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Alumni in Action

Alumni Webinar Series: Having Challenging Conversations

By Alumni Relations

September 2, 2021

The ability to navigate difficult conversations is a necessary skill in your work, community, and personal life. Being able to do it well is challenging, and sometimes we’d rather ignore certain conversations altogether. During this webinar, Harry Webne-Behrman explains why it’s important to have those discussions and provides tips and tricks to having meaningful, collaborative conversations.

Prepare yourself

The first thing to do when you know you must have a difficult conversation is prepare yourself. Get ready to listen to what the other person has to say, and focus on the underlying interests and needs. Webne-Behrman suggests taking a deep breath, centering yourself, and going into the conversation with an open mind.

Take one issue at a time

During the conversation, speak from your own experience and take one issue at a time. Break down the topic at hand so the other person isn’t overwhelmed. If the other person comes to the conversation rambling and bringing up too many topics, you have the right to slow it down. Clearly and kindly tell them you need a moment and to slow down. This is mutually beneficial to your conversation.

Generate several possible solutions

When you and another person are discussing issues, it’s beneficial to come up with multiple solutions. If you have multiple solutions to choose from, you can be more flexible and efficient in problem solving, and are more likely to see options when approaching a problem.

Clarify criteria

After coming up with multiple ideas to solve your problem, clarify what is important. Come up with a set of criteria that you will use to evaluate the fitness of a given solution. Does it benefit the most people, or does it cost the least? You may not have entered the conversation thinking through the same criteria, but it’s important that by the end you both agree what is best for your situation.

Stay flexible

The key to having a challenging but meaningful conversation is to stay flexible. Stay patient and calm while talking with the other person. It’s important to realize that there are solutions out there, and if you’re flexible and have a good attitude you should find one that works with your situation.

Harry Webne-Behrman served as senior partner of Collaborative Initiative, Inc., a private consulting and mediation firm based in Madison, Wisconsin, from 1991-2017.  Webne-Behrman has worked as a facilitator for hundreds of businesses, schools, community groups, and public agencies, leading large-scale deliberation and engagement processes, as well as mediating interpersonal disputes. Most recently, he served as founding director of UW–Madison’s HR Communities of Practice Office. In that capacity, he led development of an array of new learning communities and competency-based certification pathways that support professional development of human resources staff across the UW–Madison campus. Webne-Behrman received a BS in economics, an MS in higher education administration, and worked on doctoral studies in educational policy at the University of Wisconsin–Madison.