There’s something that we all could use a little help with: the art of challenging 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 potentially confrontational and challenging situations. You might hope that circumstances will work themselves out – which is 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 you delay or worse, do not have the discussion at all, you might even erode your own self esteem. You could lose respect for yourself and feel inadequate because you didn’t do what was needed and you took the easy way out instead. Often people become resentful and embittered when they harbor negativity that eats away at their own self worth.

Challenge Your Assumptions

It’s instinctive to view a situation from how it affects or impacts us. However, in order to sustain credibility it’s important to put the needs of the greater good first. When you are dealing with friends and coworkers, perhaps you put the needs of your team or organization 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. It’s not easy, but it’s critical to be to reflect on the part you play in a challenging situation.

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

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 ‘speaker’ (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 our benefit regardless of the truth.

Have a Game Plan

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

  • Separate the person’s actions from your opinion of that person.
  • Clarify your understanding of the situation at hand with the other person first.
  • Seek to understand through questions: ask the other person to share their perspective.
  • Ask the other person if they are aware of any issues.
  • 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.
  • Repeat back the facts back to them that you gathered from the conversation for clarity.
  • Ask the other person what they think the key takeaways 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 essential for career growth 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.

Avoiding Future Misunderstandings

During my career, over 84% of the issues I have facilitated evolved from a simple misunderstanding. Keep this in mind when you are happily typing away on an email or sending a quick text message instead of picking up the phone. Even walking down the hall to speak to someone in person is worth the few minutes of exercise to avoid future issues. 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 a vast majority of your communication. 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. By optimizing your face-time, you could avoid the need to master the art of challenging conversations!