Michael Sterling

5 Ways to Tackle a Tough Conversation


It doesn’t matter where you are in an organization – head honcho or entry level – everyone finds themselves face-to-face with sharing troubling news or asking difficult questions. Whether you need to tell your client a project is delayed; update your boss regarding a problem; ask for a pay raise or coach an underperforming team member, it’s daunting to tackle a tough conversation.


Difficult conversations may never become easy, but they can be less uncomfortable – for both parties. Having a tough talk requires courage, tact and empathy. By establishing a game plan and following some simple guidelines you’ll be prepared to take on even the most challenging conversation.


5 Ways to Tackle a Tough Conversation


  1. Map it Out. Plan, but don’t script, the conversation. Create a mind map of the message. Organize your message points on paper. Putting thoughts in writing makes them more memorable. Place the hardest part of the conversation at the beginning. Delaying the main point with small talk only drags out the discussion and makes everyone more on-edge.
  2. Design a Dialogue. Remember you’re holding a conversation. That means you want to plan for a dialogue, not a monologue. Conversations are two way streets – give and plan to take. Be compassionate in your delivery and empathetic to the message’s impact.
  3. Practice. Once you’ve outlined the message and designed your dialogue, practice out loud. Presenting to yourself in front of mirror will work for certain situations. For really critical conversations, hold a test conversation with a neutral person. Talking your message through with an unbiased individual will allow you to hear how the message flows. Get feedback on your wording, tone and body language. This will allow you to adjust words or actions which could be misinterpreted.
  4. Go Easy. Pay attention to pace. Slowing the pace of the conversation gives each of you the time to select the right words and to moderate tone. Pause to breathe and to think. Allow time for the other individual to digest what is being communicated and respond, as needed. If the subject is an emotional one, an easy-going tone will help diffuse tension.
  5. Be Helpful. Soften the blow of bad news by offering some type of assistance, when possible. If you’re telling your boss you’re over budget on a project, present a suggestion on how to help reduce future expenses. If you’re terminating someone, you might offer constructive suggestions on how they might improve their professional development.


Mastering these five steps to tackle a tough conversation will make each difficult discussion more comfortable. The ability to handle these types of challenges will make you a better professional and earn you the respect of your colleagues.


Career Wellness

Interested in more career nutrition? Check out the Career Wellness section of the SterlingFreeman website. And connect with me on LinkedIn. I welcome your comments. 


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