5 Tips for Handling Difficult Conversations at Work

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5 Tips for Handling Difficult Conversations at Work

Difficult conversations — whether you’re telling a client the project is delayed or presiding over an unenthusiastic performance review — are an inevitable part of management. How should we prepare for this kind of discussion? How do we find the right words in the moment? And, how can we manage the exchange so that it goes as smoothly as possible?

We’ve all had bad experiences with these kinds of conversations: perhaps your boss lashed out at you during a heated discussion; or your direct report started to cry during a performance review; maybe your client hung up the phone on you. As a result, we tend to avoid them. But that’s not the right answer. After all, tough conversations are not black swans! The key is to learn how to handle them in a way that produces a better and less painful outcome.

So, how do we get what we need from these hard conversations — while also keeping our relationships intact?


Change your mindset

If you’re gearing up for a conversation you’ve labeled “difficult,” you’re more likely to feel nervous and upset about it beforehand. Instead, try framing it in a positive, less binary way. For instance, 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 best when you think about it as a just a normal conversation!



Plan but don’t script

It can help to plan what you want to say by jotting down notes and key points before your conversation. Drafting a script, however, is a waste of time. It’s very unlikely that it will go according to your plan! Your counterpart doesn’t know his lines, so when he goes off script, you have no forward motion and the exchange becomes weirdly artificial. Your strategy for the conversation should be flexible and contain a repertoire of possible response. Be ready for everything!


Acknowledge your counterpart’s perspective

Don’t go into a difficult conversation with a my-way-or-the-highway attitude. Before you broach the topic, ask yourself two questions: “What is the problem? And, what does the other person think is the problem?”. If you aren’t sure of the other person’s viewpoint, acknowledge that you don’t know and ask. Show your counterpart that you care and express your interest in understanding how the other person feels!

Also –  take time to process the other person’s words and tone. Once you hear it, look for overlap between your point of view and your counterpart’s!



Give something back

If you’re embarking on a conversation that will put the other person in a difficult spot or take something away from them, ask yourself: “Is there something I can give back?”.

If, for instance, you’re laying off someone you’ve worked with for a long time, you could say, ‘I have written what I think is a strong recommendation for you; would you like to see it?’. If you need to tell your boss that you can’t take on a particular assignment, suggest a viable alternative. Be constructive! Proposing options helps the other person see a way out, and it also signals respect.


Reflect and learn

After a difficult conversation, it’s worthwhile to reflect ex-post and consider what went well and what didn’t. Think about why you had certain reactions, and what you might have said differently. Observing how others successfully cope with these situations and emulating their tactics could be really helpful in a situation like this. Learn how to disarm yourself by imitating what you see! Handling a difficult conversation well is not just a skill, it is an act of courage.



What’s your take on this matter? Have you had difficult conversations over the past few weeks and felt uncofortable while having them? Let us know how you handle these kinds of situations and drop us a comment in the section below!


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