AI Coach: find and fix deal issues before they result in closed-lost using AI


How to Coach (by Asking Questions)

7 min
Average Score

Dan Smith

Chief Learning Officer at Winning by Design

Watch Session

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.

How Triple Session works

Training, Testing, & Feedback

Triple Session's proven formula accelerates your sales performance through consistent, organized practice, backed by measurable results.

Watch a session

Bite-Sized Knowledge

Our expert-led video sessions simplify complex sales concepts into easy-to-digest 5-15 minute videos for better retention.

Test your understanding

Test Your Understanding

After each session, there will be a quiz to test your understanding and help you improve on any areas that need more attention.

Evaluate and Grow

Evaluate and Grow

Get progress snapshots after each quiz to track your improvements and achieve your sales mastery goals.