How to Have the Difficult Conversations

How to Have the Difficult Conversations

Most leaders and managers will agree that they do not relish having the difficult conversations, whether this is a leader with his/her team, a manager with one of his/her direct reports, or even a C-suite executive with the Board. Unfortunately, a leader or manager may put off having a difficult conversation for fear of upsetting a team member, or not wishing to deliver negative feedback, only for a relatively small issue to escalate over several weeks, months, or even years. In particular, if there is a performance issue to be discussed, or a team member who is being put at risk, it is best to confront the situation early on and communicate regularly. At Natural Talent during our Executive Coaching and Leadership Development Programmes clients have the opportunity to practice relevant and effective tools and techniques in a safe environment.

So how do you approach the difficult conversations?  Here is a 10 Point Plan:

  1. Prepare: make sure you are up to date with all the relevant facts and scenarios ahead of any difficult 1:1. Take time to plan a difficult conversation and not just hold it ‘on the hoof.’
  2. Give the individual enough notice of the conversation so that they may ask questions in advance and also have time to prepare. If it’s a confidential, time-sensitive topic, then give as much information as you can up front.
  3. Ensure the conversation takes place face to face or via video conference in order to show the individual that you value their time and to enable you to understand their reaction.
  4. Consider the Personality type of the individual and think about how they are likely to react. Assess potential outcomes and scenarios and identify how best to deal with them.
  5. Explain how the situation has caused issues and how these are impacting the manager/team/project/organization, or the individual themselves.
  6. If the difficult conversation relates to a performance issue, use specific examples of situations and behaviours.
  7. Use ‘I’ and ‘we’ rather than the more accusatory ‘you’ to identify issues and deliver constructive feedback.
  8. Keep calm and present the facts of the situation in a clear, concise manner. Don’t raise your voice. Ask Open Questions to establish the individuals’ point of view or how they are feeling. However, avoid using the judgmental-sounding ‘Why?’ Instead ask: ‘What is driving that behaviour?’ Or ‘What is the reason behind x, y, z?’
  9. Look out for unhelpful passive-aggressive behaviours and negative body language, such as nodding of the head, rolling of the eyes, or even tutting. Ask relevant Open Questions to ascertain why the individual is having a certain reaction.
  10. If the individual becomes aggressive or angry, maintain an even tone and stick to the plan and your notes. If they become too emotional, stop the conversation and agree a time for a follow-up.  Email a summary of the conversation and key points you covered.

    Avoiding having the difficult conversations can prove very costly for projects, teams and the organization itself. If poor performance isn’t addressed in a timely manner, the individual can have a toxic effect on other team members; as a result productivity, engagement and even retention levels can drop and the overall company culture can suffer. Addressing issues as they arise, focusing on the facts and the impact issues are having on all key stakeholders, can prevent matters escalating in to interventions such as performance improvement plans, mediation and even resignations.


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