Brian G. Burns Interviews Sean O’Shaughnessey On How To Win Large Enterprise Deals

Brian G. Burns Interviews Sean O’Shaughnessey On How To Win Large Enterprise Deals

Brian G. Burns  

How’s your rep radar? As far as being able to talk to another rep and get a sense of “Do they really understand how to sell a large complex deal, or do they just have a nice personality?”

Sean O’Shaughnessey  

As a hiring manager, I’ll be honest. I always think I have a lot of room to improve. My belief is that I can train anybody to do it. I have learned over the years of hard knocks: sometimes I can’t train somebody to do it. I can figure out when they’re bullshitting me because I was the king of bullshit back when I was rep. My boss always thought I had every answer. That was fine, so I know how to interpret it. But sometimes the rep is just not going to make it. Sometimes I’m not going to get him or her there.

That’s probably my number one hit on me as a manager. I’m probably only 60 to 75% successful in hiring the right person who will be successful in the job. Rep radar is something that I think everybody struggles with at some point in their career.

Brian G. Burns  

And what do you look for that when you know, even though they might have a delightful personality and a great smile and handshake, but they’re not going to figure it out.

Sean O’Shaughnessey  

Yeah. My big thing is, “Describe how your prospect will make their goals by using your product?” So when I’m interviewing somebody, that’s what I start with. I’ve been doing this technique for less than five years, and it’s helped me a lot in finding people that are the right kind of people. “Tell me about what you sold and then tell me why you sold it?” “Yeah, you sold that big deal. Congratulations! That was a great commission check, and you went to Club, and went on stage and got a trophy. That’s all well and good. Okay, why did they buy, though? I mean, really, why did they buy?” Because I’ve learned that if you really know your customer’s business, you’re probably going to be okay. You’ll survive some of the faults that you may have if you know the customer’s business. You’re going to do well. That’s really the number thing. I think you said it earlier: put yourself in the customer’s shoes. Tell me this, young rep or “up and coming” salesperson, “How did that work? And how did you do that?”

Brian G. Burns  

That’s a pitch too often you hear, you know what Adam Carolla calls a platypus. They take a platitude, and they make it like the most important. It’s all about relationships, all about value, all about ROI. And it’s not that it’s wrong. It’s just incomplete. It’s a little bit of each of the above: the muffins, not just sugar, there’s flour, there are blueberries, there’s heat. And if you lean on just one ingredient, you become good at that ingredient. But you miss the others. 

Sean O’Shaughnessey  

I do think being a well-rounded salesperson is incredibly important. One of the things I like to encourage every salesperson, “How much do you read?” Listening to podcasts is good. You do that when you are driving in the car between appointments. At the beginning of the day (or at the end of the day, I don’t care which), did you read five articles in our business?  

I’m in an IT technical space; I read at least five, if not ten, new articles every day in my space. Because for one, I don’t want to get blindsided when somebody asked me a question that’s something new (and there’s always something new in my world). But the flip side is just being good and well rounded in understanding all the other things. And yes, we don’t sell that one thing, but it might come up in conversation. And you can’t look to the customer and say, “I don’t know what you’re talking about, because it’s not what I sell.” You have got to be more rounded than that

Brian G. Burns  

I’m sure because we’ve sold in similar spaces. You go into meetings, and they all have their own language, their own acronyms. And if you don’t know at least some of them. You’re gonna feel like you’re in a new country or something. 

Sean O’Shaughnessey  

That also goes into the verticality of selling. If you’ve never called on banks before, you might want to read up a little bit before, or talk to somebody about, “What’s banking doing in this space? What does banking care about? What are the terms that they’re going to use?”

Now I’m going to go talk to a manufacturer. What are they worried about? Those are all the things that a well-rounded salesperson needs to be able to do.

You need to be comfortable saying, “I need to learn that as I go along because I’m not going to be an expert in all those vertical industries.” A rep needs to be a well-rounded person and needs to read. I tell everybody, “You better learn how to learn.” That’s a big deal. You do that by listening to podcasts, reading the Wall Street Journal, reading the various magazines, getting online, just read the stuff in your industry. You need to learn how to learn. It’s very, very important. 

Brian G. Burns  

That’s good advice. Just people typically just say, you know, read sales books, but I don’t think it’s just sales books. 

Sean O’Shaughnessey  

I don’t think so either. I’ve read them all. 

Brian G. Burns  

You know, you can’t read a book about basketball and become a better player. You learn the rules. You learn the mindsets, the attitudes, and some strategies. But you got to get out there. This is the most complex game I think there is, enterprise sales. 

Sean O’Shaughnessey  

it is, and it’s fun. 

Brian G. Burns  

When it works,

Sean O’Shaughnessey  

People ask me, why don’t you sell something simple? Because I can sell something hard. And therefore, I eliminate a lot of my competition just because they can’t sell something hard.

The better you are at selling hard things, the easier it is to sell simple things. Practice at getting good at those things. Practice at being a well-rounded person. Practice at being a business person as well. Be able to relate to your customer in a way that they can be successful.

Brian G. Burns  

Cool. Hey, Sean, where can people go to connect with you and learn more about you and your work?

Sean O’Shaughnessey  

You can send me an email at sean@newsales.expert. I’m on LinkedIn at https://www.linkedin.com/in/soshaughnessey/. I’m always on LinkedIn as that’s where I met you, Brian. I was on LinkedIn following all your stuff and then subscribing to your podcast. I wrote a book on sales as well. It’s called Eliminate Your Competition, and you can reach me on the contact form for that site.

This is the end of the interview and transcription. It was initially transcribed by https://otter.ai and then edited to make it more readable.

You may purchase my book, Eliminate Your Competition, from your favorite book retailer. The ebook version is available at the most popular retailers such as Apple, Amazon, Barnes & Noble. The paperback version is also widely available at such retailers as Amazon, Barnes & Noble, and Books A Million.

There is more to read. Go to the following pages to read:
Introduction
Why does Sean like the sales profession?
The transition from salesperson to sales manager
Growth milestones
Rep radar and Always Be Learning

One Reply to “Brian G. Burns Interviews Sean O’Shaughnessey On How To Win Large Enterprise Deals”

Leave a Reply