The Professional Confessional Podcast, with guest Robert J. Finn

Robert J. Finn
8 min readNov 21, 2022



Ashley Stryker [00:00:05] Welcome to the Professional Confessional: How the biggest mistakes we’ve ever made fundamentally changed our work, our careers and our approach forever. Gain wisdom and perspective through these audio absolutions.

Ashley Stryker [00:00:20] Today’s guest is Rob Finn, a successful global sales manager for an international conglomerate. However, I’d like to introduce you to who Rob was just five years ago: An inexperienced first-time closer with something to prove to the world — which led him to ignore every red flag for eight months while chasing an impossible-to-close commission.

Rob Finn [00:00:44] I was doing renewals and expansions for a software company up in Massachusetts. It was my first closing role. It was incredibly excited and incredibly ambitious, wanted to kick everybody’s ass. And I’d actually had to interview for the role like four times because I kept messing up the roleplay portion of it. I had a chip on my shoulder to go in and do big things and prove everybody wrong — show everyone how great I was.

Rob Finn [00:01:09] So that’s the headspace that I was in at the time. A lot of that I still carry with me now, where I do want to be good as I can be and be successful. But I think there was a little more vitriol in my approach and thought process.

Rob Finn [00:01:25] I was working with smaller customers. What ended up happening was, a customer of mine essentially on one phone call said, “We are interested in a huge enterprise wide rollout.” And I was doing the math up in my head and it was — like, it would have been 40% over my quota to just close this because it was so much bigger than anything else that I was working on at the time.

Rob Finn [00:01:49] For the next, I think eight months, I had this gigantic deal in my pipeline I refused to get rid of, and would always have excuses for why there wasn’t updates for it. I took time from the solutions architects and consultants to have them answer questions for these guys. They were just really, really wishy-washy.

“Essentially, not only did I waste my own time …” [02:07]

Rob Finn [00:02:07] Essentially, not only did I waste my own time — not only did I promise or keep pushing this thing out that never really had any legs, that would send up a red flag because it was so much bigger than anything else that I was working on — [but also] I took the time of my boss at the time, other people that I was working with, and other people within the company to work on and talk about this giant deal that never was in the first place.

Rob Finn [00:02:30] What I ended up finding out was, they… I think they came to us after, again, after eight months, closing this out and wasting the time of probably 20 people internally strategizing about what we’re going to do, talking with the VP, all of this stuff and when, in the back of my head, I’m thinking, just like, “We’re– I’m going to make this happen. I don’t know. I don’t know what I’m going to do, but I have to. I don’t care.”

Rob Finn [00:02:49] They just stop responding and then finally gave up. It was like, oh, I feel terrible. Wasted so much time with everyone around me on this deal.

Rob Finn [00:02:58] Then, they came back two months later, said, “The CFO said, give us your best price.” And we tried to send him something and be reasonable and undercut whoever else you might be going with. And it was clear from the response that we got — from him and from the original two people that I had connected with — we were never even remotely under consideration. All it was, was them stringing us along to get as much information as they could out of us to get our price to then go back to the vendor that they really wanted to work with and say, “Well, this is what your competitor is offering.”

“We couldn’t believe that you kept coming back to us…” [03:28]

Rob Finn [00:03:28] They said, I think in his email said something like, “From the beginning, we were very clear that this was exploratory, etc., etc.,” and basically said, “We couldn’t believe that you kept coming back to us to when we kept, you know, just dragging you along.”

Rob Finn [00:03:42] And it never really had it wasn’t some spectacular… It wasn’t like a fireworks, a spectacular explosion where there was this moment where I was so incredibly embarrassed and everyone was like, “Oh, remember when that happened?” It wasn’t like that.

Rob Finn [00:03:56] I’ve gotten away from it more, as I’ve continued in my career, I’ve looked back on it with more critical eyes and thought of some of the stuff that I didn’t even realize was a waste of time at the beginning. Like, there’s just all these kind of red flags that you pick up on.

Ashley Stryker [00:04:10] Like what?

Rob Finn [00:04:12] I would offer up an end of the month deal nearly every time. And, they would come back like, “Oh yeah, we think we might be able to get it.” And it was… It’s something that it’s hard to read between the lines when you haven’t done it a lot. But it should have been clear — and it probably was clear to everybody else other than myself — that this was not real, was never real, and was just a tactic for them again to get a better price from the person that they really wanted to.

Rob Finn [00:04:38] I did not need to spend all this time, spent all my company’s time — spend, like I said, everyone around me’s time on something that was never going to happen because of my own refusal to give it up or to accept defeat graciously.

Rob Finn [00:04:53] It’s something that when I look back on how I what I would spend my time on and what I would I think I’m still learning this. I think everybody’s always still learning. When is it a situation where, like, you are doing yourself a disservice to continue to try to pursue something — as much as I say to even to the stars that are on my team now.

Rob Finn [00:05:13] Some things are better than others to pursue, but I think it comes down to having an overly positive attitude, but only up to a point when, if someone is willing to meet with you for three hours every week and you never make any progress, that’s probably not someone that you are going to end up doing business with.

Rob Finn [00:05:31] And you can keep fooling yourself and convincing yourself that it’s going to happen. You’re going to convince them this time where you’re going to get this new person on the call. But sometimes, it’s just not meant to be and they’re not the right person for you.

“It became a running joke.” [05:43]

Ashley Stryker [00:05:43] Did your boss or any of your teammates express frustration with waste of time, or was this something that you observed in retrospect?

Rob Finn [00:05:49] It became a running joke. We were we were big jokers and would mess around with everything. It kind of became like an inside joke, almost like, “Oh, this deal is coming in, right??” — And it so never was. Never to me [did they say anything]. “I can’t believe that we wasted another half hour talking about this thing” — never anything or direct like that.

Rob Finn [00:06:09] And, it’s possible that I was a successful salesman when it came to convincing them that it was real. Probably the best selling that I did was just like, “No, no, no. Here’s here’s why you’re wrong when you tell me that it’s not worth anything.”

Rob Finn [00:06:23] Nothing but positive things to say about my team. We all had a great year; the team had a great year. Everybody went to President’s Club. It was a great time that, I think, I would have enjoyed even more if I didn’t have this big gray cloud, this fake gigantic “too good to be true, but also not even true” opportunity in front of me.

“…was something I never would have even imagined saying to someone then.” [06:42]

Ashley Stryker [00:06:42] So surely you’ve gotten those kind of opportunities since then. How have you evaluated those more carefully since the mishap?

Rob Finn [00:06:51] A lot more scrutiny, a lot more being willing to ask someone or even being willing to say to someone, “It doesn’t seem like you can get this over the line” — was something I would never have even imagined saying to someone then. But then, as time went on, that became easier and instincts get better.

Rob Finn [00:07:09] So, whenever someone comes in saying, “Oh, we’re going to buy everything your company has,” or “We’re going to do it all, we’re going to do it in the next week,” I go, “Oh, that’s great. OK, well, let’s talk about it. Let’s figure it out. Let’s figure out we’re going to do next.”

Rob Finn [00:07:21] Whereas before, I was just like, “Holy shit, I’m going to make all this money. I’m going to close. It’s going to blow everyone out of the water. I’m going to get double my quota for the year.” But now there’s a mixture of optimism and realism, and I think that’s the best way to go.

“So, Rob’s big mistake was..” [07:37]

Ashley Stryker [00:07:37] So Rob’s big mistake was letting his personal ambitions and thirst to prove himself blind him to the red flags plastered against a prospective deal that would never materialize. In what must be a mark of his personal character, Rob’s biggest regret wasn’t the loss of a giant commission. Instead, Rob’s biggest regret of the whole episode was dragging his teammates into the meetings — accidentally wasting their time, too, even if they never expressed resentment.

Ashley Stryker [00:08:05] (For what it’s worth, as someone who’s hired and trained juniors, I’d rather misguided enthusiasm than just about any other type of mistake.)

Ashley Stryker [00:08:14] While Rob admits his mistake is partially a product of inexperience — something only time and better instincts can correct for — he advises others in similar “too good to be true” situations to get excited about the potential win, but also press for practical details on moving forward if you sense hesitation or are skeptical of a prospect’s promises. Try confronting them directly with a polite, plainly worded question to see if this prospect can take the proposal to the finish line and put money in the bank today.

Ashley Stryker [00:08:46] Rob Finn is the global sales manager of an international team supporting Link, a digital platform for lifescience supply chains. You can find him on LinkedIn by going to, or by visiting his website at

Ashley Stryker [00:09:13] And you can find this and other episodes of the Professional Confessional podcast at or on your preferred podcasting platform of choice.

Ashley Stryker [00:09:24] Do you want to come on and share your biggest professional mistake? Head to to schedule your professional confessional. Again, that’s

Ashley Stryker [00:09:40] In the meantime, please share this episode with someone you think needs to hear this today — and share what you needed to hear in a review! The more often we rate and review our favorite podcasts, more people will find out about our community, and the more episodes I can make. When we reach 25 reviews, I promise will vote on a special edition deep dive into a major mistake in history that is still relevant and affects how we do business today.

Ashley Stryker [00:10:05] Anyway, that’s all for this professional confessional. I’m Ashley Stryker. Thanks again for tuning in, and I hope you’ll join us next time. Talk soon!