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Why My Teams Don't Miss Targets
I just wrapped a full day of calls with 75 MSP business owners about goal setting, and I heard all the mistakes I've made myself over 20+ years—from leading eight sales turnarounds to turning around a 40-year-old PE-backed company to its highest revenue ever. The most common mistakes? Inaccurate goals where the math doesn't map. Unrealistic goals that look good in December but are dead by March. Setting them too high so your team quietly thinks "that's never happening," or too low creating a complacent half-ass culture. Or worst of all—not setting goals at all. Here's why I'm passionate about this: the right goals manage for you, change behavior, and help people make decisions when you're not around. But bad goals make terrible people look good and great people look bad, which ruins your culture. This episode breaks down why I don't believe in "shoot for the moon, hit the stars"—that just means you're constantly missing and creating a losing culture. Learn why starting small and building a winning habit matters more than big aspirational numbers, why your goals need integrity (not pencil marks that change when you're behind), and how to rebuild momentum with bite-sized wins instead of resetting the whole target.
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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
That's wrapped up full day of falls with about 75 MSP business owners and sellers, and the topic was all about goal setting. In these conversations, I heard a lot of the mistakes that I've heard a lot of business owners make and frankly, that I've made myself, you know, from 20 plus years of sales management to CEO of a, of a piggybacked company. Like, I've set some goals, and trust me, I've made, I think, a ton of mistakes that I can share with with you as lessons. And I heard them come back up. So what I'm going to do in, in this podcast is just kind of like highlight what those those patterns are and how I think about goal setting.
Now, just very briefly, I'll tell you like my my background on this. Like I said, I've been setting goals from a sales and leadership and company perspective for over 20 years. And I've, you know, I've led eight sales turnarounds with with sales teams. I led a turnaround of a of a p back company, 40 year old B back company and within a year of rebuilding the entire executive team and setting new goals, led that that company to its highest amount of revenue.
And so I've, I've done a lot of this in different capacities, mostly around, you know, strategic objectives and, and revenue objectives and what I've seen and, you know, in my own experience in talking to, to business owners all the time and to coaching and stuff, is the the most common mistakes that we that we make are like, what is like just inaccurate goals. Like we we put numbers out there that that aren't accurate, that aren't like the math isn't mapping on these things. And we locked them in and we talk about them and then we never achieve them. And and they're not they're not believable because they were never accurate to begin with. And kind of like in the same boat, like unrealistic goals, like setting these things like, hey, this looks good on a spreadsheet in December for the following year, but come March of the following year, the numbers always read and that that dream is short lived, right?
So that's what I see. I see, you know, a setting goals are way too high, you know, like so like the unrealistic for this. And people don't buy in as a result of it, you know, so your team doesn't buy into it. And there's just a whole bunch of quiet quietly, you know, people sitting in the background like, dude, that's never going to happen, right? So it doesn't achieve the goal of of changing behavior or setting them to low and ending up with, you know, a complacent you know, half ass culture, of people thinking that they're killing it. But really, the goals just weren't weren't set right to begin with, or probably worst of all, like not setting goals at all.
So I'll tell you, like, why I'm so passionate about this topic is I believe that the right goals have the capability to manage for you and to change behavior and communicate and help people make decisions when you're not around as a leader. And when you can do that, you're able to operate asynchronously. And it requires getting these goals right. But it will tell people, hey, we're off the mark and we need to make changes as a result. Maybe it's to volume, maybe it's to what we're doing, maybe it's to something else. But we need to hit that goal and ergo, like we need to change something. So it's it's like a management tool. And I've seen you know, goals where terrible people on the team look good because they weren't set right. I've seen goals where great people look bad because they they weren't set right, which then obviously affects the culture of the organization. And you know, you've got it has the power to to ruin a really good team. You know, make them feel like they're, they're losers. Has the power to make a great team feel like winners. And they're not getting anything done, you know, like, so at the end of the day, that's kind of how I think about role. I think the impact on an organization or a team is fucking huge. And it's and it's often under underestimated in my view.
So here's, here's a handful of things that that I think about goal setting and how I've used them to to drive performance consistently. And the first thing is like just making sure that they're realistic, right? Like making sure that, you know, the team has to buy in in order for you to get the goal. The goal is obviously to achieve the target rights, to achieve the goal that you set. But really the purpose of the goal is to change behavior to get there. Right. That's the real like impact of the goal. Now, nobody believes that it's fucking real and nobody actually buys into it. And everyone's quietly saying never going to happen. Like they're not going to change what they're doing or try harder or, you know, do something differently in order to achieve it because it was never real to them in the first place.
Right? So like to determine this, like ask yourself like, hey, we achieved this before, have we achieved anything like this? And we achieved anything remotely close. Like is there any historical context for this? Is there historical context with a competitor? Is there a historical context within the industry or another industry like can I go find some science to to back this up, that this is achievable if you don't have anything like if you're a startup, like purely in a, you know, blue ocean, you know, no, no competitors, no way you can still look and say, okay, can I work the numbers backwards? Right. If it's a sales goal, okay, I'm at that. If I have to hit that many sales, what's my closed rate got to be? How many pitches do I need to make? What's my average sale need to be? How many first time appointments do I need to set? How many emails do I need to send? I mean doors do I need to knock? I'm like, just work the whole thing backwards and say this is what's needed to achieve that goal. Now, is that remotely realistic? Right. So that's just don't pull numbers out of your ass. Like don't don't make it a dream because it's really clear. And then they they don't work anyway.
And it actually works against you, especially on the second part, which is you really want to establish a culture of hitting goals within your team, right? Like when I've when I've set goals, the, the first thing like, listen, we as an identity, as a culture, we do not miss fucking goals. All right. So when we set them, if we are behind, we are going to do what is necessary to achieve them because that's what we do now in order to do that. When you're starting out, a lot of people assume a lot of people push back, like, I am not a believer and shoot for the moon, hit the stars. I think the advice is terrible. Like that means that means you're constantly missing the fucking goal, right? Like that means you're always falling short. How's that feel? That's not. That's not the culture I want. So start small and build up. I have another podcast on this about, you know, how and why I used the couch to five K app to start running again, even though I was in more than, you know, half marathon shape. There was psychology. Like I wanted some bite size wins to build on compounds, establish that identity and culture of this is what I do, this is what we do. It's the same thing with the team. Make it. Make it non-negotiable. Make it a fucking habit, right? And and like I said, the best way to do that set goals that sometimes seem too low to begin with, but you get into the habit of achieving them. And then as you ratchet them up, you with that identity, you're like, I'm not going to fucking mess that up.
Third thing is talk about them, like integrate them into the fabric of your team in your organization. Like, are you using them in the meetings? Are you using them in the one on ones? Do you have a scoreboard up? Are you sharing the reports? Is the data public? Are you talking about the progress? Are you talking about if you won? Awesome. Celebrate. Why did we win? If we're not winning, like, okay, what do we need to do to change it? Like if you're not constantly talking about it, then you're not doing the other half of the leadership role. One half is setting the goals, the other is like installing them into the fabric of of how your team operates. And we want to we want to keep it top of mind that people are focused on it. Right.
Fourth thing is tie them together. Meaning I've gone into two organizations where marketing is setting goals independently of sales and independently of, client success. I'm like, hey, guys, like you're aware this is just one system. At the end of the day, you're just different components of a of the same system. We all want technically one output here. And if you were setting goals independently and they impact that team who's setting goals independently and effects that team was setting goals independently. Like that's like you're not going to get any synergy like one. They're probably not realistic to you. You know, good system one and one equals three. That that works when you have people aligned all rowing in the same direction. So what we want to do is want to make sure that the goals finished cascade down. And we're and represent the organizational unit. So you, you can, you can kind of like waterfall those into, into other teams.
And then the last thing here also a little unorthodox is don't change them. Right. Like if you want to you need your goals to maintain integrity. The numbers have to have some integrity. If they don't, if you're constantly changing them, like if you if your goals are set with a pencil instead of a pen, then your team knows if they miss, they're just going to change the goal. Like you can't fucking establish that habit. It's maybe gets addictive, right? People set the spreadsheet looks really cool. They get the dopamine hit like short term. Like, yeah, guys was fired up. Like it's going to be fucking great year. Then two months later you're like, okay, that didn't work. Let's let's change the goal. Let's change the goal. Well, you're telling them the goal is not real, right?
So instead, if you if you're behind instead of resetting the whole goal, what what I would do is I'd take a team and say, listen, we're on. Right. Here's what I want to do. I don't want to focus on the big number right now. What I want to focus on are small, bite sized wins that we can we can get right now. Right. What's the next 30 days? The next 30 days what? This is the target? Yes. It's lower than the monthly run. Don't worry about it. Let's. Let's hit the fucking smaller number. Then let's go up a little bit. Then let's go up again a little bit and go up a little bit. What are we doing? We're changing the mindset. Listen, we're not losers. We we we don't we we can get into the habit of hitting goals. We can get into a winning habit. I'm injecting some energy and helping people feel like we start, if we start stacking some wins against the habit of of getting goals, the habit of winning, and then people start, okay, that feels realistic, that feels realistic. We dial it up and then at some point you can look at it and say, all right, is it is it possible to make up the whole the whole number here? Sometimes it is, sometimes it isn't, isn't. But what you don't want to do is change the whole goal or ignore it. Right. This guy. All right. Well, fucking year shot now, right? So if you start falling behind consider do I need to sub to not focus on the big goal right now and put in place some smaller, achievable goals to just reframe everybody, refocus everybody, inject some energy and get back to to winning again.
So again, keep them, keep them realistic. Establish the culture of hitting those goals. Make sure that you talk about them, install them with everyone else, tie them together with the organization. One one sustaining and don't change them. Break them down. I hope this has been helpful. I I would, as you may be able to. So like I feel really strongly about the science of goal setting and how you do this. And if you do it really effectively, you can you can build some killer teams, get them really focused. Not have to micromanage. And, the team will thank you for it. Open up studios.
