Home > Chewing on Leadership: Difficult Conversations

Difficult Conversations: How to get at the truth of things without causing or receiving harm.

Guest Presenters: Jane Arthur and Jody Fried

Key insights:

    • Determine to be curious
    • Drop your agenda
    • Connect to the human
    • Try not to make assumptions
    • Be willing to own our own harm we have caused as leaders
    • It is a gift to be poked, to engage in a difficult conversation
    • Hear someone else’s truth
    • Make a genuine connection so we are not talking heads trying to defend ourselves – otherwise there is no movement, no learning
    • Be willing to be vulnerable
    • Even with so much closing down right now and people isolating, there is sameness at the heart of it
    • Core values exist
    • Come from a place not of other but of both sides feeling the same
    • Listen deeply to still love and respect the person, knowing you may not get to agreement
    • Create better understanding, so next conversation can build from that
    • It’s not about win/lose
    • Be open minded going in
    • Show a willingness to slow down, listen at a different level, listen close up to core values
    • Social media is a disaster for conversations that are difficult
    • Email is impersonal, better to be in person
    • Curious vs certainty – certainty is intellectual suicide; curiosity values difference, begin with agreements that foster deep listening for understanding without judgement

How to work with nervous or avoidant people in challenging conversations?

    • Use neutral settings such as arts venues and cafes. Environment can mean so much in supporting all sides.
    • Assess what kind of relationship you want with this person; if it is a long term relationship, then we can afford to be patient, invest time, personal.

How to engage across power structures?

    • If leaders are not open to receiving feedback, it’s not leadership.
    • A best practice is for leadership to receive feedback in a separate structure. For example, an annual review structure of the ED that is presented to the board.

Annual retreats as a tool:

    • Move away from work-based agenda and focus on relationships.
    • With building good relationships, people working together can weather a lot.
    • Trust is a huge piece to go deep and this takes time to tend to common bonds and nourishment. Ultimately it is listening someone into their own wisdom, that is a fruitional listening and engaging.

Final thoughts:

    • Come from the side of poetry, which offers ways of expanding listening ability.
    • Ambiguity tolerance – identify where team members fall.
    • Be comfortable with different ways of resolution – some things are not resolvable.
    • Remain aware of White Fragility – that insulating sense of fragility that contracts and creates separation.

Additional Resources:


Jane Arthur is a graduate of VLI Class of 2012. She was the Director of VLI from 2014-16. Jane was the Director of Karme Choling Shambhala Meditation Retreat Center in Barnet for 7 years prior to her work with the VLI. Karme Choling is part of Shambhala, a worldwide network of over 200 city and residential centers teaching meditation and how to lead a meaningful life. She supervised 30-50 residential staff, managed a $1.7 million budget and stewarded over 700 acres of land with several thousand visitors a year to the center.

Jane has also been trained and practiced as an attorney and a nurse. Her nursing career included a stint in the Air Force Nurse Corps where she was awarded the Meritorious Service Award for her service as head nurse of a pediatric clinic that served approximately 200 children a day at Malcolm Grow Hospital at Andrew’s Air Force Base. She also worked for 10 years as a neonatal intensive care nurse at Children’s National Medical Center in Washington, D.C. Her law degree is from the George Washington University, National Law Center. She served as an Assistant Public Defender in Fairfax County, Virginia and as an Assistant Attorney General for the Public Safety Departments for the Commonwealth of the Northern Mariana Islands. In addition to her work for VLI and Shambhala, she sits on the board of the Northeastern Vermont Regional Hospital. She is past president of the St. Johnsbury Rotary Club.

Jane loves to travel and has done so extensively. She loves Vermont and being of service. She lives in Danville with her partner, John, and their 2 cats.

Jody Fried is a native Vermonter. He and his wife, Erin, reside in a two hundred year old farmhouse in Peacham with their four children: Molly (14), Rian (11), Liam (10) and Eliza (5). Jody has had a diverse career with direct experience in the private / corporate setting, entrepreneurial / small-business ventures, the non-profit sector and as a community activist.

As Executive Director of Catamount Film & Arts, Jody is responsible for the overall administration, management and operations of the regional arts organization and box office serving Northern Vermont and New Hampshire. The mission of Catamount Arts is to inspire appreciation of and participation in the arts, promote the arts throughout the region, and cultivate the arts as an integral part of community life. His responsibilities include supervising the day to day operations as well as providing the vision, direction and oversight of all activities that sustain and develop the organization. He supervises a small staff and collaborates closely with a board of directors of over twenty.

Catamount Arts has played a central role in the cultural life of the Northeast Kingdom since 1975. The acquisition and renovation of the historic Masonic Lodge building in St. Johnsbury in 2005 expanded Catamount’s physical capacity and greatly expanded its ability to provide service to the community. Since joining the organization in 2009, Jody’s primary focus has been to methodically move Catamount down this path. The new Catamount Art Center now serves as one of the premier art facilities in all of New England. When he’s not working or carting one of his kids to soccer practice, you will probably find Jody pedaling his bike.