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

Brian G. Burns  

And how have you found a going from individual contributor to manager and sometimes back and forth a couple times? 

Sean O’Shaughnessey  

I am probably a better salesperson then I am a manager. I had a really good manager a few years ago as I was starting to make this transition into being a manager that gave me good advice. I used to play sports when I was a young man, like a lot of salespeople do. He would say, “Your coach never ran on the court and shot the free throw for you. He taught you how to shoot the free throw. Taught you your technique. Criticized you. Yelled at you. Made you do layups or do sprints if you screwed up. But he never went out during the game and shot the free throw for you. That’s the way you have to be as a manager. You have to do all that work in advance. Then you have to let them go, see how they do, and then give them critiques afterward.” 

That advice I still live on it because I still love sports. The whole idea that the coach doesn’t play. The coach coaches, and the players play, and they don’t coach. As long as I remember that, I’ve always been good. I try really, really hard not to take over a sales cycle when I’m working with a sales rep. I try hard to just keep my mouth shut. We’ll talk about it after the meeting. We’ll talk about it before the next meeting. I try to be very careful about remembering: “I’m the coach. I’m not the player.”

Now, let’s be honest, the end of the quarter, I’m going to be LeBron James. I’m going to be Michael Jordan. Give the ball to me.

Brian G. Burns  

That’s kind of understandable because, you know, it’s not purely coaching; it’s kind of player/ coach, especially in big deals. Because you want your reps to pull you in to talk to your peer. 

Sean O’Shaughnessey  

Exactly. That’s a really important thing to remember that they need to own the relationships. But maybe there are some relationships I should own. Maybe there are some relationships our CTO or Vice President of engineering should own with the customer. So that multi-faceted, multi-pronged attack is important to keep track of as well. So everybody’s going to play a role on the team.

Once again, Michael Jordan said, “When there are three seconds left in the game, and the game is on the line, give me the ball. I will take care of it.

Brian G. Burns  

And that’s that, you know, the first year I really knocked it out of the park. I was lucky enough to have a great relationship with the CEO and co-founder of the company. And I would just say, “Paul, come on out for a week.” We would hit everything. And he was the guy. He was charismatic and knowledgeable. And he could talk at that CEO level. At the time, I was in my 20s. And I was I’d shake like a leaf in front of a CEO. I didn’t know what they cared about. But he could paint that vision from a business standpoint.

Sean O’Shaughnessey  

And that’s important, especially with a younger salesperson. You have to understand that if they’re calling on a person that’s as old as their dad, maybe they just have a hard time relating to that. So in those cases, we need to tag team and take care of that situation. And the more you’ve made sales calls in your career, the more comfortable you get with that situation of: “I’m going to talk to the CEO, or I’m going to talk to the CIO of a company.” And what am I going to say to that person? How am I going to relate to them? So the more you’ve made sales calls, you just got to do it.

There’s only so much training we can do. There are so many books that we can read, so many podcasts like watching your podcast, there are only so many you can do. A lot of sales is: “Just go do it.” And you will get better as time goes on, as long as you think about, “Okay, what didn’t work?”

We did a presentation earlier today with my sales team, and we were talking to a customer, and some things didn’t go well. So afterward, after every good sales call, we got together. We talked about it as a team. What went well? What didn’t we like? We talked about that one thing that didn’t go well, where we kind of screwed up. And we figured out what we’re going to do next time that that would come up. And that’s just part of sales. It’s part of life.

You’re probably not going to blow a long term deal, like what we do, by doing one silly thing in one meeting. You can recover from that. The goal is to not do ten silly things in that one meeting. 

Brian G. Burns  

And the challenge with larger, complex deals is that you’re not doing the same play every day. You might not do that play for three months. And so you’re out of practice,

Sean O’Shaughnessey  

You’ve got to practice. So that is where complex sales is a job that not everybody can do. Because you do have to wing it a lot, and you have to think on your feet. And you do, it does take more effort to be successful and to be successful year over year after year. Once again, that does come with just practice.

But there’s also just the confidence that “I’m going to be okay.” And it’s also okay to say, “Mr. Customer, I’m not quite sure about that one. Let me get back to on that.” And that even takes some degree of confidence in your own ability to say, “I don’t know.” That’s not a personal affront to me that I don’t know something. I’m going to have to go figure that out. I’m going to have to go talk to our developers or whomever. “We have to come back to you.” And that’s perfectly fine. Everybody understands that. And nobody expects you to be an expert at everything.

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