Five common difficult conversations and how to handle them

Thursday 29 August 2019
Managing conflict, resolving disputes, and handling difficult conversations are key management skills. What can you expect from them, and how should you prepare?
Person standing in the woods

Managing staff can be one of the trickiest aspects of being a boss – no matter how experienced you are, there will be certain issues you may find challenging. Below are five common conversations that many managers would do anything to avoid, but are part and parcel of managing a team.


Telling staff their work isn’t up to scratch is difficult – but if you don’t do it, the problem will escalate without you having given the person a chance to improve. Start by preparing a succinct document of where the problems lie, what improvements you’d like to see, and when the deadline is. Be specific about examples of underperformance and explain how it affected the rest of the team and the overall workload. Outline the measures you will take to help the person – training or bringing in another member of the team, for instance – and make sure that they understand what is expected. Going forwards, you should also have regular reviews where you can both assess progress.


How do you keep the peace when you’re applying for the same promotion as your colleague? First, talk about the situation with them. Say that you know you’re both going for the job, but that you don’t want it to have a serious impact on your relationship and that you are looking forward to working together, whatever the outcome. Second, keep your emotions in check and, above all, do not undermine or criticise your colleague’s work. Thirdly, be gracious – in defeat or victory. Finally, be prepared for the dynamic between you to change. However much you’d like the friendship to remain intact, there’s a good chance it will shift if one of you gets the role and the other doesn’t.


If you have a talker but not a doer, there are several steps you can take to improve the situation. Perhaps they book a meeting but nothing gets resolved, and there’s another meeting to address the questions raised in the initial meeting; perhaps they’ve promised more than they have the capacity to deliver; or maybe their momentum has run out since they first started a task. Often the lack of delivery has less to do with laziness and more to do with lack of focus: some people spend so long talking about their plans that they run out of steam before they do them. One way forward is to help your employee break tasks down into more manageable chunks – and setting deadlines for when you expect to see delivery. Also, if you’ve been praising the idea, hold back until the task is completed – in other words, congratulate, “I have,” rather than “I will”. Finally, stop accepting excuses and force outcomes. Nobody enjoys having a meeting to plan another meeting.


Micro-managers can undermine you, so it’s important to address the problem quickly. Helicopter bosses, as they’re sometimes called, often have control issues – but before you ask for a meeting, appraise your work honestly. Have you given your boss cause to doubt your abilities? If yes, then you will need to address these. If not, then speak to them and explain how you’re feeling. Be honest. Explain that you’d prefer more autonomy and ask if there is anything you should be doing differently to build trust.

Conversely, if you’re a micromanager and are worried about the effects your leadership style is having on your team, then it may be time to adjust your behaviour. Why do you feel you need to scrutinise your team’s work? Do you think things will go awry if you don’t keep tabs on everything? Is your lack of trust in your team based on experience or your own insecurities? Good managers delegate – start slowly, with tasks that aren’t critical and build from there.

We have lots of tips and resources to help you deal with difficult conversations including checklists, articles and bitesize videos. Find them by logging into ManagementDirect.