5 ways to get better at handling difficult conversations at work

It would be great to go through your entire working life and never have a difficult conversation. Unfortunately, challenging chats are part and parcel of the modern workplace — and if you’re going to make a bad situation good, you’re going to have some tough discussions. 

So, how can you start difficult conversations with people at work? Five business leaders tell us how they talk about tough topics with their team members.

1. Establish trust quickly

Mayank Goswami, assistant vice president at Travelex, says the techniques you’ll use to deal with a difficult conversation will depend on the challenging situations you face.

Telling someone they’re about to lose their job is a bit different to getting them used to a slight tweak to their roles and responsibilities.

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However, people who manage others will often be required to deal with internal cultural concerns, such as the result of a new initiative starting in the business.

The trick is to allay people’s concerns and make them feel more confident and assured.

“People get fear from something; let’s say if it is a technological change or position change,” says Goswami. “I think understanding what they really need, and helping them and supporting them to transition to something you really want them to do, is key.” 

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Once you’ve established trust, one-to-one conversations — even if they’re going to be challenging — should become much easier.

“Empathize with them; understand their concerns and their fears. Addressing those issues must be the first thing to do — that’s really the one thing you should look at.”

2. Probe gently for challenges

Mary O’Callaghan, director of technology engagement at British Heart Foundation, says the key to success is to try and let the person you’re talking with engage with you on their terms.

She says most people know when there’s an issue in the workplace. Good managers find a way to bring the problem up without causing a confrontation.

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“It’s very rare that somebody is completely oblivious to the fact that there’s something that needs to be improved.”

By probing gently for potential issues, you might find the individual you’re talking with already knows that there’s an issue that needs addressing.

“I usually start by asking somebody how they feel about something,” says O’Callaghan. 

“Because if I’ve noticed a problem, they probably have as well — and they’re just not sure how to broach it. So, I ask them how they feel something is going or whether they’ve got any questions or concerns they’d like to address.”

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Of course, people might sometimes need a little bit more encouragement to be open about a problem or challenge. When they do, don’t make them feel culpable.

“It’s not about blaming somebody, it’s about saying, ‘Right, there’s an issue, so what are we going to do about it?’ And then it’s about working out what we can do so that we don’t have that problem anymore.” 

3. Be open and honest

Bob Michael, head of data at retailer DFS, says experience helps. As you get used to having difficult conversations, you’ll develop an approach that works for you and the person you’re talking with.

For Michael, that approach typically involves being as straightforward as possible.

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“I don’t try and upset people,” he says. “I just try and be open and honest and do as much as I can to help people along the way.”

Michael says having challenging conversations has gotten easier as he’s moved through his career — and he provides tips for other people stepping into management positions.

“Build your own confidence, build your network, step outside your comfort zone, and put yourself in a good position,” he says.  

“I wouldn’t say I’m necessarily an extrovert. I’m on the side of things. But as you get older, you realize that it’s often easier to just say it how you see it. I tell it as it is.” 

4. Give generous feedback regularly

Adam Warne, CIO at retailer River Island, says difficult conversations should never come as a surprise to the person you’re talking with.

Good managers make it clear long before the one-to-one chat that something is amiss, and that an improvement is required.

“If you walk into the room and you’re suddenly having a conversation with someone about their performance, that’s going to be a shock,” says Warne. 

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“However, if over the past three months, you’ve had a series of conversations and, after every chat, you’ve said that they need to be improving in particular areas, then that difficult conversation isn’t a surprise.”

Therefore, if you want to reduce the chance of having a difficult conversation with a colleague, you need to make sure that you’re engaging with people as regularly as possible.

“I think feedback needs to be generous enough and often,” says Warne. “And by doing that, I don’t think difficult conversations are ever as difficult as you think they’re going to be.”

5. Leave a good impression

Rajeswari Koppala, senior manager of DevOps at United Airlines, says it’s important to listen to everyone’s perspective, even if you’re about to have a difficult conversation because you think they’re in the wrong. 

“People love people who listen,” she says. “So, listen to their perspective and start the conversation in a positive way. Even if you have to contradict someone, you need to start with something positive.” 

Koppala says professionals can use techniques to ensure the person they’re having a difficult conversation with doesn’t feel too exposed. 

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“There is one approach I learned from my mentor previously, which is the sandwich approach,” she says, explaining how it’s important to not just start your chat with encouragement but to finish with a plus point, too.

“Start with something good, give all your criticism in between, and then end with something good,” she says. 

“That way the difficult conversation is less challenging because you’ve started with something good and ended with something good.”