The Motivation Mistake Costing You Your Best Sales Rep
I was working with a tech company a few months ago. About $100+ million in revenue.
The CRO pulls me aside after our session.
“We’ve got underperformance issues. I think it’s the territory plan and comp structure.”
I asked him a few questions about the person who’s struggling. Then I asked about his top performers.
“When’s the last time you asked any of them what they’re actually trying to achieve? What motivates them?”
Long pause.
“I mean, they want to make money. That’s why they’re in sales.”
This is the mistake I see constantly. Sales leaders assume everyone is motivated by the same things. Usually money. Sometimes competition. Maybe recognition.
So they design comp plans and run contests and hope that motivates everyone equally.
It doesn’t.
I’ve worked with several hundred salespeople over the last twenty years. Here’s what I’ve learned: more people are motivated by fear than by greed. More people are driven by internal goals than external rewards. More people want development than they want cash bonuses.
But most execs and sales leaders never ask. They just assume.
That assumption costs them their best performers.
The Motivation Myth
There’s a persistent myth in sales that everyone is money-motivated.
I’ve touched several hundred salespeople through coaching, training, and consulting over the years. I don’t see many people who are greedy.
I see a lot of people who are scared.
They’re scared they won’t close enough business. Scared they’ll get fired. Scared they’ll let down their families. Scared they won’t achieve what they thought they would in life.
That fear drives more behavior than greed ever will.
I also see people motivated by:
Mastery. They want to get really good at their craft. They treat sales like something worth perfecting, not just a job.
Impact. They want to make a difference for their customers. They want to solve real problems. The money is nice, but it’s not why they show up.
Competition. Not against others, but against themselves. They want to beat their own numbers. Get better than they were last quarter.
Security. They want stability for their families. Predictable income. The ability to plan for the future.
Growth. They want career progression. New challenges. Opportunities to lead. A path forward.
Recognition. They want to be seen and valued. Not necessarily in front of the whole company, but by the people who matter to them.
Money matters to all of them. But it’s rarely the primary motivator.
And when you treat it like it is, you miss what actually drives your people.
The 4 Motivation Questions
If you manage salespeople and you can’t answer these four questions about each person on your team, you don’t actually know how to motivate them.
Are they intrinsically or extrinsically motivated?
Intrinsic motivation comes from within. These people are driven by internal standards. They want to get better. They want to prove something to themselves. External rewards are nice, but not why they do the work.
Extrinsic motivation comes from outside. These people are driven by external rewards and recognition. They want the trophy. The title. The leaderboard position. The comp check.
Most sales leaders assume everyone is extrinsically motivated. The data says otherwise. About 40% of professional salespeople are extrinsically motivated. The other 60% are driven primarily by internal factors.
If you’re only using external rewards to motivate your team, you’re missing more than half of them.
Do they love to win or hate to lose?
This sounds similar but the psychology is completely different.
People who love to win are energized by competition. They want to be number one. They want to beat everyone else. Contests excite them.
People who hate to lose are risk-averse. They’re motivated by not failing. They want to hit their number reliably. They don’t care about being the top performer. They care about not being at the bottom.
If you run contests for people who hate to lose, you’re not motivating them. You’re stressing them out.
What are they trying to achieve outside of work?
Most sales managers never ask this. But it’s one of the most important questions.
Are they saving for their kids’ college? Paying off debt? Building wealth? Pursuing a passion project? Supporting aging parents?
When you understand what someone’s trying to achieve in their life, you can connect their work to that goal. You can show them how hitting quota this quarter gets them closer to what actually matters to them.
Without that context, compensation is just numbers on a page.
What’s their career timeline?
Some people are sprinting. They want to get promoted fast. Build skills quickly. Take on new challenges every year.
Others are running a marathon. They want steady growth. Sustainable performance. They’re not trying to be VP in three years. They’re trying to build a 20-year career.
If you manage both types the same way, you’ll frustrate everyone.
The sprinter will feel held back. The marathoner will feel pressured.
You need to know which one you’re working with.
The Motivation Matrix
I use a simple framework to think about motivation. It’s not perfect, but it helps sales leaders understand the different types of people on their team.
There are four primary motivation profiles. Most people are some combination of these, but usually one is dominant.
The Achiever
Driven by hitting goals and leveling up. Wants clear targets and visible progress. Loves scorecards and metrics. Motivated by seeing themselves improve over time.
These people don’t need external competition. They’re competing against their own past performance. Give them clear milestones and show them their progress.
The Competitor
Driven by winning and external validation. Wants to be number one. Loves contests and recognition. Motivated by beating others and being celebrated for it.
These are the people everyone thinks of when they imagine salespeople. They exist, but they’re not the majority.
The Builder
Driven by mastery and impact. Wants to get really good at their craft. Loves solving complex problems. Motivated by learning new skills and creating value for customers.
These people will work harder on a difficult deal than an easy one because the difficult deal teaches them something. Money matters, but development matters more.
The Stabilizer
Driven by security and consistency. Wants predictable income and sustainable performance. Loves process and systems. Motivated by reducing risk and creating stability.
These people are your steady performers. They’re not going to blow out their number, but they’re also not going to miss it. They want to know exactly what they need to do to be successful.
When you understand which profile fits each person on your team, you can motivate them effectively.
Stop running contests for Builders. Stop giving Stabilizers stretch goals. Stop trying to develop Competitors who just want to win.
Meet people where they are.
How to Figure This Out
Most sales managers read something like this and think “okay, I’ll put everyone in a bucket.”
That’s not how this works.
You have to actually talk to your people. Ask them questions. Listen to their answers.
Here’s how I recommend doing this:
Schedule individual conversations with each person on your team. Not a performance review. Not a pipeline discussion. A conversation specifically about what motivates them.
Tell them upfront: “I want to make sure I’m supporting you in a way that actually works for you. I’m going to ask you some questions about what drives you. There are no wrong answers.”
Then ask:
“What do you want to achieve in the next year? Not just at work, but in your life?”
“When you think about your career, what does success look like five years from now?”
“What gets you excited about work? What drains you?”
“When you’ve had wins in the past, what made them satisfying? The money? The recognition? The challenge?”
“If you could change one thing about how we work together, what would it be?”
“What kind of support do you need from me that you’re not getting?”
Listen more than you talk. Don’t judge their answers. Don’t try to change what motivates them.
Just understand it.
Use assessment tools. I’m a big fan of Objective Management Group for sales-specific assessments. Culture Index is excellent for understanding personality and work style. Kolbe is great for how people do work. I like DISC, too.
These tools give you data you can’t get from conversation alone. They reveal blind spots. They confirm or challenge your assumptions.
I’ve had sales leaders tell me someone is “definitely money-motivated” and then the assessment shows they’re actually driven by autonomy and mastery. The leader was projecting their own motivations onto the rep.
Don’t guess. Get data.
Observe behavior patterns. Watch what energizes people and what depletes them.
Do they light up when you talk about a challenging prospect? Or do they prefer easier wins they can close quickly?
Do they ask about career development? Or do they ask about comp structure?
Do they want to role-play and practice? Or do they just want to go execute?
Behavior tells you what people actually value, not what they say they value.
Ask their peers. Sometimes the team knows things about each other that you don’t see.
Not in a gossipy way, but in a “what do you notice about what motivates them?” way.
The Competitor on your team knows who else is competitive. The Builder knows who else cares about craft.
Use that information.
What to Do With This Information
Once you understand what motivates each person, you can start managing them differently.
Not in a way that’s unfair, but in a way that’s effective.
For Achievers: Give them clear metrics and regular feedback on progress. Show them how they’re improving. Create development plans with visible milestones. Let them track their own growth.
For Competitors: Run contests (but make them fair). Recognize them publicly. Create leaderboards. Give them challenging goals and celebrate when they hit them. Let them know where they rank.
For Builders: Invest in their development. Give them complex problems to solve. Send them to training. Let them mentor others. Show them how they’re getting better at their craft. Connect them with customers who appreciate their expertise.
For Stabilizers: Give them clear processes and expectations. Show them exactly what they need to do to be successful. Create predictable income opportunities. Reduce chaos and uncertainty. Recognize their consistency.
This doesn’t mean you treat people unfairly or create different standards. It means you understand that the same reward affects different people differently.
A public callout for hitting quota might energize a Competitor and embarrass a Builder. A stretch goal might excite an Achiever and stress out a Stabilizer.
When you understand these differences, you can lead more effectively.
A Recent Conversation
I was working with a sales leader who had a rep struggling to hit quota.
I suggested having a different conversation first.
“Ask him what he’s actually trying to achieve. What matters to him outside of work. What’s going on in his life.”
The leader pushed back. “That’s too personal. I don’t want to get into his personal business.”
I told him: “You’re about to fire him. Maybe you should understand what’s actually happening before you do that.”
He had the conversation.
Turned out the rep’s father had been diagnosed with cancer six months earlier. The rep was flying home every other weekend to help care for him. He was exhausted and distracted and didn’t know how to tell anyone.
The leader didn’t know because he’d never asked.
They adjusted the rep’s territory. Shifted some accounts. Gave him more flexibility on travel. Created a plan that acknowledged what was actually happening in his life.
The rep’s performance improved. Not immediately, but over the next few months. He ended the year at 95% of quota. Not great, but not getting fired.
More importantly, that rep became one of the most loyal people on the team. Because someone finally asked what was actually going on instead of just demanding better numbers.
That’s what understanding motivation does. It creates loyalty. Trust. Performance.
Talk To Your People
One of the biggest mistakes I see sales leaders make is not knowing what motivates their people.
They assume everyone wants the same things. They design comp plans and contests around those assumptions. Then they wonder why half their team isn’t performing.
The fix is simple but requires effort.
Talk to your people. Ask what drives them. Use assessment tools. Observe behavior.
Then use that information to lead them more effectively.
Give Achievers clear metrics. Give Competitors contests. Give Builders development. Give Stabilizers process.
Meet people where they are instead of where you think they should be.
When you do that, performance improves. Retention improves. Morale improves.
Not because you got lucky with talent. Because you finally understood what your people actually need.
Questions our sales training programs? Email me at adam@thenorthwoodgrp.com.
