Morgan Friedman: Hey everyone, welcome to the latest episode of Client Horror Stories. I’m very excited to have today’s honored guest, Steve Perry, with us. How are you doing today, Steve?

Steve Perry: So good, Morgan. Thanks for having me.

Morgan Friedman: I am happy to have you here. Now, I have my coffee — with some whiskey in hand. Let’s jump right in. Tell everyone about your most intense client horror story.

Steve Perry: Yeah. Well, this one goes way back, but it’s crazy — I remember it still, almost 20 years later. So I was a couple of years into my career as a young financial adviser. I was just scratching and clawing to make my way and have a business that somewhat paid the bills. The managing partner came up to me and said, “Hey Steve, we’ve got this brand new guy — sharp young kid — and he’s got a very promising lead with a couple of executives who are close to retirement and need some help. He’s too brand new to know how to help them. Will you go with him?”

And I was like, “Yeah, absolutely.” For me it was like, yeah, I’ll split the comp on this, and it could be a really nice case. So me and Jesse, we talk a little bit about it. The couple was a friend of a friend of his parents or something like that. So we go over to their house and they’re super sweet — late 50s, early 60s. We go through our spiel and after a while you can tell that she’s super into it, super sweet, super engaging, and he’s kind of leaning back like, “All right, what are you guys going to try to sell me here?” Which, honestly, I don’t blame him.

We get to the end of the presentation and it turns out they have all of these retirement accounts. They had changed jobs like ten times each, so there’s a 401k here and a 401k there. What they really want help with is collecting all of those together, and then we can build a plan around that. So the homework from the meeting is that they need to go find the latest statements they could — in the mail, since this was about 20 years ago when things weren’t really online yet, it was still all snail mail — and then put them all together so we can put a plan together.

They were like, “Yep, we’ll do that. It’s going to take a little while, but we’ll get it done.” So me and Jesse leave, and I’m thinking, “Hey, this is your deal. I’m the so-called expert coming in, and you’re the one with the relationship.” We were probably 40 years old combined, but you know — in the land of the blind, the one-eyed man is king.

Morgan Friedman: That’s right. Exactly.

Steve Perry: So I said, “Your job is to professionally follow up with them once a week, just to check in and see how they’re doing, see if there’s anything you can do to help.” Week one comes and goes. Week two comes and goes. I see Jesse in the hall at the office and I’m like, “Hey man, did you talk to them? Are they making any progress?” And he’s like, “Yeah, you know, I got a couple of the statements, but they’re not getting them all together.” All right. A couple more weeks go by and I’m like, “Hey Jesse” — I was having a slow month, so I wanted this to go quicker — “Can we speed this up?”

Well, it turns out Jesse wanted it to go even quicker, because he had started calling them every day. And I’m like, “I don’t know if that’s a great strategy, bro. Like, they’re not able to find old mail from the middle of nowhere and make progress day over day on this. And they’re two executives helping run two different companies.”

Morgan Friedman: By the way, I want to pause on that for a minute. Usually — at least us Americans — think about that go-getter spirit as a great thing. Follow up, follow up. Most people don’t follow up and let things disappear. But you’re calling out an interesting risk factor, which is that too much of a good thing can be a bad thing. You want to follow up, but every single day kind of drives the other person crazy, and it’s impossible for them to keep up.

Steve Perry: Yeah, totally. It’s like, they may be the biggest opportunity in our world, but we’re nothing to them right now. They’ve got other things going on.

Morgan Friedman: Exactly.

Steve Perry: So another week or so of that goes by, and then all of a sudden I get a phone call. It’s from the husband — his name’s Ron. Ron goes, “Hey Steve, you were close, but no cigar. We’re done. We’re out. We’re not working with you.” And I’m like, “Okay…” He’s like, “Your little buddy over there crossed the line.” And I’m like, “All right, hold on — can I call you back?” He’s like, “You can call me back, but we’re still not working together.”

Morgan Friedman: Big question before we find out what the other financial adviser actually said — were there any signs from the couple or from Jesse in any direction, other than him being a bit anxious? Or did it all seem smooth up until that point?

Steve Perry: I was pretty much out of it. I had let Jesse handle the relationship, for whatever dumb reason, trusting that he had the emotional intelligence and the ability to know how often to follow up and what to say. I mean, following up is hard, right, Morgan? It’s like, how do you say the same thing over and over again? I was way too hands-off on it. But from what I knew, it had been smooth. So I go to Jesse and I’m like, “Hey, man. What did you do? What happened? I just got this call from Ron.” And Jesse goes, “I don’t know. I just kept calling her office and kept getting the runaround from the secretary.” And I’m like, “What? Something is not adding up here.” Like, I’ve been doing this for a couple years — what is going on?

So I call Ron back. I’m like, “Sir, I don’t quite understand what happened here, but I’m sorry.” And he goes, “Look, your little buddy Jesse would call my wife Charlene’s office every day. Every day the receptionist would answer the phone, take a message, and give it to Charlene. Well, this last time, Jesse said to the receptionist, ‘You’re not giving the messages to Charlene.’ And the receptionist said, ‘Of course I am.’ And Jesse said, ‘No, because if you were, she would have called me back by now. You need to do a better job at your job. In fact, maybe I’ll just come in there and talk to her myself.’ And the receptionist told him, ‘No, sir — you are not welcome in this office.'”

Morgan Friedman: So he’s telling you this and you’re cringing, crawling in your skin. But by the way, before we hear what happens next, let’s analyze why that is so cringeworthy — because people 20 years younger than us may have an instinct for it but may not really understand it. The first observation I want to make is you never really know the relationship between the people on the other side. Like, it could be a secretary — but they could also be best friends, for example. And I also want to point out there’s a classic sales technique that Jesse never learned, which is basically: the way to get to an executive is through their secretary. The secretary is the one who filters everything, and as the filter, you never want to cross them. You in fact want to become their best friend. You want to send the secretary flowers and charm them, because then the secretary will be saying good things to the boss. And this guy did the exact opposite.

Steve Perry: Yeah, you nailed it. That’s the classic lesson — you befriend the gatekeeper.

Morgan Friedman: Oh, I like that word — the gatekeeper. That’s the abstracted-out version of it. Befriend the gatekeeper. And the young financial analyst wasn’t sophisticated enough to view the gatekeeper as the person whose job it is to lift up the gate — and he was not lifting up the gate.

Steve Perry: One hundred percent. Yeah, exactly. So, cringeworthy, right? I’m just sitting there like I don’t even know what to say. Fortunately, Ron spoke next. He said: “What your little buddy Jesse doesn’t know is that the receptionist is our daughter.”

Morgan Friedman: No! A moment ago I said, oh, maybe they’re friends — but this is even worse.

Steve Perry: Literally so much worse. And I’m like, “Wow, Ron, I don’t even know what to say other than I am so sorry. And I don’t blame you for a second. I wouldn’t expect you to work with us after that whatsoever. I appreciate you letting me know what happened, though. Thank you, sir.”

Morgan Friedman: By the way, let’s analyze this for a second before continuing with the story. The intensity. I love this buildup to it being a daughter. We were saying a moment ago that you want to befriend the gatekeeper, but here it’s so much more extreme. It really shows you — you could be in a relationship that is really intimate, like mother and daughter, and you just never know. You also never really know what conversations are happening on the other side. The financial analyst thought it was just a case of a message being passed on or not, when really it was probably dinnertime conversation. Just imagine the family dinners, dude.

Steve Perry: This annoying guy called again… Yeah. No kidding. I can’t even begin to unpack all of the cringe.

Morgan Friedman: You know what, that is a good point — I hadn’t realized that “cringe” is a more modern word. It described exactly what we felt. And this is probably why the word was eventually coined. Actually, I also hadn’t realized it, but only in the early 2000s did a genre of comedy — cringe comedy — appear. And it’s my favorite type of comedy. Like Larry David saying things that make you cringe. It’s hysterically funny. But there was no word for cringe comedy back in the ’80s and ’90s.

Steve Perry: Is that like The Office too? Like Steve Carell?

Morgan Friedman: Yes, exactly. It’s a sort of comedy where it’s like: don’t do it… don’t do it… don’t do it… No, he did it.

Steve Perry: My wife literally says she can’t watch The Office. It makes her so anxious. She’s like, “That man — I just can’t do it.”

Morgan Friedman: With cringe comedy it goes to one of two extremes — either you love it and think it’s the funniest thing ever, which is my camp, or it’s like your wife where it’s so painful you can’t even watch it. This is too much information about me, but whenever I fly on an airplane, I’ll watch whatever new movie I’ve been meaning to see. The plane ride is always about three hours long, so it’ll end and I’ll have this awkward 40 minutes left. I’ll play the blackjack game for about four minutes and then I’m like, I can’t do this anymore. So I’ll turn on The Office — I’ll watch three old episodes to end every flight.

Steve Perry: I love that you’ve turned that into a ritual for yourself. Catching up on my college days of watching The Office.

Morgan Friedman: Great to watch in college preparing you for adult life. That’s a college education in and of itself — what not to do.

Steve Perry: So I go to Jesse and there’s not even any reason to chew this kid out. By that point, I knew he probably wasn’t long for the business. So it was just like, “Hey buddy, I got bad news. We lost that deal. It’s not going to work.” He’s like, “What happened?” And I’m like, “Well, you happened. I mean, it was his daughter, and you were basically accusing her of lying.” And he’s like, “Well, I didn’t know that.” I’m like, “It doesn’t even matter if you said it or not, because that’s what they think you said.”

Morgan Friedman: You made a really important point that I don’t think has ever come up in an episode before. In every episode I try to get at least one new lesson, and I think today’s is this — because you just made a very powerful point. It doesn’t even matter if you said it or not. I know so many people, so many professionals, who are obsessed with the truth and being right. “No, this happened.” “This didn’t happen.” “This was said.” And at the end of the day, the truth of the situation truly doesn’t matter in any way. All that matters is the perception and the emotional reaction that the other person had to the situation.

Steve Perry: Yeah. Perception is reality.

Morgan Friedman: Perception is reality. Oh, well said. You’re a philosopher.

Steve Perry: Well, that’s way stolen — I didn’t come up with that. Lots of people have said that.

Morgan Friedman: So here you are, still relatively new in the business, you could have definitely used these guys as clients, Jesse is exiting the business — what was your next move?

Steve Perry: So, you know, call it a last-ditch effort, Morgan, or just call it trying to do the right thing. Probably a good combination of both. Ron’s office was not too far from mine — like six or seven minutes down the road. I thought, he doesn’t want to see me, he doesn’t want to talk to me, he doesn’t want to do anything — but I’m just going to go humble myself. So I went down to his office, went to the lobby, went to the receptionist — not knowing if this one was his daughter too, by the way.

Morgan Friedman: Ha! Right, right.

Steve Perry: She’s like, “Who are you here to see?” I’m like, “I’m here to see Ron.” She’s like, “Do you have an appointment?” I’m like, “I definitely don’t have an appointment. And he probably doesn’t want to see me — you’ll probably go tell him who’s here and he’ll say, yeah, I’m not coming out there. But I literally just want to apologize to him, man to man.” And she’s like, “Wow, okay.” So she gets up, goes back there, opens the door — and you can see his office right through the window. She kind of mouths “Steve Perry,” and he looks at me and looks down. He’s like, “Nah.” So she comes back and says, “Hey, he said maybe he’ll get to you if he has time.” I said, “That’s fine.”

So I sat there. I’m not going to drag it out and say it was hours, but it was probably a good 30 or 40 minutes. I didn’t have a time limit for how long I was going to sit there. And about 40 minutes later, he comes out and basically says, “What do you want?” And I said, “Ron, there’s nothing I can say to make this right. I’m not here asking for your business. But man to man, I just want to apologize. That was wrong of us. Jesse and I were together on this, and that was wrong of us. You don’t deserve to be treated like that. You and Charlene are amazing people and you didn’t deserve that. I just want to apologize, man to man.” And he goes, “Okay, thanks.” And that was it. So I left, kind of thinking, all right — I did the right thing.

About a week later, I get an email from Ron. You know how you see the person’s name and the first few words in the preview and you’re like, “Oh no, oh no”? I’m like, I’m not getting the business — what else could be coming? And the email said: “Hey Steve, I appreciate the way you handled this. We still really need the help. We don’t know anyone else, and the way you handled yourself tells me you’re the kind of guy I want to work with. That other guy — he’s not welcome at our house.”

Fast forward, they became clients for many years. Even after I left being an adviser and moved into a leadership position — and by the way, the business they did with me ultimately qualified me to get promoted to partner in the firm. And even years later, when I had moved out of state, they would still call me and ask my opinion on things. Just developed a great relationship. I know this is Client Horror Stories and there was a lot of horror in it, but there’s a real silver lining in that one as well.

Morgan Friedman: I think it’s powerful how you were able to turn it around, and I think this is a great lesson in the power of humility and sincere apologies. I don’t know the sort of people you surround yourself with, but I surround myself with far too many people who will never apologize — even if the existence of the universe depended on it. And it’s not even just saying the words “I’m sorry.” It’s actually feeling it. You can tell from how you tell this story and the details in it — it wasn’t just about wanting to salvage a deal and make some money. You actually felt terrible about what happened and you owned it. I think that’s an important lesson for everyone listening who is scared to say they’re sorry.

Steve Perry: Yeah. It doesn’t always work out that way. It usually doesn’t work out that way, actually. But you sleep better, and you feel better at the end of the day.

Morgan Friedman: That is a good point that it usually doesn’t work out that way. I would interpret that in a few different ways. One point I’d make is there’s this deep question of who do you want to be? What kind of person are you, and what kind of person do you want to be? I think it’s impossible to always strike the perfect balance — apologizing exactly when you need to and not apologizing when you shouldn’t. It’s a fine line to walk. So fundamentally you’re going to err on one side or the other. And I think the strategic life and business question is: do you want to be the person who errs on the side of not apologizing enough, or do you want to be the person who errs on the side of apologizing too much? Maybe because I secretly have aspirations of becoming Canadian, I personally prefer the “Canadian I’m sorry” — erring on the side of apologizing a little too much.

Steve Perry: Yeah! I love that. In Canada, you bump into someone and they’re buying you flowers to apologize for it.

Morgan Friedman: I need to spend more time in Canada. Actually — I’ve never noticed that. I ran out of Canada once.

Steve Perry: You ran out of Canada?

Morgan Friedman: I got run out of Canada. You have to share this story. You can’t throw something like that out without details.

Steve Perry: All right, in 60 seconds or so: one year I thought it would be a great idea to drive from San Diego to Anchorage — in January.

Morgan Friedman: Oh no.

Steve Perry: Not a great idea. In January. So I got one of my crazy buddies to meet me in Seattle — he had bought a boat there and needed it towed up, so we’d do it together. We’re driving a Cadillac Escalade through Canada in the middle of January with a bright yellow boat in tow, and a spare set of tires with 24-inch rims just sitting in the boat as we go down the highway. It is 40 below zero. We’d been driving all day and hadn’t seen a soul, and we got to this stretch of road where there’s a big hill that goes down into this town. My buddy hit the brakes — and we hadn’t touched the brakes in like four hours — and as soon as he hit them, they froze. All four tires locked up. We’ve got this trailer behind us, we’re going down the hill, and then the trailer jackknifes. I’m looking out the window and the boat is sideways right next to me. I look over at my buddy. He says, “I’m sorry about this, Steve.” He was driving my car.

We go into the ditch — backwards — and the boat shoots off backwards off the trailer, way down into this ravine, 24-inch rims and all. We’re in the middle of nowhere — Watson Lake, Canada. It is now 50 below zero.

The first car that comes along is an appliance repairman. I’m freezing — I didn’t have good enough gear — so I get in his car, and his dog bites me. Just the randomness of all of it. It takes us two days to find somebody who can tow the boat out of the ditch. There are two tow truck companies — one on each side of town. We go to the first one. They’re like, “Nope, not going to do it.” So we go to the other one. We go back and forth, finally agree, and we drive out to meet them. But by the time we met the second company out there, the boat was gone.

We’re like, “What the heck?” And then we’re like, “I bet the first company came and took it.” So we drive to the edge of town to the first tow truck company, and sure enough — the boat is sitting right there in their yard. My buddy backs up to it, we put the winch on, load the boat, and point the car toward the exit, ready to go. Then we go inside to talk to them. “Hey — you got our boat.” “Yeah, we did.” “Well… we probably owe you some money.” “Yeah, you do.” He pulls out the bill: $2,000. My buddy looks at me and goes, “I’ve got 500 bucks. How much have you got?” I said, “I’ve got a hundred bucks.”

And just then, four of his tow truck guys — all giant, 6’6″ Canadian dudes who had been watching TV over their shoulder in the back — stand up and start walking toward us. My buddy and I look at each other, throw all the money we have on the counter, run out the door, jump in the car, and scream out of town. We didn’t turn around until we hit the US-Canadian border.

Morgan Friedman: That is an incredible story. I’m so happy we got to that. Totally off topic — but actually, I want to tie it back in, because I think that story brings out an important client management lesson. If I understood correctly, it sounds like the first company told you they weren’t going to tow it, but then went and did it anyway.

Steve Perry: Yep.

Morgan Friedman: What’s interesting about that is I’ve seen that same pattern so much in professional services. It happens to me all the time. I work with a lot of freelancers, and I’ll talk to this freelance software developer about doing a WordPress page, doing this, doing that, and he’ll just complain — “No, no, no, it’s going to be so annoying, we can’t do it like this.” Okay, whatever. He’s not going to do it. And then three days later he’s like, “Morgan, I did it all.” And I’m like, “You did what?” He’s like, “You know, that WordPress plugin to do this and this and this.” And I’m like, “I never even gave you authorization. We never discussed how many hours it would take.” He just got so into it and went and did it.

I’ve seen this type of person a lot — and it sounds like the people who run that tow truck company are like that too. They might be resistant or negative at first, but they’re doers and they want to get things done, and they want to do the right thing — whether that’s fixing a WordPress problem or pulling a boat out of a ravine. They’ll be resistant, but then they go and do it. Now, we understand their good intentions. They’re doers and they’re naturally skeptical at first. But the client risks that behavior if you don’t discuss the budget beforehand, you don’t discuss the terms, and that leads to problems — like a $2,000 bill when you’ve only got $600 on you.

Steve Perry: Yeah, definitely. That totally transcends industries.

Morgan Friedman: It transcends industries, and I think it makes a very important point in preventing client horror stories — a little bit of communication, a little preparation before the work starts, a little expectation setting, goes so far toward solving client problems. And note that their good intentions actually created two separate problems. Not only did they expect $2,000 and only got $600, but also you went to the other company, agreed to work with them, and they got nothing because the boat was already gone. So the second company got nothing out of their attempts to help you either.

Steve Perry: Yeah, it’s not just them — there’s a whole world out there that the butterfly effect will create ripples for.

Morgan Friedman: Exactly. And I think the meta lesson here is that anything bad that happens in your life, we can always learn something from it — especially a lesson about how to interact with and deal with other people, so we can all improve over time.

Steve Perry: Yes. Yeah.

Morgan Friedman: And with that, that’s a beautiful and elegant way to end this episode. Steve, it’s been so much fun. Great story, great lessons, including at least one unique lesson from the core story. And then we got the bonus story — and we actually pulled a client management lesson out of that one too. It’s been wonderful talking to you and getting to know you. Thank you for the stories. And to everyone who’s made it to the end of the podcast — thank you for watching, and we hope you’ve enjoyed it as much as we’ve enjoyed this conversation. Good night, everyone.