· Letter
Why Your Sales Training Isn't Working
The Optimism Advantage
Originally published on Substack (opens in a new tab). Subscribe (opens in a new tab) for the next letter.
Your pessimistic salespeople are costing you money.
Not because they’re bad at selling. Because pessimism kills action.
I’ve watched founders invest heavily in sales training. Objection handling workshops. Closing technique bootcamps. CRM systems. Scripts.
And then wonder why nothing changes.
The answer is usually simpler than they expect: their team’s heads are full of fear before they even pick up the phone.
The COPE Mindset
I’ve been learning about this through my work as an Outgrow Advisor (opens in a new tab). Alex Goldfayn calls it COPE:
C – Confidence
O – Optimism
P – Positivity
E – Enthusiasm
You can’t fake these. And without them, every call becomes a burden.
Sales is two-thirds mindset. One-third technique.
Most companies get this backwards. They teach the technique and hope the mindset follows. It doesn’t.
What the Research Says
Recent research from Rockefeller University (opens in a new tab) looked at the impact of optimism—not just on wellbeing, but on performance and longevity. The findings were striking:
People in the most optimistic quartile lived 11-15% longer (controlled for smoking, diet, exercise, alcohol, depression, and BMI)
They had 50-70% higher odds of reaching 85 years old
35% lower cardiovascular risk
Better stress management and faster emotional recovery
And here’s the part that matters for companies building sales teams:
Optimistic sellers and business owners consistently outperform pessimistic ones.
Not by a little. Significantly.
The research confirms what I’ve seen in the field: when your people believe good outcomes are possible, they act differently. They pick up the phone more. They follow up faster. They recover from rejection quicker.
Pessimism creates hesitation. Optimism creates momentum.
The Skill Nobody Talks About
Here’s what most founders miss: Optimism isn’t a fixed personality trait. It’s a learnable skill.
You can train it. Just like you train objection handling or closing techniques.
This was the insight that shifted my thinking. We spend so much time trying to fix behaviours: call more, follow up faster, ask better questions, all without addressing the belief system underneath.
If someone believes “they probably won’t buy anyway,” no amount of technique will fix that. The fear shows up in their voice. Their prospects hear it before they finish the first sentence.
But if someone believes “this call could help them,” everything changes.
Same prospect. Different energy. Different outcome.
How to Train Optimism
The research points to several practices that actually work:
1. Cognitive Reappraisal
This is the practice of reframing setbacks as temporary rather than permanent.
Instead of: “I lost that deal because I’m not good at this.”
Try: “That deal didn’t close. What can I learn for the next one?”
The first interpretation creates paralysis. The second creates movement.
Train your team to catch themselves when they catastrophise. Ask them: “Is this a permanent truth, or a temporary setback?”
2. Morning Sunlight
This one surprised me. 10 minutes of natural light in the morning helps regulate mood and energy throughout the day.
It’s simple, free, and backed by science. Encourage your team to take calls outside or near a window in the morning. Small shift, real impact.
3. Deliberate Breathing
Before important calls, a few minutes of slow, controlled breathing calms the nervous system. I particularly love box breathing. Try it on the Calm app. (opens in a new tab)
Fear shows up in the body first. Racing heart. Shallow breath. Tight shoulders. Your prospects can hear it.
A calm nervous system creates a calm voice. A calm voice creates trust.
4. Structured Gratitude
Write down 3 things you are grateful for daily - either when you wake up or before you sleep. Not goals. Not tasks.
This trains the brain to notice progress instead of problems. Over time, it shifts the default lens from “what’s wrong” to “what’s working.”
I’ve seen teams transform their energy within weeks of implementing this practice consistently.
What Fear Sounds Like
You’ve probably heard these from your team:
“If I call them, I’ll be bothering them.”
“If I call without an appointment, they’ll get upset.”
“I should wait until I have something new to share.”
That’s the voice of fear. And it’s contagious.
One pessimistic team member can drag down the energy of an entire sales floor. They don’t mean to. But negativity spreads faster than optimism.
The reframe is simple:
They’re your customer. You’re there to serve them. When you pick up the phone, you’re calling to help—not to bother.
That’s it.
When your salespeople believe that, COPE kicks in:
Confidence replaces hesitation
Optimism replaces dread
Positivity replaces excuses
Enthusiasm replaces avoidance
Recognition Over Bonuses
One more insight from my recent learning: recognition is more effective than money for driving behaviour change.
Most founders default to bonuses and incentives. But recognition does something bonuses can’t:
It’s public, so it teaches the rest of the team what good looks like
It reinforces identity (”I’m someone who succeeds at this”)
It motivates both the recipient and the observers
When someone on your team closes a deal or makes a great call, don’t just pay them more. Celebrate them publicly. Name the specific behaviour. Make it visible.
This builds optimism across the team, not just in one person.
The Bottom Line
You can teach someone how to pitch. You can teach objection handling. You can teach closing.
But you can’t teach them to believe they’re helping people.
That belief has to come first.
If your sales feel inconsistent, if your team hesitates before picking up the phone, if rejection seems to linger longer than it should—the problem probably isn’t technique.
It’s mindset.
Fix that first. Then add the skills.
One question to consider this week:
Is your team’s mindset helping or hurting your sales?
Sid
P.S. If you’re a leader stuck with unpredictable sales and want to build a system that creates predictable revenue growth, reply to this email. I’d be happy to share what’s working for my clients.
If your revenue growth feels unpredictable or market-dependent, this webinar is for you. Alex Goldfayn will walk through real Outgrow client case studies showing how companies add 15-30% in annual sales — predictably enough to hire and plan around it. Join us live March 2nd at 12 PM ET / 5 PM UK. Save your spot. (opens in a new tab)
Originally published on Substack (opens in a new tab). Subscribe (opens in a new tab) for the next letter.