I’ll never forget the Saturday afternoon.

I got a call from Josh, my sales manager while I was on visiting family with my girlfriend (now wife) in my hometown, Tulsa, OK.

I had to pull over as I heard the words, "hey man, there's no easy way to say this but I want to be honest… I think it's time for me transition out of the company."

This was my right hand guy.

And to make it worse, 6 months prior to this I moved up to President / CEO and took over the second profit division in this company.

I was running two companies at the time (more on this later) and immediately my thoughts started racing between…

Who's going to replace him?

I know I don't have the time.

Why is he leaving?

What did I do wrong?

Is he getting poached?

Is it his pay?

Over the next couple of day's I proceeded to get messages on slack from the sales reps on the same team…

"Hey man, do you have time today or tomorrow for a quick call?"

The equivalent of the dreaded, "We need to talk".

I knew what this meant.

We went from a team of 8, to a team of 4 in a matter of days.

To give you context as to why this was so bad… I was the president / CEO and partner at THE "sales team" company.

We were the category king in our space. We specifically did sales recruiting, training, and consulting so everyone looked to us to learn sales leadership, excellence, recruiting, etc.

I had stood on stage and taught this stuff, yet here I was processing that I just lost half my sales team.

Where did I go wrong?

What did I miss?

How could I let this happen?

Not to mention, this was years of pipeline opportunity, walking out the door.

Projections set from our last 2 day executive offsite, now meaningless.

I also knew the statistics…

87% of companies that lose more than 40% of their sales team within a 90 day period never fully recover to their previous performance levels.

I knew that.

So of course, I was staring down that statistic.

The other execs on the team including Cole, the founder, now looking to me for answers and a plan.

At first, I didn't have one.

But I'll say this, there's something about failure, especially if it's crisis level…

It has a way of stripping away the fog of ego and giving us the clear lens of humility to see what we've been missing.

And grow.

That devastating Saturday became the catalyst for building something I should have built from the beginning.

I’m genuinely grateful it happened.

Because losing everything taught me the difference between building a team on a foundation of sand VS on a firm foundation.

Building something with depth and anti fragility.

What I discovered over the next 90 days transformed how I think about leadership entirely.

And I want to share it with you.

The Honest Truth About Why Good Leaders Lose Great Teams

For weeks after the exodus, I tortured myself trying to understand what went wrong.

Was it compensation? I’d always paid competitive OTE's (on track earnings).

Was it culture? We had team off-sites, camaraderie, we had fun.

Was it my leadership style? I thought I was giving people autonomy and trust.

But the more I dug, the more I realized the humbling truth.

I had fallen victim to the Dunning Kruger effect.

If you're not familiar, the Dunning Kruger effect is a cognitive bias named after two psychologists, David Dunning and Justin Kruger.

"Pride goes before destruction, a haughty spirit before a fall."

- Proverbs 16:18

I wasn't familiar at the time, but through this experience I was eager to learn from my mistakes and grow.

So I read.

A lot.

And I learned about this unfortunate effect we can stumble into.

Essentially Dunning and Kruger's research showed that people with limited knowledge or skill in a particular area often overestimate their abilities. It's like the beginner who thinks they're a pro because they don't know enough to recognize their own gaps.

A cognitive bias.

However, on the flip side, and this is where it hit me hardest…

Those with real expertise can sometimes underestimate themselves, but more often, success breeds a subtle overconfidence where you assume things are easier than they are, or that you can handle more without consequences.

In my case, it was classic overestimation from the "I've got this" mountaintop.

See - we had been crushing it at Closer.io for years.

Record month, record quarters, over and over again. We had the sales team that was the envy of the industry.

And honestly, no major screw ups, just steady wins.

I started feeling a bit invincible.

So when the opportunity came to step up as President/CEO and take over our second company (RCA, our B2C division), I jumped at it.

This came up during an executive offsite.

Me, Cole, Brian, Sasha…

"Mitchell, you should run both companies. It'll be seamless."

"Yea Mitchell, I think you've earned it and it'll free up Bryan for xyz."

I mean this was everything I had worked for.

Sounded brilliant in the moment, but it was a massive miscalculation.

"No one can serve two masters. Either you will hate the one and love the other, or you will be devoted to the one and despise the other."

- Matthew 6:24

What proceeded was a slow train wreck.

Hindsight's 20/20…

And so over the next several weeks after Josh quit, I began to see exactly what went wrong.

Simply put, I got spread way too thin, juggling two companies while trying to keep everything afloat.

Our core value was "Get and stay in sync," but I was completely out of it.

I wasn't close to the front lines anymore…

The market feedback, team feedback, the customer feedback…

Which is a common pitfall and I knew that.

See - leaders in a company have ALL the authority, but often the least context.

Yet, the team on the front lines have ALL the context, but the least authority.

I used to avoid this with QC (quality control), sales audits, and reviews but now I didn't have time for it.

I stopped creating systems to pull that vital intel up to me.

I was making decisions in a vacuum, excelling at nothing and instead I was doing "ok" at everything.

When this happens, cracks begin to form.

The team started slowly moving away from what worked. Close rates began to decrease, CAC (cost to acquire a customer) began to rise.

The team's earnings decreased along with their performance.

I didn't catch it early because I was too far removed.

And the gossip kicked in because I didn't over communicate why it was happening.

Remember, silence fills itself.

So if you don't communicate, a narrative whether right or wrong will manifest.

Usually, it's not the narrative you want, and negativity spreads like a virus.

And spread fast, it did.

Eventually… Josh quit, then the rest of the team.

Looking back, I see the collateral damage I could've prevented.

So what did I do about it?

Because now it was up to me to fix it.

In about 90 days, I not only learned all of the heard lessons but I did turn the team around, rebuilt, and with the help of my team we did this in about 90 days.

I'm going to share exactly what I did AND what I could've done to prevent the exodus on the first place.

The Sales Team Resurrection Framework (How To Build Something Unbreakable)

The framework that saved my team - and has since helped dozens of other leaders navigate similar crises - starts with a counterintuitive principle:

Build the vehicle before you add new passengers.

Step 1 - Stop the bleeding

Look - if there's smoke there's fire.

I was caught off guard with this whole mess, but I was at least aware enough to know that the reps that hadn't left were probably pretty close.

So I got on 1-1s with them right away to temp check, get feedback, and make sure they didn't leave.

Similar to how I'd put an employee on a PIP (performance improvement plan), I put a PIP on myself FOR them.

"If I just fired you without any prior communication, would that be fair to you? Look, I will always over communicate to you, if you're anywhere close to termination. In a similar way, I'd want you to over communicate to me, if you're close to leaving. So honestly… where are you at right now mentally?"

We had brutally honest conversations, I listened to them, put a plan together and I asked for 60 days to make these changes.

Step 2 - Find the root problems

Once the immediate crisis was stabilized, I conducted a brutal audit of what actually caused the exodus.

This process is now standard for every single client we work with now.

It consists of two core analysis.

1- Quantitative analysis

2- Qualitative analysis

So I stared at spreadsheets for hours. Every single key success metric we have for this department, I analyzed and took notes. This was the quantitative part.

Then I moved on to the qualitative part.

I pulled a random selected batch of sales call recordings and binged them for hours.

  • Intro calls from SDRs

  • Demos from AE's

  • Follow up calls

  • Sales meeting recordings.

Then I did something that no one wants to hear lol…

I took calls myself.

I know a lot of CEOs out there will say this is a waste of time, but it was incredibly insightful.

"The first principle is that you must not fool yourself and you are the easiest person to fool."

- Richard Feynman

I got a very very clear picture of exactly what changed on my team.

I learned…

  1. The general avatar the sales team was talking to, had slowly drifted from who we used to talk to a year ago. Not necessarily a bad thing, but we definitely needed to adjust the pitch to accommodate

  2. The whole team felt very silo'd and so I initiated a weekly sales meeting where the fulfillment team came on as well to get more in sync on what's happening after clients onboard with us

  3. A lot of deals where getting lost in the follow up. Meaning when we had initial demo and couldn't get them across the line on that call, deal were dropping off, so I hyper focused on pitching and follow up on our daily sales meeting over the next 4 weeks.

Step 3: Reset the culture

All of this would be in vain if the culture (narrative) didn't change.

I've written about culture, a lot, so I won't spend too much time on this.

Just know this, HOW you're team works together is predicated on beliefs and narratives.

So if you want to change the culture on your team to be resilient, high performing, and somewhere that pulls the best out of people…

You have to change the beliefs and narratives.

So that same week I took over the team I called a reset huddle on a Sunday afternoon.

We got clear on focus: Individual targets, calendar tweaks, but more importantly, who we wanted to become as professionals but more so people.

Prep work included a similar agenda to an offsite, just more brief.

So this included…

  • 90 day reviews (calls booked, closed, upfront collected)

  • Goals and aspirations

  • Feedback for each other to achieve those goals

  • It surfaced silos for example, resentment toward fulfillment because we were disconnected.

  • We laughed, built camaraderie, and it sparked that iron-sharpens-iron effect where reps started helping each other

Things like this, team dynamics, is a process.

Not an event.

This requires more than just a reset meeting, although that's a good place to start.

So I made an intentional shift in my overall leadership style.

We addressed negativity head on. Studies show it's the top predictor of job failure.

It's actually worse than skill gaps.

And lastly if I wanted my team to do something, the way in which you do that is everything.

I shifted a lot of my communication, feedback, etc to transformation and transcendent leadership.

If you want to learn more on this, check out this newsletter where I break this down in depth.

How it Ended

So the product of these changes, was quite remarkable. I'm proud of that team.

In a matter of just 4 weeks, we saw collective close rates jump from 19% to 28%, CAC drop from $1,696 to $1,420.

The top rep, Tyler went from 13% to 31% close rate, CAC from $2,969 to $982.

We even beat the previous November's numbers despite historical B2B challenges due to holiday season.

And that's with a smaller team.

I could keep going with many more lessons I learned, micro lessons in communication, leadership, culture, and so on.

But this was the core of it.

Looking back, I understand WHY it happened and I’m genuinely grateful for it.

It forced me to confront my own blind spots.

And learn the difference between leading through hierarchy and leading through principles and by example.

The crisis stripped away my illusions and forced me to build something sustainable.

I hope this gives you insight in 2 things…

  1. How to avoid an exodus and what makes a sales team great

  2. How to use crisis to your advantage

The leaders who emerge from crisis stronger aren’t the ones who never face adversity.

They’re the ones who use adversity to build resilience and better teams that can handle anything.

"Consider it pure joy, my brothers and sisters, whenever you face trials of many kinds, because you know that the testing of your faith produces perseverance."

- James 1:2-3

Till next time,

- The Miles Memo

-Mitchell Miles - CEO

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