Back to sessions
Coaching

How to Coach (by Asking Questions)

Dan Smith

Chief Learning Officer at Winning by Design

Watch session
Duration
7 min
Rating
4.8/5

In the world of sales leadership, being a great coach is a skill that can set you apart from the rest. Effective coaching is not about telling people what to do but rather guiding them with well-crafted questions. Not all questions, however, are created equal. In this session, we will explore the art of asking the right questions to empower your team and drive results. So, how can you become a good coach? Let's dive in.

The Pitfalls of Bad Questions

The Common "Does That Make Sense?" Trap

One of the most common pitfalls in coaching is asking, "Does that make sense?" More often than not, you'll receive a resounding "yes" in response. However, this question can be misleading. It might imply that your message wasn't clear, or worse, the person doesn't truly understand but doesn't want to admit it. Instead, try asking, "How would you apply this to a scenario?" This encourages action and engagement rather than passive agreement.

Giving Advice in Disguise

Another pitfall is asking questions that are thinly veiled advice. For instance, "Do you think it would be better to come prepared with a report next time?" These leading questions do not promote independent thinking. Instead, focus on questions that stimulate thought and self-reflection.

Crafting Great Questions

Starting with Open-Ended Curiosity

Begin your coaching sessions with a powerful open-ended question: "What's on your mind?" This prompts your team to share their thoughts, whether they relate to personal or business issues. Understanding their context is crucial to guiding the conversation effectively.

Navigating the Challenge Zone

Address challenges by asking, "What challenges are you facing?" Most people tend to blame external factors initially. Follow up with a more introspective question: "What challenges are there for you?" This shift encourages self-reflection and personal growth. Keep the momentum going by asking, "What else?" It leads them to explore new perspectives and solutions.

The Cautionary Tale of "Why"

While "why" questions can be valuable, they often trigger defensiveness. When providing constructive feedback, opt for "what" or "how" questions. They convey partnership and collaboration rather than criticism.

Ending on a Positive Note

To ensure your coaching session leaves a lasting impact, conclude with a self-reflective question. Instead of simply asking, "What did you learn today?" try, "What was the most useful thing you learned today?" This question encourages individuals to find value even in challenging conversations. It's a powerful way to gauge their emotional investment in growth and development.

Enhancing Your Coaching Skills

To delve deeper into the art of coaching and learn practical strategies, watch this video session featuring renowned experts in the field. This session provides valuable insights on how to be a successful coach and transform your sales leadership.

Mastering the art of coaching as a sales leader involves asking the right questions that inspire, challenge, and empower your team. By avoiding common pitfalls and embracing the power of well-crafted inquiries, you can elevate your coaching sessions to drive better results and foster personal and professional growth. Remember, it's not about what you tell your team; it's about the questions you ask to guide them on their journey to success. Watch the recommended video session to deepen your coaching skills and unlock your full potential as a sales leader.

Free plan, no credit card. Watching opens this session in the Triple Session app.

How Triple Session works

One coaching loop, running every week

Coaching fails when it is an event. Triple Session turns it into a loop: measure the gap, train against it, and check whether the next call moved.

  1. 01

    Identify the gap

    Every call is recorded and scored against your own playbook, so the distance between what your team says and what the playbook asks for stops being a guess.

  2. 02

    Surface the insights

    Patterns roll up across reps, deals, and objections. You see which behavior is costing pipeline, not just which rep is behind.

  3. 03

    Train the people

    Training is assigned against that specific gap: short, expert-led sessions tied to the behavior you just measured.

  4. 04

    Deliver the feedback

    Managers coach from evidence instead of memory. A scorecard, the moment in the transcript, and the one thing to practice next.

Your team's next call is already on the calendar.

Start with the free plan and run the loop on your own playbook. No credit card, no procurement conversation.