Revenue Storm Insights | Sales Strategy Blog

Why Your Sales Team Doesn’t Feel Coached — Even When You’re Coaching

Written by Vince Corica | Feb 24, 2026 4:22:33 AM

A Disappointing Reality

This image shows a disappointing situation, doesn’t it? Are you sure your team would agree with you on how often they are coached? If you’re concerned about how your team would answer this question, this article is for you.

Why would such a shocking disparity exist? Are Sales Leaders lying? Are Sellers forgetting their coaching sessions?

Neither of these things are happening.



The Definition Gap: Coaching vs. Inspection

What’s happening is a definition gap. Sales Leaders perceive themselves to be COACHING when, in fact, they are INSPECTING. Sellers immediately and totally feel the difference. They understand that inspection is a part of life, and they undoubtedly accept it.

What Sales Leaders need to do to close this definition gap is simple. We need to reflect on HOW we conduct a coaching session to ensure that the Seller experiences coaching, and we need to adhere to a process that effectively guides and enables a coaching collaboration.

Note the use of the word collaboration. Collaboration is the North Star of an effective coach.


Three Areas for Self-Inspection

Our experience is that a great place to start avoiding unintentionally entangling inspection with coaching is with a self-inspection of our mindset on these three coaching aspects:

  1. How committed are you to doing more listening and collaborating versus talking and directing?
  2. What about the questions you usually ask?
  3. To what extent do you feel like you need to be the smartest person in the room while coaching?

Let’s talk about each one of these.

Listening and Collaborating vs. Talking and Directing.

How committed are you to doing more listening and collaborating versus talking and directing?

You genuinely want to help the Seller, of course. You see a better approach than the Seller indicates they’re following. You want to quickly get to that better approach so the Seller can start executing.

That’s great for a Pipeline or Top Five Deals Review. But the Seller was promised this would be a Coaching Session. This is where the Definition Gap starts to intrude on your intention to coach.

The cure for this is simple…it’s PREPARATION. Not just from you. From both of you.

The Seller needs to provide you with whatever documents from your CRM you require prior to a coaching session. If you don’t require one or more documents prior to the coaching session, you and the Seller immediately descend into a wasteful, two-dimensional chat about the deal, when what you needed and wanted was meaningful, executable progress on the opportunity.

A Sales Leader who shifts to three-dimensional coaching (You, the Seller, one or more documents) can study the documents provided before the session and prepare topics to discuss, which you design to be collaborative.

Coaching topics prepared in advance save time, boosts an atmosphere of collaboration, and improves mutually beneficial outcomes exponentially.

The Questions You Usually Ask.
Are they questions that sound like this?

  • “What’s taking so long?”

  • “Why didn’t you…?”

Those kinds of questions, of course, sound like inspection, not coaching. Here is a short list from our almost limitless collection of collaboration and co-creation coaching questions:

  • What would you like to accomplish in this session?

  • Tell me about your last meeting with your most positive client.

  • What specific elements of our Value Proposition have the most traction with the clients so far? Which ones are not getting traction?

  • What other courses of action have you considered?

  • What do you think about trying this…?

  • What concerns or objections do your most concerning Detractor have?

When questions such as these have provided collaborative outcomes in Strategy, Tactics, and Next Steps, these kinds of questions keep the coaching experience very much intact for the Seller:

  • Can you review the Next Steps we agreed to with me?

  • What concerns or questions do you have about any of these?

  • What additional resources might you need in taking those steps?

  • When do you think we should have our next session?

  • How well did we achieve the objectives you set at the start of this session?


The “Smartest Person in the Room” Trap

This commonly used term is surely a double-edged sword if there ever was one.

On the one hand, it feels good. It feels powerful. It’s great to have everyone value your expertise and your opinions.

On the other hand, it limits input from others, which stifles your own growth. It increases the burden on you, which is already extensive.

This can be debated forever. But unequivocally declare one thing on this topic…a Sales Leader who presents themself as the Smartest Person in the Room is NOT coaching. They’re inspecting/directing.

So, let’s quash this instinct if it sneaks up on you. Good leaders never confuse power with greatness. Forget chasing Smartest Person in the Room. Instead, strive to be the MOST CURIOUS, MOST COLLABORATIVE person in the room.

Ask the best questions, ones that assertively open the gates of exciting ideas, energizing what-ifs, and the joy of being part of a problem-solving team!

Closing Thoughts

So, Sales Leaders. I hope you embrace the reality in the image at the top of this article and honestly assess whether this chart might represent your team.

If you sense a gap might exist in your team, I hope this article gives you some ideas on how to significantly increase the likelihood that your team’s two Coaching Frequency curves soon lie right on top of each other.