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Hitting Sales Quotas: From Underperforming To High-Performing With Donald Kelly [Episode 83]

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What makes a top performer different from others when it comes to quota?

Doug C. Brown speaks with Donald Kelly, podcast host, founder, and CEO of the Sales Evangelist, about the skillsets and strategies that separate top performers from the rest. Doug and Donald also discuss how to go from an underperformer to an overperformer, and when you should accelerate a sale, and how to hit – and go beyond – your quota.


In this episode you will learn:


Episode’s guest – Donald Kelly

CSS 82 Donald | Hitting Sales Quotas
Donald Kelly believes that anyone can sell if they have the desire. Early on in his sales career, Donald struggled with sales, but through the proper training and coaching, he became a top-performing seller. He has since taken it upon himself to “evangelize” the message of effective selling to struggling entrepreneurs, salespeople, and anyone looking to improve their sales hustle. Donald hosts a popular sales podcast called The Sales Evangelist, which has over 2.3 million all-time downloads and is heard in over 150 countries. Donald and his podcast have also been mentioned in Entrepreneur Magazine, Forbes, Inc, and HubSpot as a top B2B sales podcast. 
Visit his website: www.thesalesevangelist.com


Hitting Sales Quotas: From Underperforming To High-Performing With Donald Kelly

We have an amazing guest. His name is Mr. Donald Kelly. Donald owns a company called The Sales Evangelist. We are discussing why 57% of individuals who are selling are not hitting quota and why 67%, reported by Gartner, a research group of companies, say they’re not hitting quota collectively. We’re going to discuss why A-players, in other words, the top 1%, do differently than the ones who are average or performing. What’s the difference and why this happens? How companies can use these types of individuals to up their quota and no longer be part of that terrible statistic when it comes down to it? Without further, let’s go talk to Donald.

Donald, welcome to the show. Thanks for being here and I appreciate you being here.

I’m excited about this, Doug. I appreciate the opportunity to be in front of your audience and share some insights. I get passionate about selling so I may get too excited. Tell me to calm down. I’m supposed to be here.

You and I have known each other for a couple of years. As I always say, I learned something from everybody but when I come off the call with you, a lot of times I’m writing things down. I’m like, “I didn’t think of it in that capacity.” I appreciate you being here. I know everybody is going to appreciate this because we’re going to talk about one-percenters, the elite performers, as we go along.

The stats that come out and the recent one is why 57% of individual sellers are not hitting their quota regularly. It blows my mind every time I see these statistics because, over the years, I see different statistics but that tells me 43% of people are. There’s 57% aren’t and 43% are. What do you think the difference is between those two?

It’s an age-old challenge. What a lot of it comes down to is that they’re disciplined in their craft. We can pull together folks who may be entrepreneurs, coaches or people who are small business owners selling in that as well. Oftentimes, I find that the sales professional side, the individual who contributes, is working in an organization feels that they have the gift of God or the capabilities to be able to woo someone. Therefore, they feel that they’re a good seller. They’ve got lucky so often enough that they go on that luck and think that that’s great selling.

Say, for instance, if you were to throw a ball in the woods, there’s a likelihood you’re going to hit something. That’s what a lot of salespeople do. The top performers always hit. They’re targeted and focused because they have a plan. They understand that their craft is a craft and they need to be disciplined at it. Some of the underperforming sellers may wing it when they make a phone call. They know what the messaging could be so they play with that.

They don’t have a consistent verbiage that they’re utilizing. Their emails are sporadic. Their social outreach game is not necessarily quite there fully. Opportunities come in so they feel that they’re good. Is 70% or 60% dictating and showing that you’re a good seller? Of course not. We oftentimes agree and accept that rather than looking and saying, “What’s making the top performers hit 100% or 150% of quota?” It’s because they have a plan.

It translated and it’s the same thing with businesses. Oftentimes, I see business owners, coaches or SMB companies where their technician knows their craft. They understand their industry. They’re an engineer, go back to the E-Myth. With that, they don’t necessarily want to do the selling. They figure sales will come.

If I build it and do my craft well enough, people will come to me. People don’t know what you have to offer until they know what you have to offer. It’s imperative that we, as an organization, have a plan, process and system that allows us to be able to bring a net new business inside of our organization because it doesn’t matter how good you are as an engineer. If your sales department is not generating net new revenue, your organization is not going to last.

It doesn't matter how good you are as an engineer. If your sales department is not performing, your organization will not last. Share on X

It’s the most critical role within any company because that function needs to be on point. We’ll go back to look at it when it comes to the sales professional. Sometimes, these small businesses will bring in A individual contributor when they’re ready to grow their business even further and say, “The salesperson could take care of that.”

If you don’t have a system and process for these salespeople, they come in with nasty habits that they will learn. Maybe when they’re doing car sales because you thought they were great at that, they’re trying to figure that stuff out and translate it into your business. You need to have the process, have the system and know how to sell the product best. Get that in place first before you bring somebody on so they can follow that system.

The same idea as a sales leader. If you’re reading this or an individual contributor, you need to make sure the company that you’re working with has that system and process so you can be set up for success. In our company, we follow this principle called we strive for excellence and all that we do. This means that every individual on our team, whether it’s in the sales side or any matter of the functional departments, needs to be able to thrive for excellence in every single craft that they’re doing. We don’t want to get that 60% or 70% quota. That’s money but that’s not what our goal is. We want to hit and surpass our goal. That’s excellence. We’re performing to the best of our capabilities and that’s what we want to strive for.

It’s interesting to me when you say 70%. Imagine we drive 100 times a month and we’re going to go down the highway. 70 out of 100 times, we don’t wreck our car but 30 times out of 100, we wreck our car. No one would accept that. Firstly, you’d never get insurance again. You’d probably hardly even have your license. The insurance companies wouldn’t take it.

The regulatory board that issues our licenses for driving wouldn’t take it. I’m sure the attorneys on the other side that would be involved in the lawsuits that would happen wouldn’t accept that. They’re like, “You’re 70% good.” People in sales like owners of companies, leaders of organizations, leaders who have sales VPs or presidents of sales, why are they going, “70% is okay?”

One of the pieces to that too is that the top performers are taking the cake and bringing up the rear. Unfortunately, they may be getting the results from that and they’re fine with it or it’s acceptable and they compensate for it. They might say, “We know that the bottom rung of our sellers is not going to hit their numbers. We know Jake, Lisa, Amber and Scott are going to hit their numbers so they’re going to be able to take care of the load for us but that doesn’t make sense.

Oftentimes, it comes back because the organization doesn’t have the processes in place. It’s been going on like this for a long time. It’s not new underneath the sun. I give a speech at Outbound in 2022, a sales conference. One of the things that I spoke about was going back to attorneys. You never find an injury attorney or any type of attorney that’s going to pick a case unless they know they can win that case.

CSS 82 Donald | Hitting Sales Quotas
Hitting Sales Quotas: Attorneys only pick cases they know they can win. The same goes for salespeople. Don’t pick deals that you’re hoping or guessing to win. You need precision in your craft as a salesperson.


Oftentimes, what happened with salespeople is that they pick these deals or “cases” that they’re not necessarily sure they can win but they’re guessing and hoping. We need to have precision with our craft. We need to evaluate and ensure that the people or the cases we are going after or the deals are the highest probability of closing. That requires us to be able to have a function behind it. I can go back to why the sales leaders. It’s because it’s been going on for a long time.

I’ll give you another example that proved this too. Most sales leaders will tell their sales team, “We need you to have 3X to your pipeline because crap happens.” We know that. Somebody gets sick, leaves their job and so forth. This is incentivizing my sellers to say, “You could have 2/3 of those deals. We know we’re not going to close. It’s okay if you have 1/3 of crap in there. Put it in a pipeline so we can have the pipeline because we are not expecting all of it to close.” That’s not striving for excellence in all that you’re doing. That’s not even precision in your craft, is it? No way.

This comes down that there’s no 1% manager on that thing. A manager’s job is to grow a team. Let’s take professional sports. “Guys, go out there. Let’s lose 1/3 of the game or the season.” They’re not doing that. That’s because they’re pro sports teams. There’s a lot of money involved in those things and their job is on the line. When it comes to sales, people have that mediocrity. When it comes to the top 1% and you and I have talked about this in the past, they don’t look at quota as the quota. They look at quota as a baseline. It’s like, “If I don’t hit this month, I failed.”

They’re not looking at quota as the failure point. They’re looking at quota as like, “That’s so far downstream. I don’t even think about it. I’m hitting 150% to 200% every single month as my baseline.” That’s who’s carrying the team. I’m going to brag a little on my end here. I was a major account executive for a company and I had nine people on my team. Every single month, without fail, I outsold all nine of them combined.

Sometimes in some months, I was outselling 2 or 3 teams combined with teams of 9. People went, “What is this kid doing?” All I did was created a massive prospecting process coming into the thing and I had systems. The point being is my manager used to take credit for having the best team in the company because they looked at top-line numbers. The reality is I was making up for the bottom third and ensuring it up.

Why don’t people go out and find the top one-percenters? They’re not as easy to find as the lower end of the producers. Why not make that your bottom line standard and then like, “Everybody is hitting 110% quota. That’s our bottom line standard. We don’t have to raise quota but we’re going to find people who are going to look at that and go, ‘I’m going to blow that out 200% to 300%?’”

Go back to the baseball analogy that you’re sharing. There’s a Law of Averages that falls in there. I would say overall, there are two points. I would go back to one, the Law of Averages, that not everyone is going to live at that expectation and do or be that type of seller. That’s going to be a top-performing seller. You’re going to have folks that are role players and so forth. The other side to that too is that the overall industry where most salespeople could have a decent living. They can make $60,000 or $75,000 a year and then commission on top of that. If you get another $30,000 or $20,000 a year, $90,000 is not bad for somebody living in Alabama or Midwest somewhere.

It’s living okay and living well. Therefore, they don’t feel that push or incentive. Imagine if the sales industry was pushed even further on the idea of your performance and individuals needed to be judged based on that. Even more so, I find that more people would step up to the game or the plate because they’re being coddled. If it’s okay for me to hit 70% or 60% of my numbers, be a good person and I’m still fine, then that’s great.

CSS 82 Donald | Hitting Sales Quotas
Hitting Sales Quotas: Salespeople are earning enough that they can live okay. They don’t feel pushed to perform. If the sales industry focused more on performance, more people would step up to the plate.


The organizations that want to get those top performers are hard to find because 1) The Industry is allowing for underperformance and then 2) Either way, we are still going to always find the Law of Averages. I do feel that companies could have more than 20% that are top performers. We should expect more than that but we accept it too far too often and far too consistently.

What I have found is that the more demanding the management side of it is, the more people step up. It’s like in the military when I was in the military. There were a lot of guys and there were no women back then because I’m that old. Back then, guys were coming in. Many of the guys that I served with came in and they had a choice. Either you go into the United States Army or to jail. That was their choice.

It surprised me because I was a kid from a small middle-class neighborhood that I never met those types of individuals. There were enough of them that it was pretty prominent. What never ceases to amaze me is when they got into a highly structured, highly disciplined and highly demanding environment with high consequences. If they didn’t perform in that environment, they stepped up and admittedly said, “I’m a better person. I feel better and more confident about myself.”

They would make rank quicker. I remember the movie Rambo. Rambo would say, “In the military, I would have $25 million pieces of equipment that I would run but here I can’t park cars. Get a job parking car.” I find that if we structure that environment, it doesn’t have to be boot camp, guys and gals. I’ve always done this with the people that I managed. I’ve brought them to a place and they’d be like, “I got 40% close.” I’m like, “Are you sure it shouldn’t be 47%?”

They’d be like, “You’re a jerk.” I’m like, “Am I or you are not living up to your potential?” If we hold people to that potential, what I find is people bring that potential up anyways. As individuals, it’s easy. It’s like, “I’m not fat but I’ll keep eating an extra cookie every day.” Six months from now, I look and go, “I gained 8 pounds.” If we had a personal trainer on the other end going, “You ate a cookie?” Slap. Not maybe a physical slap but you want to hit your goal type of thing.

A lot of these are like, “I’m sorry, managers, vice presidents and presidents. I’ve been there. I’ve done that.” The reality is if we don’t hold them accountable, then the people will tend to take the path to the least resistance. As you said, Donald, if they live in Alabama and they’re making $90,000 a year, they’re living a decent life. If you’re in New York City, you’re going to be sharing a pizza with a rat. The environment will sometimes hold people accountable. You gave me a stat before we started this. It was 60%. Could you quote it, please?

LinkedIn launched a tool called Deep Sales. In the report, they shared some figures from Gartner’s latest reporting that showed that 67% of sales leaders reported that their organization missed their target in the month of July 2022.

There’s a myriad of reasons why that’s probably the case. Certain companies are economics all of sudden whack them in some cases. Here’s the thing. Being old, I can say these things when I was in my twenties. I’ve been in the game a long time selling and what I have found and I’m looking for your feedback on this, Donald, is in a recession, I have always taught people, “It is the time to gain market share more than ever.” Traditionally, what happens in a recession is people get nervous so your competitors get nervous and they start pulling back. They pull back on two things initially, marketing and sales.

I don’t want to say anything about this because I’m giving secrets away here with you. We’re going to get people too far ahead.

Experience dictates something here. Between the two of us, we’re not Centurian yet but we’re getting close. I always found that’s the craziest thing to do. You cut off all the leads that you can get and get rid of the people who are converting sales. The sales engineer will have nothing to do. It’s a death of spiraling.

My point being is do you believe, because I think you do based on your reaction, that leaders of companies should be stepping up more than ever, training their people, helping their people and pushing their people to be in that top 1%? Even if they get to the top 3% versus the top 1%, it’s still a marked improvement. That person that’s making $90,000 a year is making $140,000 or $150,000 a year in sales. The quality of life is so different from that, I suspect in Alabama. What are your thoughts on this?

Let me start by saying this. I want to give another visual compared to what you’re saying. I ran track in high school and when you’re doing the 400 meters, that’s one time around the track. Inevitably, where people are going to fall out is at that 200-meter mark. The 400 meter is a cruel race. It is a sprint. What will happen is people will jump out the gate, start going fast, try to get ahead of you and “get more market share.” That’s fine. Everything is great. All things are created equal. When you get to that 200-meter mark, that’s when the economy “starts to go bad.”

What I want to do at that point is you can say, “I want to conserve my energy until the 100. No. I’m going to start at that 200 and start my sprint there. I’m going to take as much market share and get in front of more people as possible. At that point, when they’re the weakest and they think they’re going to wait until they get some juice or energy at the 100, I am going to kill you starting at 200 and bring that thing down until the very end of the race. When I get to that 50-yard line, I’m going to waste you even further because I’m so much further ahead.”

The same concept applies. I didn’t mean to say kill because I don’t want people to get crazy about that idea. Metaphorically, I’m going to take over at that point. When it comes to this idea, I’m 38 in 2022. Back in 2008, I went through that. When I finishing up college, in 2010, I started in the workforce. It was challenging trying to sell during that period and getting into software sales.

Eventually, we saw the same idea. Coming back in 2020, we saw some little issues. Both times, what I saw with people before me, there was a sales guy. I don’t ascribe to his way of selling. However, you can’t beat the idea in this industry. Grant Cardone, in 2008, recognized that. One of the things that Grant did was wrote several books. In 45 days, he wrote a book with the whole idea up the 10X and he was everywhere.

When everybody was running back to the hills because they retreating, he decided to go everywhere and saturate the market when it comes to sales. He killed it on YouTube and all over this place. Eventually, he got the TEDx event and all the stuff that came from it because he was going out hunting and taking over market share when everyone was running back and hiding. The same concept applies when 2020 came around and we saw the crisis that was going on.

A bunch of people were trying to figure out, “What am I going to do?” I was scared. I’m telling you, Doug, because I saw a lot of reoccurring revenues started drying up. I was like, “What do I do at this point? Do I sit back, go in the house and be afraid?” I started to go on a podcast and everywhere as much as I could and that helped a lot. Eventually, opportunities several months later came. This is why I’m telling you this because I saw the data. What I saw happen is companies started to realize that they weren’t making money.

After around June 2020, summertime, we started to see an uptick where they’re like, “We needed our salespeople. We have to be better.” They started looking at me to do more training and we got a lot more opportunities. 2020 became a good year for us. There was this dip and then we saw the uptick. I started looking ahead of this and then as soon as I started hearing people say stuff like the R-word, news and so forth, I was like, “This is a time to punch on the gas.”

We did polls and saw things within our industry. We said, “We’re punching double in our gas.” This is a strategy. It seemed like I’m everywhere doing everything because that was the idea. If you follow me on social media, I’m trying to take over my market share in places where competitors want to cut back because I know what’s going to happen. When it gets to that 100-meter mark, they’re going to try to hit that sprint. Once they get to the part where they see their number is dipped enough, they’re going to say, “We need to put some more resources.” This is a critical component and period where we need to push on a gas.

Going back to the idea of a sales professional, it takes a skillful seller to be able to sell during challenging times. This is where it separates the kids from the adults. It separates the professional from the amateurs because the amateurs wing it. They sit back and send out these basic emails. They send the crap that you get from old-school emails.

It takes a skillful seller to be able to sell during challenging times. That is what separates the kids from the adults. Share on X

If they send enough out and throw enough spaghetti on the wall, something is hit. In a market like this where it’s a little more challenging and people are being cognizant about the money that they’re spending, talented sellers can create business cases, reasons or what we call blindside challenges. It points out to companies, decision-makers and stakeholders. It’s the importance of problems that are not even focused on that will be a hindrance to them. That takes skill, craft, persistence and a process.

That’s why top performers will thrive during this period. I want to give a big shout-out to Jeb Blount on his book, Selling in a Crisis. You can see a lot of those components that Jeb released in his book about how these top-performing sellers are, how they’re strategic and how they can sell during a crisis and still be successful compared to the underperforming sellers. I got all my soapbox there for a minute.

Donald, how do people get ahold of you? I’m sure your passion is coming through here for sure.

You can find me on any of the platforms. You can find me on Linkedin, Donald C. Kelly, Insta @DonaldCKelly and Twitter @DonaldCKelly. I spend a lot of my time on Insta and LinkedIn. If you want to get free content that we have, you can go to TheSalesEvangelist.com. On that page, we have a Resource tab. We have free training courses. If you’ve taken advantage of LinkedIn, we have a free general sales training course teaching you the fundamentals of outreach. We have a ton of podcast episodes on which we share a lot of insights.

Alan Weiss once said to me, “You got to get out there and get into the public square.” That’s what I heard you do. You’re out there and you’re in the public square. If people don’t know what the public square is, in the old days, you had a town center. You would get up there and you would speak. I saw this when I was in North Hampton, Massachusetts. This guy was out in front of a church in the public square and he was going off about something.

I didn’t even know what he was talking about but the fact that he was out there, deliberately going out, getting a message out and doing this stopped me enough to say, “What is this guy talking about?” He was a terrible speaker so he didn’t keep my attention but the reality is he got my attention. The top 1% don’t wait for other people to tell them to get out into the public square.

They go and start getting out in the public square. They don’t look at it and say, “If they’re working for one, maybe my company is the only one who pays for this.” They will look at their sales processor or career as part of their responsibility for going forth and doing that. Going out, networking events and doing these things because they treat this as their separate business when it comes down to it. Donald, I could talk to you all day long as you and I both know. I’m very grateful you’re here. A lot of people have probably written about three pages of notes on this. I’d love to have you back on another episode if you’re up for it.

I always love to come back.

I’m going to thank you, Mr. Donald Kelly, from The Sales Evangelist, for being on the show. I’m very grateful you’re here.

I appreciate it, Doug. Thank you.

Respected discipline. Think about those words for a second. That means we respect the discipline that we have to invoke the result we want so we’re committed to that process. Respected discipline is one of the reasons that most people and companies are not hitting their quotas. Respected discipline on the company side could be the managers and the leaders.

They’re not holding accountability to the actual numbers. They accept things like, “I hit 80%, 85% or 90% quota.” Why would you want to do that as an owner of a company? Why not say, “This is quota. This is what I’m paying you for. This is why you’re here. If you can’t hit quota, you can’t be here. We’ll find other people to hit the quota and exceed that.

If you’re the individual thinking and they say, “I have a bad month.” Everybody has a bad month but are you having bad month after month? Look at what you’re doing. Do you have systems, processes, details and procedures around these things? Do you have things holding yourself accountable? If you do, you will sell more. If you don’t, you will sell less.

It’s that simple. One percent of earners in the world don’t look at quota as something they have to achieve. They look at it as a baseline. In other words, it’s like, “So what? I got a quota. I don’t care about the quota. I’m going to double-triple that anyways.” They don’t look at it as like, “I got to reach quota.” That’s the minimum viable starting point in the process.

I loved what Donald said about running the 400-meter. He said that the best companies and his company and what Pete teaches his people to do is you are going to sprint at the 200 marks. You’re going to stay the pace and ahead of people up to the 200. Halfway through, you’re pushing the pedal down and you’re going because you blow away the competition doing that. That’s what one percenter does.

They don’t look at and say, “Average is good.” They look at it and say, “I’m not average. I’m going to be above that and way beyond that. That is my new baseline.” If you like this episode and you love the subject matter, let me know. If you feel you have a subject matter that you would like to hear more about or let’s say you might be the subject matter expert and you want to get onto our show, reach out to us at YouMatter@CEOSalesStrategies.com.

If you love this show, give it a five-star review. Tell other people about it. The more people they know, the more people we can help. If you want, yourself, someone you know, your sales team or your company to get into the top 1% of earners, which means you raise your revenue or if you’re a company and you’re looking for these top 1% earners and elite sales performers, reach out to me at Doug@CEOSalesStrategies.com. @DougBrown123 on LinkedIn or call the company direct at (603) 595-0303. That’s it. Go out and sell something. Sell a lot of it. Play win-win. Sell it profitably. Make someone happy. Make yourself happy. Make people’s days brighter through what you do through selling. Until next time. To your success.


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