How to Give Difficult Feedback to Your Sales Team

constructive feedback conversations difficult conversations feedback techniques leadership tips management tips sales team management May 18, 2025

Avoiding feedback might feel easier in the short term, but it leads to long-term problems.  Your team deserves direct, respectful coaching that helps them improve. Giving honest, constructive feedback isn’t about confrontation.  It’s about helping your team succeed.

The Simple Formula: When–Then–Ask

One of the best ways to take the pressure off these conversations is by using a structure.  Here’s how it works:

  1. When – Describe the specific behavior you've observed
  2. Then – State the consequence or impact of that behavior
  3. Ask – Invite change with a clear, respectful request

Example:  "When you're late to a client meeting, it reduces our credibility with the customer. Can you commit to being on time moving forward?"

This structure keeps the feedback focused on observable actions, not personality, and ties the issue to job effectiveness, which is what coaching should be about.

Why This Formula Works

  • It’s easy to remember – You don’t need extensive prep to use it
  • It’s grounded in facts – Focus on what actually happened, not how you feel about it
  • It’s action-oriented – You’re not just pointing out a problem, you’re asking for a change
  • It’s repeatable – Use it in the moment or in a one-on-one with minimal friction

When to Give Feedback

Timing matters.  It is recommended that you wait until you see a pattern — typically the third time a behavior occurs. This prevents overreaction and gives your team member a chance to self-correct.

Also, only give feedback on behavior you’ve personally observed. Secondhand feedback often feels like gossip and can create distrust.

Tailoring Feedback with DISC Profiles

Not every one of your team members will hear feedback the same way. That’s where DISC profiles come in.

If you know your team members’ DISC styles (Dominance, Influence, Steadiness, Conscientiousness), you can frame feedback in a way that connects better. For example:

  • A D-style rep may prefer direct, concise feedback.
  • An S-style rep may need you to ease into the conversation with rapport first.

You don’t need to soften the feedback, just deliver it in a way that the person is most likely to receive it constructively.

Feedback Doesn’t End With Correction

Once you’ve given feedback and the behavior improves, affirm the progress.  Recognition reinforces change and shows your team members that you’re paying attention to not just when things go wrong, but when they go right.

The When–Then–Ask framework gives you a simple, effective way to lead those conversations without hesitation. Combine it with DISC insights and consistent follow-up, and you’ll create a culture of trust, accountability, and growth.

Ready to level up your feedback skills?
Download your free DISC Profile for Sales Teams today!