• Dr. W. Craig Gilliam

The Art of Difficult Conversations: Best Practices

Prepared by Dr. W. Craig Gilliam. . . a collaborative partner with the Wi2CoLab Team, and founder and owner of Gilliam and Associates, LLC, (www.gilliamandassociates.com ). (Revised, March 2021)

The following is a list of some best practices I have observed, utilized, and practiced

over the years working with business and congregational leadership as they prepare

for difficult conversations. The challenge is how to increase the opportunities for these

challenging, anxious interactions to yield positive outcomes, or, at least, how to

improve the possibilities for productive ones? There are no guarantees in the dance of

human interactions, especially around hot topics, but good practices and self-awareness

yield better outcomes and responses.

While not exhaustive, Wi2CoLab and I make this hand-out available, hoping it will help

you and your organization prepare for those problematic encounters and discourses

on the horizon.

Prepare in advance both the space around and within you.

Seek wise guidance from a trusted, wise friend, associate, or professional.

• Have a clear focus or purpose for the conversation. When possible, put your

focus or intention for the conversation in the form of an honest question because

questions open space and invite conversation.

Focus on curiosity, compassion, and understanding. Pete Senge refers to a

focus on inquiry and vulnerability rather than advocacy (The Fifth Discipline, 2006).

• Manage yourself first and foremost. Focus on regulating your own anxiety and

reactivity. When needed, take a three deep breaths to calm and ground self.

Take a break, if needed, to calm emotions.

Use silence for heavy lifting. Do not be afraid of the pause or deep silence. Silence

is its own language.

Take clear stances without steamrolling or sugar-coating. Practice beforehand

on stating your stance, focus, or question in a calm, non-anxious, non-reactive way.

• Stay connected to the other person(s) in a genuine way, if possible.

• Honor their agency, even if you do not like his/her choices or decisions.

• Regardless of what happens, be fair, honest, and a person of integrity.

• What would you add to this list? What are you learning?

If we can be of assistance to you, please let us know. Thanks for your courage and for

reaching out.


Senge, P. M. (2006). The fifth discipline: The art & practice of the learning organization.

Revised and updated. New York, NY: Currency.

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