How Often Should Sales Leaders Practice With Their Team?

The Power of Scrimmaging-and Why Most Leaders Skip It

By Nathan Jamail | Sales Keynote Speaker

Let’s start with a hard truth:

If you’re not practicing with your sales team, you’re not leading them.

You’re managing them.

And that’s a big difference.

Here’s what I’ve seen over two decades as a Sales Keynote Speaker and coach:

Most sales leaders know practice matters.
Almost none of them do it consistently.

Why? Because it’s uncomfortable. Time-consuming. Awkward.

But it’s also the secret weapon of every high-performing sales team.

Let’s dig into why it matters, how often you should be doing it, and the real reasons leaders avoid it.

1. Scrimmaging Isn’t Roleplay – It’s Leadership

When I say “practice,” I don’t mean reading a script or playing make-believe.

I’m talking about scrimmaging–running real scenarios, real objections, and real conversations just like a sports team would.

Think about it:

  • NFL teams don’t just watch film-they scrimmage before every game.

  • Musicians don’t just wing it on stage-they rehearse every chord.

  • Even surgeons rehearse complex procedures before performing them.

But salespeople?
We too often expect them to “figure it out on the field.”

If your team isn’t scrimmaging regularly, they’re using live client conversations as their practice field.

And that’s a recipe for lost deals.

2. How Often Should You Practice With Your Sales Team?

Short answer: More than you are now.

Long answer: At least weekly.

  • Run a 15-minute scrimmage in your weekly sales meeting.

  • Do 1:1 role practice before important calls.

  • Launch a “scrimmage of the week” challenge around common objections or new product pitches.

Bottom line?
Make it a rhythm, not a random event.

When scrimmaging becomes part of the culture, performance skyrockets.

3. Why Most Sales Leaders Don’t Scrimmage

Let’s be honest-there are lots of reasons leaders avoid practice:

  • “It feels awkward.”
  • “I don’t want to make reps nervous.”
  • “I don’t have time.”
  • “I trust my team to figure it out.”
  • “They’ve been doing this for years-they don’t need practice.”

I get it.
But here’s the truth:

The best teams in the world still practice.
Every week. Every day. Even during winning seasons.

So if your team isn’t practicing… are you really giving them the tools to win?

4. What Happens When You DO Practice Regularly

  • Objections become easier to handle

  • Pitches become tighter

  • Confidence goes up

  • Close rates go up

  • Coaching becomes real (not just performance reviews)

Oh-and morale goes up too.

Because when you scrimmage, you’re showing your team that you’re in it with them. You’re not just pointing fingers from the sideline. You’re preparing them to win.

Final Thought: Lead With Practice, Not Perfection

Practice is where growth happens.

It’s where trust is built.
And it’s where the difference between average and great shows up.

So, Sales Leaders:
Get uncomfortable.
Scrimmage more.
Coach better.

Your team doesn’t need a perfect leader.
They need a present one.

Let’s go coach. Let’s go win.

– Nathan Jamail
Sales Keynote Speaker