Your goals are sabotaging your team

I just wrapped a full day with about 75 MSP business owners talking about goal setting.

And I heard the same mistakes over and over again—mistakes I've made myself over 20+ years of leading sales teams, managing turnarounds, and running companies.

Here's what stuck with me: most business owners are sabotaging their own teams with the goals they set. And they don't even realize it.

After two decades of setting revenue targets, leading eight sales turnarounds, and rebuilding a 40-year-old private equity-backed company from the ground up, I've seen (and done) every flavor of bad goal setting.

Inaccurate goals where the “math ain’t mathing.”

Unrealistic targets that look great in December but fall apart by March.

Goals set so high that nobody believes them.

Goals set so low that you end up with a complacent, half-ass culture.

Or worst of all—no goals at all.

Why does this matter?

Because the right goals manage for you.

They change behavior, help people make decisions when you're not around, and tell your team when something needs to change. They're not just numbers on a spreadsheet—they're a management tool.

I've seen terrible people look good because goals weren't set right. I've seen great people look bad for the same reason.

Bad goals can make a winning team feel like losers. Or worse—make a mediocre team feel like champions when they're not getting anything done.

The impact is massive. And it's almost always underestimated.

Here's how I've consistently driven performance across multiple companies and teams:

Your team has to buy in. If everyone's quietly thinking "that's never going to happen," they won't change their behavior to achieve it. The goal isn't just to hit a number—it's to change what people do every day to achieve them.

Ask yourself: Have we achieved this before? Has anyone in our industry? Can I work the numbers backward and show this is achievable?

If you're setting a sales goal, map it out: closed rate, number of pitches, appointments needed, outreach volume.

Does the math work? If not, you're pulling numbers out of thin air. And that’s not goal setting, that’s dreaming. Fun for you, terrible for teams.

I don't believe in "shoot for the moon, hit the stars" advice. That means you're constantly missing targets. How does that feel? That's not the culture I want.

Start small and build up. I'd rather set goals that seem almost too easy at first, establish the habit of winning, and then ratchet them up. Once your team has the identity of "we don't miss goals," they'll fight like hell to maintain it.

(I wrote a newsletter on the psychology behind this and why it led me to downloading a Couch-to-5k app to start running again—even though I was conditioned to run a half-marathon. Check it out here.)

Integrate goals into everything. Are they in your meetings? Your one-on-ones? Is there a scoreboard? Is the data public? Are you celebrating wins and dissecting misses?

If you're not constantly talking about progress, you're only doing half the leadership job. One half is setting the goal. The other half is installing it into how your team operates daily.

I've walked into organizations where marketing sets goals independently of sales, who sets goals independently of customer success. That's insane. You're all part of the same system working toward one output.

Goals should cascade down from the organizational level. When marketing, sales, and customer success are aligned and rowing in the same direction, one plus one equals three. When they're not, you get dysfunction and finger-pointing.

This one's unorthodox, but critical. If you want your goals to have integrity, set them in pen, not pencil.

If your team knows you'll just change the target when things get tough, they'll never take it seriously. You can't establish winning habits when the goalposts keep moving.

So what do you do if you're behind?

Don't reset the big number. Instead, shift focus to smaller, bite-sized wins. "Forget the annual target for now. What can we achieve in the next 30 days?" Hit that. Then dial it up slightly. Then again.

You're not abandoning the goal—you're building the winning habit back up, injecting energy, and helping people feel momentum again. Once you're stacking wins, you can reassess whether the bigger number is still reachable.

Goals done right can build killer teams that don't need micromanaging. They focus effort, change behavior, and create accountability—all without you having to be in every room.

Goals done wrong destroy morale, waste time, and make great people look bad.

The difference? Being honest about the math, building winning habits, and treating your goals like the management tool they actually are.

Set them right, and your team will thank you for it.

Adios,

Ray

P.S.— Have a question about your 2026 goals? Share it with me in a comment on this post by clicking here and I’ll give you some feedback.