Leadership Culture

How True Leaders Change Everything

Member-only story

How to Talk to Someone You Don’t Like

5 min readApr 14, 2025

--

Above: President Donald Trump at an April 10 Cabinet meeting at the White House. Public domain government photo courtesy of the White House.

Imagine dining with someone who tells the whole world he hates you. What do you say?

Bill Maher described his recent dinner with Donald Trump and offered 10 key lessons that can be applied to any encounter with anyone (friend or foe). These tips illustrate the art of difficult conversations.

Call these lessons “Effective strategies for engaging with disliked individuals.” Or better yet? Call it the Art of the Awkward.

Mastering the Art of Difficult Conversations: Tactics for Uncomfortable Situations

We enjoy watching and hearing about awkward moments when two people who can’t stand each other have to get close (but we rarely enjoy being part of such moments — unless you happen to be Donald Trump or Bill Maher).

They thrive on arguments. These moments also make for the best TV:

Dallas did a special episode with J.R. and Bobby Ewing (the battling brothers) trapped in an elevator, forced to get close (both physically and emotionally) just talking and sharing a case of wine.

All in the Family very similarly showed conservative Archie Bunker and his liberal son-in-law (the…

--

--

Leadership Culture
Leadership Culture
Joseph Serwach
Joseph Serwach

Written by Joseph Serwach

Story + Identity = Mission. Leadership Culture, Journalism, Branding Education. Inspiration: Catholic, Polish. https://medium.com/@serwachjoe