I went from getting elementary school students in central PA to sell chocolate bars, magazines, and cookie dough… to being the CRO of a publicly traded company.
We’re all busy…too busy. Every once in a while, you get reminded to look back.
When that happens, if you are like me, your reaction is usually, “How the heck did I get here?”
Well, it wasn’t all sunshine and unicorns.
I wanted to share the 3 toughest learning lessons I had on my way to CRO so you don’t make the same mistakes I did:
- Shield the Field
- Don’t doom the PIP before it even starts
- Why hiring “The Best” almost broke us
These 3 experiences created beliefs that continue to influence my sales leadership career daily.
(1) Shield the Field
Sales leaders must protect their reps’ time. It may be the first law of sales leadership. Reps doing busywork are not selling.
I got confused by this as a young sales manager. I thought that helping my reps to sell better was more important than selling.
It’s not, and I learned that the hard way.
18 months into my first sales leadership job, I thought I was rocking: I came up with a million new trainings, fun contests, team meetings, and ways for reps to share their learnings.
Each week was packed with valuable things for my reps.
Then, I got a call from one of my most tenured and successful reps, M.S.
He said, "Mark, this stuff is taking me away from actual selling. It's busy work."
I got defensive, hit "forward," typed my VP's name, and wrote something like: "Can you believe this guy?"
I hit reply (not forward). My VP AND my rep got the email. Uh oh.
An hour later, my rep's name was on my phone, and I didn’t answer. A few hours later, I summoned the courage and called him back.
He let me have it. That was my "oh shit" moment.
I realized I had no idea what I was doing. So I called a few mentors.
This is when I learned the concept of “Shield The Field.” A lot of times, as leaders, you want to put all of these trainings and meetings on the calendar in an attempt for you to feel like you're being useful in doing your job.
But you actually need to keep your sellers focused on selling as much as humanly possible and block distractions.
So the next “fun” thing or random training you suddenly want to throw at your reps ask yourself:
Will it create more noise or create focus and more room to sell?
(2) Don’t doom the PIP before it even starts
One of my reps, C.H., was a mid-performer. He wasn’t listening to prospects and over-pitching was preventing him from leveraging a ton of amazing strengths he had to become a top rep.
We coached him. He couldn't change. I decided to put him on a PIP.
I’d put 10-15 reps on PIP by this time in my career. I hadn’t had a single one result in retaining the rep.
In other words, something was broken with PIPs for me.
I think he knew it was coming because he was ready as I started the call. He had data to make his case on why he didn’t need a PIP.
C.H. said, "You're putting me on this PIP because you're trying to fire me."
That’s when I had to ask myself: Do I actually want to keep CH? Or do I really just want to fire him?
A lot of managers put reps on PIP that they really just want to fire. If you're doing that, just make the hard decision and let the rep go.
And that’s what every rep thinks going into these conversations that makes them defensive.
But I actually wanted to keep CH around.
So I told him this PIP conversation is more important than the PIP itself.
I said that if he wanted to turn it into a you versus me conversation, I knew it wasn't going to work out, but if he wanted to take it as an opportunity to coach him, I told him I would be there to support him.
C.H. realized in the PIP conversation that I was on his side and became the first rep to crush his PIP.
It wasn’t the PIP itself. It was the fact that he committed to being coached in the PIP conversation.
And it was because I realized at that moment that I needed to make it clear that I wasn't just trying to get him out of the organization. I actually wanted him to stick around and take the coaching.
(3) Why Hiring "The Best" Almost Broke Us
At Outreach, we hired 10 reps who were #1 at their previous companies.
They were built for established markets with established brands, whereas we were doing an evangelical sale in a new category.
Those are completely different jobs.
Every single one of them failed. Why?
- We didn’t need someone with perfect pedigree experience (hiring for background)
- We didn’t need someone with a perfect discovery call (hiring for skills)
We needed reps who could thrive in ambiguity of the early stages (hiring for traits).
That’s when I learned: You have to hire for traits over skills and background.
I can teach someone skills. But I can’t teach someone how to work hard or thrive in ambiguity.
So I reworked my interview process to test for traits instead of skills.
For example, I might still have them do a mock cold call. But I'm actually going to test for coachability by having them do the cold call twice and seeing how they react to coaching.
I don't care if the cold call is good. I care that they have the train of coachability.
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I learned a ton leading outreach from 0 to 250 million dollars in ARR, and I've shared a lot of my mistakes so that you don't have to make the same ones.
And if you want to become a great sales leader: I've broken down everything I've learned in our Sales Management OS course.
It covers everything from how I hire to how I forecast to how I coach my reps. And I hope it helps you be a better sales leader because I made a lot of mistakes along the way:
