Lost in Baltimore: Selling to the Worst Buyer in the World, the Brand New Executive

After giving one of my talks at the Association of Proposal Management Professionals conference this summer, I grabbed a drink with an experienced salesman. I always love hearing war stories and tips and tricks, so I was excited about the opportunity. I was most certainly not disappointed.

Eventually, we got around to discussing who the best and worst buyers are. I was arguing that the worst buyers are the guys who think everything is a commodity and don’t believe in the concept of value. He shook his head. This is the conversation we had:

“If you have to rate who the absolute worst buyer is,” he said, “it’s the brand new executive who just got promoted from right hand man to running a department.”

I raised my eyebrows. “Worse than the price-only, just-fill-out-the-damn-spreadsheet procurement guys?”

“Definitely. With those procurement guys, you know what you’re dealing with. So you just ask them what they can live without. They see quality as fluff.”

I went to object, but he cut me off.

“I know. I know. It’s stupid. But you ask them what their absolute bare minimum is and then that’s what you give them so you can cut your price as much as possible. And then you try to talk to other people at the company to show them what they’re missing.”

“OK,” I said. “I’m listening. Why is a hot shot new guy the worst?”

“Because politicking and responsibility are two very different things. Once you get to a certain point, everybody is smart. They’ve all got their fancy MBAs. So intelligence isn’t the issue with getting to the top. Politics is. You get to know a customer after a while and they’ll start telling you stories about what’s really going on. Who’s throwing who under the bus.”

“Or worse.”

“Or worse. But that’s how you advance. Playing the game. But the skills of moving up the ladder are almost completely unrelated to the skills of actually running a department. So the result is that they’re too scared.”

“Of what?”

“Being exposed. Accidentally showing that he feels like a fraud. Or at least like an impostor. So he’s scared of making a decision that puts his lack of experience up on a billboard for the world to see.”

“But he still needs new equipment for his department. Or new people or whatever.”

“See, that’s the thing. The department needs it, yes. But he doesn’t know he needs it. That’s why he’s the worst customer. He’s so terrified of his own judgment that a salesman can’t convince him. If someone doesn’t trust themselves, they don’t trust anyone.”

“Sounds like a fortune cookie.”

“Maybe, but it’s true. Think about the last time you were in a new city. It’s late. You’re surrounded by shady people. You don’t know which way to go, where to find a taxi. Remember any time like that?”

“Sort of. My first time in Baltimore, I accidentally turned off on the wrong exit. And it was not a good neighborhood. People drinking out on the stoops of rundown, boarded up houses. People dazed out of their minds on drugs, wandering in the middle of the street.”

“OK. Right. So you were totally lost and didn’t trust yourself, right? Why should you? It’s your first time there.” I nodded. “Alright, so if one of these guys had gotten up off a stoop and walked over to your car, what would you have thought?”

I laughed. “Thought? I think I would have slammed down the gas pedal too fast to think.”

“Because you didn’t trust him. Not without reason, of course. But did you ever end up in that area later on?”

“Yeah. Still not a great neighborhood, so it’s not like I went there on purpose. But if I had to drive through, it was no big deal. And you learn to spot the real trouble from the ones who are just doing their thing.”

“Exactly. That’s experience. And that’s what these young guys don’t have. When they take over a department, they’re lost in Baltimore. And everyone who comes up to them – including salesmen – is a threat to ruin everything. What makes it so hard is that these new executives are so self-confident – sometimes irrationally, but also because that’s part of what it takes to succeed – that they don’t realize the fear.”

“How’s that possible?” I asked. “I mean, aren’t they feeling it in the pit of their stomach? How do you explain that?”

“Oh, sure, they feel it. But the mind is a crazy thing. If you’re the salesman and you talk to this executive, they suddenly believe you’re the reason for that feeling. Just because you happen to be there when they notice they’re having the feeling. So they blame you. And, when I say blame, I mean it. He’ll treat you like you’re a criminal. Exactly like you would have thought about anyone coming up to your car in Baltimore.”

“But,” I protested, “if his department needs something… ”

He smiled and shook his head at me sympathetically. “Well, think about it. First, and most important, if it’s a battle in someone’s head between emotions and logic, emotions win every time. And it’s not even close. You know that.”

I nodded. I knew that. I didn’t like it, but I knew it.

“Second, how often is something really, truly make or break for a company? Usually, what we’re talking about is increasing profits and productivity or reducing costs, not life versus death. So, even if he’s unsure whether he should trust his emotions – and this is just academic because they’re never unsure – but even if he is unsure, it’s not that big of a deal to push it off for a quarter or two.”

“But you can’t push it off forever.”

“No, you can’t. But you can in the beginning. You can blame the previous guy for at least a year, maybe a year and a half. And after a year or two, the new executive starts getting experience and this fear wears off. Although, and this is really frustrating, they continue to associate you with what they were feeling. They’ll almost never learn to trust you.”

“What?! Are you joking?”

He chuckled. “No. Not joking. Remember, to the new executive, these feelings are real. So he really thinks you’re trying to pull a fast one. Usually, you have to switch salesmen. That gives the exec the opportunity to save face by saying it was the old salesman who was the problem.”

“People are idiots.”

“That brings up the third reason why new executives will act against their department’s interest – and their own – and reject something that will make the department more profitable. They actually believe what they’re feeling. We’ve been talking about it from a psychological kind of perspective. But that’s not how people experience life, is it?”

“What do you mean?”

“If someone cuts you off in traffic, do you get mad or do you think to yourself, ‘I am now experiencing the feeling often described as anger, which has resulted from the stimulus of the automobile-‘”

“The first one.”

“Right. Same with the baby executive. When he feels that a salesman is bringing up all these fears, he doesn’t analyze it. He blames the salesman. Literally, just like in Baltimore, sometimes they’ll look at you like you’re about to pull a switchblade out of your briefcase. They interrupt you constantly. They disparage your evidence. They raise ridiculous objections. They certainly won’t answer any consultative questions.”

“But how do they respond to hearing, you know, that they could increase their profits by $300,000? Doesn’t that grab their attention?”

“If the guy in Baltimore knocked on your window and said, ‘I know how you can earn an extra $300,000 this year,’ what would you say?”

I laughed. “I suppose I wouldn’t say anything. I’d drive away.”


“Why? I mean, because it’s a scam. He can’t do that.”

“How do you know?”

“Well,” I paused to think about it. “I don’t know. I just know.”

“You feel it?”

I leaned back in my chair.

He looked at me with a wry smile. “Are people still idiots?”

I crossed my arms. He watched me for a moment. Finally, I sighed and uncrossed them. “Fine. So, what do they say? What’s their excuse?”

“Usually, you can’t really pin them down to any definite reason. Like I said, evidence is no good, projections are no good. You have to remember that this is all about fear. So he won’t make a decision to go forward with you. But, a lot of times, he also won’t decide against you.”

“Really? Why? If he thinks you’re a crook, why not just kick you out?”

“Because it’s about fear. He’s afraid that, if he says no to you, someone higher up might think that’s the wrong decision. Especially if you’ve shown evidence and projections and identified needs.”

“So, he won’t even just get out of the way and send you to talk to someone more experienced?”

“No way. He’s terrified of losing his new-found power. Plus, except for the CEO, who’s a new exec going to send you to?”

“I suppose. And he’s not going to send you to the CEO.”

“Certainly not. Look indecisive to the CEO? No way.”

“Alright,” I said. “I give in. These guys are worse than the spreadsheet guys. Waste of time. So you skip them.”

“No way!”

I looked at him in shock. “Haven’t you just been saying… ?”

“I said they’re the worst to sell to, not that you can’t sell to them. Once you know the trick, they’re actually great customers because nobody else is selling to them either.”

He paused, tapping his finger on his empty glass. (I told you he was an experienced salesman. My glass was barely a quarter empty.) I knew he wanted to make me ask what the trick was. I didn’t want to, but I had to know. I signaled the bartender for another drink for him. “Alright, what’s the secret?”

He smiled. “First, let me give you a quote. Napoleon said, ‘The herd seek out the great, not for their sake but for their influence; and the great welcome them out of vanity or need.’ Keep that in mind.”

“OK. Makes sense, I guess.”

“My secret is a two-step process. As soon as you realize that you’re dealing with a fearful new exec, you need to leave as soon as possible with your dignity. You say something like, ‘I seem to be annoying you today. I really think we might be able to help you make money, but I’m afraid that it must be coming out wrong. I didn’t sleep well last night, so I’m sure that’s the problem. At any rate, I’ll let you go and would love to discuss this with you further some other time.'”

I looked at him in surprise. “Whoa. Really? Just leave?”

“Yep. Then you go. Sometimes, with the guys who have manners deep down, that alone will be enough to break him out of his spell and he’ll say something like, ‘No, no. It’s my fault. Please, have a seat.’ And with those guys, you can oftentimes get a starter sale because they feel bad for having offended you. It harms their image of themselves as courteous and a good person.”

“I wish.”

“It happens. Maybe 20 percent of the time. People say morals are declining, but I find it’s pretty constant.”

“Well, 20 percent is better than zero, but what about-”

“The other 80? Right. So that brings up step two. You leave. This automatically puts you in a different category as those other guys who get desperate and keep trying to sell until they’re told the time is up and the exec will think about it.”

I groaned. “The ol’ ‘I’ll think about it.'”

“Nothing worse. So then you wait a while and you call up later. A month or so. You don’t bring up business at all. Instead, what I do is I say that I need some data for our company newsletter that I thought he might be particularly well positioned to give me.”

“But, if he was afraid-”

“Hold on. Let me finish. Yes, he gets suspicious. He asks what kind of data. So I tell him I need data on something that is a little obscure, but would be basically known to anyone in his position. Not something you can find on the internet. But not proprietary stuff either. This is why it’s so important to leave the first time with your dignity. He has you in a category all by yourself. Not trusted yet. But also not untrusted anymore like the other desperate salespeople are.”

“Like what’s an example?”

“So, for example, if he’s now the head of consulting for an IT company, you ask what they keys to running an effective consulting practice are and how he knows his clients are satisfied. If he asks how that’s relevant to you, you say that you want to apply some of those best practices to your own people to make sure that they are true consultants. Or, say he’s at an engineering firm and he’s the head of the group that designs and constructs data centers for companies. You say you want to ask what the critical things about data centers are because you’d like to apply that to your salespeople, who are like a data center. If he’s in charge of building hospitals, then you want to build a sales culture devoted to the health of your people and your company.”

I grinned. “If he builds educational centers, then you want your salespeople to be lifelong learners.”

“Exactly. So you ask for 15 minutes of his time. You ask him some questions. Let him talk. It will always go more than 15 minutes. I’ve had some go an hour. In one case, I explained that I was nearby with another client and, after mentioning what I was looking for, I offered to treat him to lunch in exchange for some expertise. In that case, by the time we were halfway through our sandwiches, he had already filled up four or five napkins with diagrams and org charts and on and on. And he was giving me advice on how I could use the principles of quality control in pharmaceuticals to improve the quality of my sales force.”

“Just because you asked?”

“No. Not just because I asked. Because I asked to interview him to write a ‘View from the Expert’ article. Because I wanted his judgment. I was recognizing his skill. Plus, you mention that your newsletter goes to the company president, so it’s a big deal for you. That shows how important he is in your eyes. How much his insights mean to you. And then when you actually ask him the questions, whether right then or later on his drive home or whatever, the whole time you’re being nice, asking about his family, mentioning yours. You’re generally making yourself a human that he can trust. Not a ‘salesman’ he fears.”

“Isn’t that manipulative if you’re not going to actually use it?”

“Why wouldn’t you use it? It’s great stuff. Remember, these guys are really smart. They’re just afraid. But that doesn’t mean that they don’t have great things to say about how the principles of, you know, designing an efficient hotel apply to managing the sales force of a telecom company.”

I smiled. “I guess so.”

“So you write it up and send him the article. View from the Expert. ‘From Building Bridges for Clients to Building Bridges with Clients: How Civil Engineering Best Practices Can Keep Us the Number One IT Consulting Firm.’ And you start it off with some praise for him and his department – under the guise of explaining to your reader why he’s worth listening to. You quote him, apply it to the company. Easy.”

I chuckled. “I like it. Everyone wins. But do you get the sale?”

“That’s the question, right? Typically, what I’ll do is send it to him, oftentimes with a quote from the president saying how clever it was or something similar. Along with my thanks, of course. He’ll usually send back a short email saying I’m welcome and well done. A couple weeks later, I’ll call up and say thanks again and that I’d love to talk with him further about our company, but that I don’t want to abuse his time, and so I’d like to send a colleague over to explore if our services makes sense for them.”

“You do?”

“Yeah. Most of the time, he’ll say, oh, no, it was his pleasure and that I’m welcome to come over, even though he can’t promise they’re in the market.”

“What prospect ever says he is?”

“Exactly. So you go over. He trusts you and likes you. Nobody else has been able to talk to him. If you have the skills and your service makes sense, you can make the sale.”

“What if he says, ‘Sure. Send him over?'”

“Then you do. You can figure out the commission later. Ideally, if it’s someone who’s as smart as you, you’ll do this for each other and it all balances out. But, lately, I’ve added a new wrinkle.”

He paused again, waiting for me to ask him. I hated being led like that, but I needed to know. “OK, what’s the wrinkle?”

“So, for really big prospects, I’ll have a VP or someone of at least his equivalent rank ‘communicate’ to me” – he made quotation marks around communicate with his fingers – “how impressed they were with the article and ask to set up a lunch or dinner between the VP and him. As long as it’s not too far of a drive, some VPs are really good at it. They do the usual schmoozing thing. Ask lots of questions. Share some funny stories about previous places. And now, suddenly, the executive is even more comfortable with your company. That firsthand knowledge trumps the diffused fear of his new position.”

“And then you take it up from there?”

“You got it.”

I shook my head in respect. “I like it. I’m convinced.”

“If you’re smart about it, a person’s vanity can truly be a wonderful thing.” He tapped on his glass, which once again sat empty. “And you’re just the sort of smart, clever, diligent person to make use of vanity.”

I rolled my eyes. But I also signaled the bartender for another drink for him. So I guess he was right again.