Some of the most challenging times in sales coaching are when sales reps have been on your team for just a few months.

They’re starting to get a handle on how your process works, how to connect with customers, and how to value-sell your offerings. They are starting to produce results.

Yes, you want to be encouraging to these sales reps. But being too lavish with your praise can backfire. I’ve seen newbie reps who are praised effusively misinterpret those kudos as an indication that they have already made it. They become satisfied with their progress and quickly plateau at what is an unacceptable level of results.

On the other hand, you don’t want to be so harsh that you discourage the rep. Being too critical —even though they likely still have a lot to learn — can destroy their confidence and make it even harder for them to succeed.

How you handle this phase can determine the rep’s level of achievement in the future.

The key is to communicate your high expectations when the sales rep is hired. By that I mean talk about the standards of performance that apply to all team members. But also discuss key milestones — interim levels of achievement — that you’ll be looking for from the rep as they get established.

When talking with the sales rep, consistently send the message, “You’ve reach this one milestone, and I’m pleased to see your progress. But I know you can be even better and get closer to the expectations for the team. Let’s see how good you can really be.”

To help them move from milestone to milestone, do ride-alongs (or “call-alongs”) so you can observe them in action. Don’t wait until a deal has been won or lost—if you do that, any advice you give will be too late. Instead, keep in touch throughout the sales process. Along the way, ask the rep to self-assess:

  • What did you do well here?
  • What do you want to do differently the next time around?
  • What do you need from me so you can make the needed changes?

Offer your own opinion after they’ve shared their comments, and reach agreement on where the sales rep should focus. Be sure to offer help in the form of coaching, mentoring, or additional training to help the rep develop the skills that will help them achieve the next level of performance.

As the sales rep improves, gradually increase the height of the bar — your expectations — until the rep is performing at a peak level.

This blog is part of TopLine Leadership’s series called Sales Coaching 101. On the first Tuesday of every month, we’ll cover a fundamental skill that helps sales managers interact more effectively with their sales reps. Here are other articles from this series:

Kevin F. Davis, author of “The Sales Manager’s Guide to Greatness: 10 Essential Strategies for Leading Your Team to the Top.”

Kevin F. Davis is the author of “The Sales Manager’s Guide to Greatness: 10 Essential Strategies for Leading Your Team to the Top.” The book is available for purchase on