7 Tips for Difficult Conversations

7 Tips for Difficult Conversations – Daisy Wademan Dowling – Harvard Business Review.  One key skill that separates good leaders and others is the ability to have difficult conversations.  Almost anyone can manage a group if everyone is performing well.   It is easy to give raises and bonuses to strong performers.  The harder part — the part that separates good leaders from others — is the ability to have difficult conversations — telling people that they are not performing, not getting a promotion, or addressing conflicts with clients or other departments.

Ms. Dowling provides useful tips for having difficult conversations including “3.  Adopt the ‘And’ Stance.”   Use “and” instead of “but” in difficult conversations.  I first saw this approach in Difficult Conversations:  How to Discuss What Matters Most by Douglas Stone, Bruce Patton, and Sheila Heen.  For example, consider using “and” instead of “but” in a conversation breaking up with a girl/boyfriend — “I like spending time with you and it is time for me to go my separate way and I know this is sudden and I am sorry and I still need to break up with you and I wish things were different andandand”  By using “and” instead of “but” it changes the conversation from being something where one person is right and the other is wrong to a discussion where both views are acceptable and true.

Daisy provides another good tip “Pretend it’s 3 months or 10 years from now.”  This is hard to do but if you think back to a difficult time in your past, you realize you got through it.  Imagine it is 10 years from now and try to imagine how you will remember this difficult conversation.

Daily offers useful tips for having difficult conversations; they won’t make magically change difficult conversations into pleasant conversations, but they will make the conversations less difficult.


  • Nathan S. Gibson

    Nathan S. Gibson is an independent worker compliance business partner who provides expertise and creative solutions to enhance workforce flexibility and maintain compliance. He helps mitigate the risks associated with the misclassification of self-employed consultants, freelancers and independent contractors.

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