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Having challenging conversations

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Use this page to understand how to approach challenging conversations with your board.

Impactful leaders have the ability to have effective conversations about difficult things in ways that resolve problems, improve relationships and help their organisations to thrive.

These conversations may happen in a group setting, as part of decision-making with a board of trustees, or one-to-one. When the situation comes up, it’s important you're ready and able to take steps to move forward to a positive outcome.

When difficult conversations arise

Difficult conversations may be needed in a variety of situations. These might include when:

  • there’s been a complaint or grievance
  • someone's behaviour or opinions are creating challenges
  • there’s general or entrenched conflict
  • inviting challenge or feedback
  • you need to give or receive feedback
  • acknowledging mistakes or failings of an organisation or leader
  • someone is seeking or needs support with personal issues.

There might also be other causes of conflict or disagreement such as when there’s a:

  • lack of clarity or confusion - for example around expectations or roles
  • difference in beliefs, opinions or approaches.

Conflict is not necessarily negative, but it is inevitable because it is part of how we build relationships. Being able to discuss different opinions is an essential part of healthy decision-making. In fact, organisations that cannot disagree well are more likely to end up reaching a consensus without critical reasoning or evaluation of the consequences or alternatives and make poorer decisions as a result.

Debate, discussions and differences of opinion lead to better more robust outcomes and greater diversity of thought.

What makes a conversation difficult

The conversation may feel particularly difficult if you need to cover a sensitive subject, need to deliver bad news or receive or give feedback, and if you’re not sure how the other person (or people) in the conversation will react.

Negative reactions are more likely when people feel personally judged or criticised, and so it’s important when preparing for your conversation that you think about approaching the situation as objectively as possible.

How to begin to approach a difficult conversation

It’s worth trying to explore the issue informally before starting a formal procedure or conversation. Consider the following aspects or steps to help you when having an informal difficult conversation:

  • Prepare for the conversation:
    • Reflect on what you want to say to the other person. You might even write it down.
    • Think about what your thoughts or feelings are about the issue and how they might be affecting you. Your mindset will have a big impact on even an informal conversation.
    • Identify the top outcome you want out of the conversation.
    • Get ready to be curious and think about what might be going on for the other person.
  • Prepare your opening sentences:
    • Try writing them down. Ask yourself how the other person will hear what you have to say. Try to replace anything which could sound judgemental with neutral observations. For example ‘I noticed when…’
  • Plan the conversation:
    • Ask permission to have a conversation. Plan to have it in a private and comfortable situation when you’re both likely to be at your best and allow time for it.
  • During the conversation:
    • Listen - try and listen to the other people in the disagreement
    • Be curious about what might be going on for them - try and understand where they are coming from
    • Show empathy by reflecting back the things that you hear
    • Say what you need to say in a way that can be heard
    • Be future-focused. Once you have listened to each other, which may require reflecting back on what you’ve heard until you have a consensus, move on to focus on the future or the outcomes. Think of options together and ways to move forward and agree on any outcomes together.
    • Talk about how you would like to approach this or other issues if they were to come up again in the future.

Approaching a difficult conversation formally

If you’ve tried the informal approach and there was limited success, Acas recommends a clear structure to help you have the best chance of moving forward.

  1. Plan
    Decide who should lead the conversation, considering whether you have any emotions which may make the conversation more personal than necessary. Make sure you are clear about the issues you want to address in the conversation, and what the purpose of the conversation will be.
  2. Prepare
    Set a time, date, and location for the meeting, and think about whether it’s possible to hold the conversation in person. If you are meeting in person, think about the room layout and try to make the space comfortable and non-confrontational. Make sure you allow enough time for the conversation.
  3. Structure the conversation

Acas recommends that you have a clear structure to your conversation so that you reach a clear outcome. The steps they set out are:

  • Opening
    • Begin by explaining the subject of the meeting, while being clear that the conversation will be two-way and has the aim of resolving the issue.
    • Set standards of behaviour for the meeting.
    • Introduce the issue, giving examples for clarity.
    • Explain why it is important to resolve the issue and demonstrate your willingness to do so.
  • Middle
    • Invite the other party to share their views, making sure you understand their perspective and are ready to hear what they have to say. Do not be so fixed on your plan for the meeting that you are unable to listen.
    • Acknowledge their feelings.
    • Keep the conversation on track.
  • Resolution
    • Work together to develop options which take into consideration both of your perspectives (as far as possible).
    • Check if anything unsaid needs to be shared.
    • Summarise the conversation.
    • Confirm the decisions you are making, the next steps from the meeting, and how these will be communicated.
  • Review
    • Take time after the meeting to review the issue and process. Encourage the other party to do the same.
    • Reflect on what you have learned and what you can take forward.
    • Consider what you might do differently if the situation comes up again.

For a formal conversation, Acas has online guidance on Dealing with a problem raised by an employee.

Where to find help with difficult conversations

Acas provide advice on raising issues at work.

Another organisation who provides practical support and advice in preparing for a challenging conversation or managing conflict, is Crux. They are a social enterprise who offer a wide range of advice and support including coaching, mediation, facilitation and training.

NCVO worked with Philip Guthrie from Crux to create this guidance.

This page was last reviewed for accuracy on 29 April 2022

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