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Published on:

18th Jul 2025

How to Apply the RIGHT Amount of Sales Pressure (Without Being Pushy)

Ray breaks down a real coaching scenario where an MSP salesperson lost a deal to an inferior provider despite proving compliance issues and security vulnerabilities.

The prospect chose to give their current provider "one more chance" instead of switching to better service.

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Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

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YouTube | LinkedIn | Facebook | Twitter | Instagram


Transcript

00;00;00;00 - 00;00;17;06

Speaker 1

Like the Socratic method of asking the right questions to lead them to the fact that it's a dumb decision, but on their own. Every Tuesday, I spend a few hours coaching people who are selling MSP services on how to close more deals. Some of them are business owners, some of them are, you know, full time salespeople, but they're all closing it deals.

00;00;17;06 - 00;00;47;51

Speaker 1

And it's something that I've done for a couple of years. I'm a sales sales management expert in residence at the largest IT mastermind TMT. We hop on for several hours a week and answer questions. We go through sales process, we do Q&A, take office hours, and one of the questions that we got last week, I thought was really good around losing a deal to a current incumbent provider who was inferior in the prospect, acknowledged was inferior in terms of service and delivery.

00;00;47;51 - 00;01;03;37

Speaker 1

But they were going to stay with that provider and it wasn't about price. This is a scenario I see come up a lot and it's, you know, losing deals to, you know, people, incumbents or not, that we know are not nearly as good. And I want to address it head on the way that we did on this call last week.

00;01;03;37 - 00;01;27;09

Speaker 1

So let's dive in. Hey what's up? I'm Ray green, founder of MSP Sales Partners, where we help IT companies scale sales. So here's the scenario. We've got Jane the salesperson. We've got Mark, the business owner okay. Her prospect. All names have been changed to protect identities or address. So Jane says all right so I worked with Mark. He basically came to us because he was concerned about the the compliance issues.

00;01;27;09 - 00;02;02;48

Speaker 1

Right. Like they that's an important part of their business. Not being compliant is a pretty significant risk. They had some suspicion or concern that they weren't, compliant, even though their current provider said they were. So they went out and started talking to other providers and wanted to essentially understand where they stood. Jane runs her process and, you know, does some of her discovery, does an assessment, you know, goes in and does like a, you know, an assessment to find out who owned the workstations, looks at the compliance issues, looks for other things, and sits down to do the proposal and they go through it and sure, shit, they're not compliant.

00;02;02;53 - 00;02;24;56

Speaker 1

Okay. So like that is is a pretty significant issue on its own. They also found other issues on the assessment. She sits down with Mark says listen I confirming unfortunately, you know, you're you're not compliant like here the gaps we've also found several other issues on your, on your network that are, you know, pretty, pretty clear and goals and you know, some leaving you're pretty pretty vulnerable.

00;02;24;56 - 00;02;53;18

Speaker 1

So, you know, she goes through this whole thing and, you know, presents the proposal. And Mark says love everything you've done. I really appreciate it. What I'm going to do is essentially take this back to my current provider, and I'm going to give them one last chance. And I asked, asked. And so why why would they go with somebody who just basically violated their trust, left them vulnerable, put them in a position where they're they're not compliant and potentially face pretty steep fines.

00;02;53;30 - 00;03;15;18

Speaker 1

Why would they choose to go with that person? And by the way, it wasn't price. She said. Well, you know, they they said they have a long standing relationship. They've worked at them for a number of years. They think they deserve one more chance. I said, you know what? Like maybe, like what I hear is I don't want to make a hard decision, and I don't want to have a tough conversation.

00;03;15;18 - 00;03;29;27

Speaker 1

Like, that's what I hate. That's what I hear. But okay, here's the overarching issue. And what I talked to Jane about. Why would they go with an inferior provider? That's what I asked Jane. I said, you know, like so so what is the what is the motivation here. Like it was it was it price was it. This was she said no.

00;03;29;27 - 00;03;46;50

Speaker 1

Like we barely came in like a few dollars more than their current provider. Like in terms of relative to the issues that they were facing, like it was completely insignificant. It wasn't price. And so I asked Jane, I said, okay, what did you did you challenge that decision to said, no, I don't I'm not really I don't want to be pushy.

00;03;46;50 - 00;04;05;01

Speaker 1

I don't want them. I don't want to be like high pressure sales. I don't want to feel like a timeshare person. So that's not the way I saw most of us selling it. Services are not arms twisters are not high pressure salespeople like we are part of a, you know, consultative sales process. We're guiding people through. We're solving problems.

00;04;05;01 - 00;04;26;04

Speaker 1

We're, you know, we're being strategic with the information. But and we should absolutely should have some rock solid closing capability, the ability to ask for the money and close deals. But we're not high pressure. So I completely get that as a salesperson, part of your job is to coach people into making decisions that they would not otherwise make.

00;04;26;06 - 00;04;44;03

Speaker 1

Because if you don't, I mean, first of all, it's then you're not really need it, right? Like if all we're doing is guiding people through the process of making a decision that they were already going to make, we don't really need a commission for that. Part of that job is also helping them make decisions that are in their best interest, and challenging them when they aren't doing that.

00;04;44;03 - 00;05;01;55

Speaker 1

Just like a good coach would, just like a good consultant would like. Forget the sales part of this just for a minute. Like take your commissions, take your deal off the table. If you sat down or you talked to somebody who was just making a really bad decision, right. Like, because this sounds kind of like a relationship soccer, like, oh golly, they did it again.

00;05;01;55 - 00;05;17;21

Speaker 1

But, you know, I think this time is going to be different. Let me go back to them and see if you know, they'll they'll make changes. And I and I think this time that gets it's going to be different. Like what would you do if you were coaching that person. That was your friend, that was your sister? Like you'd go, do you really think that's that's the best approach here?

00;05;17;24 - 00;05;38;12

Speaker 1

Now, that doesn't mean you've got to necessarily throw people under the bus, and it doesn't mean you have to be disrespectful, but it does mean you have to be willing to challenge and you have to be willing to apply some healthy pressure in order to get the different decision that they are otherwise going to make. If you don't challenge them at all, then they will make the default decision that they were going to make.

00;05;38;12 - 00;06;04;37

Speaker 1

And in this case, this is unequivocally, absolutely a bad decision, right? This is a business that has compliance issues, fears, concerns enough to go out to the market. They are in fact not compliant. They are in fact vulnerable to ransomware and other things. There are real problems in the business. It is not a good decision to go back to the person that has been does put you in that spot, if for no other reason.

00;06;04;50 - 00;06;25;48

Speaker 1

Technology is changing so quickly right now, right? Like, I mean, you know this, like this. If you go back, you fix it today, it's not going to the what are they going to do in six months if they don't have the expertise, if they don't have the knowledge, if they don't have the bandwidth, if you don't solve the root cause of this problem, you, mark, are going to end up in the same exact scenario in six months.

00;06;25;48 - 00;06;47;45

Speaker 1

But here's the thing as a salesperson, I'm not coaching you to say that this is this is where I believe this is where I think this is how I frame this. This is why I believe the best approach to this is, in fact, to apply a little bit of healthy pressure. Now, what I wouldn't do is go on that exact, you know, monologue or that exact soapbox and say, okay, now do do you agree with me?

00;06;47;45 - 00;07;05;46

Speaker 1

Right. So I'm just I'm, I'm setting this up and I'm framing this so that, you know, where I'm coming from. That is one of my beliefs like that, that sales is about helping people make decisions that is in their best interest. And sometimes that means creating some friction and applying some healthy pressure. Now Jane wants to know, okay, so cool, I agree with you.

00;07;05;48 - 00;07;22;52

Speaker 1

What should I have done? I told her there's a couple of questions that I would that I would ask. And you can ask one. You can ask both, but you know, or you can ask a different version of this, but something along the lines of, hey, you know what, Mark? I understand, like, I respect a long standing relationship and frankly, like, those are the kind of people that we love to work with.

00;07;22;53 - 00;07;50;39

Speaker 1

Let me ask you one question, though. If I may. Do you really want to take on delivering the technology roadmap and the compliance issues and vulnerabilities like, do you want to take that on as part of your role as a, as a business owner with your I.T company, or is that something that you think they should take? And what I'm getting at here is, hey, you know, when you take this to them, like you're basically enabling a behavior, right?

00;07;50;39 - 00;08;13;46

Speaker 1

And you're now becoming the person that's responsible for doing that. Do you really want that to be in your job description? Mr.. Mrs.. Business owner, another way to to apply some healthy pressure maybe. Hey, you know what, Mark, I completely understand. You know, the, you know, long standing relationship and I respect that. We would we would love to, to earn the right to to have that degree of loyalty with you, too, if I may ask you just one question.

00;08;13;46 - 00;08;43;41

Speaker 1

And I don't mean this to to come across the wrong way, but with the rate of change in technology and I mean, frankly, I haven't seen anything like it, like the, you know, the development with AI, with cyber threats, with, you know, solutions that are coming around for, for security, and, you know, the, the bad guys that are coming up with the ways to, to beat those, like, we specialize in staying ahead of the curve and at the rate of change that I've seen, which is unprecedented, what leads you to believe that in six months this is going to be a different?

00;08;43;41 - 00;09;03;07

Speaker 1

What I want to do is I want Mark to think through what is going to be different about this. I want Mark to tell me his dumb excuse. Right. Like that's like when you're talking to somebody, it's like, well, I'm going to go back to him because he did this and you know, maybe like you're like, no, like that's this is that's a bad decision.

00;09;03;08 - 00;09;21;35

Speaker 1

The best way to get them to make a better decision is not to tell them it's a bad decision. It's like the Socratic method of asking the right questions to lead them to the fact that it's a dumb decision, but on their own. That's how you sell with pressure, without feeling pushy, without feeling high pressure, without feeling like you're twisting people's arms.

00;09;21;40 - 00;09;48;04

Speaker 1

You ask the right questions, but you ask the right questions. You don't shy away from the questions that left unasked. Leave them to make a really terrible decision. Like, how would you feel three months from now when you find out they got held up for ransom where they got, you know, do they get something happened? You went, damn, you know, if I had asked a couple more questions, I bet I could have gotten them to understand.

00;09;48;09 - 00;10;07;34

Speaker 1

This is not good like you should. You shouldn't do that. That's a bad idea. If you have trouble with that concept, like of of challenging and, and applying a healthy dose of pressure. Think about it this way. Some of my best coaches in life have been coaches that were tough on me. They have been the people that pushed me a little bit more when I couldn't.

00;10;07;49 - 00;10;27;34

Speaker 1

They are the people that got me to do what I couldn't otherwise do. They are the ones that said bullshit right? Like try this. Like you can do more, you can do better. My best coaches, the ones that I respect, the ones that I appreciate the most, are the ones that were a little tough on me. Right? And think about what would you do with somebody that you that you liked or that you loved?

00;10;27;34 - 00;10;46;20

Speaker 1

What would you expect a psychologist to do? Like just a good one, like sit there just okay, like, yeah, you should just continue to make bad decisions like people that care about other people, challenge them. Right. And that's all we're doing. It's a reframe on how and why we do it, but get to the same outcome. So I hope this has been helpful.

00;10;46;21 - 00;11;06;57

Speaker 1

By the way, if you like these breakdowns where we go through like specific scenarios, just comment below. And yeah, I'll, I'll do more of them. If they if you do find them useful in the meantime, you can hop on my email list. The link to that is below. And if you're an MSP or night business, go ahead and hop over to MSP Sales toolbox.com and you can get access to a whole pile of resources.

00;11;06;57 - 00;11;29;23

Speaker 1

It's it's playbooks. It's templates. It's frameworks things that we use to, you know, hire good salespeople, manage good salespeople, forecast, build revenue and grow all that stuff. I put new resources in every month. You'll have lifetime access, absolutely free. So hop over MSP sales toolbox.com. Otherwise I'll see you in next video. Adios. Love.

00;11;29;28 - 00;11;30;40

Speaker 1

You.

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About the Podcast

Repeatable Revenue
A podcast for MSPs and B2B business owners who want to scale sales.

Repeatable Revenue is hosted by Ray J. Green, an investor, entrepreneur, and strategic growth advisor to MSPs and B2B businesses. He's led national small business for the U.S. Chamber of Commerce, run turnarounds as a CEO for private equity groups, and advised 100s of MSPs and B2B businesses on how to build sales teams and scale sales from Cabo, where he now lives with his family.

This podcast is a collection of interviews, lessons learned, and other infotainment to help you build your business... and the best version of yourself.