Category: Prospecting

I recently spoke to Robert Gillette, the host of the podcast Reclaiming Sales. It was a great conversation! We discussed many things that will benefit beginning sales professionals. Specifically, we discussed:

1. Get to know your prospects better, understand how they make and lose money.
2. Get curious, and stay that way… even when you’ve heard your 100th prospect tell you the same thing.
3. Build your belief, it will keep you company when times get tough.

You can listen to our conversation by subscribing to Robert’s podcast here. You can also subscribe by going to Apple Podcasts, Google Podcasts, Spotify, and many more that are listed here.

The following is a transcription of our conversation for those that prefer to read rather than listen. The transcription is as close as possible to the spoken word but effort was made to try to make it a little more readable with fairly grammar correct phrasing, sentence structure, and paragraph structure. Where the commentary overrode grammar or the use of synonyms, the spoken word was chosen.

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Announcer 0:30  

You’re listening to Reclaiming Sales because you don’t need to sell your soul to be successful with your host and fellow salesman, Robert Gillette.

Robert Gillette 0:41  

Hey everybody, welcome back to the show. My name obviously is Robert Gillette, and I have a new friend of mine. I know everybody I meet on the show, I say my new friend, but it’s true so far—a gentleman named Sean O’Shaughnessey. Honestly, the reason why you’re on the show, to be totally honest, is he, you engage with me, you commented on the things that I post, and you send me messages. And you know, when you’re doing a podcast, it’s like screaming into the void. And so when the void reaches back out and gives you feedback, it’s incredibly helpful. I’m used to performing on stage, in general, so I just wanted to have you on the show, first of all, to get your perspective on what we’ve been talking about so far. But, still, you also have some pretty deep claws into this whole sales game as well, and you have some perspectives that I just want to explore and see what we can uncover over the next 20 minutes or so. But before we get onto that, Sean, why don’t you, I guess before you take off your sales guy hat, what do you sell and who do you sell it to.

Sean O’Shaughnessey 1:42  

I am the CEO of a company called New Sales Expert. I sell sales management to companies with bad sales management or don’t know how to have sales management.

Robert Gillette 1:56  

Okay, and we don’t have a lot of, you know, people on the show who aren’t salespeople. But I guess my first question to you before we move too far into this is. Do you think it’s harder to sell to salespeople or to sell to non-salespeople? Is it hard to sell to people who sell for a living?

Sean O’Shaughnessey 2:16  

So it’s I think it’s easier to sell to salespeople because we like to hear a good pitch. I actually sell, though, to the CEO that is frustrated because he doesn’t know how to manage a sales force. So that’s actually whom I sell to. And that’s the problem I solve.

Robert Gillette 2:32  

Okay, so you’re actually selling to a CEO or someone at that C suite level.

Sean O’Shaughnessey 2:37  

Correct. I’m usually selling to the founder of the company. And he is in a situation where he can’t figure out how to manage salespeople, how to recruit salespeople, and how to make salespeople better. So that’s what I do for him or her.

Robert Gillette 2:51  

Unfortunately, mostly him, but we’re working on that diversity by brute force. We’re doing it as a country anyways. 

So let’s, let’s roll this back to the beginning of your career, how did you get into sales. And why did you stick with it all those years?

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