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Using Role Play in Executive Coaching

How many leaders struggle with having difficult conversations? Some leaders struggle with telling their manager what she doesn’t want to hear? Some struggle with giving critical feedback to a direct report? And others struggle with confronting a peer who is sabotaging his ability to be successful. As executive coaches, we hold leaders as the expert. However, if used effectively, role play can be a highly efficient tool to teach, rehearse, and coach leaders through a challenging work relationship.

Advantages of using role play include:

  • Models direct communication
  • Learning / skill development is highly transferable
  • Highly efficient use of leader’s time
  • It’s used in a non-judging environment
  • Can create early wins in coaching engagement, increasing leader buy-in to the process
  • I personally think it is the best way to help leaders who are struggling with a difficult conversation


  • Can be overused, creating a dependency (remember, you want the leader to develop both competency and confidence)
  • You, as the executive coach, are relying only on your leader’s viewpoint and have limited data
  • You are telling the leader what to do, which positions you as the expert


  • Pre-emptive to prepare for a difficult conversation
  • Post process a conversation that didn’t go well)
  • Entire conversations or brief interactions: Start fresh or jump in – “can we just go there now?”


  • Executive Coach plays Leader only
  • Executive Coach models / plays Leader then Leader does the Role Play
  • Leader practices, debrief, practices again, debrief – 3 times’ a charm

Rule for engagement

  • Ask permission
  • Qualify the role play (I’m making up stuff)
  • Process / debrief – what’s likely to go wrong
  • Keep leader as expert and remind when needed
  • Target to specific need of leader
  • Get enough details to be an informed participant (of person with whom Leader is in conflict) then no more (like in regular coaching, this isn’t about getting the story – you’re not doing an investigation, you’re helping Leader develop a skill. Ask a few rounds of “what did she then say, what did she then do” enough to get a sense of the other person and the relationship.  You need less than you probably think but you do need some of it.
  • Connect to values and to the bigger development opportunity (this isn’t just about the situation with John, this is about your ability to … give feedback / influence / stand your ground / develop managerial courage / repair & strengthen all relationships, work and non-work)

-Dr. Jeff Kaplan

Dr. Jeff Kaplan is a business psychologist and executive coach who coaches executives and high potentials to lead with heart. Jeff helps leaders to work more collaboratively with others, recognizing that people are an organization’s greatest asset.