Best Practices for Difficult Conversations

By Caitlin Percival
April 20, 2019
3 min read

Summary: We’ve come up with five best practices to reduce the number, and severity, of difficult conversations you may have to conduct in the office. Spoiler alert: the number one best practice is to eliminate the need for them!

We’ve all been there – have an all-encompassing sense of dread towards a conversation you know you have to have. Whether it’s giving an employee a poor performance review, asking for a raise or delivering unflattering results to your client, the anxiety leading up to that conversation can be debilitating. With that in mind, we did the research and found five best practices to ease the issues faced when conducting difficult conversations.

1. Be Proactive

The best way to deal with difficult conversations is to be proactive and eliminate the need for them. I’m sure you’re saying ‘well that’s easier said than done’, and we totally understand. That being said, we’ve provided some tips below that will get you on the fast-track to success.

Tip: Communication is key! Make sure you have an effective way of distributing information to the team (intranet software could really help you here).

2. Preparation

If there is an issue that needs to be addressed, the ideal solution is to identify and resolve it immediately and professionally. To articulate the outcome you wish to see and the actions to get there during your conversation, be sure to have a clear outline of your goals before entering into it. Ask yourself some of the following:

  • What is the purpose for holding this conversation?
  • Are there any facts or data supporting your position?
  • What factors or behaviors have led you to this conversation?
  • What objections could they have?
  • What outcomes, or actions, need to happen to resolve the issue?

Tip: Jot down bullet points of the key topics you’d like to address during the conversation. Do not write out full paragraphs or make preemptive assumptions on how the conversation will go. This could result in your conversation sounding scripted and encourage un-organic responses.

3. Stay Objective

Do not hold conversations based solely on your observations. If you struggle separating emotion from objectivity, make a list of what to avoid saying. Make sure you are presenting facts, not feelings and that you remain constructive, not condescending.

Avoid passive use of words such as:

  • I feel
  • I think
  • This might
  • It could
  • Maybe

Instead, try using active phrases and concise examples:

  • I did
  • I am
  • This will
  • The numbers are
  • The data indicates

Tip: If there is a particular individual you have an issue with, separate them from the issue at hand. Take the problem, set it on the floor and speak to the issue, not to the person.

4. Practice

The best way to get comfortable with an awkward situation is practice. Consider the following options to ensure you are comfortable with your delivery:

  • At home in front of the mirror.
  • With a friend.
  • With your partner.

Tip: Do not discuss details of the issue with a colleague who is not on a ‘need to know’ basis.

5. Follow-up

The aim of the meeting was to instigate change. It is vital to document the action items and follow up to ensure they get done.

  • Document the main points.
  • Document action items with reasonable timelines such as within employee goals.
  • Schedule check-ins to facilitate motivation and communication.

Tip: Discuss timeline during the meeting to come up with a mutually agreeable schedule.

It is crucial for managers and colleagues to be able to communicate effectively, which can sometimes require a fair amount of preparation. Avoiding situations altogether will only escalate the issue and can lead to stagnation,  losing employees or having a dis