Why Your MSP Sales Hires Keep Failing
I burned through $50,000 and four virtual assistants trying to fix my operations and tech stack, and things only got worse. The problem? I was trying to skip the hard part - actually understanding what needed to be fixed before hiring someone to fix it.
Dan Sullivan's "Who Not How" advice is brilliant, but there's a critical piece missing that cost me nine months and left my business in worse shape than when I started. The real formula isn't just "who not how" - it's "you, then who, somehow."
I see MSP owners make this exact same mistake on the sales side constantly. They hire agency after agency, SDR after SDR, trying to outsource their way out of a problem they don't fully understand. If you've burned through multiple people in the same role, the role is probably wrong - not the people.
You don't need to become an expert, but you need to understand the problem well enough to know who you're hiring for, what success looks like, and how to measure progress. Otherwise, you're just throwing money at a problem and hoping it goes away.
This was an expensive lesson for me. Hopefully you can learn it without paying the same tuition
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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
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right. So this is really embarrassing to admit, but last year
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I burned through four virtual assistants and about $50,000 in operations consultants.
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And after nine months,
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we were worse off than we were before.
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We had broken processes. We had tools that were half migrated and operations.
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The tech side of it was was basically in disarray.
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if you're an MSP owner or an IT business owner, then listen really closely to this, because
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this is actually a mistake that I see technical founders make
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all the time, the exact same mistake, just on the sales side of things, which is interesting because I kind of knew what the mistake was when I made it.
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I'm just used to not doing it on the sales side. So here's what I mean.
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Maybe you've heard of Dan Sullivan's advice. Who? Not house a dance a little bit is from Strategic Coach, and he's got a great book,
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called Who Not Hal. And
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the gist of it is, you know, instead of you as a business owner, figuring out how to do everything right, like, you see the problem, you go, okay, we need to fix that.
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Instead of diving in
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you go, you hire a who, right? You hire somebody who can tell you how to fix the problem and it's brilliant advice,
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I've employed it successfully many, many times. But there's a really critical piece missing, and it's, it's the one that actually cost me the $50,000 and the money invested in the four VA's.
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And all the time that I invested. And here's what happened.
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I spotted a problem, right? Like our funnels, our ops, our tech. The automations, like all of that happening in the background just wasn't running smoothly. It was kind of patched together with different platforms and different tools. And because of that, it was impossible to get data out of it.
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without data becomes very difficult at a certain point to grow because you're just like yours, you know, trying to figure it out. So I knew I needed data. I knew that meant, you know, cleaning up a lot of the tech.
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And what I did first was I went and hired a VA, right? Like somebody that was affordable, somebody that knew the tech, somebody that knew the platform.
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Somebody could come in and kind of be an extension of me
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just start ripping through and kind of implementing what I wanted. And the first VA that I had didn't work. All right. Well, yes, it's probably on them. They weren't that good. The second VA came in and they didn't work. All right. So that's kind of bad luck.
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The third VA came in
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It didn't work. Like, what are the odds of this
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fourth VA comes in? I'm like, for fuck's sake, are you kidding me? Like, this is clearly on me, right? Like at this point, there's the old Peter Drucker quote about,
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more than three people fail on a roll. It's not the people.
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It's the it's the roll.
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and I got a light bulb moment, you know, I know the answer to this. It is what Dan Sullivan recommends. It's who not how. Like what I'm doing is I'm making the mistake of trying to figure out how to do something and by because I need to know how to do it, to tell the VA how to do it.
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So what I'll do is I'll go spend more money, better money, hire a who to come in and tell me how to do it. So I hired a, you know, $50,000 consultant.
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know, they had stellar credentials. We we came with a recommendation from somebody that I knew. They talked a really good game, which, by the way, is not hard to do with me when it comes to ops and tech, because I only know so much. Right. So it's not hard to talk a really good game to me, because I don't know nearly as much as any ops person supposed to know.
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they get to work, and months go by and by and by. It's supposed to be like a 90 day sprint project or something turns into nine months plus, and at the end of nine months, we actually, like we said the agreement, we said like this clearly isn't working.
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Now, keep in mind we're talking about a small business here.
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we're not talking about, you know, a $20 million company. We're talking about a small digitally based business. This was, you know, last year, you know, more on like, the solopreneur, like, you know, had a had had just a few people on the team.
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like, this shouldn't have been that complicated.
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But after nine months, after 50 grand, we basically ended up in what was a situation that was worse than when we started, because we now had shit halfway implemented, right? Halfway migrated.
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we were in this CRM and they told us we need to go to this CRM. So we start migrating here. We need to move our website to this.
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And we started to like, so you start moving all these pieces around and you get to a point. And if you kill that project, you're like, shit, this is this is now twice as bad as it was before.
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I decided to go a different route. I said, you know what? I'm just going to I'm going to violate the rule. Like who? Not how. Like I'm just I want to roll up my sleeves
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I'm. I'm. Well, whatever.
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Like, I'm. I'm gonna roll up my sleeves. I'm going to dig in. I'm gonna figure it out. I'll solve this shit myself.
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So that's what I did. I spent several months, diving in, understanding the platforms, understanding tech, understanding, you know, things that are at a deeper level than what I knew before and just ripping through it, like, piece by piece, like understanding why we were using this, why this wasn't working, and what I found was,
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massive redundancy in our tech stack.
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Right? Like, I saw, half a dozen tools that were using 20, 30% of,
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hey, this tool can actually do everything. This tool can maybe at like 89% effectiveness. But the the complexity that's created by having multiple tools. So I just see like all this overlap, all this redundancy, I see us not using the tools that we have to capacity.
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I see us
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spending a boatload more money than we needed to on tech. I mean, thousands of dollars per month that were being completely wasted on things that not only
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didn't make much of a difference, like the, you know, the fact that one tool did something slightly better, it didn't really move the needle, but it did make things more complicated.
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It did require automations to connect the two things, and they were just like situation after situation after situation.
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But more importantly, what I learned in that process was
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what was needed to fix it.
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Right? Like what was actually the skills in the specific problems that I was solving instead of I've got an ops mess,
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or I've got an automation mess, right?
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Instead of saying like, hey, I've just got this big blob, here you go, solve it. I dug in enough to know these are the specific things that I'm looking for. These are the specific skill sets that I'm looking for, and I now knew enough to ask some some tougher questions. I now knew how to ask some questions that I was like, hey, this starts to smell like bullshit, right?
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And I now knew what success actually looked like, because I knew enough about the problem that I was trying to solve, to know what the solution looked like, and at least know what the solution architect needed to look like.
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Dan Sullivan is not wrong,
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the who not how
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is hands down the best way to build a business that you don't become a prisoner to. Right? Like that's at the end of the day. That's what that advice is for, is that as a founder, if you continue to go in and solve all the problems yourself, if you continue to be the source of the information, if you continue to be the source of answers, if you
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continue to be the center of your universe within your company.
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You will never break free of that because each extension of you is still dependent on you.
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I fundamentally absolutely agree it's who or not how. But there's a critical piece missing and it's you.
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It's you. Then who somehow. Right. Because sometimes, frankly, it's a problem that you jump in and you're like, hey, I can I can get a VA to to do this.
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They don't necessarily need to have a full skillset to tell me how to solve the problem. And you're okay. Like, I know enough about the problem to to hire somebody, just simply execute what I need.
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Sometimes I'm going to need a who. I'm going to need somebody that I go, hey, this is a this is a behemoth of a problem.
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This has more strategic implications. This has more complexity that's involved. This has whatever for whatever reason. But you you are the front end of that.
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I don't mean you need to become a master of it like you don't. You don't need to, like, become an expert on the thing that you're trying to solve. I did not go into this ops in this tech problem thinking,
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hey, you know what? Like this is going to be my new thing. Like, I'm going to this is I'm going to I'm now going to take over the OP side of the house, and I'm just going to like, I'm going to go hog wild on, you know, making everything I can I and order like that's now like that wasn't my plan.
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My plan was I've got to get in here and figure it out and either fix the damn problem or get a really good idea of
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what's needed to actually solve it from the person that I'm hiring to solve it right, I need to know how to screen people. I need to know who I'm looking for. I need to know how to define success.
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I need to know how to measure progress. And I can't do that if I refuse to understand what I'm working with.
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you're not looking to master it. You're looking to understand it just enough to know who you're hiring for, whether you need a who or how and basically what what the definition of success is going to look like.
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I
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literally coach spies and IT businesses
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on this exact same advice all the time in sales. Right? Like this was an ops problem, but in sales, I have this conversation repeatedly and it is with technical founders who don't really want to. They don't want to get involved in sales.
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Like, I'm not a salesperson. I don't know how to sell. I don't like selling. I like I've heard it over and over and over, and I think I completely get it
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understand it. You now know, for example, on the upside, I completely understand where you're coming from.
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however, the challenge is if you never take the time to learn the process, to actually sell to to get in there and, and close some deals, to create some leads, to do the process first.
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Again, not trying to master it like I'm not trying to turn you into a sales savant,
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but I am saying the pattern is strikingly similar. Right? It goes something like this with most, most MSPs, it's business owners. It's I'm going to hire, you know, I need to get some lead generation.
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Here's what I'm going. I'm
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going to hire I'm going to outsource it right to an agency. Try an agency. It doesn't work. Try an agency. It's super expensive. Try an agency and it works for a minute and then it peters out. All right, well, you know what? We need to bring this in-house. It's not consistent enough. I want to own the asset.
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I want somebody who's updating my own list, things like that. Okay, let me hire an SDR. Doesn't work. Let me hire another SDR. Doesn't work. Let me hire another SDR. Doesn't work.
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Okay, tell you what. Let me let me hire a salesperson. You know what? If I got a good, experienced salesperson, maybe if they've done this before, they can come in and just solve it all for me.
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Like, they can figure out the process and all that stuff
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doesn't work. Okay, you know what? Maybe what I need to do. I need a who. I need a sales manager. So I'll go higher sales meters, those build the whole thing. I want a sales manager that's going to sell, generate some leads, build a sales team like, you know, do the whole like.
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And that doesn't work. And this, this pattern or these examples or what I'm, what I'm talking about is something that is
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very, very consistent
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that I see all the time with MSPs. And when I did the same thing, on the upside, there was this like this, moment of I'm doing the exact same thing.
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I'm trying to avoid the problem that I don't want to fully understand. I'm going to I'm trying to avoid the side of the house that doesn't excite me as much. I'm trying to avoid the like the the the the roles or the responsibilities or the problems or the things that I'm not. I don't have the experience in. And rather than getting the experience, rather than rolling up my sleeves and getting in there, rather than like understanding it enough to know how to direct that, I try to just like hired away
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and I suffered the same fate that you will suffer if you decide I'm not going to take the time to understand sales at all.
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I'm going to try to abdicate it. I'm going to try to like it's not even delegation. Like if you don't, if you don't know what you're what you're delegating for, if you can't semi manage it and you can't, you know, measure progress on it because you don't understand it, that's not even real delegation.
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that's why even our our fractional management programs like we have the SDR accelerator and the outside sales rep accelerator where we do fractional management coaching, run sales meetings, listen to calls, all that stuff.
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We do that with you,
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yes, we take the heavy lifting. Yes, we carry the vast majority of the sales management load of it, but it's not fully outsourced and it's not fully outsourced by design, because I know the relationship that's created.
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When you try to say here, you take all of sales and I just don't want to deal with it,
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don't want to be involved with it. I don't want it connected to our strategy. I don't want to like, you know, integrated into everything else that we're doing. It just doesn't work as well.
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like I look at I'm like, you know, I know these lessons and I've even built our services around the lessons that I've learned. So yeah, imagine it's it's a little embarrassing when you go make the exact same mistake
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that you advise people not to make, just in a different part of the business. So.
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if you're stuck on on something right now, you know, don't don't try to hired away immediately. Right. Like make sure that you understand. Do I know enough about this problem to know who I need to solve it? Do I know enough about this problem to know whether they're on track to solve it?
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Like, am I just going to, you know, waste nine, nine months and 50 grand only to find out, hey, we haven't gone anywhere. Like, how do I am I able to measure the progress along the way? Do I know what success looks like?
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And if you have a role where you've had multiple salespeople or multiple ops people or multiple admins or techs or whatever it is that haven't worked. Take a step back, like look at that and say,
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I'm either wildly terrible at hiring or is the role wrong? And more often than not, I'm telling you, the role is wrong.
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It's it's trying to combine different roles because we don't fully understand all. We're actually combining like three jobs into one. You know what, if we break these up, it's going to make it easier to hire.
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Before the who in the how conversation. There's a you conversation. And for me, that was a $50,000 tuition bill. And all I got to show for it was this YouTube video.
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I hope you don't have to learn it the same way that I did. Don't be like me.
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And if you thought this was helpful. Pop on my email list. I actually send out, weekly emails on on sales and sales training and general business building. You can the link is below in the description. You can hop on the list, absolutely free. And if you're an MSP and want access to the MSP sales toolbox, it's a it's a resource that we just we put a bunch of stuff that we work with clients on.
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So we've got templates,
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playbooks, SOPs. You know, some, some scripting things like that. We drop in new stuff every month and, you can get access to that links also in the, in the description, it's also MSP sales toolbox.com. When you get access to that it's free. And we drop in more stuff, basically every month.
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So you have access to that for life. So again, I hope it's been helpful. If it has hit subscribe,
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sign up for one of the emails. I'll see you next video. Adios.
::Unknown
You.
