How to Expertly Handle Difficult Conversations

There’s something that we all could use a little help with: that’s the art of difficult conversations.

We all have one that we either need to make or plan to have in the future. Insights into how to handle these types of conversations are not only helpful to leaders but are applicable for parents, to friends, and with coworkers as well.

The problem is, most people routinely avoid these potentially confrontational and challenging situations. In avoiding the conversation and the potential confrontation, we hope that circumstances will work themselves out. Usually, that’s a very unwise decision to make. Challenging issues frequently become bigger and harder to diffuse if ignored. Rarely do things just go away.

Time is of the Essence

Don’t wait to have that challenging conversation with your employee, coworker, child, friend, or spouse. The more time passes, the more difficult it becomes to address the situation. To most people, silence is approval! When you realize you need to gain clarity in the face of potential confrontation – make plans to meet with the person as soon as possible. Facts are fresher and more relevant if the topic is recent.

If we delay or worse, do not have the discussion at all, we are also subjecting ourselves to ‘inner erosion’. Erosion of our own self-respect because we didn’t do what was needed and we took the easy way out instead.

Challenge Your Assumptions

It’s instinctive to view a situation from how it affects or impacts us. For leaders, however, it’s important to put the needs of the organization first. When you are dealing with friends and coworkers, perhaps you put the needs of your group or team first.

Successful outcomes are not necessarily about what we want. Especially if, during the discovery part of your research into a situation, it becomes clear that the source of difficulty is yourself. Be introspective!

Three questions to ask yourself before you have that difficult conversation:

1. Is this conversation difficult because of the issue/circumstances?

2. Is this conversation difficult because of the person you are dealing with?

3. Is this conversation difficult because of me?

Don’t always assume it’s the other person that is the problem.

Carry the Right Attitude

It’s critical to come to the meeting with the right attitude. The outcome is balanced upon whether or not you are able to be objective and clear. You are going as a listener not as a ‘talker’ (or as an interrogator). Make sure you stick to the facts and remove as much emotion from the circumstance as possible. The conversation does not have to be confrontational. However, you cannot control another person’s reaction or feelings concerning a situation. You may need to deal with a difficult person in addition to a challenging conversation!

Remember to keep calm, balanced, and centered. Do not allow the other person to pull you into an emotional state. Also remember that you do not have to be right, but you must do what is right. Open yourself mentally to the opportunity that you could be wrong and remain objective as possible. The worst thing we can do is have our ego dictate the outcome of a situation to your benefit regardless of the truth.

Have a Game Plan

It’s a good idea to have an action plan when dealing with a challenging conversation and especially when you are also dealing with a difficult person.

  • Separate the action from the person or your opinion of that person.
  • Clarify your understanding of the situation at hand with the other person.
  • Seek to understand through questions: ask the other person to share their perspective.
  • Listen, listen, and listen some more. Listen longer than you normally do!
  • Do not succumb to the desire to fill in words for the other person.
  • It’s not you vs. them. You do not need to be right. You must do what is right.
  • Ask the other person if they are aware of issue at hand.
  • Repeat back to them the facts that you gathered from the conversation for clarity.
  • Ask the other person what they think the key take-aways are from the situation and the conversation.
  • Set action items with the person and determine the next steps.

Remember that you have the right to end the conversation immediately if the situation becomes negative or destructive. Even if you are talking to a client! Should you feel the circumstances warrant the intervention, seek the help of HR first.

Try to End on a Good Note

Ask the other person what they learned from the experience. Privately, ask yourself the same question. It’s always a productive to learn from every engagement. You can take notes after the conversation is over for your future development. If possible, try to end on a good note with the individual – even if the outcome wasn’t rosy. Let the other person know that, regardless of the outcome of the discussion, you harbor no negative feeling towards them. In my experience, I find that the entire situation was often a misunderstanding.

Avoiding Misunderstandings

During my career, over 80% of the issues I have addressed are rooted in misunderstandings at some level. Keep this in mind when you are happily typing away on an email or banging out a text message instead of picking up the phone or walking down the hall to speak to someone in person. I have found that the value of in-person conversation is poorly understood in our digitally-dependent society. Your written message is entirely at the mercy of someone else’s interpretation.

Body language and tone of voice comprises 90% of human conversation. Do yourself a favor, put away the keyboard or text message and call or speak to the person face to face. In reality, you aren’t taking more time to do this – you are actually saving time. You could also be avoiding the need to develop the art of difficult conversations!

Erin Urban
Erin Urban

Founder, UPPSolutions

Erin Urban, Founder of UPPSolutions, LLC, is a certified professional & leadership development coach with a mission to lift others up to defy their limits and exceed their goals. Erin is an experienced speaker within the professional community, a published author and a member of the Forbes Coaches Council.

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