Top Tips for Handling Difficult Conversations at Work

By Miriam Rogers, experienced facilitator and an executive, business and life coach.

Difficult conversations have become part and parcel of our working lives. Most people shy away from these situations and few relish the prospect of sharing difficult messages. Fears about what to say, how to deal with the other person’s response, and concern for the individuals impacted, can knock even the most experienced leader’s confidence.

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Business is not always plain sailing and having difficult conversations is an inevitable part of the role of the leader.

Here are some tips on how to prepare for THE conversation


While it is important to take action when something is not right, it is also important to have a clear evaluation of the situation before having the conversation. Take some time to review behaviours and attitude. Consider how the person interacts with others and what impact that is having. Be clear on the issue and have evidence to support it.


Take some time to review what is going on. Try not to jump in until you have gathered all the facts particularly if there are other people involved. Make your own judgment of the situation and remember people do have an off day sometimes.

Develop a Plan

Based on your assessment decide what is your best course of action. By doing this before confronting the situation you will be well prepared when you have the discussion with the individual concerned. Consider :

  • Is this behaviour out of character – is there something else going on?
  • Does the person need some coaching which will help them review their behaviours and values and what they might consider changing
  • Are there bigger issues at play? Perhaps suggesting getting some counselling support might be of benefit.
  • Does the person have the necessary skills for the job? Would training help resolve the situation?
  • Is it a disciplinary matter? Discuss with your HR advisor.

Confront the problem

Don’t put off the conversation. Delaying confrontation of the issue will not help and it doesn’t get any easier by putting it off. Find a private space to ensure privacy.

Focus on the behaviours, not the person

Be calm and keep your focus on what you have observed and what has been brought to your attention. Try to keep the focus on the issue so that the person doesn’t feel it is a person attack.

Try to draw out the reasons behind the behaviour

This is where you need to draw out information from the person. Active listening is needed here so that you can understand the issue from the other person’s perspective. Using open questions, i.e. questions that require more than a yes or no answer are best here. Reflect back what you hearing to ensure understanding. This is your opportunity to find out what has been going on and will help you when working on the solution.

Develop the solution together

The best outcome is an agreed solution. The person needs to understand what it is that they are doing that is causing the problem and that it is unacceptable. They also need to know what they need to do to rectify the situation.

Plan next steps and follow-up

If the issue is a minor offence, then agreement on what is needed may suffice. Bigger issues may require a more direct approach and an agreed approach may take longer to achieve. Be patient – set some milestones and have regular review.

It is important that you know your limitations and don’t be afraid to seek help or advice.

Want to know more? Our 1-day Handling Difficult Conversations course will give you the opportunity to work with people in similar situations and build your confidence in communicating negative or difficult messages.  The day will be a combination of trainer led tuition, case study review, role-play and peer group discussion.


About Miriam Rogers

Miriam Rogers is an experienced Facilitator and an Executive, Business and Life Coach who has over 30 years experience in financial and private sectors. She has a keen interest in supporting managment and staff in driving performance and achieving business success.

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