How to have difficult conversations at work


No one likes having difficult conversations at work. Thankfully, there are a few things that can make them a little easier.

A feeling of dread often overcomes us when we have to tell someone something they won’t want to hear. Maybe you need to address a performance issue with a struggling employee. Or perhaps you need to present unfavourable employee feedback to a senior manager. In either case, when you know you’re about to have a difficult conversation that could end in tears or anger, it can be very tempting to put it off. Some research even suggests people would rather quit their job than have a tough conversation with a colleague.

But avoidance helps no one. You just have to roll up your sleeves and dive in. Here’s HRM’s six-step guide to get you started.

1. Have a plan

Anna Blackett, a founding consultant at Level Up Collective, is a facilitator for AHRI’s short course ‘How to Have Difficult Conversations’. Blackett has navigated a few tricky topics in her time and believes that, with the right skills, HR can have more effective conversations to achieve outcomes that will benefit both parties.

To start, she says you should always go into any important conversation with a concrete plan. 

“Sit down beforehand and think about exactly what you hope to get across.” 

A loose plan will help anchor the conversation because it’s easy to get sidetracked by your own nerves or discomfort. 

However, don’t over plan. Blackett says this can lead you to become narrow-sighted and therefore miss out on hearing what the person is actually saying, or on reading their body language.

“You want to enter these difficult conversations with some concrete things to consider, but also walk in open to what they might say. Come prepared with open-ended questions to ask.”

2. Pick your moment to have a difficult conversation

Felicity Mildon, director at Felicity Mildon and Associates, is also a facilitator of AHRI’s short course. She says it can feel tempting to hide behind an email or phone call, but urges HR professionals to have a face-to-face conversation where possible.

“You miss a lot of body language cues if you can’t see the person, so I would never recommend phone or email conversations.”

Of course, virtual working means this is often the only option, so try to have the conversations with your cameras turned on, and allow more time for information to sink in. 

These conversations should never be rushed, so if you’re conducting them online, take into account possible video lags, patchy internet, interrupting children/pets, etc.

“Turn everything else off and face them straight on. Then when they talk, make sure you’re not listening to respond, but actually listening to understand.” – Anna Blackett, founding consultant, Level Up Collective.

Once you establish the ‘how’, you need to organise the ‘when’. 

“If it’s something a bit more informal, you might be able to grab someone at the end of another meeting and just say, “Hey, can we arrange to chat about this?” says Mildon.

But some issues might need more of a lead-up, perhaps with an initial email to arrange a further face-to-face meeting, so you’re not ambushing anyone.

It’s also best to communicate with the employee before scheduling the meeting. Receiving an invite for a ‘Very Important Meeting’ is unlikely to put the employee in the best headspace for a productive conversation – and you don’t want them stewing on it for days.

3. Keep your cool

We often worry about having difficult conversations because we respect the other person involved. While respect is important, you also need to avoid letting the conversation become  derailed by your own discomfort, says Blackett. Remember, it’s not about you. It’s about them.

“You don’t have to agree with someone to empathise with them,” says Blackett.

“Just because you say, ‘I understand this is making you upset,’ that doesn’t mean you’re agreeing with them or that you’re going to let it slide. It just means you’re taking their reactions and feelings into account.”

If you find the conversation has moved off topic or the person has become upset, Blackett suggests pausing and returning to the conversation when you are both in a more positive mindset.

4. Listen to understand

The most important part of the conversation is actually hearing what the other person is saying and ensuring they know you’re actively listening.

“Turn everything else off and face them straight on. Then when they talk, make sure you’re not listening to respond, but actually listening to understand,” says Blackett.

During a conversation, we sometimes spend a lot of time thinking about what we’re going to say next. This means we might miss what the other person is saying or fail to pick up on their tone/subtext.

If you find yourself distracted by your own thoughts, Blackett recommends acknowledging the thought and letting it pass. Then you can put your focus back onto the other person.

“Using phrases like ‘It sounds like you’re saying this’ or ‘Am I understanding you correctly?’ lets the other person know you’re actively listening, and they’re more likely to respond positively,” she adds.


If you want to get better at having difficult conversations at work, try AHRI’s short course.


5. Follow up

“You shouldn’t leave a conversation without talking about next steps,” says Blackett. 

Schedule the next meeting there and then, she suggests, so the other person knows they’re being held accountable for what was discussed.

It is also important to remember the other person in the conversation – you – and the emotional impact the conversation might have had on you.

Blackett recommends taking a moment to check in on how you’re feeling and, barring any confidentiality issues, debrief with a co-worker about the conversation.

“Especially in remote workplaces, you sometimes hang up a call and you’re all alone. That’s when it’s really important to have a colleague you can call to debrief.”

6. Share your skills

The duty of having difficult conversations too often falls to HR. But everyone experiences difficult conversations at work, so it’s worthwhile training others in your organisation too. 

“I’ll often have someone come to me and say, ‘I need you to have this conversation with so and so about XYZ’ and I’ll say to them, ‘Okay, here’s how you can have that conversation yourself’,” says Blackett.

“I don’t think you’ll ever unlearn being uncomfortable, but you can certainly learn techniques to have more productive conversations and build better relationships with people.”

This article first appeared in the March 2021 edition of HRM magazine.

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Kate Neilson
Admin
Kate Neilson
6 months ago

Test comments

Dawn
Dawn
24 days ago

What happens if you are the manager & the employee has no respect/likeness for you & they have accused you of micromanaging, when you’re not… they clearly do not like taking direction or being accountable for their actions? They have been there for a very long time prior to the new manager coming in?

More on HRM

How to have difficult conversations at work


No one likes having difficult conversations at work. Thankfully, there are a few things that can make them a little easier.

A feeling of dread often overcomes us when we have to tell someone something they won’t want to hear. Maybe you need to address a performance issue with a struggling employee. Or perhaps you need to present unfavourable employee feedback to a senior manager. In either case, when you know you’re about to have a difficult conversation that could end in tears or anger, it can be very tempting to put it off. Some research even suggests people would rather quit their job than have a tough conversation with a colleague.

But avoidance helps no one. You just have to roll up your sleeves and dive in. Here’s HRM’s six-step guide to get you started.

1. Have a plan

Anna Blackett, a founding consultant at Level Up Collective, is a facilitator for AHRI’s short course ‘How to Have Difficult Conversations’. Blackett has navigated a few tricky topics in her time and believes that, with the right skills, HR can have more effective conversations to achieve outcomes that will benefit both parties.

To start, she says you should always go into any important conversation with a concrete plan. 

“Sit down beforehand and think about exactly what you hope to get across.” 

A loose plan will help anchor the conversation because it’s easy to get sidetracked by your own nerves or discomfort. 

However, don’t over plan. Blackett says this can lead you to become narrow-sighted and therefore miss out on hearing what the person is actually saying, or on reading their body language.

“You want to enter these difficult conversations with some concrete things to consider, but also walk in open to what they might say. Come prepared with open-ended questions to ask.”

2. Pick your moment to have a difficult conversation

Felicity Mildon, director at Felicity Mildon and Associates, is also a facilitator of AHRI’s short course. She says it can feel tempting to hide behind an email or phone call, but urges HR professionals to have a face-to-face conversation where possible.

“You miss a lot of body language cues if you can’t see the person, so I would never recommend phone or email conversations.”

Of course, virtual working means this is often the only option, so try to have the conversations with your cameras turned on, and allow more time for information to sink in. 

These conversations should never be rushed, so if you’re conducting them online, take into account possible video lags, patchy internet, interrupting children/pets, etc.

“Turn everything else off and face them straight on. Then when they talk, make sure you’re not listening to respond, but actually listening to understand.” – Anna Blackett, founding consultant, Level Up Collective.

Once you establish the ‘how’, you need to organise the ‘when’. 

“If it’s something a bit more informal, you might be able to grab someone at the end of another meeting and just say, “Hey, can we arrange to chat about this?” says Mildon.

But some issues might need more of a lead-up, perhaps with an initial email to arrange a further face-to-face meeting, so you’re not ambushing anyone.

It’s also best to communicate with the employee before scheduling the meeting. Receiving an invite for a ‘Very Important Meeting’ is unlikely to put the employee in the best headspace for a productive conversation – and you don’t want them stewing on it for days.

3. Keep your cool

We often worry about having difficult conversations because we respect the other person involved. While respect is important, you also need to avoid letting the conversation become  derailed by your own discomfort, says Blackett. Remember, it’s not about you. It’s about them.

“You don’t have to agree with someone to empathise with them,” says Blackett.

“Just because you say, ‘I understand this is making you upset,’ that doesn’t mean you’re agreeing with them or that you’re going to let it slide. It just means you’re taking their reactions and feelings into account.”

If you find the conversation has moved off topic or the person has become upset, Blackett suggests pausing and returning to the conversation when you are both in a more positive mindset.

4. Listen to understand

The most important part of the conversation is actually hearing what the other person is saying and ensuring they know you’re actively listening.

“Turn everything else off and face them straight on. Then when they talk, make sure you’re not listening to respond, but actually listening to understand,” says Blackett.

During a conversation, we sometimes spend a lot of time thinking about what we’re going to say next. This means we might miss what the other person is saying or fail to pick up on their tone/subtext.

If you find yourself distracted by your own thoughts, Blackett recommends acknowledging the thought and letting it pass. Then you can put your focus back onto the other person.

“Using phrases like ‘It sounds like you’re saying this’ or ‘Am I understanding you correctly?’ lets the other person know you’re actively listening, and they’re more likely to respond positively,” she adds.


If you want to get better at having difficult conversations at work, try AHRI’s short course.


5. Follow up

“You shouldn’t leave a conversation without talking about next steps,” says Blackett. 

Schedule the next meeting there and then, she suggests, so the other person knows they’re being held accountable for what was discussed.

It is also important to remember the other person in the conversation – you – and the emotional impact the conversation might have had on you.

Blackett recommends taking a moment to check in on how you’re feeling and, barring any confidentiality issues, debrief with a co-worker about the conversation.

“Especially in remote workplaces, you sometimes hang up a call and you’re all alone. That’s when it’s really important to have a colleague you can call to debrief.”

6. Share your skills

The duty of having difficult conversations too often falls to HR. But everyone experiences difficult conversations at work, so it’s worthwhile training others in your organisation too. 

“I’ll often have someone come to me and say, ‘I need you to have this conversation with so and so about XYZ’ and I’ll say to them, ‘Okay, here’s how you can have that conversation yourself’,” says Blackett.

“I don’t think you’ll ever unlearn being uncomfortable, but you can certainly learn techniques to have more productive conversations and build better relationships with people.”

This article first appeared in the March 2021 edition of HRM magazine.

guest
2 Comments
Inline Feedbacks
View all comments
Kate Neilson
Admin
Kate Neilson
6 months ago

Test comments

Dawn
Dawn
24 days ago

What happens if you are the manager & the employee has no respect/likeness for you & they have accused you of micromanaging, when you’re not… they clearly do not like taking direction or being accountable for their actions? They have been there for a very long time prior to the new manager coming in?

More on HRM