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A practical introduction to coaching conversations

Develop the skills to be a more empowering leader, teammate, and friend

Heidi Helfand

Listening is power. By tuning in and applying self-management and directed curiosity, you can help others solve their own problems instead of telling them what to do, giving them the tools they need to be leaders in your organization rather than “order takers”. In this interactive workshop, Heidi Helfand leads a crash course in coaching conversations - teaching you practical communication techniques to draw out the leader in others.

Heidi first teaches you listening and self-awareness techniques. Next she digs into skills and behaviors you can exhibit to verbally and physically “show” other people that you are listening. Following that you practice techniques for asking questions focused on curiosity and the benefit of the other person instead of for your own personal “information gathering”. The workshop culminates into a framework for having opt-in coaching conversations that are helpful for mentors, managers and anyone who wants to help others succeed. You’ll be able to apply these skills and techniques to all areas of your life.

What you'll learn-and how you can apply it

By the end of this live, interactive online course, you’ll understand:

  • How to design coaching conversations to help the other person unearth an action or desired change
  • How to refactor your one-on-one meetings so you can incorporate a coaching approach
  • How to design coaching conversations to include accountability and follow through
  • How to invite people into coaching conversations and not surprise them with it
  • The three levels of listening and how building an awareness of your own listening can help you control yourself and regulate your attention
  • How to show others that you are listening through mirroring and paraphrasing with words and actions
  • How to draw people out and help them discern what they really want by asking open-ended, powerful questions
  • How to connect coaching into Individual Development Plans (IDPs)
  • How rank and privilege impacts coaching

And you’ll be able to:

  • Distinguish the difference between coaching and mentoring and when to use each skill set
  • Understand why always telling people your opinion first gives them less options
  • Identify coaching ethical issues and know when to refer people to talk to specialists like your human resources team or therapists outside your company

This training course is for you because...

  • You’re an engineer who wants to improve your communication skills
  • You’re a manager and want to shift your approach to be more growth-based
  • You want to become a manager
  • You are an architect and you want to encourage others to determine their own solutions to grow their skills instead of just telling them what to do


  • No specific prior experience besides working with people in a corporate setting

Recommended preparation:

  • Complete this intake survey before the course. Although it is optional, it would be helpful for your instructor to gather this information in advance of the course.
  • Watch Defining Coaching & Mentoring (video: 4m 16s)

Recommended follow-up:

About your instructor

  • Heidi coaches and influences fast-growing companies using practical, people-focused techniques. Her approach is based on experience at highly successful startups. The first was ExpertCity, Inc. (acquired by CitrixOnline) where she was on the development teams that invented GoToMyPC, GoToMeeting and GoToWebinar. Heidi helped the company scale from 15 employees to 800. Then she was Principal Agile Coach at AppFolio, Inc. makers of workflow software for property management and law verticals. There, she built a coaching group that supported dynamic, cross-functional teams as the company scaled from 10 people to 650. She is currently at Procore Technologies – a leading provider of cloud-based applications for construction. At Procore, Heidi is in R&D leadership, coaching and consulting on software development and reteaming best practices as this company scales globally.


The timeframes are only estimates and may vary according to how the class is progressing

Introduction to coaching (20 minutes)

  • Presentation:
    • What is coaching and what isn’t coaching?
    • What are the differences between coaching, mentoring, consulting and therapy?
    • Can you use skills from all these disciplines?
    • What does using these skills look like in technical workplaces?
  • Q&A

Why is coaching important in today’s world? (10 minutes)

  • Presentation: A look at current trends in management that show a shift to growth and learning.
  • Q&A

The Coaching Conversation Model - an Overview. (20 minutes)

  • Presentation: A brief overview of the components to a coaching conversation.
  • Q&A
  • Break

Eight Skills to a coaching conversation (70 minutes)

  • Presentation: A deep dive into the coaching conversation model.
  • Exercises: Interactive practice within each skill section.
  • Wrap-up and Q&A