Difficult Conversations

Navigating Difficult Conversations

by Megan Zirger

This article is one of six articles in the mini-series “Feedback Is A Gift” to help you navigate these uncomfortable conversations year-round.  

According to a recent study approximately 70% of employees opt to steer clear of challenging discussions in the workplace, while around 53% of them choose to overlook “toxic” situations when encountered.

But having these difficult conversations are necessary and helpful to: 

  • improve performance and engagement
  • progress careers
  • achieve our goals 
  • build strong relationships on teams 

Difficult conversations are inevitable in the workplace as they appear any time there are high stakes, high emotions or opposing opinions. If you are committed to your career growth, you should commit to learning how to have difficult conversations. 

Here is a detailed guide to prepare and approach a difficult conversation:

1. Reflect on Your Intentions

  • Purpose Over Outcome: Be clear about your primary purpose. Instead of being fixated on a particular outcome (which you might not control), focus on the intent of the conversation. Is it to inform, understand, resolve a conflict, or something else?

2. Gather Relevant Information

  • Facts Over Assumptions: Ensure you have all the necessary information and that you’re basing your points on facts rather than your assumptions or feelings. It’s easy to create narratives based on hearsay or our own biases. Confirming facts minimizes the risk of the conversation derailing.

3. Plan Your Communication

There are many different ways to structure your plan to communicate. 

One simple framework to express concerns / give feedback is DESC: 

It can help you articulate your concerns without coming across as confrontational.

  • Describe the specific behavior / situation to be addressed. 
  • Express how it makes you feel or its impact on the work at hand. Add some open-ended questions for the other person to understand their perspective and show them that you’d like the discussion to be collaborative. 
  • Specify the change you’d like to see moving forward or request you have. 
  • Convey the positive outcomes possible if the change occurs and set a time to check-in on changes. 

4. Anticipate Reactions

Empathy First: Put yourself in their shoes. How might they react? What concerns or objections might they raise?

Keep in mind that the person listening may resist the conversation and 

  • divert the conversation bringing in irrelevant topics
  • shift the focus to blaming you for the matter at hand
  • show a strong emotional response 

By anticipating these reactions, you can prepare responses that are empathetic, but still bring the person back to the matter at hand and focus on reaching a solution. 

5. Choose the Right Environment

  • Neutral Ground: Find a location that’s neutral and free from interruptions. This shows respect for the individual and the conversation.
  • Timing Matters: Ensure the chosen time is convenient for both of you. Avoiding end-of-day, pre-weekend, or pre-vacation times can be considerate.
  • Avoid digital communication: Don’t try to have a difficult conversation digitally. It’s difficult to understand tone of voice and things can quickly escalate or be misunderstood. 

6. Practice with a Trusted Colleague or Friend

  • Role-play: Rehearse the conversation. This can help you to refine your points, anticipate possible reactions, feel more comfortable and adjust your approach based on feedback.

7. Mental and Emotional Preparation

  • Mindfulness: Engage in mindfulness practices like deep breathing or meditation to center and calm yourself before the discussion.
  • Positive Affirmation: Remind yourself of the positive intentions behind the conversation. This is not a confrontation but a step towards clarity and understanding. Rather than being married to the outcome you desire, be committed to the purpose of the conversation. 
  • Stay Open: Be prepared to listen, adapt, and adjust your perspective based on what you learn during the conversation. 

8. Set Clear Boundaries

  • Determine Duration: Decide in advance roughly how long the conversation should take, and try to stick to it. Extended discussions can sometimes lead to more conflict or confusion.
  • Keep on topic: Don’t let resistance from the other person undermine your conversation. Respect their point of view, but keep them on topic and keep the conversation constructive. 

9. Reflect and Learn 

After the conversation, take some time to reflect. What went well? What could have been better? Record your learnings and keep them somewhere that you can revisit them the next time you need to have a difficult conversation. 

Difficult conversations are a part of work-life and with the right approach can be helpful to achieve our goals, build stronger relationships and develop as professionals. 

The more difficult conversations you have, the greater your confidence and skill in handling them will be.

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