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Published on:

29th Aug 2025

MSP Owners: Stop Getting Stuck in Limbo (Here’s 3 ways to force decisions)

I recently coached an MSP seller who spent over 20 hours chasing a $5,000 deal only to get completely ghosted at the end - sound familiar? If you're tired of getting stuck in sales purgatory, chasing deals you were never going to win, I'm going to show you three specific strategies to break free and force more decisions.

First, use your discovery phase strategically to understand their actual buying process by asking the right questions about urgency, decision-making structure, and stakeholders involved.

Second, after your proposal presentation, get them to quantify their interest on a 1-10 scale and then ask the crucial follow-up question: "What would make it a 10?" This reveals the real objections you need to address.

Finally, make it easy for prospects to say no by giving them permission to tell you if they've gone a different direction - you'll either stop wasting time on lost deals or they'll put themselves back into the buying process.

These three techniques will help you allocate your time more effectively and stop chasing deals that are already dead.

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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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Transcript

00;00;00;00 - 00;00;29;52

Speaker 1

I was cooking MSP seller who had invested over 20 hours chasing a $5,000 meridian at the end of it. He got completely ghosted and his question to me was how do I keep from getting stuck in limbo? I feel like I'm getting stuck in sales purgatory and I can't break free. How do I prevent this from happening? And I'm about to show you three very specific things that you can do to keep from getting stuck in sales purgatory, to break free so that you can get more decisions and stop chasing deals that, frankly, you were never going to win.

00;00;29;54 - 00;00;50;34

Speaker 1

Let's dive in. Hey, what's up? I'm Ray green, founder of MSP Sales Partners, where we help IT companies and MSPs scale our sales team. Last week I was coaching a salesperson from an MSP. They specialize in the health care industry and they're relatively well known. And he said, we ran a really good discovery. Found some what I thought were some good pain points, some good challenges that they had, things that we we could definitely address.

00;00;50;38 - 00;01;06;36

Speaker 1

We moved on to the assessment. So they did like a network assessment, found some, some vulnerabilities, found some things that he thought was going to be really helpful in the proposal stage, then put together a proposal, uses the slide deck that that we recommend, like, you know, don't make it just like a long 50 page quote.

00;01;06;36 - 00;01;24;31

Speaker 1

So, you know, he walks through the slide deck, they get to the ends and he feels like they've got a good conversation, like the, you know, the prospect was asking questions, seemed engaged and said, you know, just need to to think this over. And, you know, there were a couple things they needed to do on their end. And then we'll we'll get back to you in later on.

00;01;24;42 - 00;01;47;05

Speaker 1

But as I dove in, I realized, like, this is happening to him a lot. Like there's a pattern. And what I said was there are basically three things that that you want to look at to, to help avoid this, to, to basically force more decisions going forward. I will tell you this like it's this is one of the hard things with B2B sales is when you're in a buying process that is just really slow, but still has a good chance of moving forward.

00;01;47;05 - 00;02;04;46

Speaker 1

And when you are chasing a lost deal, right, like, how do you how do you distinguish between this, but more importantly, how do you prevent it from happening in the first place? And the first thing that you can do is work to really understand what the buying process is for that particular company. Early in the discovery things okay.

00;02;04;46 - 00;02;30;00

Speaker 1

So let's assume that you run like a qualifying process. You've got like a discovery call. Maybe you do an assessment, put together a proposal. Well, the closer you get to asking for money and the closer you get to negotiating and closing, the tighter they're going to be with information. Okay. So the most open they're going to be is basically in discovery, right after you've established some initial rapport and you're asking your your initial discovery questions, that's when they're going to be more forthcoming with the information.

00;02;30;00 - 00;02;52;15

Speaker 1

That's the time that you want to understand what is the buying process that we're going to have here. And the way to do that is just ask the questions that are going to help you get those answers. Don't waste your time in the discovery phase, asking questions that you're going to get in in the network assessment that you could have gotten on a form that are super easy to get from a database like number of employees and revenue and, you know, even like estimated workstations, things like that.

00;02;52;16 - 00;03;13;08

Speaker 1

Most people are asking these technical questions and they're missing the opportunity to ask good questions like, how are you going to buy services and make a decision? So one question that I like to start with is, hey, so what makes this a now conversation or not? You know, six months ago or six months from now. And what I'm getting at here is, do we actually have something that you're trying to make a decision on?

00;03;13;12 - 00;03;28;34

Speaker 1

Right. Like, are you shopping or are you just kicking tires? Are you just exploring some things? Is there any urgency here? And when I get the answers to that question, I can start to gauge. All right. Are we in a real buying process? Are we in a shopping process. And frankly, that's okay. Like even if you're in a shopping process, that's okay.

00;03;28;34 - 00;03;49;24

Speaker 1

Like everybody's not ready to buy right now. But it helps your expectations and it helps you be more strategic with your process. If you would identify, hey, there really isn't any urgency. On the other hand, if they tell you, yeah, actually, you know, we we have a major issue with our current mSRP or we've just had, you know, we've been compromised or we're having issues with compliance or you go, okay, cool.

00;03;49;24 - 00;04;07;36

Speaker 1

We've got real problems to solve. So that gives me a sense that we're in an actual buying process. Another question that I like to ask is as direct as it is. Hey, so how do you typically make these decisions, like when you're buying new services or switching service providers? Is there a committee or a board? Is it, you know, like how do you how do you guys usually walk through this process?

00;04;07;36 - 00;04;29;08

Speaker 1

Now when you're asking early and you're asking with the totality of curiosity, then chances are they're going to give you some information that helps you understand what you're going to go through here. And so if you know early there's a board thing, if you know early, there's another decision maker. If you know early that there's these steps that they're going to go through, or you can start to gauge for that and adjust your process to move it forward more quickly.

00;04;29;09 - 00;04;46;43

Speaker 1

And then another question that I like to ask is, hey, so when you're having it, conversations like network and who the provider is and that current challenges and all of that, who's usually involved in that conversation. Now I'm not going to ask, hey, are you a decision maker? Are you qualified to make this decision like that's a it's a it's not a good question.

00;04;46;48 - 00;05;03;44

Speaker 1

Like they say, there's no bad question. Sometimes there's a bad question in bits because buyers prospects, we've all been trained to know what that is. That's a sales question. And if you're asking that out of the gate, it's kind of like, now I'm just going to view all of the questions that you're asking through the lens of, you know, through through that.

00;05;03;44 - 00;05;20;24

Speaker 1

And they start to to get tight with the information. So I just want to ask like, hey, when you're having conversations around it and network and speed and, you know, some of the challenges you guys have had, who, who's been involved in that conversation. And I want to identify who the other stakeholders are, whether they're involved in the decision making process or not.

00;05;20;24 - 00;05;37;32

Speaker 1

They're going to be involved in the conversation. And that's just as important. But really, all you want to know is, how can I ask really strategic, targeted questions that are going to help me understand what this decision making process is going to look like, when they are going to make a decision? Who else might be involved in the decision.

00;05;37;36 - 00;05;54;49

Speaker 1

And that is the best way to use your discovery time. Now, the second thing I like to do is a little bit further in the process is after you've gone through discovery and you've given the proposal and you've asked for the sale and they've said, hey, this all looks great, right? Like typically what we're gonna do is we're going to talk about it, we're going to meet next week, and then we'll give you a call.

00;05;54;56 - 00;06;11;00

Speaker 1

Right. And so of course you bam, bam, you book a meeting from a meeting and you book the next, the next meeting. You don't leave that that meeting without an an action item on the counter. But the more important thing is what you do right then and what you do right then is you say, hey, I totally understand.

00;06;11;00 - 00;06;29;24

Speaker 1

It's a big decision. Don't want to rush it. If I may ask, like if you had to make a decision today on a scale of 1 to 10, with one being not a chance in hell, and you guys are definitely not my partner in ten is. We know, like, you guys fit like a puzzle. We've got a there's some formality here, and we feel really good about this direction.

00;06;29;24 - 00;06;48;50

Speaker 1

Where would you say you guys are in in going forward for this? Just so I can I can gauge you from my end. Now, you can ask that question a million ways, right? Like you do one with that. That's your style. I've had some people say, you know, hey, on a scale of 1 to 10, with one being we missed every major thing that we could have been, ten being we went above and beyond.

00;06;48;55 - 00;07;08;40

Speaker 1

How well did we answer all of your questions and meet the expectations and get you everything that you needed in this process? And and like I said, you could reword this a ton of ways, but here's the important piece. We want them to quantify it because it's the follow up question that matters most. What we're going to say after they say it's usually six, 7 or 8, by the way, like it's typically what you're going to say.

00;07;08;40 - 00;07;26;16

Speaker 1

And if it's six usually leaning towards no. And if it's higher than eight you're like basically you got to ask. And when they say seven or they say eight, you say, okay, no problem. Hey, what would make it a ten? Like what was missing. And what we're doing now is we're having a conversation about the gap. We're having a conversation about the gap in their decision making process.

00;07;26;21 - 00;07;44;42

Speaker 1

And that is the resistance. That is the objection. That is the reason you will not win this deal. It's whatever is between 6 and 7 and eight and 10 or 1 and ten, whatever that number is. That's the reason it's not going to move forward. You don't want to leave them with that. The last thing you want to do is leave them with that gap to figure out on their own.

00;07;44;56 - 00;08;06;22

Speaker 1

You want to pull that out, you want to identify in or address it because you need to resolve it. Right. Like you've got to resolve that if you're going to win this deal. So at the move, quantify it, put it on a scale, take the difference. Ask what it would take to get there. And then when you're having that conversation, you are now having the conversation about objections in a much more strategic and a much less defensive way.

00;08;06;31 - 00;08;26;32

Speaker 1

Now, the third thing, as counterintuitive as it sounds, make it easy to say no. You know, if you're in the follow up process. So you've done everything that I've said. You still end up in a follow up process and you feel like, hey, I'm not going anywhere. Am I annoying them or is this really a no? Just ask, like, pick up the phone, shoot an email, leave a voicemail, do whatever you need in order.

00;08;26;32 - 00;08;44;27

Speaker 1

I would do phone and then, you know, leave that voicemail, then send an email. But, you know, go ahead and ask if they've, you know, decided to go a different direction. You don't have to be arrogant about it. You don't have to be, you know, you're entitled to anything about it. But you can say, hey, Joe, you know that we had a good call.

00;08;44;28 - 00;08;57;18

Speaker 1

Things seem to go, well. I know you were thinking things over. I'd followed up a couple times, and frankly, I don't want to be annoying. Like, I don't want to be a pest to you. But, of course, it's. It's my job to follow up until I get a decision is you decided to go a different direction. No hard feelings.

00;08;57;23 - 00;09;15;08

Speaker 1

Totally understand. If you don't mind, just let me know, because I don't want to continue to to be a nuisance or flood your inbox or anything like that. So if you have gone a different direction, you'll go ahead and let me know if we're still in the in the process or you need some more information. Would be happy to hop on a call, you know, tomorrow and and we can go from there.

00;09;15;13 - 00;09;34;11

Speaker 1

Something along those lines, really? What you're saying is, hey, if you've gone a different direction, you've made a decision. Can you tell me? A lot of people don't like they they don't want to communicate the tough decisions or conversations. It's I think some of it's human nature. And I know I've had millions of conversations with the salesperson. This is why don't you just tell me, like, why don't you just tell me, you know, like, I get it.

00;09;34;18 - 00;09;50;12

Speaker 1

Like I get it, but you're not entitled to a no. Like you've got to earn the no. You got to earn the decision. Whether it's a yes or no. So what we want to do is make it easy to say no so that if they've if that deal's lost, you can just stop wasting your time. And if it's not, they will put themself back into the buying process.

00;09;50;12 - 00;10;04;54

Speaker 1

I promise you. Now, one thing don't do is in that process, there's some some breakup emails that I've seen that just sound arrogant. It's like, hey, you know, or they're they're not even truthful, you know, it's like, hey, this is the last email you're ever going to get. For me. It's clear that we're we're going in a different direction.

00;10;04;54 - 00;10;18;33

Speaker 1

We haven't met your needs. And, you know, we're taking you off the list tomorrow unless you respond to this or something like that. And, you know, when you sound like that, it's it's not how. It's not how I want to come across. And frankly, as a buyer, I would I would tell you to fly a kite, like if I ever got an email like that.

00;10;18;33 - 00;10;37;51

Speaker 1

And I have seen emails like that, they were trained by bad traders. Be genuine and make it easy to say no. And if you do those three things, if you work to really understand their buying process early in the process, you ask them to quantify it. And you know, you know, Chris, scale, at the closing process and really suss out some of those objections and, and the resistance with their reservations that they have.

00;10;37;52 - 00;10;51;37

Speaker 1

Then you make it easy to say, no, you're going to get more decisions you're going to in which ultimately, how you allocate your time is one of the most important things. As a salesperson, the last thing you want to do is be wasting your time on deals that are lost or deals that are that you're never going to win anyway.

00;10;51;41 - 00;11;07;32

Speaker 1

So you make that happen. You get more decisions. Don't avoid the know. Like lean into it if that's the case, so that you can use more of your time on higher probability prospects. Hope that helps if it has. Subscribe to the channel and check out MSB Sales Toolbox. Dot com, where I put a new resources every single month.

00;11;07;37 - 00;11;24;06

Speaker 1

It's things that we're working on. So I've got comp models, I've got, you know, objection playbooks, I've got scripting playbooks, I've got a bunch of different sales tools and resources that are in there. And like I said, we're adding to them every month. You have lifetime access and it's absolutely free. So Mssp Sales toolbox.com and or subscribe below.

00;11;24;11 - 00;11;31;57

Speaker 1

Hope to see you next video. Adios.

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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.