full

full
Published on:

31st Oct 2025

Why Nice Reps Lose MSP Deals

Ever been on a sales call where your gut tells you something's off, but you say nothing? That disconnect between what you're sensing and what you're saying is killing your deals and destroying your confidence. In this episode, I break down why ignoring red flags wastes your time and erodes your self-respect, and I share a real story where addressing the tension in a call turned a disengaged prospect into a signed client in 50 minutes. Learn how to trust your intuition, have candid conversations the right way, and why prospects will actually respect you more for it.

/

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

//

Follow Ray on:

YouTube | LinkedIn | Facebook | Twitter | Instagram

Transcript

0:00

If you're sensing something is off in a sales call and you do nothing about it, then you are

0:04

killing the deal before it ever got started. One of the reasons that you may be struggling in

0:09

sales may have nothing to do with your process, may have nothing to do with your your product may

0:14

have nothing to do with the actual pitch. It may very well have to do with what's coming out of

0:21

your mouth and what you're saying, and how you're engaging with your prospects doesn't actually

0:25

align with what's going on in your gut. Say you're 15 minutes into a discovery call with someone, and

0:30

everything about this prospect in this meeting is basically telling you there's no need here.

0:36

There's no urgency. The problem doesn't seem big enough. They don't seem very interested in this

0:41

thing. They don't seem to be in much pain. And you say nothing. You know what's going on with your

0:47

gut. Like, your intuition is telling you something and it doesn't align with what your actions and

0:52

what your words say. That creates a misalignment that has two really significant impacts on you.

0:59

And the first is super practical. It's on your sales, right? So if you were seeing these things

1:04

early in the process and you choose to do nothing, you choose to say nothing. You choose just like

1:09

you just go with the flow. Then the likelihood of those deals is low, right? Like the probability of

1:15

actually closing those very low. You end up wasting a bunch of time. You end up wasting a

1:20

bunch of resources, a bunch of energy. Like even as you're creating the proposal, you're like, I don't

1:26

think this is going to work, right, but you do it anyway. Like you're just like you're investing the

1:30

time. Sure, you get to the end and you get ghosted. You get told like fly a kite or your prices are

1:36

way too expensive and you don't even have the ability to kind of overcome that. And the worst

1:41

part about this whole thing is you get to the end and you're like, I kind of knew it, right? Like, I, I

1:47

kind of knew it was going to be too expensive. I mean, in fact, when I mentioned price like two

1:51

weeks ago, like they, they basically, you know, got up out of their chair, but I didn't do anything.

1:56

Right. And that's the frustrating part. You haven't gotten the deal and you've wasted a lot of time.

2:01

And time is. It is your most precious asset. It is your most valuable asset. And how

2:08

you allocate it is going to determine how successful you are as a salesperson or not. So

2:11

when you're spending it or investing it into these deals that you know, have obstacles that you

2:17

know, have objections, and you spotted those things days, weeks in advance and never address them at

2:23

that time. All of that time is just basically lost. And that's again, not good on sales and not good

2:28

from a time allocation standpoint. Now the second issue is actually internal, right? Like what it

2:33

does to you as a person when you're when you're going through the motions and you're doing this.

2:38

And I think this is a the bigger issue actually, because when you as a salesperson

2:45

just play the nice guy, right? When you avoid candid conversations, when you don't address

2:52

things that your intuition and your gut says need to be addressed when you spot an obstacle or

2:59

an objection and you're afraid to talk about it because you don't want to create tension in the

3:05

room or you don't want to, you know, like upset the apple cart like you wanted to keep this, you know,

3:10

nice and steady. And if I address that thing, it might get a little uncomfortable. So those candid

3:14

conversations about price, you avoid them. Those times that you sit and let somebody just waste

3:20

your time. Right. Like completely disengaged, curt, rude answers, you know, sitting on their phone. Like

3:27

I said, like. And and you don't do anything when you do that consistently. When you quiet yourself,

3:32

when you when you make yourself smaller in order to protect the feelings of the other person

3:37

across the room. It's like creates this internal conflict because you are

3:43

suppressing what you think you're suppressing what you what you want to say. You're avoiding

3:48

saying what you really need to say and what you want to say. And what that does is it just erodes

3:54

your confidence. Over time, it chips away at how you feel and it changes the energy that you bring

4:01

to meetings. Over time, it changes the the way that you project yourself. And it changes. Obviously,

4:08

like I was saying before, it changes the results that you're getting, which also adds to this. So if

4:13

you're not getting results on top of going into meetings and feeling like, gosh, let that person

4:17

run all over me, or I was afraid to say this thing or, you know, I didn't address like something that

4:22

was clearly obvious and it bit me in the ass later. Doing that over time isn't a good way to

4:28

make a living. That is not how you as a person build yourself up over time and you spend a lot

4:33

of time working. So that is, at least for me, how I want to spend the better part of my day. Okay, like

4:39

I want to be real. I want to be honest. I want to be, like, aware of what my my intuition is telling

4:45

me. I want to be able to trust it. I want to have human conversations, authentic conversations, even

4:49

if those are candid conversations, even if it creates a little bit of tension, even if it

4:54

requires challenging a prospect. Those are the things that when you do that consistently over

4:58

time, you will build your confidence as a person outside of sales like. But you will build your

5:04

confidence as a person and you will end up getting more deals and feel better about it in

5:09

the process. Okay, now let me tell you about a call that I had recently where this this played out

5:14

and I was on it was a virtual sales call. And he was he was talking about our fractional sales

5:19

management program. He had booked in a call. And so we get into this and it was like maybe, maybe ten

5:24

minutes or so. And his body language is like most of the time his head was down.

5:31

Um, you know, his answers were were few sentences here and there, uh, just the tone of the

5:38

call and the energy and, like, it just it just screamed, dude, you don't want to be here or you're

5:43

angry or you're distracted, or I said something like, I don't know, I don't I don't know what that

5:48

is. So I stopped and I said, hey, Gary, can I ask you a candid question? He He's like, yeah, sure. Why are

5:54

we here today? I mean, you booked the call. I'm sure that you don't have have time to waste. Um, like, as

5:60

we're going through this, I just kind of sense maybe you're you're distracted or or disengaged

6:05

or or maybe somewhere else, and I. Is it is it something that I asked or something that I said

6:10

or is it's not a good time? Do you want to you want to reschedule this any pause? Any chuckled a

6:16

little bit and he says, I don't have any of the answers that you're you're asking questions to.

6:20

And I, I know that you're just trying to get a lay of the land of like, what you what you'd be

6:25

working with and everything you said, but I, I feel like an idiot. Okay, first of all, thank you. Like,

6:30

that's like, thank you for being candid. Second of all, completely understood. That's that's not how I

6:35

intended it. So sorry if it, you know, if it made you feel that way. So tell you what. Why don't we

6:39

just scrap all that? Let's just pretend that we're building on an empty lot, and you tell me what you

6:46

want this to look like when, you know, 18 months from now, right? Like we've gotten this process

6:51

going and it's rolling, and you've got a rep hired and they're, you know, they're they've got pipeline.

6:57

Go. Just walk me through that. Let's start there and work backwards. And he said, okay, Eddie. And he

7:02

starts mapping that out. Right. And he starts and he sits up. His body language changes. His energy

7:08

changes. My energy changes. 50 minutes later, he is signed up. We are going to help him build the

7:14

sales process. We're going to help him with the playbooks. We're going to help him recruit a rep,

7:17

and then we're gonna help him manage them. 50 minutes later, that's what happened. And it was

7:20

because stopped and said, ah, it's I sense something is off here. Let's address

7:27

that. Instead of me continuing to go through my process, which, by the way, would have been a

7:32

complete waste of time and maybe, maybe made him feel more like shit. I had more questions to like,

7:37

understand now. Hopefully I would have picked up on it, but you know what I mean. Like, I would have

7:41

wasted my time in that call on something that was already making him uncomfortable. And you know, if

7:47

the purpose of, you know, discovery is identifying pain and probably cool. Done. Got it. Now let's move

7:52

on. Let's talk about the prescription of what this is. Right. So that's what I mean by calling it out

7:58

by trusting your intuition in your gut. So this happens a lot actually. I mean when this pricing

8:04

is a really common one, you know, when, when we mentioned pricing or when you mentioned pricing,

8:08

you may see somebody shift, you may see a body language change or a facial expression something.

8:14

And a lot of people just let that go. Well, if it's me, I'm going to say, hey, I

8:20

noticed, you know, if it was Gary. Hey, hey, notice Gary when I mentioned the, you know, the price

8:25

there, you kind of made a shift a little bit. If I, if I may ask, is that because it's way more than

8:30

you were expecting, or is that because it's it's way less than you're expecting? Um. And they'll

8:35

tell you. Right. But instead of ignoring it and never addressing it or trying to address it way

8:41

later in the process, just hit on it, right? Like just actually stop, pause. Human to human. Have

8:48

the conversation. I'm not saying you don't have to be a douche about it, you know, to be, you know,

8:51

disrespectful. Like you don't want to be an asshole. Tonality is everything. Delivery is

8:56

everything. Also, don't make assumptions about what you think it is. Like with Gary, I could have

9:00

thought, wow, maybe he's just an asshole, right? Like, maybe. Well, that's not it, right? So don't make

9:04

assumptions. Don't, you know, don't deliver it the wrong way. But when you do this the right way, you

9:10

will earn credibility from your prospects because they will respect you more for being willing to

9:17

deal with a little bit of tension and a little bit of discomfort in order to have some

9:22

boundaries, right? Like and have some self-respect and, and demonstrate, you know, project some

9:27

confidence so your earned credibility you will close more deals, which, by the way, also feels a

9:32

lot better, like sales is a lot more fun when you're when you're closing deals and you as a

9:38

human will feel better about yourself in this process, and you won't let sales be

9:45

something that chips away and makes you feel Feels smaller and instead allows it to be a

9:51

platform for you to get stronger, for you to get more confident, for you to step into those

9:56

conversations. And they get easier over time. Way easier. So you'll be shocked at how many times the

10:01

prospect will actually appreciate the candor, because it's a it's a show of respect, in my view,

10:08

and I have yet to actually have it backfire on me when it's when it's delivered the right way. So I

10:13

hope that's helpful. If it has been subscribed to the channel, we've got more sales tips every

10:17

single week. We also have a weekly email that you can get access to, as well as our entire sales

10:23

toolbox, the MSP Sales toolbox. If you're selling MSP services, it's got playbooks, scripts,

10:29

frameworks. We're adding new stuff in every week, like stuff that we we use with clients that's at

10:34

MSP sales Toolbox, comm. So just drop your email in there and you can get more sales tips. Hope to see

10:39

you in the next video or the next email. Adios.

Show artwork for Repeatable Revenue

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.