February 22nd, 2012

Questions: The Fabric of Effective Coaching Conversations

If you watched Super Bowl XLVI earlier this month, you might think that professional coaches, who manage winning teams, deploy a robust coaching strategy balanced between scowling and screaming. But look closer — professional sports coaches scowl and scream to motivate or “remind” their players of the need to execute the game strategy, in both real time (during the game) and beforehand in preparation for the game. While the game is being played, individual coaching does take place all around the head coach (on the field, in the booth, and on the sideline). It is no different in business, except maybe the screaming part. Business leaders know to use effective coaching conversations, not commands — and the fabric of effective coaching conversations is woven with questions.

With questions, you guide your team members to develop their own strategies and solutions to situations they’ve just encountered. Here’s a quick overview to using questions that coach your team to improve their own sales performance.

What should you ask to have effective coaching conversations?

Good coaching questions tend to be open-ended. Whether you’re discussing a current opportunity, a past situation, preparing for an upcoming challenge, or working on a specific skill issue, strive to get your sales reps to assess the situation and come up with the answers themselves.

Ask questions like these:

  • What did you do well? What could improve?
  • How did you think you handled the client’s question on “x”?
  • What led you to approach it this way?
  • What are the customer’s risks, and how are we mitigating them?

The power of coaching is that it takes place in real time, and the closer to the activity for which you are coaching, the more likely it is that behavior change will occur. Be ready to ask questions at key moments, not just in scheduled meetings. Read Different Questions, Different Results (A Note to the Sales Manager)” to see what Anthony Iannarino of The Sales Blog says about asking the same questions over and over. And for more thoughts on coaching, read Sales Coaching Strategy – Make Sure You Focus on Definitions” to see what Brian Lambert of Forrester says about how important it is to define sales coaching for your organization.

Let the sales rep answer your questions

Once you ask the question, be quiet. Give the sales rep a chance to think it through. Resist the urge to jump in with direction.

This is not to say that you should never provide assistance. Different people need different levels of direction. If it’s clear that the sales rep is struggling, make some suggestions that will guide the sales rep in the right direction. Example: “You might think about it this way …” or “When Joe had a similar problem, he …”

Don’t take the monkey!

Remember that good sales reps are good at asking questions. While this skill is extremely valuable with customers, it’s something to be mindful of during a coaching conversation.

Whether you accept primary responsibility for a salesperson’s problem or action item, you may not realize it at that very moment, but it is as though you have allowed the “monkey on the back” of the salesperson to be transferred to you. Ken Blanchard describes this problem as a monkey on a person’s back. Make sure the monkeys stay on your sales reps’ backs. Use questions to help empower your sales reps to figure out how to take care of their monkeys themselves.

What is your most effective coaching question?

Learn more about Richardson’s comprehensive sales training and coaching solutions by visiting http://www.richardson.com

By David DiStefano, President and CEO of Richardson

About The Author: David J. DiStefano

David DiStefano is a seasoned executive with nearly three decades of successful senior management experience with both early-stage and global organizations. Over his career David has managed finance, operations, sales, and demand generation functions. For the last 17 years, David has been instrumental in leading Richardson to its place as a premier global sales performance organization.

David J. DiStefano

4 Responses to “Questions: The Fabric of Effective Coaching Conversations”

  1. February 23, 2012 at 7:39 pm, Dave Stein said:

    Important post, David. Thanks.

    For some salespeople, asking them questions that prompt them to consider alternatives is very helpful. It promotes 1) creative thinking, 2) analysis, 3) decision-making, and 4) valuable dialog between the coach and the salesperson.

    “Joan, think of a few alternative approaches to the challenge you are facing, and let’s talk about what you think the best course of action is and why.”


  2. February 23, 2012 at 8:20 pm, Todd Spare said:

    I am a proponent of sales management being a (mostly) field based position. When traveling with reps I was willing to let them fail in order to learn. Whenever we would leave a sales call, they knew the four questions thy were going to have to answer.
    1. What did we do right?
    2. What did we do wrong?
    3. What could we have done better?
    4. What do we do next? (What action step did we set expectations for)
    Sometimes it was painful, but it was always instructional.

    I agree….open ended questions are the best teacher…

    Thanks for the post….


  3. March 15, 2012 at 5:34 pm, Gerhard Gschwandtner said:

    I loved your insight: “The fabric of an effective coaching conversation is woven with questions.”
    Questions are like a Swiss Army knife that can cut through knotty issues, or unbottle fermenting spirits that are way past their expiration date. Here are my two key questions after a joint call:
    1. What was good – and why? I want the salesperson to articulate the skill used on the call.
    2. What could be improved- and how? I don’t want to block the salesperson’s creativity by asking them to describe what went wrong. We both know that. I want to shift the focus on what could be done better and have them describe how they’d do it. This little nuance can turn the fabric of a coaching conversation from stitching a sow’s ear to creating a custom suit.


  4. April 05, 2012 at 2:53 pm, tim hagen said:

    Awesome blog entry!


Leave a Reply

Previous Post:


Next Post:


HE Blog Directory Business Blogs best blog sites