How to ask for the sale without feeling sleazy

Sep 2, 2021
Author: collin stewart

Despite their best efforts, a lot of salespeople today are coming across as sleazy. Donnie Boivin, a recent guest on the Predictable Revenue Podcast has experienced this over and over in his career. Salespeople are full of nervous energy, they rely on passed-down greaseball tactics, and they put the pressure on because they’re taught to “always be closing.” The sleazy salesperson didn’t materialize from nothing, though. The sleazy salesperson was created and bolstered by the old-school sales leaders who created the traditional sales methodologies founded on strong-arming, reverse psychology, and bravado. Unsurprisingly, buyers got smart quickly and learned to put up defences against the salesperson in the form of objections, one-word answers, and phones slammed into their (virtual) cradles. In response, the sleazy salesperson only got sleazier, memorizing ways to subvert, dodge, and coerce in the face of disinterest.  

As effective as these strategies may have been in the past, they’re losing their lustre as consumer preferences (b2b and b2c) shift in favour of ethics and humanity in business. Consequently, Donnie prefers to leave his prospects and customers feeling that their conversation was a positive one – that they learned something, they got value out of it, and they’re leaving better than when Donnie found them. Although after decades of the traditional (sleazy) buying experience people hate being sold to, they still love to buy. And if salespeople treated sales calls a little more like Donnie does, they’d have an easier time sleeping at night and they’d actually sell more.

*Just a quick note that neither Donnie nor I am claiming that all salespeople following the traditional methodologies are sleazy – but you’ve got to admit that they make it pretty easy to sell that way.

Two people working and pointing at a laptop screen


In traditional sales you are taught to qualify everybody, and quickly. Stop that. You don’t need to be big-headed about it but go into every sales conversation with the mindset that each customer needs to prove that they are ready to work with your company. Not everybody is going to need your product or service, and there are certainly companies out there that you would be better off not working with, so start any conversation with the assumption that the prospect is not a fit. With this mindset, you can enter a call with curiosity and discover new things about this prospect and their company without reeking of commission breath. After a good, thorough conversation, when they’ve ticked all your boxes and you’re sure that they’d be a good client, then you can shift into selling mode. 

If the company won’t work for you, be honest. Prospects will appreciate the change of pace. Donnie often says, “Look, I don’t think you guys are ready to work with a company like ours,” and prospects often turn around to explain to him why they are ready. If you find yourself, as a salesperson, handling objections and trying to force the prospect into a next step, you’ve lost the real, honest conversation somewhere down the line and you are dangerously close to sleazy territory.   

To disqualify a prospect, you need to know everything characteristic they would need to meet to be qualified. From there, you need to come up with the questions you can ask that will uncover those characteristics. For instance, Donnie might open up a call by saying, “Hey {first name}. Tell me about yourself, what’s your story, how did you get here?” and a prospect might respond that they own an accounting firm. Then, Donnie will ask a follow-up question, like “Do you have any other accountants working for you?” because a) he’s genuinely curious and b) he’s looking to make some assumptions. Those assumptions might include how big a business is, what stage it’s in, etc. Those assumptions will tell Donnie whether this company is a fit to work with him. Along the way, he’s also likely to uncover some personal similarities with his prospect that he can use to forge a connection. At the end of the conversation, Donnie has qualified or disqualified his prospect without asking any generic, canned qualification questions.


Asking for the meeting without being sleazy starts with the initial connection between you and your prospect. The old-school methodologies would tell you to look for a photo in the office of your prospect and try to bond over your mutual love of baseball or summers in the Poconos. While this particular tactic doesn’t apply much today, you can look for those similarities on LinkedIn. 

Donnie is trying to create a personal connection with his prospects. He starts by sending a connection request with no message, just to see if they’re active on the platform and willing to interact with new people. Once they’ve accepted, Donnie drops them a “hey, thanks for connecting. Tell me a little bit about your story” message. Prospects are used to being on the receiving end of a connect and pitch, so this casual message is a pattern interrupt. How the prospect responds dictates Donnie’s next move. If they give him all business, he digs in one layer deeper with another question. If they go straight for personal, great. Either way, Donnie is gathering information and looking for a connection. Once he has them talking a little bit, he asks them if they’d like to have this chat over zoom. Finally, when they’re on the zoom call, Donnie asks them to tell him their story again: “Hey {first name}, you told me such a great story on LI, walk me through it again. I’d love to hear it in your words.”


The first part of the live conversation isn’t about Donnie, it’s about information gathering. But, eventually, once he’s checked off his qualification criteria through subtle exploratory questions, Donnie has to pivot the casual conversation into a sales conversation. The way he sees it is you have two options rooted in permission-based sales:

Option 1: You flip the call right then and there. You say, “{first name}, I’ve got to be honest, I’m really enjoying this, would it make sense if I were to tell you a little bit about my world, and then we can decide if it makes sense to do something together? Are you ok with that?” If the conversation has been valuable and relevant to the prospect, they may just say yes.

Option 2: You schedule a sales call. You say “{first name}, I’ve got to be honest, we’ve been talking about {business function}, and I think you and I could really partner up on some things. I don’t want to take any more of your time – are you okay if we schedule another call and we really dive into what my company does and how we can help your company move forward with that?” If they say yes, you schedule the next call right then and there.


Again, asking for the next step at the end of a meeting actually begins with how you open up the meeting. Donnie suggests you do it gently, recapping the first call or conversation you had. Then, give your prospect an out. Say something like, “I just want to let you know that if we get to the end of this thing and there’s no fit, it’s 100% okay if you say this is not what you’re looking for.” This relieves some of the pressure on the call right away.

At the end of the call, when it’s clear that there is a potential opportunity, Donnie asks his prospect, “What do we do next?” He asks this question already knowing where the prospect stands and what they want to do. If they seem unsure, Donnie knows he lost them somewhere earlier in the conversation, and that’s okay. He lets them know that it’s all good, they can still be LinkedIn connections and can still give each other referrals but it’s not a fit, and that way he can let them go without coming across as a sleazy salesperson. At this point, the prospect will either agree or will re-engage in the buying process. Either way, Donnie is pushing for closure – not a close.

If the prospect sees the value, they’ll ask him how to get started. Donnie will then give a synopsis of the prospect’s current situation and ask, “Are you okay if I go away, put a game plan together of how this might work, and we’ll come back together to discuss?” Then he’ll get a next step on the calendar. If the next step is not in the calendar, or if both parties don’t know when they’re meeting, why they’re meeting or what the expected outcome is, it doesn’t count.


Asking for the close should be just like asking for a meeting or asking for the next step – genuine and gentle. Talk to your prospect the way you’d talk to a friend. If, on a call, you feel your prospect’s tone suddenly shift and they suddenly become standoffish and cold, ask where you went wrong. Most salespeople will try to recover the conversation without even knowing what they’re trying to recover it from. With Donnie’s approach, you give yourself the best opportunity of actually finding out what your prospect’s barriers are. 


Even when a prospect is not a fit, Donnie wants to leave them better than he found them by providing value. And, in b2b sales, there’s nothing more valuable than an introduction. As Donnie is disqualifying someone, he will ask, “Who was your best client? Walk me through it.” As they do, he’ll rack his brain for someone who fits that profile that he can introduce them to. If you’re a coach or consultant, give your prospect free advice that they can take action on right away. If you work in marketing, tell your prospect 2-3 things they can do on their own right away to improve their marketing.

Just pour into your prospect and don’t worry about your own ask. Pouring into people creates champions. The more you pour into people, Donnie asserts, the more people celebrate you and your name and the more prospects come knocking on your door.


Donnie Boivin is a veteran sales guy who doesn’t do sales like a veteran sales guy. After growing up under the tutelage of old-school methodologies like the Challenger Sale and questionable role models like Jordan Belfort, Donnie had all the makings of a sleazy salesperson. But he quickly realized that what these selling styles lacked was humanity – something customers want more of now than ever. Society is shifting and both those who sell and those who buy like the traditional methodologies taught us are a dying breed. Treating sales like a regular conversation is the new frontier.


More on how to avoid being sleazy and keep up with the times:

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