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Executive communication expert Dianna Booher shares tips for tough conversations

I wish had the proverbial nickel for every participant in one of my sessions who has approached me after the program with a comment that began, “Have you got a minute for a question? My boss and I just don’t get along. We need to have a conversation, but he/she…” From there, the story and details diverge.

But here’s the commonality: The conflict has been ongoing, stress has clearly altered productivity and results, and both parties have crashed against a communication barrier that seems insurmountable.

If you find yourself in that same predicament, consider these tips for a straightforward conversation that helps you break through that wall of hard feelings and misunderstandings.

1. Realize that two sides can be right. Conflict is not a competitive sport. The other person does not have to lose for you to win.

2. Communicate what happened, what you have concluded about what happened, and how you feel about what happened. Then listen for the same information from the other person. You will uncover hidden invalid assumptions, wrong interpretations, and inaccurate information.

3. Make a conscious choice about whether you will accommodate, compromise, overpower, or collaborate to come to resolution. Backing people into a corner rarely serves good purpose. But you yourself may decide to accommodate the other person’s wishes to “bank a favor” when something is not all that important to you. Remembering that you have a choice in the matter helps.

4. Define areas or issues that you agree on and move forward from there. Refocus on your goal rather than the obstacle.

5. Work to create alternatives. When locked in a stalemate, try brainstorming to generate new ideas to meet your goals.

6. State the real reasons for your feelings or objections—not just logical ones. Otherwise, the other person may remove the obstacle you’ve mentioned, and the problem will remain unsolved.

7. Prefer statements to questions during conflict. Instead of “Why didn’t you tell me about car?” State, “I wish you had told me about car.” A question typically generates an argument. A statement typically elicits a response—either agreement or disagreement.

8. Discuss a problem sitting down. You’ll be less likely to use intimidating body language or make a dramatic exit from the conversation in a huff.

9. Describe; don’t label. People can respond to statements like, “Your reports are missing key information.” They can confirm or deny that “fact.” Descriptions of what you see or what happened most often generate explanations. On the other hand, people can’t respond to a statement like, “You’re evasive.” Labels and value judgments generate arguments.

10. Avoid “hot words.” Just like radioactive material, they trigger an explosion: anger, defensiveness, denial, or blame.

Granted, you and your boss may never become BFFs. But tactful, yet direct conversation goes a long way toward understanding. And a stress-free life.

Dianna Booher, an expert in executive communications, is the author of 46 books.  Her work has been translated into 23 languages.  Her latest books include Creating Personal Presence: Look, Talk, Think, and Act Like a Leader  and  Communicate with Confidence, Revised and Expanded Edition.  National media such as Good Morning America, USA Today,  the Wall Street Journal, Investor’s Business Daily, Bloomberg,, CNN International, NPR,Success, and Entrepreneur have interviewed her for opinions on critical workplace communication issues. As CEO of Booher Consultants and as a high-caliber keynote speaker, Dianna and her staff travel worldwide to deliver focused speeches and training to address specific communication challenges and increase effectiveness in writing skills, presentation skills, interpersonal communication, and organizational communication.   Clients include 22 of the top Fortune 50 companies.  1-800-342-6621

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11 thoughts on “Communication Skills: Top 10 Tips for Tough Conversations With Your Boss, Business Partner, Or Best Bud”

  1. Terrific suggestions, Dianna. I've always found that intention — on the part of both participants in the dialog — is what will determine the outcome. It's what determines the willingness to do all the things you suggest … Or simply dig in heels. No?

    1. Very true, Sharon. And the tendency is to assign ourselves good intentions and excuse the actual action (or inaction or behavior) and then doubt someone else’s good intentions when things don’t things don’t turn out well.

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