't know.
And so they don't understand the nuance of let's say, the service that you're providing. Let's say you're a CPA and you do some kind of tax planning.
Maybe they don't understand the nuance of your background as a tax litigator against the IRS or some kind of specialist inside the IRS that dealt with audits because you don't explain your difference there and how you understand all of the limits.
Or you're maybe you're a tax strategist and you went to, you worked at a high level law firm and you know all of these amazing strategies for high net worth people. If you're not explaining those differentiations to the prospect, all the prospects going to look at is your price.
And if you're triple the cost of your competitors, they're going to keep throwing the ball and looking at price and their basic objections and they're never going to sign up for you with you. So that's the problem of a golden retriever salesperson is that they chase whatever ball that prospect throws.
And they're typically just basic questions that aren't headed in any strategic direction and they come back and say, here's the answer. Okay, what's next? Do you have any more questions? Well, what would you like to do next?
And so I work with salespeople on getting out of that rut of continually giving the prospect all the power. And I like just using the reframe of sell like a surgeon. I had a pre med background, I sat in on surgeries, I worked in an er.
So I saw high level surgeons and ER docs working and saw the difference between the best of the best and the average ones. And the best of the best maintain control even if they're not certain. They don't let the chaos ensue.
And the nurses that work with high level surgeons that maintain control are so much more calm and they all work so well together. Even if they deal with huge surprises and somebody coding or whatever. This control and the structure and the piece from that control is amazing.
And in sales, all of these prospects are coming to us for a solution. They need help and often they don't know exactly what they need. And so we do, we know most of the time what is best for them.
If we're good at our craft and if we deliver a great product or service, we can sell like a surgeon because we know exactly what works best for their situation. And so it's not a control thing to try to overpower them, but it's a control thing. A control is the goal.
So that they feel confident that they're getting expert help and that we're providing certainty that they're going to get the outcome they want. And so when I say sell like a surgeon, there's a place for answering questions.
But it's not always chasing whatever question the prospect throws or the great joke I say with salespeople is a surgeon would never say so do you want to bring anybody else in to review this X ray that I looked at or hear my opinion for you? No. They deal directly with the decision maker, they make their case and then they say take it or leave it. Essentially.
Now in sales we don't say take it or leave it because that's kind of an asshole ish thing to say.
But we change the dynamic from chasing whatever ball that prospect's throwing to establishing a process, demonstrating that we understand their needs, prescribing a solution and then standing behind that solution. So that's the biggest stuff in coaching that I see needed in sales.
And if you don't feel like you're a good salesperson, you don't feel like you can coach others to close, well then maybe there's a need for bringing in a coaching, a sales expert to help coach them, to help set a baseline of coaching. And I'm not saying that I, I'm the one to do that, but there's lots and lots of sales training out there. I enjoy doing it, it's fun. I like closing.
But Sandler is a great sales training system out there.
My buddy Tom Schaff, he, I can't remember what he calls his program now, but he's a great sales trainer and he used to be a Sandler trainer and went off and did his own thing. There's lots and lots of great sales training companies out there.
So if you don't feel like you have a process or a framework to coach around, go get that.
But I think for most business owners, they're great salespeople and they just need to define the process and coach the salespeople in improving each of these metrics or areas that I, that I pointed out. The other thing that I look at when I'm helping sales teams is I want to remove minutiae.
A lot of companies view salespeople as kind of like this multi talented tool jack of all trades. They can do a little bit of prospecting, they do a little bit of marketing, they do some reporting, they do some account follow up.
But at the end of the day, the whole point of a salesperson is to close. That's it. I Try to remove everything possible that isn't closing. Because the number one activity to get revenue is to close prospects. That's it.
And so if you've got a salesperson who's talented and can close, then you want them spending all day, every day, closing. So what about all the other activities, right?
Filling out reports, sending proposals, chasing leads to get them qualified, following up on account frustrations where maybe the support team dropped the ball.
All the things you have salespeople do, those are all things that I would look at either delegating, offloading, automating, figuring out where in the system you can streamline it. I hate chasing people for sales conversations, so I use calendar system. I live on calendly.
Calendly is my favorite and it's so streamlined and you can have it in a team environment. So every time somebody sends in an inquiry to the website, just put a calendly link right there.
After they qualify, after they fill out a questionnaire, after they demonstrate some level of competence or engagement, let them schedule right on the salespeople's calendar.
So if a salesperson's going from appointment to appointment, that's already pre structured and the show rate is high and they're closing on those calls, you, you could expect, you could see a salesperson's performance double, triple or quadruple easily by removing all that minutiae and chasing unqualified leads or whatnot.
And I know it's scary to think of, gosh, if they just sit around and are only dealing with pre scheduled appointments, then we're missing out on a lot of business because maybe there's not enough leads and maybe we don't know exactly who's qualified and maybe it's just once we get on the phone we find magic happens and people show up with money all of a sudden.
But the reality is the more structured you can make this process and the more streamlined you can make it, the more profitable your salespeople will be. My goal again is to reduce minutia, get rid of TPS reports, get rid of manual entry across systems.
I mean most CRMs are sophisticated enough, there's APIs for everything. You can connect systems, disparate systems with zapier most often.
And I think there's no reason to have salespeople spending the bulk of their time filling out data, chasing people, making cold calls, following up on, trying to get people tied down to appointments. I think that whole dynamic just wastes so much time and so much potential of the salespeople's closing ability.
Then the other piece That I think is really critical is getting marketing support. So oftentimes as companies grow, marketing and sales become two divided relatives or siblings under the same house.
And my personal philosophy is that marketing should be overseeing sales because marketing sets the strategy, they deal with the communications, they build the demand, and then sales closes on that demand.
And so oftentimes the sales will be this silo off to the side and they deal directly, maybe with the CEO or the founder, and then marketing's off doing its own thing. And there's no cross pollination, there's no collaboration.
And so my view is that marketing does long range bombing to soften the front lines for sales to go in and take over and close leads on. But what happens so often is that marketing views their activities more like branding.
They've got to get some educational material out and they've got to show up to the trade shows and they've got to have a good booth, but they're not thinking about short term leads or any kind of direct ROI on their activities. And so they don't build things that sales needs. So my recommendation is to have marketing focus on building assets.
So those are case studies, testimonials, explainer videos, guides, download reports, things of that nature that sales can use to smooth out their sales process, to not keep repeating themselves over and over and over and make the prospects move through the sales process more easily.
So that to me is where marketing can really get involved and really stop going from promotion to promotion or long term brand building and focus more on okay, what's next, what do we need, what channel do we need to build out for the sales team to get consistent lead flow? What assets do we need to create that make it easier for them to engage prospects?
And some business owners think, well, that's sales job to get the testimonials or to create the case studies. But the reality is salespeople aren't necessarily multi talented at all that stuff. They're really good.
The best salespeople are really good at building rapport, finding out need, pulling people through with motivation and getting them to make a decision, getting them closed. None of that is related to writing case studies or creating marketing collateral or any kind of sales collateral.
And so I think that's where marketing really steps in to add value and create the one, two punch between marketing efforts. Communication, building demand and getting sales closed. And then the final piece of getting sales dialed in is getting their comp plan dialed.
And so I think a lot of companies go one extreme to the other where they either put everybody Commission only or some aggressive comp commission based plan or they go salaried, which I've never found anything more lazy than a flat salaried salesperson. And you may say, oh well, my salespeople are different. They have morals, they follow through, they're motivated.
But the reality is once you put an upside on their performance, on their compensation, they meet it, they're hungry, they're competitive. It's what gets measured, gets rewarded, what gets measured and rewarded improves.
And so I think that having some incentive on their upside is critical for all salespeople.
And then on the other side of the spectrum, the commission only side that says, oh well, if they're worth their salt, they'll live on what they kill, they'll eat what they kill. And the problem is that most companies don't have a proven sales process. The owner's doing it all.
There's not been somebody that's been able to come in from the outside and do it and it's unproven. And so the owner is deferring all the risk, the salesperson's taking all the risk, and they're really set up to fail.
And so because it may take three to four months to get up to speed without even having a base, most salespeople are gonna flame out and they're not gonna last.
And, and so you're just going to go from frustration to frustration trying to get commission only salespeople to come in and take all the risk on your company when it's you get all the lion's share of the reward as you grow.
So that's the basics to me of becoming a better sales manager and overcoming the biggest issue why salespeople fail of being that they're just left up to their own devices and they're not coached to achieve their potential. And so if you have any questions, I'd love to get them.
You can email podcastottleneckbreakthrough.com and if they're worthwhile and useful for future episodes, I'll answer them directly on the podcast. And if they're useful enough, or if they're quick enough for me to reply, I'll happily reply via email. And then I'd love your reviews.
So go to Apple Podcasts or wherever you're listening to this at.
And I would love your reviews to keep helping more people find this and appreciate the feedback that you send in and hope you got a ton of value on how to dial in your sales team and get salespeople achieving their full potential, because that's the name of the game is helping you grow your company and get sustainable results that last. This podcast theme music is an excerpt from Triptych of Snippets by Septahelix. It's used under Creation of Commons.
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