“The last time we missed quota? It's been about 18 months.”

I was asked this question while on a Q/A panel at an event for founders and revenue leadership. I knew that he probably wouldn't believe me and if he did he'd want to know the "silver bullet".

"Are you serious?" he asked.

"100%", I answered.

"So… I guess what's the secret?"….

I'm glad he asked because it gave me the opportunity to unpack the "secret", if you want to call it that.

My answer that followed was broken into 5 main points I want to share with you in this letter.

Before I do that, I want to challenge one particular thought I think will stop you from really getting this.

The reason why is because I asked this gentleman the same question he asked me.

"How often does your team hit quota?" I asked.

"We stay steady between 60-67%, for us that's pretty good", he answered.

And honestly? In his world, it probably was "pretty good".

So here's the idea I want to address first…

Most leaders in this industry have unconsciously accepted that 60% quota attainment is “pretty good.”

They’ve normalized systematic underperformance to the point where missing targets 40% of the time feels normal. Maybe even expected.

Why is that?

Most revenue teams I get the privilege of working with either can and end up increasing quota attainment to 90%+ OR have a competitor already doing that.

It can be the same industry. Similar product. Comparable market conditions.

That's not insignificant.

The difference isn’t merely talent, some magical sales process, or tech…

It’s that one company treats 60% quota attainment like a systemic defect, while the other treats it like the weather.

And the psychological frameworks that create this difference run deeper than most leaders realize or care to admit.

Let me explain…

First, we have to agree the normalization of consistent underperformance is in fact a problem.

“Sales is just unpredictable. That’s the nature of the game.”

I've heard this. You've heard this.

Otherwise, very competent executives have convinced themselves that revenue teams are inherently chaotic. That consistent performance is naive or wishful thinking.

That 60% quota attainment is just “how sales works.”

This is the most expensive lie in business.

Do we accept this in other departments?

Let's use manufacturing for example…

What if Toyota accepted 60% quality standards? That'd be insane.

When a manufacturing line produces defective products 40% of the time, you fix it.

Now, in order to do so, you need to diagnose the problem and you have to diagnose correctly. In my experience, most don't.

Remember, if you misdiagnose → you mistreat.

It's either…

A people problem (talent)

A vehicle problem (the system)

You can take the best driver in the world, but if you put them in a Honda Civic they're not going to win the Daytona 500 my friend.

You can take the best SDR, the best AE and put them in a role where the revenue systems are broken at worst, sub optimal at best…

And good luck.

The good news is, the vehicle, is within your control. Which means it deserves your attention.

Things you can't control (market conditions, competition, individual rep performance), are not worth your attention.

Control what you can and make it 10 out of freakin 10: the systems and environment you create.

The psychology here is fascinating and predictable.

A professional basketball player can’t 100% control whether any single shot goes in…

But they can control their shooting percentage over hundreds of attempts through deliberate practice and systematic improvement.

The same principle applies to revenue teams.

You can’t completely control whether any individual deal closes, but you can absolutely control your team’s closing percentage over time through systematic optimization of the variables that matter.

After analyzing endless amount of underperforming revenue teams, I’ve identified exactly five reasons companies get stuck in the 60% trap.

Most organizations suffer from 2-3 of these simultaneously.

The companies hitting 90%+ quota attainment, they've systematically eliminated all five.

I'll break down all five…

But before we dive into it, I want you to understand something important about human psychology and organizational behavior.

Every system is perfectly designed to get the results it gets.

I'm not saying this as a motivational platitude, it's just a fundamental truth about cause and effect.

If your team consistently achieves 60% quota attainment…

It MUST be true that your current systems, processes, leadership, and organizational health are perfectly designed to produce that outcome.

It's not a fun pill to swallow to admit, that changing those results requires changing the system that creates those results.

That's exactly why most leaders psychologically justify their teams performance and label it "pretty good". The best of us do sometimes.

As Scripture says in Proverbs 27:5-6:

“Better is open rebuke than hidden love. Wounds from a friend can be trusted, but an enemy multiplies kisses.”

Sometimes the most loving thing I can do for a leader is wound them with truth instead of multiplying kisses with comfortable lies.

However, it's worth it.

Let's unpack these 5 reasons…

#1: You Promoted Your Best Rep Without Teaching Them To Lead

This might be the most common and most expensive mistake in revenue leadership.

Your top performer crushed their numbers, three years running. Natural choice for sales manager, right?

Except that, if being good at the craft was the only criteria for leadership then why don't we have many examples of great players being great coaches?

A quintessential example of this would be Magic Johnson. I mean, he was an NBA champion five times over and earned three MVP awards during a Hall of Fame career.

Yet…

His brief stint as the Lakers' head coach in the 1993-94 season ended with a 5-11 record before he stepped down.

In fact, Michael Jordan refused to coach and admitted he wouldn't have the patience or ability to transfer his approach to the game to other younger athletes.

There are many other examples of this.

Because the best players don't automatically make the best coach.

Individual performance and leadership are completely different skill sets, but we keep promoting based on sales ability and wondering why team performance plateaus or declines.

When you take a step back and zoom out, it actually makes sense…

  • We promote the top rep to manager→

  • New manager defaults to teaching what worked for them personally →

  • When that doesn’t translate to others, they can’t diagnose why →

  • They mistake activity management for performance management →

This is a double whammy because now you have one less superstar individual contributor and one ineffective leader managing a confused team.

Very expensive learning lesson.

Why does this happen?

Think about it. For years, this person’s identity was built around individual achievement…

Their self image came from personal performance metrics. Now suddenly, their success depends entirely on other people’s performance.

It's a skillset that needs to be learned, but also it's a psychological issue. More specifically, identity shift.

And we expect them to make this transition overnight, with no training, no support, and no understanding of the psychological work required.

It's foolish. Fixable, but foolish.

One of the toughest adjustments for top reps who get moved up is they unconsciously judge others by their own standards.

In other words, when team members don’t perform at their level, the new manager assumes it’s a motivation problem or a talent problem, or what have you.

They rarely consider that it might be a systems problem or a development problem or a clarity problem.

This is called the “fundamental attribution error.”

We attribute other people’s failures to character flaws while attributing our own failures to circumstances.

Elite revenue organizations understand this and hedge against it.

They separate individual performance from leadership potential

Systematically develop management capabilities

Provide frameworks for diagnosing performance issues that go beyond “work harder” or “want it more"

That's the right way to think about it.

Promote based on leadership potential and systematically develop management capabilities.

Understand that great leadership is about creating conditions where others can access their highest capabilities.

As John Maxwell says:

“A leader is one who knows the way, goes the way, and shows the way.”

-John Maxwell

Knowing the way (personal excellence) is just the beginning.

Going the way (modeling excellence) is the middle. Showing the way (developing excellence in others) is mastery.

Most promoted sales managers get stuck at stage one.

Here's the second reason…

#2: You’ve Accidentally Created A Culture That Tolerates Mediocrity

This one may seem obvious, but you’ll want to lean in and hear what I share here.

Remember this → you get what you tolerate.

If missing quota doesn’t trigger systematic investigation and intervention, you’ve unconsciously communicated that underperformance is acceptable.

Your team will not "rise" to your stated goals. They will optimize to "fall" to the level of your expectations.

I’ve watched this play out over and over and over…

Leadership sets stretch goals (which feels ambitious) but accept sub stretch results (which feels reasonable) and then they praise effort (which feels positive), but don’t address outcomes (which feels negative).

Look… culture isn’t JUST what you say in team meetings (although that's important). Culture is what you systematically reinforce through your actions.

It's not enough to communicate verbally how you want your team to show up.

That's not how humans work.

Culture (or let's call it subconscious standards and expectations) are created by what you tolerate, what you celebrate, what you measure, and what you ignore.

Everyone talks about excellence. Everyone agrees excellence is important. Everyone has good intentions about pursuing excellence.

But the actual systems, consequences, and reinforcements all optimize for “good enough.”

Your intentions can be admirable, but if the preparation doesn’t match the goal, there's a big gap between what you say you want and what you expect.

And your team knows the difference. They do.

They might not articulate it consciously, but they feel the gap between what you say you want and what you actually reinforce.

And over time, they calibrate their effort to match your actual expectations, not your stated aspirations.

If consistent under-performers keep their jobs with minimal consequences, everyone learns that underperformance is tolerable.

If top performers don’t receive meaningful differentiation in recognition, compensation, or opportunities, everyone learns that exceptional effort isn’t particularly valued.

The system is the ultimate teacher and everyone eventually learns what it tolerates.

Teams that achieve 90%+ quota attainment have one thing in common: they’ve created environments where anything less than excellence feels uncomfortable.

Through systematic support and clear accountability.

They understand what ancient wisdom has always taught.

“When the sentence for a crime is not quickly carried out, people’s hearts are filled with schemes to do wrong.”

- Ecclesiastes 8:11

Clarity is underrated power.

When people know exactly what’s expected and exactly what happens when those expectations aren’t met, they can focus their energy on performance instead of wondering where they stand.

Ambiguity creates anxiety. Clarity creates confidence. And confidence performs.

To sum this up:

  1. Create crystal clear performance standards

  2. Crystal clear consequences for not meeting those standards

  3. And crystal clear support systems for helping your team meet those standards

Engineer the conditions that make excellence achievable.

Reason #3: Your Systems Were Designed For Someone Else

This problem fascinates me because it reveals something profound about organizational dynamics.

We’re all systems thinkers when it comes to other people’s problems and individual thinkers when it comes to our own.

When a competitor is struggling, we can easily see their systemic issues.

  • “Their pricing model doesn’t make sense for their market.”

  • “Their sales process is too complex for their deal size.”

  • “Their management structure creates too many bottlenecks.”

But when our own organization struggles, we default to individual explanations.

  • “We need better salespeople.”

  • “Our reps aren’t working hard enough.”

  • “The team lacks motivation.”

This is another manifestation of the fundamental attribution error (micro), but at an organizational level (macro).

So let me flesh this out as to why this is important for you…

People adapt to the systems they operate within.

If your comp plans incentivize competition over collaboration, you’ll get competition.

If your org structure creates silos and lacks transparency, you’ll get internal conflict and eventually dysfunction.

If your management tries to win by hierarchy instead of merit, you’ll get communication problems and politics.

The system shapes the behavior, not the other way around.

Now, there are certain people that come along (leaders) that will influence those systems and create a "greenhouse effect", if you will. They force positive change and most leaders would never even see the systemic problems until those leaders leave.

Those leaders are anomalies, there are always exceptions to the rule, but most of the time you're going to have to fix the system.

I notice most leaders resist this because rebuilding the architecture is hard.

I was reminded of this while reading about Toyota’s production system.

They have a concept called “jidoka”…

It's the idea that you stop the production line the moment you detect a defect.

Most American manufacturers in the 1970s thought this was insane. “Stop the entire line for one defect? That’s inefficient!”

But Toyota understood problems (like this) are similar to mildew. The more you ignore it, the more it grows.

In other words: fixing problems at the source is always more efficient than fixing problems after they compound.

It's the same for you and your revenue team.

It starts with asking questions like:

  • What behaviors are our systems actually incentivizing?

  • Where are the bottlenecks in our process creating frustration or inefficiency?

  • How do our compensation, territory, and management structures support or undermine our stated goals?

The best teams treat systematic problems as system problems.

The systems and processes that worked at $5M might be actively sabotaging your growth at $25M.

But admitting this requires acknowledging that your previous approach has limitations.

Most leaders would rather blame external factors than confront the possibility that their own design choices are creating their current problems.

My advice…

Regularly audit your architecture for scale mismatches.

Understand, what got you here won’t always get you there.

#4: You’re Ignoring The Performance Optimization Gap

I was asked one time by a room of sales professionals, "what's the one thing that had the biggest impact on your income?"…

I said, "easy, having a bed time".

Optimizing my sleep.

If you were to ask all of the top performing sales pros in my network I bet most would agree or close to it.

They all obsess about most or all of…

  • Rest and recovery

  • Movement

  • Nutrition

  • Longevity

  • Spiritual health

The truth is all of these more connected than you think.

Your physical health, mental health, spiritual health… they all effect how you show up, make decisions, your capacity for pressure and learning, etc…

The one I notice top performers on revenue teams obsess about it their physical health.

Now, the question is why? I can assure you, it's not a coincidence. There's good, better, and best. The BEST understand something about mental resilience, physical energy, and personal optimization.

Let me explain…

Peak performers in any domain share common characteristics. They manage energy as carefully as time. They’ve developed frameworks for handling pressure and rejection. They understand the connection between physical wellness and cognitive performance.

If your job is to play mental chess all day at a high level, then that means your greatest asset is you.

If you want to sharpen the axe, you're the axe.

But let me go deeper on this, because I think this might be the most overlooked factor in revenue performance. We live in a culture that treats business performance and physical performance as separate domains.

This is a incredibly short sighted.

Sales is one of the most mentally and emotionally demanding professions in the world.

  • Constant rejection

  • High pressure conversations

  • Emotional labor

  • Cognitive complexity

  • Relationship management

  • Time pressure

And the travesty is most organizations provide zero training on the mental, physical, and emotional foundations that sustain high performance in demanding environments.

We expect peak performance without providing peak performance support or at least a supporting environment.

This is frankly such a lost opportunity and I personally try to change this everywhere I go.

It's a ridiculously high leveraged concept if you have a revenue team.

Every single elite producers I've ever rubbed shoulders with, they exemplify patterns similar to professional athletes.

For example…

  1. They prioritize sleep and recovery. They have a consistent sleep and wake cycle and they know the inputs that lead to high quality rest.

  2. They manage their energy systematically. In other words, they know when they’re most mentally sharp and schedule their most important calls or most leveraged work during those windows.

  3. They’ve developed mental frameworks for handling adversity. Like a "rut" for example, doesn’t derail them because they literally prepare for this kind of thing like a professional.

  4. They understand the mind / body connection. They know that their physical state directly impacts their mental state. They optimize sleep, nutrition, exercise, and stress management because they understand these aren’t “nice to haves”, it's the epitome of working smarter, not harder.

  5. They think systematically about their self improvement. They analyze their performance, identify specific areas for development, and systematically work on those areas with a schedule, deadlines, and targets.

This may seem intense to some, but it really just comes down to priorities. The best leaders, sales professionals, entrepreneurs, athletes, etc that I know…

They prioritize these things and it shows. It works. And it works for organizations too.

Companies that systematically develop these capabilities across their entire team create sustainable advantages. Their people perform better and they perform better for longer.

It's almost an unfair competitive advantage, but very few foster this kind of thing on their teams, for various reasons.

But the ones who do…

They have lower turnover because their people feel supported rather than burned out. They attract better talent because peak performers want to work in environments that help them optimize their potential.

And most importantly, they scale more predictably because their performance isn’t dependent on finding naturally gifted individuals.

They’ve built systems that help average performers access higher levels of their capability.

I like how Aristotle put it:

“We are what we repeatedly do. Excellence, then, is not an act, but a habit.”

-Aristotle

Elite revenue organizations understand that excellence is a systematic capability.

It's possible to build it and maintain it for a long time.

#5: You’re Treating Symptoms Instead Of Diagnosing Root Causes

This is the reason most consulting interventions fail.

Most companies approach revenue challenges backward:

  • Notice poor performance

  • Guess at the cause

  • Apply tactical solutions

  • Hope for different results

Let's be honest this is like taking a pain killer for a broken leg.

It just ain't gonna cut it…

I sound like a broken record, but again, if you misdiagnose → you mistreat.

Start with systematic diagnosis.

Turn your frustration into curiosity by asking thoughtful questions.

  • Is this a leadership issue or an individual contributor issue?

  • Are our processes creating the behaviors we see?

  • What specific capabilities are missing and why?

Only after you understand the root cause should you design interventions. This is hard to do because we tend have a bias toward action over analysis. When something isn’t working for example, our natural instinct is to do something different. The discomfort of poor performance creates psychological pressure to act quickly.

This feels productive. It feels like leadership. It feels like problem solving.

I get it.

But it’s actually the opposite.

Each intervention might provide temporary relief. But if you’re treating symptoms instead of root causes, the fundamental problem never gets solved.

And it's expensive.

Every failed intervention costs time, money, team morale, and opportunity cost. More importantly, it reinforces a culture of tactical thinking instead of systematic thinking.

This creates learned helplessness at an organizational level.

Avoid this by starting with a systematic diagnosis:

If you misdiagnose the problem, even perfect execution of your solution won’t create the results you want.

But if you accurately diagnose the problem, even imperfect execution often creates significant improvement.

Let me sum this up…

In my experience, salespeople are the hardest to hire, hardest to train, and the hardest to lead.

However, once you learn how, every other department gets easier.

In fact, the same principles that creates revenue excellence creates excellence in every other area of business.

Operations become more predictable.

Customer satisfaction becomes more consistent.

Team engagement becomes more sustainable.

Strategic execution becomes more reliable.

Organizations that learn to optimize their revenue team learn to reengineer it in every department.

So here's what I want you to consider…

What would change in your organization if your revenue department became absolutely, systematically predictable?

Not just hitting numbers, but doing it with such consistency that every other department could build their strategies around that reliability?

  • What investments would finance approve?

  • What risks would product take?

  • How would operations plan differently?

  • What talent would want to join your team?

I've seen too many teams underestimate how much organizational energy gets wasted managing around revenue unpredictability.

They don't realize the full potential of every department that depends on those numbers being real.

The best organizations understand this though.

They engineer the conditions for 90%+ quota attainment because they know it's the foundation that allows everything else to operate at the level they say they want.

Once you see how revenue predictability cascades through your entire organization, accepting 60% quota attainment starts feeling like accepting 60% organizational potential.

And leaders who think systematically about organizational performance rarely accept that trade off for long.

Hope this helps.

Until next time,

THE MILES MEMO

P.S. - If you found yourself nodding along to this breakdown, you already know your revenue dept could be the leverage point that transforms your entire org.

And the most successful transformations I've witnessed always start with just one leader asking: "What if our revenue operations actually worked the way they're supposed to?"

Forward this to someone you'd like to have that conversation with.

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