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Published on:

13th Jun 2025

You're Only Scratching The Surface On Discovery Calls

In this episode Ray shows you how reps with all the right questions still blow the deal—and how one simple shift in how you run discovery can help you outsell competitors, even when your price is higher.

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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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Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

Transcript
Speaker A:

If you've got a good sales playbook to run your discovery process, you've got a head start.

Speaker A:

But if you are using that playbook like a checklist and just asking the questions that you think you're supposed to be asking, you're missing more than information.

Speaker A:

You're missing deals.

Speaker A:

Because a lot of reps ask good questions.

Speaker A:

The problem is they don't strategically follow up on those questions at the right time and they just work through the playbook and leave a ton of information that could help them close the deal and edge out their competition and understand the objections and the obstacles that they're going to face in the process.

Speaker A:

They leave all those things aside because they're treating this thing more like a checklist than an actual diagnostic process.

Speaker A:

Hey, what's up?

Speaker A:

I'm Ray Green, founder of MSP Sales Partners where we help MSPs and IT businesses build high performance sales engines.

Speaker A:

And a couple of weeks ago I had a client ask me to review some sales calls.

Speaker A:

They have been struggling with their close rate.

Speaker A:

It's not abysmal, it's not terrible.

Speaker A:

The reps are decent, you know, like the, they're, they're closing deals.

Speaker A:

But if you look at where they were 12 months ago and where they are today, there has been a fall off and they couldn't quite put their finger on whether they were doing something different, whether there was an opportunity to improve.

Speaker A:

So they sent us over some calls and said, hey, can you have a listen?

Speaker A:

When I listened, what I heard was a pattern that I hear very consistently in consultative sales, meaning any sale where you've got multiple steps and at least one of those steps is a discovery process where you are asking questions to understand your, your prospect.

Speaker A:

Right?

Speaker A:

Like I want to understand the problems that you're facing today.

Speaker A:

I want to understand the pains that those problems are caus, right?

Speaker A:

Like what are the symptoms that are associated with those pains and what are the obstacles that I'm likely to face in this deal?

Speaker A:

What are the objections that I'm, you know, potentially going to face as we move through this process and get a little further along, you know, budget, timing, all those things.

Speaker A:

That's what discovery is.

Speaker A:

And this is true whether that discovery process is 15 minutes or that process is an entire meeting, right.

Speaker A:

Like it's the same concept and running the process more like a checklist than a true diagnostic process where you are really trying to understand what's going on.

Speaker A:

And this is the challenge with a great playbook, because a great playbook will give a rep the framework that they need to move through that process.

Speaker A:

If you just follow a checklist by the end of that meeting or by the end of that discovery process, you'll have more information, right?

Speaker A:

Like, it's not like you're not going to get any information, you're going to be asking questions, you are going to be hearing the answers.

Speaker A:

So you will get information that will help you close the deal.

Speaker A:

The problem is if you only run the process according to what you've got in front of you and you like check the boxes as you go through, like, okay, cool, okay, cool, okay, I got this.

Speaker A:

And you're not really listening and you're not really thinking, whoa, wait, that's a flag or that's a clue, or that doesn't make sense, that's inconsistent.

Speaker A:

Like if you're not paying attention and you're not actively listening, and most importantly, following up your questions with strategic follow ups, you're trying to frame your prescription, which is your service.

Speaker A:

Assuming you know where they're at, you know the problems, and your company can solve those problems.

Speaker A:

When you go to sell, you're effectively offering a prescription to those problems, right?

Speaker A:

If you've only gotten to the surface and you've not dug in and truly understood what's below that, you're at a disadvantage.

Speaker A:

Especially if there are other players involved, right?

Speaker A:

If there are other vendors that are involved in this process, the person that understands the prospect best and really understands the emotional drivers, the why things are frustration, which ones are more important to which buyers in the process, the person that knows that is going to have a better opportunity to frame the prescription in a way that the buyer wants it.

Speaker A:

Now let me give you a couple of real life examples like from these calls early in the discovery process.

Speaker A:

They're talking and the rep basically asks, hey, why are we talking?

Speaker A:

And the prospect says something along the lines of, well, you know, we've got a provider, we've got an IT company today, and they're okay, but we kind of think that we may have overkill here, that they may be selling us a whole bunch of stuff that we don't necessarily need.

Speaker A:

And the rep says, oh, hey, totally understand, I've heard that before.

Speaker A:

You know, what we'll do is I've got a few more questions that we'll walk through, then we'll do a network assessment.

Speaker A:

On the network assessment, we can take a look at how many machines you have, what tech stack, they have, all that stuff, and we can give you a really good answer on that by the second meeting, if that's cool with you.

Speaker A:

And they, and they move on.

Speaker A:

And then they change the subject.

Speaker A:

They move on.

Speaker A:

Now, the rep.

Speaker A:

That wasn't terrible, right?

Speaker A:

The rep acknowledged it.

Speaker A:

The rep said, hey, I'm going to help you answer that question.

Speaker A:

And I think for the most part, like, it comes across as a person that's providing a service.

Speaker A:

So it wasn't the worst answer.

Speaker A:

However, if it were me and what I coached them on was if I heard, I think I might be, this might be overkill, or I think that I might be paying for too many services.

Speaker A:

Instead of saying, I'm going to help get you an answer, what I'm going to say is, tell me more about that.

Speaker A:

Like, what makes you think that this might be overkill?

Speaker A:

I'm going to pause and I'm going to let them tell me.

Speaker A:

Why is that?

Speaker A:

You know, the fact that it might be overkill?

Speaker A:

I think that that probably means, hey, we might be paying too much for a whole bunch of services that we're not using.

Speaker A:

That's possible.

Speaker A:

But what that could also mean is, well, I think it's overkill because, man, like, we.

Speaker A:

Every time we log on, things just seem really slow all the time, right?

Speaker A:

Like page pages loading and getting access to stuff just seems really slow.

Speaker A:

And I think it's because of some security stuff that they put on.

Speaker A:

Or they might say, I don't know, they talk to us about, you know, the cybersecurity stuff.

Speaker A:

And I just don't think it's like that big of a deal for us.

Speaker A:

Like, we're a small business, then the likelihood of us getting hacked is like, is.

Speaker A:

Is basically zero.

Speaker A:

So I just don't know why we're.

Speaker A:

We're investing in all this stuff.

Speaker A:

Well, all of those very different concerns, right?

Speaker A:

Like, if it is like the one that you assume, and it is, hey, we're paying too much for services.

Speaker A:

Okay, well, I would address that one way in a proposal if it was, hey, it's super inefficient and it's annoying and I've, you know, I've got to do notifications and tokens and this and that and your authenticator apps.

Speaker A:

And it's just, it's like, really frustrating for me and my team.

Speaker A:

I'm going to address that differently in a proposal.

Speaker A:

And if they tell me, well, you know, I mean, we're paying for all this cyber security stuff, and I just don't think it's worth that now.

Speaker A:

I know that because I'm going to perhaps be talking about the exact same thing when we Come into the proposal.

Speaker A:

Now if I walk into the proposal and I say, hey, I know you thought it was overkill because it was too much money.

Speaker A:

Here's what we've managed to do.

Speaker A:

We've managed to get your cybersecurity a lot cheaper so that it's more cost effective for you.

Speaker A:

And they go, I still just don't, I still don't feel it.

Speaker A:

Or they go, that's not really at all what I was trying to address.

Speaker A:

In that scenario, what you hear is what's on top of the surface without digging in, without double clicking, without understanding what is below the surface.

Speaker A:

What is driving that, what is the thought process behind that, what are the frustrations behind that, what are the pains or the problems or the actual symptoms that they are dealing with on a day to day basis or the real concerns that they have, then you potentially miss the deal.

Speaker A:

And you miss the deal because you don't have all the information that you need to come into the proposal with a strategy.

Speaker A:

And that is crucial.

Speaker A:

But if another rep, say they're talking to a couple companies and I ask those questions and then I bring in a proposal, guess what?

Speaker A:

Even if I come in a little bit higher, as long as I'm hitting their actual concerns and what their real problems and pains are, chances of me winning the dealer higher.

Speaker A:

Another example came up and this is actually, this is a really common one in it anyway.

Speaker A:

And they said, you know, well hey, like what's, what's not working with your current provider.

Speaker A:

And the prospect said, well the response time sucks.

Speaker A:

And the rep immediately goes into like a two minute monologue of, of well, you know, we've got, you know, here's our CSAT scores and you know, here's our response time metrics and here's a chart that shows how quickly we respond.

Speaker A:

And you know, you aren't going to have that problem with us.

Speaker A:

Let me just flood you with information to kind of like deal with what I think the objection is and then move on.

Speaker A:

Right?

Speaker A:

And again, worse things could happen, right?

Speaker A:

Like that's not, it's not like that's an F on the report card, but it's not an A because an A is understanding what that means.

Speaker A:

Right?

Speaker A:

So if somebody says response time to me, I'm going to think, well let's, what does that mean?

Speaker A:

Right?

Speaker A:

Like what is, what is a good response time?

Speaker A:

Like what is the response time you're getting today?

Speaker A:

What is your expectation of response time?

Speaker A:

Like what if the prospect just has a wildly irrational expectation around what response time Is you should know that before you go into the proposal, by the way, it can still be addressed, but you need to know that.

Speaker A:

You need to understand what the deal is.

Speaker A:

Even more importantly, what I want to know is what's behind the response time issue?

Speaker A:

Why is that a problem?

Speaker A:

So, all right, response time sucks.

Speaker A:

Okay?

Speaker A:

Like, so what is the response time today?

Speaker A:

What's.

Speaker A:

What's.

Speaker A:

What's your reasonable expectation?

Speaker A:

Like, what are you.

Speaker A:

What are you anticipating with the new partner?

Speaker A:

Cool.

Speaker A:

What is the response time costing you when that happens?

Speaker A:

Like, what.

Speaker A:

What does that mean for you and your team?

Speaker A:

Like, has it led to any missed deadlines?

Speaker A:

Has it led to any frustrations with clients?

Speaker A:

Has it led to any miscommunication?

Speaker A:

Like, what.

Speaker A:

What is the reason that that is a problem?

Speaker A:

Because that's the fact.

Speaker A:

Right.

Speaker A:

But that's not the feeling.

Speaker A:

That's not the thing that's really motivating.

Speaker A:

It's not response time.

Speaker A:

It's what response time causes.

Speaker A:

And you can't fix a problem that you don't truly understand.

Speaker A:

So if you think about this process more like a doctor, who would you trust more from a prescription standpoint?

Speaker A:

Would you trust a doctor that came in with a script and off their clipboard said, let me ask you this, and this and this and this and this?

Speaker A:

And at the end of it said, based on your score, here, here is the thing, and that was it.

Speaker A:

Right?

Speaker A:

Or you talked to a doctor that said this, this.

Speaker A:

Wait, what do you mean by that?

Speaker A:

Right?

Speaker A:

Like, what is.

Speaker A:

What's behind that?

Speaker A:

How often has that happened?

Speaker A:

How long has that been going on?

Speaker A:

How intense is that pain?

Speaker A:

Okay.

Speaker A:

Is it related to something else?

Speaker A:

Okay.

Speaker A:

And let me continue to work through my process.

Speaker A:

It's not that I'm throwing the clipboard out as a doctor.

Speaker A:

It's that I'm using this as a guide, but I'm using this and these to help me truly understand what is going on with you.

Speaker A:

So the prescription that I offer actually matters, right?

Speaker A:

Ends up being something that you want to buy.

Speaker A:

Now, there's three reasons this matters.

Speaker A:

First is obviously the information, right?

Speaker A:

Like, if you are working through the process and you get more information that helps you close a deal, then that's.

Speaker A:

That's good news for you, right?

Speaker A:

Like, you increase the probability of success.

Speaker A:

The second reason, though, is when you get them talking about the frustrations, when you get them talking about the problems that they're facing, the pains that they have, the symptoms that are associated with it, what you're doing is like you're activating some Emotion.

Speaker A:

Instead of me telling you what the problem is, I'm saying tell me more about that.

Speaker A:

So response time, okay?

Speaker A:

Like has that, has that led to any challenges?

Speaker A:

Has that led to any, you know, customer complaints?

Speaker A:

How long has that been a problem?

Speaker A:

Have you talked to the current, your current provider about that?

Speaker A:

What was the outcome of that discussion?

Speaker A:

When I'm having a discussion about that, what I'm doing is intentionally activating the emotion that's associated with that thing.

Speaker A:

Right?

Speaker A:

And if it's a negative emotion, that's good news for me.

Speaker A:

And it creates emergency.

Speaker A:

Like you're kind of transporting them back to that exact time when that was a problem.

Speaker A:

Because I'm now getting you to talk about that.

Speaker A:

Okay.

Speaker A:

Now the third thing, it gives you an opportunity to position yourself as a consultant instead of a salesperson and coach them through the decision making process.

Speaker A:

Because I can't tell you how many times I've been in a discovery process and somebody says something is important to them but they haven't fully thought it through.

Speaker A:

Me asking the follow up questions is essentially helping them make a better decision.

Speaker A:

And I'm coaching them, right?

Speaker A:

So you know, for example, if somebody says price, cool.

Speaker A:

Nobody wants to pay more money than they need to pay for services.

Speaker A:

I get that.

Speaker A:

But if somebody says, well you know, hey, what are the most important considerations for you?

Speaker A:

And they go, well, price.

Speaker A:

Chances are they haven't fully thought that through.

Speaker A:

And if you're selling something like IT services, chances are they don't know how to buy IT services.

Speaker A:

Like it's not something that you buy every week, okay.

Speaker A:

So they may say price.

Speaker A:

You asking the right follow up questions helps them understand that it's more than price.

Speaker A:

A simple question like, well, how are you going to know when you're getting a good price?

Speaker A:

I've had people sit back and go, well, I mean it's I guess, you know, and you can see them go through the thought process of I guess it's more than the actual price, right?

Speaker A:

Because nobody's actually just going to buy the cheapest shit on the planet because we wouldn't be talking like in a consultative sales process.

Speaker A:

So it's value, it's always value.

Speaker A:

We know that.

Speaker A:

But how do you convey that?

Speaker A:

How do you help them come to the same conclusion?

Speaker A:

It's really targeted follow up questions.

Speaker A:

Now this is mostly about discovery, right?

Speaker A:

But I will tell you this kind of a bonus tip.

Speaker A:

This is actually great for objection handling too, like knowing when to ask targeted follow up questions.

Speaker A:

And the right questions to ask will help you Overcome objections better than trying to like hit them head on.

Speaker A:

Because if you try to hit them head on and try to address them in like the old fashioned, let me overcome this objection type of thing, like I've got this silver bullet rebuttal that's going to make you go, oh my God, I completely changed my mind.

Speaker A:

Usually doesn't work that way.

Speaker A:

The way it usually works if you want to be effective at handling objections is you ask really good follow up questions that enable you to really understand what the underlying objections are and get them to come clean on where they're at on things.

Speaker A:

An example would be somebody says, I've got a, you know, I need to talk to a couple decision makers, right?

Speaker A:

Like I've got to talk to some other people or I've got to talk to my partner, I've got to talk to somebody.

Speaker A:

And you know, by the way, if you've done a good discovery process, then you should be ahead of a lot of these things.

Speaker A:

But inevitably like you, you get this deal and instead of saying, oh okay, great, like, so I totally understand this is a, you know, normal in the process, why don't we give you some information, you can take that to talk to him, we'll schedule a follow up.

Speaker A:

Like, no, no, no, you say, okay, great, not a problem at all.

Speaker A:

Totally understand.

Speaker A:

Just out of curiosity, where are you on in this process?

Speaker A:

Like on a scale of 1 to 10, you know, with 1 being you want me to get the hell out of your office right now and 10 being you're waiting for me to hand you a contract to sign so you can give me a credit card, where are you at in the process?

Speaker A:

They will, you know, usually tell you, well, you know, I'm a seven or eight.

Speaker A:

Okay, great.

Speaker A:

Like what's, what's missing to make that a 10?

Speaker A:

And now you're having a completely different conversation.

Speaker A:

Well, I mean you're actually, now you're continuing to have the real conversation, right?

Speaker A:

Because what they were trying to do is like say, hey, let me just, let me put off making this decision.

Speaker A:

And by asking the right targeted follow up questions, you're saying, let me help you through the decision making process and let me help me understand where you're at in this process so that I can understand the right next move for me to make.

Speaker A:

Now here's the main point.

Speaker A:

The thing that I really want you to take away from this is a playbook is phenomenal and it is a guide.

Speaker A:

It is a framework to help you run great discovery.

Speaker A:

But it is not a replacement for an actual conversation.

Speaker A:

And if you are selling in a consultative sales environment, you have to be adept at listening.

Speaker A:

You have to be adept at understanding and processing the information that you're hearing while you're working through your playbook, while you're working through that process and determining what's a clue that needs to be followed up on what is, what is the thread that you need to find to pull, right?

Speaker A:

Like what is something that when you hear, you're like shit, we need to double click on that.

Speaker A:

Like there's something below the surface on that.

Speaker A:

And I have found personally that has been the thing that helps me close more deals than most other people.

Speaker A:

Without feeling like I've got to twist people's arms, without feeling like I've got to create this high pressure environment and without feeling like I've got to have this silver bullet rebuttal in my back pocket that's going to overcome the objections, right?

Speaker A:

Like I.

Speaker A:

Because I know them early on and been super helpful for me.

Speaker A:

So I hope this has been helpful.

Speaker A:

If it has, subscribe to the channel or jump over to MSP salestoolbox.com and you can get access to our, our sales toolbox for free.

Speaker A:

It's a collection of resources and playbooks and templates and, you know, forecast models.

Speaker A:

Like we're putting stuff in there almost every single month so you can get access to that lifetime access MSP sales toolbox.com I'll see you in the next video.

Speaker A:

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.