Overcoming Sales Challenges (EP811)

Robert Gillette from MSP Dojo shares practical strategies to help MSPs strengthen their sales skills, build a cohesive sales engine, and close deals with confidence. Discover how to overcome common sales challenges and apply actionable tips to grow your IT business.
Join Uncle Marv and Robert Gillette from MSP Dojo in this engaging episode of the IT Business Podcast. They break down what it really takes to build a strong sales engine for MSPs, from overcoming the awkwardness of asking for money to the power of teamwork in the sales process. Robert offers a fresh perspective on sales, treating it as a co-op game where collaboration between sales, technical, and executive roles is the secret to success.
You’ll hear why keeping your sales muscle strong is essential, how to avoid the trap of relying solely on marketing, and why consistent, small actions can make a huge difference in your sales pipeline. Robert shares actionable tips, like using personalized scorecards and referral calls, and explains how the MSP Dojo helps IT professionals practice and perfect their sales techniques. Whether you’re a seasoned MSP owner or just starting out, this episode is packed with insights and real-world advice to help you close more deals and grow your business.
Building a Strong Sales Engine: Robert explains the importance of having a structured sales process to ensure consistent client acquisition and business growth.
Overcoming Sales Challenges: Learn how to address common fears and obstacles in sales, including the discomfort of asking for money and dealing with objections.
Sales as a Team Game: Discover the value of collaboration between sales, technical, and executive roles to create a seamless and effective sales process.
Actionable Tips for MSP Growth: Robert shares practical advice on how MSPs can strengthen their sales skills, generate leads, and close deals with confidence.
The MSP Dojo Approach: Explore how the MSP Dojo helps IT professionals refine their sales techniques through practice and repetition, much like training in a batting cage.
Companies, Products, and Books Mentioned
- MSP Dojo – https://mspdojo.net
- Iceberg Cyber – https://www.icebergcyber.com
- Pandemic (Board Game) – https://www.zmangames.com/game/pandemic/
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[Uncle Marv]
Hello friends, Uncle Marv here with another episode of the IT Business Podcast, the show for IT professionals and managed service providers, where we help you run your business better, smarter and faster. So, I took a little break and had a discussion with Robert Gillette from MSP Dojo, and we are doing part two of our conversation. I had to stop the last one because it was on a good note about being happy where your MSP is.
[Robert Gillette]
Yeah, that's probably, yeah, it happens so rarely, you should probably just be satisfied in the episode.
[Uncle Marv]
Yep. But we wanted to get back and dig into what we should all be doing in, you know, facing those challenges with sales, closing deals and all of that. And Robert, let's just do a very quick recap.
So, MSP Dojo was something that you saw that MSPs were just needing a little bit of help. And was it more of, you know, closing appointments and deals? Was it confidence?
Was it, you know, just not getting the right guidance on where they should focus? What do you think you saw?
[Robert Gillette]
Yeah, it's such an interesting one because I don't tell, I don't sell people on what it really is. The sales is, well, we're going to fine tune your pitch and, you know, we're going to give you the, help you try out your silver bullets and, you know, we're going to work you through the 52 most common objections that you'll come across and all those things. Yeah.
Some of that's true. Some of that's not. I don't think there are really silver bullets, you know, that's fine.
But I think the honest part of it is that most of us are just weird. Like sales meetings, it's just, it's weird to ask people for money, you know, it's weird to be the expert. And when someone says, Hey, will you, will you tell me this?
And you go, yeah, but pay me. Like, that's just weird. I don't think we acknowledge it.
So not how human, humans built societies. That's not how it worked for a really, really long time is that I know a thing and I'm not going to tell you that thing unless you pay me. Right.
And so I think it's, it's not human nature typically to ask for money to just help people. We're so used to, Oh, you want this bucket full of potatoes? Makes sense to pay for that.
And I think this is the same reason why people will spend $2,000 on a new phone, but then like pause for $2.99 app. Like it just doesn't mathematically and logically makes no sense, but it's the, it's true. And Steve Jobs even called it out.
And so there's somewhere in there is the right answer. So what I believe the real value of the MSP Dojo is, comes from just the sales muscle being strong. Just getting to the point where you can ask people for money without making it weird for them or for you is it's a perishable skill.
It's like a muscle, like any other muscle in your body. And if you ignore it and you don't train it properly, it doesn't work very well. And so I think that's the real challenge.
That's why a lot of my members come to me and they run MSPs that are successful and they've been doing it for 10 years or 20 years or I just signed a guy up today that's doing it for 25 years. He's owned his MSP, but he hasn't signed a new client in three years. And he's just like, that's probably a bad idea.
So he invested in some marketing. He's paying a bunch of money for a bunch of leads. And he's like, I should probably figure out how to close those leads.
And it's not for any other reason that he's like, I just need to be the kind of company that closes new clients or I'm going to be in trouble. So I applaud him. I think that's the right attitude.
And it's just about keeping that muscle strong.
[Uncle Marv]
Now without giving away details, you know, that would identify anybody. Is this a small, large MSP?
[Robert Gillette]
The one I just referenced to you about is a two and a half million dollar MSP. Okay.
[Uncle Marv]
So got some people.
[Robert Gillette]
Yeah. I generally try and not work with MSPs that haven't like closed their first client. Usually around maybe half a million is where they start to poke around.
And most of them sign up somewhere around 750 or a million, you know, because the reality is you can probably, if you're in a decent market and you charge the right price, you can probably build a half a million dollar MSP by just telling your friends about it and being good at what you do. And you probably didn't start your MSP after working at Wingstop. You know, you probably have some connections in the industry or at least with your old job.
And so you can build a half a million dollar MSP with just some gold old grit and activity. And you don't have to be good at it because you're getting lots of referrals. And, you know, then it's somewhere around that half a million to a million point where you're like, well, I got to start selling to some more strangers, which means I have to be a little better at this.
[Uncle Marv]
All right. Enough about me. Let's move on to...
[Robert Gillette]
Take it personally, Uncle Marv.
[Uncle Marv]
So one of the things I think that I liked about the dojo is you've been talking about sales as a team game. You know, we talked last time where, you know, the owner just hiring the marketing person or the salesperson and saying, just go out and save me. It's more of a holistic thing with, you know, the owner taking some responsibility.
How many other team members can be involved in that, you know, beyond the owner or sales or marketing?
[Robert Gillette]
Man, you're... Yeah. Gosh, such a great question.
Yeah, you're good at this. So there's... Oh, camera.
How far do I go on this? In the MSP Growth OS, we talk about how there's three circles that are like a Venn diagram for any deal to get done. And this is just on our side of the table.
On our side of the table, we have this Venn diagram of what we call sales, technical, and executive. Like, somebody's job has to be to run the sales process, to walk someone through the steps of stranger to signed contract. Someone has to own that.
Then there has to be the technical component, like someone has to make sure we can do what they need from a technology standpoint. You don't want to sign them up and then find out they got like 28 Linux servers. Now, that might just blow up your whole thing.
You know, some people don't work with Google at all. You got to be Microsoft or die. So there is this technical component where you have to be sure you can actually do the job.
And then there's this third component, which we call executive, which is owners like to buy from owners. This is a mission critical part of your business, whether you want to acknowledge it or not. And so at some point, we have to be able to speak one executive to another so that the executives are comfortable with who they are working with.
And that's just on our side of the table. But then there's the buyer side of the table, which is they have a technical component as well. They have an executive component as well, and they have a buying component as well.
So it just kills me when people say, like, well, I won't take a meeting with an office manager. Well, why not? They're the one running the buying process.
Now, they may not be the executive. They may not know the technical components. But someone over there has to run the process of gathering the vendors and choosing one, you know, even though they may not sign.
So like there's the way I like to think about this particular flavor of sales is it's not it's competition. It's like a co-op game. So, you know, in chess, I make moves, you make moves, and whoever has the best strategy wins.
And that's not how I like to think about MSP sales, maybe car sales, but not MSP sales. MSP sales is more like a co-op game, like the game Pandemic. I don't know if you've played that game.
It's one of my favorite games. My wife loves it.
[Uncle Marv]
I went through the Pandemic. I did not play it.
[Robert Gillette]
Yeah, it's thankfully it's probably maybe what turned us on to it. I don't know. But it's this co-op game where it's like I have certain skills and requirements as a player, and the other people have certain skills and requirements as a player.
And if we don't all do what we're supposed to do, we will lose the game. The board will beat us. And so I don't think we're competing against the client to position them into a way where we win.
It's more like, hey, I have certain skills and I have certain requirements. You have certain skills. You have certain requirements.
How do we work with each other to beat the board? And the board is you have crappy IT outcomes, and that needs to change. So how do we work together so that both of us can fulfill our requirements while using our strengths so that when we win, you no longer have bad IT outcomes?
[Uncle Marv]
So I partly ask that question for me in the sense of I have seen some very good sales combinations when I've been looking for stuff. I love it when a salesperson is teamed up with a tech person because it's nice for the salesperson to say, you need this, you need that. But it's nice for me to get the technical reason, OK, well, why do I need this?
And I just ran into a situation with a prospect. Yes, I have them. Where I was talking to somebody about upgrading their network and stuff like that, and the comment came across, you're just trying to get us to buy something.
Like, no, no, no, I'm not. Trust me. And here's the reason.
And I was able to give them, here's the age of your equipment. Here's the mean time to failure. Here's this.
And if this happens, your downtime might be this. The whole conversation changed.
[Robert Gillette]
Yeah, and that would be loosely what I'm referring to when I say executive. You know, and you see this a lot of the time with, you know, technical account managers where they go, hey, I'm really nervous. I have to go ask these guys to spend $10,000 on a server, you know, or some giant Windows 11 upgrade or something like that.
And then, you know, what they're really saying is, like, I feel like I have to go beg for money. And that's a very understandable fear or concern to have. So the question I always ask is, well, why should they pay for that?
And if your answer is, because it's a best practice, no wonder you feel like you're begging for money. But if the answer, if I said, like, well, why should they buy a new server? If they say, oh, so they could reduce their employee turnover by enabling work from home.
You're not going to have any concern getting that approved. If work from home is one of the big business challenges they have. And the same holds true for new client acquisition as well.
You have any idea how easy it is to just do nothing? Like, man, I have this MSP and they're not terrible. I haven't been hacked.
I don't like this guy's stupid face, but it technically works. But then I clicked on an ad and now I'm here reading your blog article. And sure, I'll hear what you've got because you've got a good chat bot that pops up and they talked me into an appointment.
So now we've got 30 minutes on your calendar and a team's meeting at the end of my day, which doesn't really cost me a lot. Do you have any idea how easy it is for that prospect to just do nothing, to just ignore the problem?
[Uncle Marv]
The devil I know.
[Robert Gillette]
You know? I mean, it's just so easy to do that. And then let's say you can even somehow convince them that they need to change providers.
Why would the business spend a dollar more than they're spending now? What do they get out of it? And it can't just be better IT, can't just be better technology support.
Don't make them do the hard work of figuring out what's in it for the business. Help them figure out what's in it for the business because businesses have lots of problems. They don't spend any money and don't fix.
I mean, how many problems do you have in your own business right now that you go, yes, I fully acknowledge that's a problem. I'm not fixing it. Just not going to.
It's not a top priority for me. We're just going to learn to walk with that limp.
[Uncle Marv]
I'm not going to answer that question.
[Robert Gillette]
Well, I mean, let's say the metaphorical you is you as the owner listening to this. Well, you're already vulnerable enough on these, Mark.
[Uncle Marv]
Yeah. Oh my goodness gracious. So very good answer.
Very, you know, thanks for rolling with the punches there because I didn't prep you for that.
[Robert Gillette]
That's all right. I'm here to do what I can.
[Uncle Marv]
But let's turn that back now to when we were talking last time, you mentioned sales engine. And part of the sales engine is having this process in place so that we're not trying to flip a switch when our largest customer leaves. So I imagine that this process of having the sales, the tech and the exec is part of that engine.
Am I correct in thinking that?
[Robert Gillette]
Yeah. Okay. Certainly part of it.
[Uncle Marv]
All right. So from a perspective of somebody that's like me at a point where I need to start doing something, what would be the first steps in developing this proper sales engine?
[Robert Gillette]
Yeah. And I'm going to do a little plug for a friend of mine just because like this is if I was going to, if I woke up tomorrow morning and I was the owner of a half a million dollar MSP and or a million dollar MSP and my client informed us, hey, we have plans to be acquired in three months. And just to let you know, they have an IT department.
We've loved working with you. You're amazing. But, you know, about 25% of your revenue is going to disappear, we're guessing sometime around the summer.
Here's what I would do. I would wake up every day and the first day I would go over and visit Michael Bakaic at Iceberg Cyber and I would sign up for his tool that would allow me to identify five businesses a day and I would send them their scorecard. And I'd be like, hey, Uncle Marv, here's a handwritten letter.
You are a pillar in our community. I've heard your name, I've seen your ads, whatever. I have this tool that does a cyber scorecard and I was surprised to see your score was so low.
I don't know who does your IT, but I'd be happy to talk to you about how this works and how this was calculated, if it would serve you. Have a great day. And I would drop that in the mail and I would send five a day to local businesses and take me about a half an hour and I am, I would be willing to bet my entire MSP that I would close 25% of my revenue before I lost that client.
I'd be willing to bet. That would be the only thing I did differently and I'm pretty sure I could pull it off. Now maybe your market doesn't support that.
Maybe that's a tool you never want to buy. Maybe that's not authentic to your personality. I would have no problem sending that to people, but maybe that feels icky to you.
It doesn't really matter. Don't do what I did, but do something. What most people do is nothing.
Because here's the deal. If you give a sales guy two jobs, your job is to make 100 cold calls a day and clean this toothbrush with your toilet, or clean this toilet with your toothbrush, okay? So those are your two jobs, make 100 cold calls every day and go clean the bathrooms with your toothbrush.
They will wake up in the morning and go, I might as well get the toilet thing out of the way. Because it's just, this is hard. Sales is hard.
It's not normal. If you feel like it's normal, congratulations. You've got the gene or maybe you're a sociopath, I don't know.
But even for me, who's made a ton of money doing this, it doesn't always come naturally to me. I have to take steps to will myself to do it. And so the very first thing is just do something and do it every day.
Call up someone in your phone book and ask them for a referral. Seriously, just how hard would it be? Call up if you've got, just do the math on this, if you've got 35 clients and you wrote down five things, you know, every client uses like payroll, a bank, insurance, whatever.
And you just said, I'm going to call one person every day and ask them who you're using for that and asking them if they're satisfied. And if they're not satisfied, if I could refer them to someone I trust. You'd probably uncover one to two referrals for your network every single week.
And imagine what your business would look like if every single month you were creating eight to 10 people that owe you a favor. What would that do to your the referrals incoming? Like the biggest, most important thing for a sales engine is are you doing something?
That's the first lever you can pull on its inputs. Even if you have a bad machine that's inefficient and broken parts, if you just double the material that goes in the front end, you're going to spit something out the other. Does that help you?
Is that what you were looking for?
[Uncle Marv]
A little bit. I was thinking of something a little beyond that, but that's obviously a good start.
[Robert Gillette]
I mean, and if you're already doing that, give me a call. I'll give you 30 minutes free consulting. We'll figure out the next part.
But I'm willing to bet most people aren't doing that. This is the most common problem.
[Uncle Marv]
So now I can't speak to the numbers, but I know that a lot of a lot of people that listen to this show, a lot of MSPs that I have spoken with over the years, the first thing that they do is look to some marketing template based system. They're posting on social media. They're getting a mailing list and sending out blanket, spray and pray type mailers.
Yep. I'm saying this at the risk of hurting anybody I've had on the show before, because I think a lot of them do a good job in putting together, you know, marketing campaigns and systems and stuff like that. But the idea of a cold call versus referrals, there's a lot of people that, I mean, when you mentioned, you know, just calling up people and asking, it sounds more like a cold call than a referral call.
[Robert Gillette]
It could be. I mean, but here's the thing. I'm speaking from my personal place of excellence.
I told you what I would do. Because I can do that. I've done a lot of sales.
And so I'm not saying these are, these are not prescriptions. These are just examples. And I think one of the reasons why marketing guys get a bad rap is because someone does.
They sit there and they go, oh crap, I need to close a bunch of revenue. And so they pay a marketing guy four grand to send out 800, you know, or 8,000 postcards or something. I don't know what the going rate is, but they send out a bunch of postcards and then they sit there and they wait for the business to come rolling in.
And then it doesn't. And they blame the marketer. With each of those things I mentioned, if I just asked for referrals for my network, or if I just sent the letter, I might get, I'd get more than nothing.
But there's a reason why we call it a sales funnel. You put things in the top and they funnel down to further steps. Nobody has a one step funnel unless you sell flashlights on Amazon, where I make listing people buy flashlight, you know, that's a one step sales funnel.
That's not what we have here. We have to warm people up to the idea of not only like changing IT providers, but changing for a certain reason and then asking us about it and then negotiating with us and then eliminating other providers. And then following our, like there's so many steps that have to happen to go from even referral to closed revenue.
Like we have to understand that it's not just do something. It's do something every day or every week or whatever works for you. But it's have this consistent momentum towards the thing.
And that's just the first lever. So let's say you double or triple or 10x your input of what you're dumping into the machine. If you do that for a time and you're still not having enough come out the other side, well, the first level is, am I doing enough?
The second level is, am I doing the right thing? That's the next lever you get to pull on. And then the third level is, am I any good at it?
So those are like the three big levers we have in our sales engine or to creating a sales engine is, am I doing enough stuff? Is it the right stuff? And when I do it, am I good at it or is there something off?
The dojo specifically is about, am I good at it? But there still is it the right thing? And am I actually doing it?
Those are the three big levers. OK. So there's this get a little heady, this is a little, yeah, I'm trying to be delicate with my questions and my comments, because you're not going to hurt my feelings.
[Uncle Marv]
No, it's not you. It's not you. It's the other people I've had on the show.
The other marketer is like, oh, he just poo-pooed on marketing campaigns, which I'm trying not to do. I'm trying to find a way where they all work together.
[Robert Gillette]
And I'm not trying to either. I love marketing. It has its place.
I think we expect too much from marketing.
[Uncle Marv]
All right. That, that sounds fair. Now you mentioned the dojo again, because really this all comes back to regardless of what you're doing, are you doing it well?
Because that's where it sounds like the dojo really can come in and say, OK, listen, this is what you need to focus on to make it work for you. So how tailored can you be with the dojo?
[Robert Gillette]
So with the dojo in our open sessions for our just our, you know, you join and it's just the minimum we offer, it's, it's not tailored to the individual MSP. It's tailored to the prospect. What is the prospect going to say to you?
And then we give you some examples of how you might respond to that. And if you really don't know what you're doing, we can give you some suggestions. But I like to think of the dojo specifically.
It's like, if you want to hit home runs, someone has to teach you how to hold the bat, where to stand, put your feet, spot the pitch, swing through. And this is a baseball analogy. So maybe this doesn't resonate with everyone.
But like there's a there's a knowledge component to how do I hit home runs? That is mission critical. But then you don't just go straight to a game and try and hit a home run.
What you usually do is you get into the batting cages and a machine throws you the same pitch over and over and over and over again while you try and do the thing you've learned. That's the MSP dojo. We are just the batting cages.
So if you don't have a coach, if no one has taught you how to do this, you will catch a fastball to the dome and it's going to hurt and you will learn something. But it is realistically the last step of the process. It's the are you any good at it?
Are you any good at swinging at this fastball that comes at you the same way every time? And then once you feel really comfortable with that, you can then step into the game and deal with all the other variables that come from trying to hit a home run. And that's what a client meeting is, is all the other variables.
[Uncle Marv]
So in the dojo. I've tried not to ask you specific.