“You have no idea how long I've been trying to get my sales team effective call coaching…”
“Can I ask what’s kept you from doing it?”
“Well, the CRO Bill (not his real name) hasn’t been CRO for long, that was recent and he’s just so busy.
“Oh ok, so he’s a recent hire?”
“Not exactly, the previous CRO recently transitioned out, so Bill, who’s also COO recently stepped in to fill his role.
This conversation happened last week with a prominent company doing $50M+ in revenue. And it perfectly illustrates something I’ve been thinking about lately.
Why is the average tenure of a CRO only 17 months?
And more importantly…
Why do otherwise competent leaders keep making the same (very) expensive hiring mistakes when it comes to revenue leadership? These types of mistakes cost companies millions in lost growth, demoralize entire teams, and turn promising executives into career casualties.
It'll usually get chalked up as, "not a culture fit"… Or, "we mutually decided to part ways"…Sure, ok Bob (lol).
Let's be honest. These are hiring failures.
And the biggest problem here is is that the failure rarely has anything to do with the person being hired.
It’s almost always the mental models and cognitive biases of the people doing the hiring. The worst part is that these are otherwise brilliant leaders. People who’ve built successful companies, navigated crises, and made hundreds if not thousands of good decisions.
But when it comes to hiring senior revenue talent? They’re operating with frameworks that were maybe relevant 20-30 years ago.
Let me explain…
Last year, I watched a CEO hire what should have been a home-run CRO. This person had scaled 2 or 3 different companies past $50M. Had testimonials from previous CEOs that sounded like love letters.
Let's fast forward 14 months…
Demoted to a fractional VP of sales essentially. If you ask me they're just keeping him busy until they find a replacement and the cycle continues.
Tragic. What is going on? Let's break it down.
The CEO had unconsciously hired someone "familiar". In other words, he hired someone who fit the profile of past successful hires instead of strategically hiring for the obvious future bottlenecks along the road ahead.
And this is costing him roughly millions and counting, plus another $200K+ in recruiting, onboarding, and transition costs when it's all said and done.
But... this is a pattern.
The same psychological traps that cause this CEO to make this mistake are operating in businesses across the country every single day. Even research from Harvard Business Review agrees. 40% of senior revenue hires fail within their first 18 months.
It gets worse.
40% of senior revenue hires fail within 18 months.
89% are mis-hires by the hiring leader.
Why do you think that is?
— #Mitchell Miles (#@mitchellbmiles)
12:15 PM • Sep 19, 2025
Only 11% of those failures are due to lack of technical skills or experience.
That means the other 89% are simply mis hires on the one doing the hiring.
I'm convinced it's the psychological misalignment between what the hiring leader thinks they need and what the business actually needs.
Cognitive biases.

Richard Phillips Feynman was a multifaceted American theoretical physicist and Nobel laureate. He made groundbreaking contributions to quantum mechanics, quantum electrodynamic (QED), and particle physics.
The first principle is that you must not fool yourself — and you are the easiest person to fool.”
Feynman was talking about physics, but this applies perfectly to leadership decisions. The leaders who consistently make great hires, in general as well as revenue specific hires, aren’t necessarily smarter. They’ve simply built systems to counteract their own psychological blind spots. Again, cognitive biases.
Once you see them, you can’t unsee them. Let's break down all 4….
(To be completely transparent, I didn't give the name to these biases much thought until now as I'm writing this. Don't judge too hard 🙂
Bias #1: Competence Substitution
This CAN be the most insidious one because it masquerades as rigorous thinking. It happens when you unconsciously evaluate candidates based on competencies that are measurable rather than competencies that are predictive of success in your specific context.
So it can go like this…
You know you need someone who can "scale revenue systems." But what does that actually mean for your business? Instead of wrestling with that uncomfortable ambiguity (which would be the right thing to do) your brain substitutes somewhat "easier to measure" vanity metrics:
• Years of experience
• Size of previous companies
• Recognizable brand names on their resume
Let's roll play this… You're the CEO of a hypothetical $15M SaaS company. You have two final candidates to hire your CRO.
• Candidate A: 15 years at enterprise software companies, had "scaled revenue" from $100M to $500M at a Fortune 500 company.
• Candidate B: 8 years of experience, had built the revenue engine from $5M to $50M at two different mid market companies.
Why one are you choosing?
Many would choose Candidate A because the experience "looks more impressive."
Right? No. Why?
Because scaling revenue inside a $2B company with established product market fit and massive marketing budgets is a completely different competency than building revenue systems from scratch.
Especially in a, more than likely, resource constrained environment. Don't fall victim to substituting "impressive experience" for "relevant experience" because impressive experience is easier to evaluate.
Feynman warned against “cargo cult science”, rituals that look like science but aren’t.
Leaders fall for the same trap in hiring: resumes and rituals that look like proof of performance… but aren’t.
— #Mitchell Miles (#@mitchellbmiles)
4:52 PM • Sep 25, 2025
When we're uncertain about what we actually need, we default to evaluating what we can easily measure. It's a cognitive shortcut that feels "right" but is actually just lazy.
Before you write the job description, spend time defining what "success" actually looks like in your specific context.
Ask yourself…
"What are the top 3 scenarios this person will face in their first 18 months, and what specific capabilities do those scenarios require?"
Then design your evaluation process around those specific scenarios. It'll save you time, money, and a lot of frustration.

Bias #2: Attribution Error
This is when you misdiagnose why your previous revenue hire didn't work out, then optimize for the wrong variables in your next hire.
Remember: if you misdiagnose, you mistreat.
I think the majority of costly mistakes are made from a misdiagnosis, not necessarily the inability to solve problems. Most leaders think they're learning from their mistakes.
In reality, they're often learning the wrong lessons because they're misattributing the causes of failure.
(Misdiagnosis)
• Previous hire doesn't work out →
• You create a story about why →
• That story becomes your hiring criteria for the next person →
• You hire someone who looks different but has the same underlying skill gaps
We have a psychological need to believe that our decisions are logical and our problems are solvable. So when a hire doesn't work out, creating a clear narrative about WHY makes us feel in control.
But often the real causes are systemic issues we don't want to acknowledge because those are harder to fix.
As opposed to just "hire better next time".
Before you diagnose why your last hire didn't work, do a ruthless audit of the conditions they were operating in.
• Did they have clear success metrics?
• Did they have authority over the systems they were accountable for?
• Were there organizational dynamics that would have sabotaged anyone in that role?
Many times the problem isn't the person, it's the system you're asking them to succeed in.
Your brain sabotages your best hires.
You need "revenue scaling" but substitute:
→ Years of experience
→ Company size
→ Brand names
"Impressive" ≠ "relevant"Define success in YOUR context first.
— #Mitchell Miles (#@mitchellbmiles)
1:50 PM • Sep 23, 2025
Bias #3: The Functional Fallacy
This is the unconscious belief that revenue leadership is a fixed function rather than adaptive. Most leaders hire revenue executives the same way they hire other functional leaders…
The look someone who has "done the job before". But revenue leadership is fundamentally different because it sits at the intersection of so many other functions:
• Sales
• Marketing
• Customer service
• Product
• Operations
• Finance
The specific combination of capabilities needed depends entirely on your current context, growth stage, market dynamics, organizational structure, etc...
Remember that CEO I mentioned earlier? He hired a CRO that's now an overpaid VP of sales essentially. He hired someone who had "done exactly this before" This CRO wasn't incompetent by any means.
He scaled a similar company from similar revenue to similar targets in a similar market. But what he missed was that their organizational context was completely different.
This may seem trivial, but hear me out…
Organizational context is more important than you might believe. The CROs previous company had a rather prominent and strong brand. The founder had a large following (intentionally) and this means a lot of market clout.
This influences sales in a very positive way.
In addition, the founder had kept their team somewhat lean and gave them a lot of autonomy. Now, this new company, had hardly any market clout at all. This required a very strong sales team to make up for that and so their existing sales department was strong.
Hardly any organic following, essentially all lead generation was cold. And this team was also rather large and their organization valued transparency and accountability. This meant a lot of check ins, meetings, and reporting.
The previous company was selling to mid market customers with 1-3 month sales cycle. This new company was moving up market to enterprise with 6-12 month cycles.
As you can imagine… this didn't pan out very well.
The CRO kept trying to apply the playbook that had worked before, but the underlying conditions were different. What looked like "exactly the right experience" was actually the wrong experience.
This is called "pattern matching".
Pattern matching feels safe. When we see someone who has "been there, done that," it reduces our anxiety about the uncertainty of the hire.
But pattern matching only works when the patterns actually match. Revenue leadership is so contextual. Surface level pattern matching often leads you astray.
So here's my advice…
Instead of hiring for experience, hire for learning and diagnostic ability. Look for people who can quickly understand your specific context, identify what's working and what isn't, and adapt their approach accordingly. That's the dream.
Ask candidates to walk you through how they would diagnose your current revenue engine and pay close attention to the questions they ask. Watch what they DO, not necessarily what they say.

Bias #4: Shortsighted Bias
This is the tendency to overweight immediate needs versus lon term requirements when making hiring decisions.
Most revenue leadership hires happen because there's an immediate pain point…
• Missed quarters
• Stalled growth
• Team dysfunction
• Founder burnout
When you're in pain, your brain prioritizes solutions that promise quick relief over solutions that address root causes. And so this leads to psychological pressure to "fix things fast", which leads to hiring decisions optimized for short term comfort rather than long term success.
It's the age old cycle…
• Company misses targets for two quarters →
• CEO feels pressure from board/investors →
• Decides to hire a CRO to "get revenue back on track" →
• Hires someone who promises quick wins →
• Initial improvement followed by plateau or regression →
• Cycle repeats
Quick wins aren't bad, but the issue is optimizing hiring decisions around quick wins attracts people who are good at quick wins but bad at building sustainable systems. When we're experiencing pain in our business, we discount future value in favor of immediate relief. It's the same psychological mechanism that makes people choose $50 today over $100 in a year.
Before you start interviewing, separate your immediate needs from your long term requirements. Broaden your time horizons.
Zoom out.
Ask yourself, "What do we need this person to accomplish in the next 6 months versus the next 2-3 years?" Then design your hiring process to weight long term capability at least as heavily as short term fit. It doesn't need to be an either / or thing either…
Look for candidates who can address your immediate needs while building the foundation for sustainable growth.
Carl Ransom Rogers was an American psychologist who was one of the founders of humanistic psychology and was known especially for his person-centered psychotherapy.

Carl Ransom Rogers was an American psychologist who was one of the founders of humanistic psychology and was known especially for his person-centered psychotherapy.
“The curious paradox is that when I accept myself just as I am, then I can change.
This quote is about therapy, but this applies to organizational change too. Here's my last point and I'll follow it up with three tips…
The companies that make great revenue leadership hires (or great hires in general) start by accepting exactly where they are instead of hiring someone to fix problems they’re not ready to acknowledge.
In other words, the quality of your hire is directly proportional to the quality of your self awareness as a hiring leader.
So here's what I recommend…
1- Audit your own assumptions
Before they even write a job description, they spend time examining their own mental models about what revenue leadership looks like.
They ask themselves hard questions:
• What stories am I telling myself about why our previous hire didn’t work out?
• What am I optimizing for? Quick wins or sustainable systems?
• Am I looking for someone to execute my vision or to challenge and improve it?
When you’re clear about your own biases, you can design an interview process that counteracts them.
2- Focus on "systems thinking" over accolades
The best revenue leaders aren’t the ones with the most impressive individual track records.
They’re the ones who can look at your business and see the leverage points. The small changes that create orders of magnitude improvement. When I interview candidates now, I spend more time understanding how they think about problems than what specific results they’ve achieved.
Past performance is still important, don't get me wrong. The difference is I want to make sure the way they think aligns with that past performance AND what my business will need within the next 3+ years.
3- Optimize for learning speed over experience depth
This might be controversial, but I’ve started to believe that learning agility matters more than domain expertise when it comes to senior revenue roles.
Almost any role, but especially senior revenue level roles.
The business landscape changes so fast these days that someone’s experience from even five years ago might be irrelevant to your current challenges.
But someone who can quickly understand your specific context, identify what’s working and what isn’t, and adapt their approach accordingly?
This is also a high indicator or IQ. In other words, speed.
That’s gold.
The leaders who get this right hire for cognitive flexibility and systematic thinking, then invest heavily in helping that person understand their specific business context.
Last thing I'll say is this… Everything I just laid out here isn't limited to hiring. This translates to every strategic decision.
Because the same psychological skills that help you hire great revenue leaders…
• Self awareness
• Systems thinking
• Bias recognition
It also help you make better decisions in every area of your business, and every area of life. Because as someone said before (not sure who said it first):
"Business is life on all levels."
You see clearer when you develop the meta skill of recognizing and counteracting your own cognitive biases.
Even ancient Biblical wisdom says:
"Trust in the Lord with all your heart and lean not on your own understanding" Proverbs 3:5
That's a whole other article, but the point remains that we should question our own understanding and look for high levels of wisdom.
When it comes to our business, revenue leadership is leveraged enough to warrant pausing and evaluating our own mental models.
The companies that figure out how to make consistently great hires are going to have a massive advantage.
Because they’ll attract better talent across the board.
Top performers want to work for leaders who make thoughtful, systematic decisions about people and strategy. But the companies that keep falling into these psychological traps are going to keep burning through good people and wondering why their growth feels so chaotic and unpredictable.
Every failed revenue hire represents someone’s career being set back, a team losing confidence in leadership, and opportunities that will never be recovered.
In fact, I’m genuinely curious about your experience with this…
Have you caught yourself falling into any of these cognitive biases when making senior hires?
What systems have you built to counteract your own psychological blind spots?
And if you’re a revenue leader yourself, how do you help hiring leaders see past their own assumptions about what they think they need?
Let me know, my inbox is always open.
Until next time,

THE MILES MEMO
Insights and stories on leadership, sales, and performance from someone who's been in the trenches.