Building AI Workflows with Claude Cowork Skills
Brock Mesarich | AI for Non Techies
YouTube creator
Dan Smith
Chief Learning Officer at Winning by Design
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.
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.
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.
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.
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.
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.
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.
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.
Brock Mesarich | AI for Non Techies
YouTube creator
Eric Nowoslawski
YouTube creator
Oleg Melnikov
YouTube creator
How Triple Session works
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.
01
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.
02
Patterns roll up across reps, deals, and objections. You see which behavior is costing pipeline, not just which rep is behind.
03
Training is assigned against that specific gap: short, expert-led sessions tied to the behavior you just measured.
04
Managers coach from evidence instead of memory. A scorecard, the moment in the transcript, and the one thing to practice next.
Start with the free plan and run the loop on your own playbook. No credit card, no procurement conversation.