top of page

Top Ten Tips on Managing Difficult Conversations

1. Do Not Avoid the Conversation 

OK you are a people pleaser, you don't like to upset people. But think about:

a) If you don't have this conversation, what will be the impact in the next week, month or year? 

b) What impact will not having this conversation have on other stakeholders such as other staff and the children. Are the children getting

what they deserve and need from this member of staff? 

2. Reframe Difficult Conversations 

If you build it up as a difficult conversation, it can become overwhelming. But try to reframe it as you’re not giving negative performance feedback; you’re having a constructive conversation about development. You’re not telling your boss: no; you’re offering up an alternate solution. A difficult conversation tends to go better when you think about it as just a normal conversation. 

3. Prepare

It's important to prep for the conversation. A script may help but remember this is a dialogue, not a monologue. There are lots of frameworks out there e.g. Fierce conversations, COIN. Stick to the facts, don't exaggerate and use 'I' statements. 

4. Be Upfront

Make it clear what the conversation is going to be about. I've sat in on many 'difficult conversations' where the member of staff didn't know why they were there, were confused about why they were having that conversation and none the wiser when they left the room. Their line manager was a typical people pleaser, terrified of upsetting people. Instead of dealing upfront with a situation, they worked themselves up into a state and achieved none of their objectives for that conversation. As a result nothing changed. 

5. Win/win? 

So it's important to have a goal for the conversation. Is the purpose to win? Then you need to think again. Whilst they may not get what they want, both parties should feel heard, valued and respected. This is an assertive conversation. 

6. Empathise 

Try to understand the other person's viewpoint. What do they believe is the issue? If you don't know or understand the other person's viewpoint, ask. Gain clarification. You may not agree but understand that this is how they see things. 

7. Listen

Really listen. Summarise what they have said. Ask clarification questions. Reflect back what the other person is saying. Reflect back emotions. For example 'So it sounds like you feel this situation is down to..... And it has left you feeling frustrated.' Acknowledging their feelings helps to calm a situation. They feel you understand but you have not agreed with them. You haven't dismissed how they feel either. 

8. Anticipate Bad Reactions

Be prepared for bad reactions. Denial, arguments and tears are all possible outcomes of tough conversations. You cannot control the other person’s reactions, but you can anticipate them, and be emotionally ready. However, if you feel the situation is getting out of control and the other person is getting aggressive, stop the conversation immediately. Pick up the conversation again when you have both had time to calm down. 

9. End with Joint Problem-solving 

Explore solutions or walk away, both agreeing to disagree. Even if you know the solution, it's essential to try coming to it together. If you can reach an understanding, create a plan or roadmap toward a solution that works for both of you. 

10. Self-care

The stress of a challenging conversation can be immense. It's essential you look after yourself by venting to your work husband/wife or your coach. Once again it's important to frame things differently - instead of 'that was a difficult, challenging and horrible experience', see it as a necessary, important conversation that will ultimately have a positive impact on the children, staff and school. I recently had to have a difficult conversation with someone I care deeply about. It went better than I thought, but the anxiety around the conversation, the tension and absolute fear of the other person's reaction left me drained and exhausted. After a long siesta I felt relieved and like a weight had been lifted. Sometimes the fear is worse than the reality.

Final Thoughts

Difficult conversations don't need to be difficult. But as human beings some of us are hardwired to over empathise, worry about upsetting someone and fear not being liked. Taking the emotion out of a conversation may seem alien for those of us who wear our hearts on our sleeve. But it's not always about us - we need to take our ego out of the equation. The ultimate aim of the conversation isn't to win but to move forward together and to have a strong working relationship.

Professional Development

If you would like support to work on your communication skills, get in touch for 1:1 coaching. 

If you feel your team would benefit from assertive communications training, get in touch regarding the Assertive Leadership course


Malarvilie is a former senior leader and history teacher. As an Education Consultant and Executive Coach she supports leadership development through InstituteLM recognised leadership and coaching skills courses. Contact her now if you'd like a complimentary 30 min coaching call to discuss some of the above.

417 views0 comments

Recent Posts

See All


bottom of page