Sean O'Shaughnessey, CEO and President of New Sales Expert, storied background in sports, including his experiences with basketball legend Bobby Knight, has deeply influenced his approach to sales and leadership. As a high school basketball official and former athlete, Sean understands the transformative power of coaching. He draws a compelling parallel between the guidance athletes receive and the direction needed for sales professionals to thrive.

One of the most striking points Sean made was the importance of humility and the willingness to learn in sales. He noted that some salespeople are hesitant to have their calls recorded, often due to negative past experiences with coaching. However, Sean argues that constructive coaching is crucial for improvement, much like the training athletes undergo to enhance their performance.

To learn more about Sean's work, check out their website at https://newsales.expert/.

Connect with Sean on LinkedIn at https://www.linkedin.com/in/soshaughnessey/.

 

Key Points

• Sean O'Shaughnessy helps small and mid-sized companies optimize their sales strategy, transform their sales culture, and implement new sales procedures and processes (0:13)

 

• Sean talks about the importance of coaching and critiquing employees in a supportive way, using examples from athletics and sales (6:52)

 

• Craig discusses how some salespeople may resist having their calls recorded due to fear of critique, but emphasizes the importance of coaching and learning from others (8:35)

 

• Both speakers discuss the small difference between success and failure in competitive fields like sales and athletics, and the need for coaches to help employees improve and reach their full potential. (11:31)

 

•Sean compares salespeople to athletes who constantly work to improve their skills and need coaches to help them do so (13:41)

 

• Sean explains that he helps small companies with sales by bringing big company best practices and teaching them how to do sales (16:38)

 

•Craig asks about dealing with sales team members who may not be receptive to coaching, and Sean explains that he sets expectations from the beginning and focuses on making the team better without taking anyone's job or hurting their promotions. He also works with CEOs to address any roadblocks in the company that may be hindering sales. (18:50)

 

• Craig asks about the economy and what sales teams should do, Sean says small businesses can still sell products in billion-dollar markets and not to worry about the economy or competition (20:28)
 

Transcript

Craig Andrews 00:09

All right, today I want to welcome Sean O'Shaughnessy. He is the CEO and president of New sales Expert. Sean concentrates on helping small and mid sized companies optimize their sales strategy. But you know what? He has not always worked with small companies. He comes from an enterprise environment and now is devoting his time to helping small or mid sized companies do it. He helps them with their process and education. He also helps companies transform their sales culture, implement new sales procedures and processes, and install best practices. Sean has a book titled Eliminate your Competition, A Trapper's Guide to Increasing your commission. Interested in learning more about the Trappers angle? And not only that, Sean has his own podcast called Two Tall Guys Talking Sales. Sean, welcome.

Sean O'Shaughnessey   01:07

Thank you very much, Craig. I appreciate you inviting me on.

Craig Andrews 01:11

Well, I'm looking forward to this conversation. And one of the things that you said is that you're taller than you look on Zoom, and apparently you're tall enough that you mix it up with the basketball community on a regular basis.

Sean O'Shaughnessey   01:26

That's correct. I'm a high school basketball official, so for those of you who can see me and are watching me on video, you'll see that I have lots of gray hair. So I've been doing this. I've been around the world for a long, long time. But I played high school basketball, of course, played college football a little bit. And then after coaching my son in AAU basketball for several years and he got old enough and he had to go off to college and play basketball for them, I could no longer be his coach anymore. I was kind of bored, and I talked to a person I ran into that was a basketball coach or basketball official. I said, how do you become an official so well into my forty? S, I became a basketball official, and now I officiate high school basketball in the greater Cincinnati area. Cool.

Craig Andrews 02:11

Okay, so you said you played basketball in high school, but football in college. Did I hear that correctly?

Sean O'Shaughnessey   02:17

Yeah, I actually played both. Football actually ended my basketball career when I was in high school. It was one of those second to last game of the year, broke my arm pretty severely. Basketball coach was a bit of a jerk, and I won't say anything bad about the past people, but he wouldn't put me on red shirt or anything like that. So here I was in a cast I couldn't try out, I couldn't make the team my junior year, and they had a relatively successful junior year without me. And so my senior year, he's like, no, you're done, you're out. So I just played football at that, so. But I still love the sport of basketball.

Craig Andrews 02:52

Now, you're from the Midwest, this went Bobby Knight or something, was it?

Sean O'Shaughnessey   02:56

I have met Mr. Knight. It was a sad day. I was born and raised in Indiana, and the only time I ever met him was when I was just done taking a shower after basketball practice, when that same high school coach thought I was going to be much bigger than I really am today. But he thought I was going to be six, eight, because I was growing fast as a very young kid. And so he wanted to make sure that I met Bobby Knight. So Bobby Knight came in right after my freshman practice. I shook his hand when I was still wearing a towel. So that's my only time I ever met Mr. Knight. But I'm a big fan of Bobby Knight.

Craig Andrews 03:30

So what was he like in person?

Sean O'Shaughnessey   03:32

He was just like my dad. So he was a big guy, strong guy, had strong personalities, kind of encouraged me. Keep working out, keep playing basketball, go to the Parks, play against really tough kids, play against kids that are guys that are older than you. But he was very uplifting and supportive, and he was like, good luck in the season. You're going to do great. You have a great coach. Complimented my head varsity coach several times because he was trying to get a kid that was a couple of years ahead of me. He was trying to get that kid into IU. So I think it was more about impressing the varsity coach than impressing this little freshman that he was seeing with a towel wrapped around his waist.

Craig Andrews 04:13

Boy, what a story. You meet a basketball legend and you're wearing nothing but a towel.

Sean O'Shaughnessey   04:21

That's right. I would guess that there's a bunch of people that have met basketball coaching legends that have wear nothing but towels because they come and they watch the practice when they're recruiting and they say, who should we talk to? Should I talk to? And they walk in the locker room and we just got done, take a shower. So, yeah, a lot of people that he meets are probably half dressed when they first meet.

Craig Andrews 04:45

I guess the other way of looking at it is, thankfully, you were wearing at least a towel.

Sean O'Shaughnessey   04:49

That's right. That's exactly right.

Craig Andrews 04:53

So now you referee high school basketball?

Sean O'Shaughnessey   04:57

Yes. And this is kind of a shout out for everybody out there that has any kind of athletic inclination. And even if you're really not, because there's a fair number of officials you can be, that you don't have to be very athletic. Most places in the country need officials really badly. It's a big deal. It's bad when a freshman team can't get a game played because they don't have officials. That could be in football, that could be in baseball, that could be in wrestling, that could be in volleyball. We just don't have enough officials in the world. So that's my first message to everybody out there. If you have any interest in giving back to your local community, to the kids that are trying to get better and beat athletes, and just learn about winning and losing and the challenges of working hard, go be an official of some kind. Whatever sport you enjoy. If you don't think you're athletic enough, go do volleyball, where you don't have to move very much. Go do swimming, where you don't have to move very much. If you do have some athletic capabilities, if you can still run up and down a field or a quarter or a diamond, then go do baseball, go do soccer, go do one of those. Every sport across the country needs officials. And if you really, really don't want to do that, remember, yelling at the official is not a sport. That's why we don't have enough officials.

Craig Andrews 06:14

One of the things we like to talk about here is leadership. And I think about the challenges of high school basketball versus college basketball versus pro.

Craig Andrews 06:30

I think Coach K was wise in knowing his sweet spot and not going up to the pros. But what would you say that you've played high school and you've played college, and now you're refereeing? Now you're refereeing. What have you learned about leadership in that journey?

Sean O'Shaughnessey   06:52

So the thing that I've learned more and else watching good coaches and bad coaches, and I probably learn more from the bad coaches than I do from the good coaches. Right. But the good coaches are very supportive of their kids. They understand that kids make mistakes. They understand that kids are going to get better, that they need to be taught what's working, what's not working for them. They need to be coached, not yelled at, not told what to do, they need to be coached. And that's the same thing in real life as well. In real life, meaning in business life, not to say the athletics isn't real life, but in business life, the thing that people need to understand is you need to coach your employees, your people that are on your team. Coach them through their problems, coach them through their losses, coach them through their successes. Why did that play work? Make sure if you're coaching in a sport, you want to make sure that the kids understand. Why did that play work? If it's football, we blocked it this way because in football, it takes eleven guys to do the play, and if one of them doesn't do it, you might blow the whole play. Why did that play work? What was the strategy of the play? So the more you coach your kids on doing the right things, the better off they're going to be. They learn and they can do it themselves and they can do it when you're not coaching them. Same thing with real life and sales is which my specialty, coaching on why did that pitch work? Why did that presentation work? Why didn't it work? Those are really important things. And just saying you aren't making your number, you're out of here, which is one bad management technique, just doesn't work anymore.

Craig Andrews 08:35

Something I've run into is I've seen sales folks, so we work with folks using HubSpot, and HubSpot has a great feature where it will record your sales calls and what have you, and you can go back and review that. And I run into sales folks that don't want to have their calls recorded. And my gut tells me is they don't want to be critiqued. But when I think about, you have multimillion dollar athletes on the field and what do they have?

Sean O'Shaughnessey   09:06

They have coaches. Yeah. So every golfer, every professional golfer. And I say every because I don't know them all. So I got to be careful when I say every. Of course, every professional golfer travels with a coach. If you go to a golfing match and you go early, or you don't even have to go early, just go before some of the last people go off and you go to the practice range and watch them warm up. There's somebody there that is watching their swing, watching what they do. Give them a little bit of advice. Hey, that one went a little bit left of where you wanted to go. That one went a little bit right. Let's make sure we got our hands perfectly. They'll look at them, they'll watch it. And these are men and women that have probably hit 1000 to 2000, maybe even 10,000 balls per day for most of their lives. And they still have a coach standing by them, watching what they do, critiquing what they do, trying to get just a little bit better. And I think that's important for every sales professional to realize, probably every professional to realize that as good as you are, you can always learn from somebody else. And the goal of leadership is to allow that learning to happen and to make it such that it isn't a put down. You're doing this wrong, cussing at them, doing bad things, but instead encouraging them. Let's just try this. Let's try this little technique. Let's try this a little bit differently and see how that works for you. And understanding that everybody's different. Your grip is going to be different if you're a golfer, if yOu're a salesperson, the way you talk, the inflections in your voice, all of those things matter. And having a coach walk you through that and help you with that, it just makes sense. So I think that when people say, I don't want to be recorded because I don't want anybody to listen to my sales call, I think it's more because they've had a bad experience where they literally have not had the help. And there hasn't been any good suggestions that have come out of those conversations. They've been all bad suggestions, not so much bad suggestions, but they've been put in a bad way. And they haven't been with the desire of coaching and getting people moving forward and telling them why it's going to work and why we should just try it. If it doesn't work for you, then we'll go back to the old way. Right? So always have humility when you're a leader, when you're a coach, that you're actually saying you might not have the perfect answer, but let's experiment together and let's get this better. And it gets people more excited.

Craig Andrews 11:31

One of the stats I love to look at is the difference between a top ten batter and somebody that's getting sent back down to the miners. So in this season, there were nine people that batted over 300 and there were only two that batted below 200. And so what that means is the difference between being in the top ten, not top 10%, top ten batters in the league and being sent down to the minors is your ability to connect with one extra pitch out of ten, right?

Sean O'Shaughnessey   12:09

That's exactly right. And it's a great thing to remember when you're in sales that you're not going to succeed every single time. And that's okay. You got to keep on going. And in fact, there's lots of studies out there about the success of sales, and it's one of my pet peeves in life that we don't train our salespeople enough. But most studies that are out on the market say at least 25%, and some would say up to 50% of people don't make their quota when they're in sales. Now, you could argue that in some of those cases it was an unfair quota. THey had no chance of making it, blah, blah, blah. That's fine if you want to say that. So take out 10% or 20% for the bad managers, bad CFOs that gave out stupid quotas, but you still had an amazing amount of failure. If we had failure that we expect of our salespeople in any other profession, bridges would collapse, buildings would collapse, and planes will laying upside down.

Craig Andrews 13:04

That's such a great point. That's just an amazing point. And that's true.

Craig Andrews 13:13

When I think about that difference in the batting average. This is so competitive. It's just a small difference, right? It's a small difference. And if you're going to be at the top of your game, the difference between you being at the top of the game and maybe looking, being let go is so small, you need a coach that's going to help you squeeze out that extra.

Sean O'Shaughnessey   13:41

You know, they talk in the NFL about, everybody's always worried about getting replaced by the younger guy that's right behind them because the difference in somebody, the speed difference in a wide receiver, the ability to do something on the line is so small, and the number two player is so close to being the number one player, the starting linebacker or whatever, it's very close. Now, you always have those superstars that do amazingly well, and they're fantastic. But the vast majority of the team is not done by superstars. They're done by guys that just work hard. They're working hard every single day. And they have weight trainers to make them strong. They have flexibility trainers to make sure that they don't get hurt. They have massage therapists to make sure they don't get hurt. They have people that are on the sidelines saying, you didn't quite hit that guy just right or you didn't quite use your hands just right. And that's why he got by you. Let's not do that again. Let's watch that tape. You know that every football player, every baseball player, every basketball player is watching tape all the time of themselves trying to get better, trying to refine their craft and get that little bit extra. And they have coaches that are doing it for them as well. They have a team of coaches that are actually watching and giving them suggestions how to get just a little bit better. And this is something that we need to accept as salespeople, that we need to get a little bit better because if we would close one more deal per year, it'd be amazing with that change in our W two or commission rate.

Craig Andrews 15:14

Yeah, and kind of putting a bow on that, I think if somebody like Michael Jordan, who would he make? 1020, 30 million a year, right, I forget, but tens of millions. If somebody like Michael Jordan values a coach in his life and he's making that much money, you would have to be the exceptionally rare salesperson to make an argument against having a coach in your sales life.

Sean O'Shaughnessey   15:42

Exactly right. Which is why sometimes you don't get your coach in your manager and that's too bad, right? So it's unfortunate. So you have to find coaches other ways. Podcasts are great, like what we're doing here. Books are great, there's lots of great books to go out there and read. There's blog articles to read. You should always be trying to get better, to craft. There's so much stuff that's put out on LinkedIn, literally. You probably couldn't read it all in a day with all the good advice on sales that is happening on LinkedIn right now. So it's a great place to learn. So every salesperson needs to dedicate their life to Am I learning about sales? Am I learning about my industry? Am I learning about my competition? Am I learning about my customers industry? Do I know how to actually talk about business with my customer? You have so much to learn as a salesperson. You need coaches to help you get through it all.

Craig Andrews 16:32

So what do you do? You help people with sales.

Sean O'Shaughnessey   16:38

That's right, I help people with sales. So you alluded to this a little bit at the top of the podcast. I spent 35 years helping big companies primarily with sales, and I learned a lot of great practices, great best practices in sales. I also learned some things not to do and some of those things I learned not to do were through the school of hard knocks, and I'll admit that. So I didn't always have great coaches in my life and sometimes I just made mistakes and figured out what I did wrong. But about three years ago I said I am tired of traveling the world. I literally had enough freaking flyer points. I could go around the world a couple of times. I can probably stay in a hotel room every night for the next two years and not pay a dime. So I have all kinds of hotel points. I don't want to do that anymore. I lived out of a briefcase, in a suitcase for a long, long time. And so I got to that point in my career when I looked around and I go, there's so many companies just in My network, in My area, My Southern Ohio, Ohio, Northern Kentucky area, which is where I live, there are probably 5000 companies that struggling with sales almost as a Rule if you are a small Business person, there's kind of two reasons why you're small. One, you haven't figured out how to scale to be big. The other reason is you don't want to, and that's fair. If you don't want to be big, if you don't want to grow and have lots of employees, that's perfectly fine. But if you want to be bigger, if you want to be $100 million versus ten, if you want to be $500 million versus $50 million, probably the reason you're not being successful is sales. That's what I see over and over again. You can figure out how to manufacture that part. You can figure out how to hire the right people to deliver the service if you're a service provider. But the challenge that most people have is I can't bring enough revenue in. And that's why you should be really understanding that sales and marketing is hard. And so let's get professionals in there to help you to get actually it all better. And that's what I do. I bring those big company philosophies and Best practices, take out some of the overhead that makes those that big companies can afford, the small companies can't. And I bring those Best practices into small companies to teach them how to do sales.

Craig Andrews 18:50

One of the challenges I would imagine you face is, let's say the sales manager brings you into a company. And back to what we were talking about earlier. There's one of the members of the sales team that takes that as a chastisement rather than a resource all the time. How do you navigate that?

Sean O'Shaughnessey   19:09

So the first thing I do with the sales team is the very first meeting I have. I explain to every single one of them that I am fractional, that I am not here to be here for very long, and I'm not here to get promoted. I don't want the CEO's job. I don't want the senior VP of sales. I just want to be the sales director or whatever. Most of my clients aren't big enough to really, truly have vice presidents. I'm just here to help you guys. So I'm going to help run the company. I'm not going to take out anybody's job. I'm not going to hurt them on their promotions because I am not here to do that. I need to leave the customer. My client has to, in my terms, graduate. They have to be able to run without me and being around all the time. So I tell them that straight up, that my job is to make them better to make them more money on commission to make their job easier. Because I also know that a lot of times those small companies, part of the reason that the salespeople aren't as executing as well as they should has nothing to do with them. They're trying really hard. But there's some roadblocks that are in the company. And I can go to the CEO and say, look, you hired me to fix this. You've got to fix this portion of the company because that's what's holding you back on sales. So I can give that advice when potentially they can't, or maybe their advice isn't being taken.

Craig Andrews 20:28

Yeah, that's so shrewd. I think that's a lesson in leadership for me as a marketer. I'm always trying to think, what's that voice of insecurity speaking in someone, and how do we comfort that voice and how do we address those fears? One of the fears is what's going on in the economy. There's different views, and I'm not here to debate what is and what isn't. Let me ask you, what are you seeing happen in the economy and what would you recommend to sales teams out there?

Sean O'Shaughnessey   21:06

So there's no question that if you are doing Multimillion dollar deals, that that will be a bit of an issue with your client because they have to finance that. They have to figure out if that's the good use of their money. Their internal rate of return on that investment in your product is probably pretty high and higher than it's been because they're a little worried about putting that kind of money into any individual project or product. However, that's not the case for most small businesses. So I made the Illusion or talked a little second ago about companies that are under $50 million in revenue. Most companies, not all, but most companies that sell a product, and let's just assume they're not a distributor, a reseller, that has a geographic Territory that they have to worry about. But if they're making a product, if they're making a thing, they can probably sell that product nationwide. They may be able to sell it globally as well, depending on if that product is acceptable in foreign countries. And in those cases, just about every one of those products is competing in a market that's probably measured in the billions. There's very few markets in the United States that are not at least a billion dollars in revenue strong. And so I look at them, I go, so you're a $20 million company, and your market that you're going after is a $2 billion market. Do the math on what that means on your market share. So they do the math. I do it on the board with them. We do the math right there on the board. Everybody out there, iPhone, they do the calculator, they figure it out, and they find out that they have an exceptionally Small market share, a market share that is so small that who cares if the market goes back down 5%? Who cares if that $2 billion market goes down to 1.9 billion? Do the math on that, and you find out that you still have an exceptionally small market share. So most salespeople need to come into life thinking that there is more to sell, more customers to help, more prospects to find than they can ever do it in any given day. And so don't worry about the market. Don't let the economy scare you. Like, don't even watch the nightly news. And I tell people, don't watch the nightly news, but go ahead and do it because you need to be well informed. You need to be a smart salesperson. But don't pay attention to what the economy is doing. Don't let that get in your way. You have people that are taking dollars from you on a regular basis, your competition, and you might have hundreds. I have a client that has 10,000 competitors, at least. We've did a search, and we found out there's 10,000 people, companies that do almost exactly the same thing they do. Who cares if the market goes down 2% or 3% or 5% in their marketplace, they have 10,000 people that are trying to take their money away from them. And that's how you got to think of it. You alluded to the fact that I wrote a book called Eliminate your competition. The goal is to beat your competition. In all cases, it doesn't matter if your market has gone down 5% or 10%. Most likely it's not, and most likely it's a short term blip anyway. Just hurry up and go get more customers. The sign of a great company is a company that grows when times are bad.

Craig Andrews 24:09

So, well said. Well, Sean, this has been an amazing conversation. I really want to thank you for being on leaders and legacies. You have your own podcast called Two Tall Guys Talking Sales, and you have your book, eliminate the competition. How can people reach you? Where should they look for you?

Sean O'Shaughnessey   24:29

The best place to find me is on LinkedIn. I post almost every day something on LinkedIn. Some days I'll take off, not so much on weekends. So I post on LinkedIn a lot you can find me Sean O'Shaughnessy. I'm sure the show notes is going to have my name and how to correctly spell my name on the show. Um, so you can always reach out to me there. Happy to talk to everybody that reaches out to me. You can also just drop me an email. And that's Sean. Sean at Newsales expert. It's not. It's newsales expert.