Nick and I have made just about every sales leadership mistake you can think of.
We’ve made bad hires, coaching mistakes that lost us top performers, and led trainings that people forgot about in a week.
So today I’ll be sharing 4 sales leadership lessons we learned the hard way:
- When Hiring, Proof of Performance > Everything Else
- Tell Your Team to Stop Replying to Your Slacks
- Have Hard Conversations Early and Let People Opt In or Out
- Train 20%, Reinforce 80%
Let’s dive right in.
1. When Hiring, Proof of Performance > Everything Else
Nick was interviewing sales reps to work for 30MPC: he’d bring in reps with the killer resumes on paper and ask a question like:
“What’s your approach to discovery?”
Every candidate crushed it. They’d talk about doing research on the client’s business, setting clear agendas, digging into pain that impacted the business.
They sounded like discovery experts. In theory.
But when they actually had to run a discovery call, it would completely fall apart.
- They knew how to set an agenda conceptually… but forgot about it when they started building rapport.
- They knew how to uncover pain conceptually… but they peppered me with 100 surface-level questions that went nowhere.
So Nick switched from theoretical questions to proof of performance where he literally made them “do the thing” live.
Instead of asking “what’s your approach to discovery?” he would roleplay:
“Let’s pretend we’re on a live call. Set the agenda and give me your first two discovery questions.”
This accomplishes two things:
- It mimics a real discovery call to see if they can do it in action.
- It tests for adaptability because you can throw uncomfortable situations into roleplays.
You will be amazed how many reps sounded like they knew discovery, but could not ask good discovery questions for their life when it came to the mock call.
2. Tell Your Team to Stop Replying to Your Slacks
I know a rep that looks like this has a massive pipeline problem:
- Make 5 dials.
- Check Slack.
- Make 8 dials.
- Check email.
- Go to bathroom.
- Make 10 dials.
Your reps will drop everything to respond to a Slack, especially if it’s from you.
So the answer is not to stop slacking them.
Tell your reps to close Slack entirely outside of 3 windows at 8am, 12pm, and 4pm.
This relieves the pressure on your reps to reply to you right away and forces them to tunnel vision on prospecting instead of getting derailed every 2 seconds.
I would literally tell my reps “I will assume you are not prospecting if you reply to me.”
And to this day, they still laugh (and delay their Slack responses).
3. Have Hard Conversations Early and Let People Opt In or Out
Week 1, rep misses their dial goal.
Week 2, rep misses again.
Week 3, rep misses… again.
Week 4 you decide to say something, but it’s way, way too late.
- Now your rep has a pipeline problem.
- Your rep has also engrained a bad habit.
- And the conversation is 10x more awkward because it’s a big correction.
The longer you let mediocre performance linger, the harder it becomes to correct.
The moment someone misses a dial commitment, call it out immediately.
3 things happen when you do this right:
- The good reps rise to the occasion.
- The bad reps self-select out.
- Both reps realize you’re serious about your expectations.
If you want to avoid whiplash performance improvement plans, say something early.
If you want your reps to actually respect your word, say something early.
4. Train 20%, Reinforce 80%
When I was at Carta, we spent $100k+ on Sandler sales training.
72 hours after the training, people are eating, sleeping, breathing Sandler.
Upfront contracts. Negative reversals. Give-get commitments.
Our VP of Sales was stoked. For approximately 3 weeks.
I’ll never forget when he asked:
“Why isn’t anyone using the upfront contracts anymore!?”
It’s simple. If you don’t reinforce a training, you might as well consider it deleted.
When I became a VP of Sales, I was determined to solve this problem.
Any time I teach my team something I follow the 20/80 rule: 20% training, 80% coaching.
If I’m teaching my team discovery, it’d look like this:
- Week 1: Discovery Training
- Week 2: Roleplay
- Week 3: Tape review
- Week 4: Roleplay
- Week 5: Tape Review
Try to stuff 10 concepts per quarter in your reps' heads and they will remember none.
Instead, hammer one concept home per month that actually sticks.
And that’s a wrap, folks!
Like these 4 lessons? Hear all 8 stories from me & Nick in our latest YouTube drop.
