How To Have Difficult Conversations At Work

Conversations can be difficult for a number of reasons, but usually it’s because we’re worried about how the other person will react, or that we will make them feel bad. We can pendulum-swing between overthinking the issue, or rushing to resolve the problem, emotionally charged. But what if you could re-frame them? To see difficult conversations through a growth mindset lens - as something that can make you and the other person stronger and better. 

Be clear in your communication

You might be letting someone go, disciplining poor performance, or declining a request for a raise or promotion. Bad news is always bad news, and difficult conversations become more difficult when the delivery is muddled. But when we are clear – and throw in a bit of communication strategy – we can create a positive, even successful outcome for everyone involved.

You’re going to need the right preparation, the right mindset and the right approach, so let’s dive right in:

The right preparation

Before you do anything else, it’s important to fully understand the issue of the person or people involved. Listening attentively at the beginning will go a long way to smoothing things at the end. And when we ask the right questions, we might find an entirely different answer is required.

You don’t always have advance warning of a difficult conversation, but when you do, that time is a gift.

Getting your objectives in order is imperative. When you write them out, it’s rare that “making them feel bad about themselves” will be on that list. Usually it’s about addressing a behaviour so that they can change the way they act in future. Once you’re clear on your objectives, you will be able to frame your approach accordingly. Planning ensures that any emotional reaction in the moment won’t cause the interaction to go off track. It’s quite possible you already feel a degree of anger or irritation towards the person involved, but if you deliberately plan against venting, you are much more likely to create a positive outcome.

(When there’s no warning) Winging it

Sometimes difficult conversations need to happen in the moment, or they are thrown upon us whether we are ready to catch them or not. Quick words need to be had before things get out of hand.

When this happens it’s important to engage your empathy as quickly as possible. Ask questions to understand where they are coming from, but afterwards be specific about the action that they need to take now. Confusion will just be another spanner in the works.

It’s worth being open to discussion and to let them ask questions of their own. This will help them to be equipped to respond in a positive way. But once again, be sure to clarify the specific action they need to take before the conversation ends.

Starting as you mean to go on

If you have time to prepare, you can include the following in your prep. Otherwise, you might have to make it work on the fly.

After the initial small talk, how do you begin? Well, providing you understand their goal, you can state how that goal aligns with yours, “I know that you want to complete this project to the high standards we’re used to,” or “I know that you want to show us what you’re capable of.” By starting out this way, you remove the notion of accusation, showing that this discussion is part of helping them achieve their goal.

Affirmation and support

Consider what they are doing well and bring it into the conversation. If they’re underperforming in one area (let’s say closing deals) but meeting or exceeding standards in another (perhaps creating leads), then refer to the latter to show how they can apply the same attitude to the former.

It may be that they need some help to do what you are asking, or to process disappointment. Asking what support you (or others in the company) can give, might go a long way. They might need a little mentorship, or to talk about a personal issue that has been affecting their work.

Letting someone down in a positive way

There’s potentially two scenarios here. One is that someone wants something (a pay rise, a promotion) and you can’t give it to them yet. Maybe you need to negotiate the term – ask them, “Tell me how I can justify this pay rise? What are you going to do between now and the end of the year?” This is meeting someone halfway - and most people would respond well to it.

The other scenario is that a pay rise or promotion is just not possible, not now, maybe not in the foreseeable future. That’s much harder to hear – and it’s not easy to say either. So what can you do about it?

Start by thanking them – you can commend them, saying it takes courage to ask. You can affirm the reasons behind their request and explain that in different circumstances, you would love to give them better news.

Second is to motivate them, to make them feel valued and appreciated in other ways. And as long as you’re not overpromising, you can tell them you would like to revisit this conversation in a few months, in case circumstances change.

Creating an empowering environment

Primarily there are two ways to handle difficult conversations. You can do it with authority or with empathy. And while you don’t want to throw authority completely out of the window, its role should be secondary in challenging conversations. Empathy will – almost always – produce more positive results.

The aim of a coaching style is to bring out the best in others – and it is still possible to bring the best out of someone, even when you’re handed the worst topic of conversation. It requires you to be open to feedback so that you can give feedback without just giving orders. It hands more power to the employee so that they have more power to change.

If nothing else, adopting a coaching style in difficult conversations will inspire loyalty. Because after all, who doesn’t want to work hard for someone who brings out the best in them. If you handle the challenging moments with care, others will respect you for it, and likely give you less challenging moments to handle. Their sense of safety will increase, and with it their willingness to take risks and be creative.

So while a difficult conversation will always be a difficult conversation – it doesn’t need to be a negative one. If you handle it right, it might have positive implications that spread way beyond the issue in hand. With a team growing in confidence and in performance, you might well think that bad news never felt so good.

I hope you find some great nuggets in here to help you with your team communication. Here's an acrostic I made to help you remember - breathe:  


Instead of automatically going into a defensive state of mind, take six seconds to breathe and exhale, allowing your cerebral cortex to kick in and compose you.


Get onto their energy level and build rapport. If they are irate and you are acting completely unbothered, this will frustrate. 


Listen out for the values - take a moment to think about why they felt abandoned, why did that affect them in that way? 


Get the detail you need to fully understand the situation. By asking them questions, you are encouraging them to talk it out, lose the heat and show that you care. Give them the space to articulate their concerns.

Take responsibility

Have a growth mindset. Always be in a place of willingness to take responsibility, even if you don't believe you did anything you shouldn't have done. Tell them that you can see from their perspective why they felt that way, and that you hear their point and understand. 


Tell them how you plan to deal with the situation going forward.


Make sure you're on the same page. Ask them "how does that sound?" and ensure that you've reached a collaborative solution.


For more on how communication can enhance team performance check out our custom courses for business.

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