How to have difficult conversations at work

Tips for navigating tough conversations with employees and colleagues

Sylvie Thrush Marsh, Chief Evangelist
By Sylvie Thrush Marsh, Chief Evangelist

In our working lives, we all have times when we’re faced with difficult situations and conversations that we’d rather not have.

As an employer, you might have to deliver negative feedback to an employee who hasn’t been performing. As a manager, you might have to tell a customer that their important order isn’t going to be ready when expected. Or as a worker, you may clash with a colleague’s way of working or strongly disagree with an idea they had.

Employee hands on table

Regardless of the circumstances, these conversations can trigger all sorts of emotions and make us want to avoid having them at all.

But there are some really good reasons why we need to grasp the nettle and have those tough conversations.

So let’s have a look at the issues around having difficult conversations at work, why avoiding them isn’t the answer, and how we can approach and reframe them to ensure that we’re getting the best outcomes for ourselves, our co-workers, and the organization.

You’re not alone

There’s quite a bit of research that proves just how common it is for people to avoid difficult conversations at work. One study by professional training and coaching platform, Bravely, found 70% of employees avoided difficult conversations with their boss, colleagues, or direct reports.

A UK survey by the Chartered Management Institute (CMI) found that two-thirds of workers felt anxious or stressed if they knew they had to have a difficult conversation and that 57% of respondents would do almost anything to avoid it.

Fear is one of the top reasons cited by both studies, whether that is fear of confrontation, fear of the consequences, or repercussions from within the organization. Other factors include wanting to be liked, previous bad experiences, a lack of time, or being worried about getting emotional or upsetting the other person.

Avoiding the situation isn’t the answer

A survey by Leadership Training Company, Crucial Learning, estimated that every failure in having a tough conversation costs an organization US$7,500 and more than 7 work days.

The ineffectual avoidance behaviors included ruminating about the problem, getting angry, complaining to others, and doing extra, unnecessary work.

That’s not the only cost. Another Crucial Learning study found that instead of having a difficult conversation, 11% of respondents quit their job and 37% considered quitting their job or taking a different job. 50% of respondents said they avoided the other person at all costs, which is hardly good for team productivity and collaboration!

These downstream effects of avoiding a simple conversation can cost your business in tangible ways, like lost revenue and increased employee turnover, and less obvious ways like increased absenteeism and presenteeism (being at work but not focused or productive), a drop in team morale, or the formation of cliques within your team.

How to turn difficult conversations into courageous conversations

It’s clear that instead of putting off a difficult conversation - thinking there will be some ideal future time or waiting until the situation reaches boiling point - it’s far better to be courageous and tackle it so you can resolve the issue and move on. It’s better for your own wellbeing and performance, the other person’s, and the wider team’s.

The key is learning how to handle uncomfortable conversations in a way that produces positive outcomes. Here are some tips for having difficult conversations or delivering negative feedback:

Have the conversation in person

It may not be the easiest way, but talking face-to-face and in private is always better than sending an email, messages on the business’ communication channel, or a phone call.

There are so many cues and subtleties that get lost in text, and it’s much easier for meanings to be misconstrued. Talking in person also shows a lot more respect and willingness to work out a solution.

When an in-person conversation is not possible in remote work situations, a video meeting is still superior to opening an email chain or going back and forth via a messaging platform.

Get in the right headspace

It’s important to be in a good mental space before you have a thorny conversation. Everything from getting enough sleep, food, and hydration can help you stay calm.

Do some preparation. You want to have an idea of how you’d like things to go but be flexible enough to adapt. Think about what the situation is as you understand it - what information might you be missing? Also ask yourself what you’d like to happen as a result of the discussion.

If you need assistance getting prepared for a difficult conversation, MyHR can help with expert guidance and tailored scripts to make sure you get the best outcome.

Take off the armor

Our feelings affect our ability to think, problem-solve, communicate, and listen effectively, so try to lower the emotional tone in your own head. Reframe the conversation. Instead of thinking of the conversation as “difficult” or confrontational, approach it as a way to work with someone on a solution.

We often approach difficult conversations thinking we are the ones who are right, overlooking the fact that the other person’s perspective may also be quite rational. It’s better to assume the best of others rather than the worst.

Learn to be comfortable in discomfort

The situations and your reactions to it might make your head scream: “Run!”, but try to sit with those uneasy sensations. Again, your reactions are valid but they aren’t the only ones you can have. Breathe deeply and take a step back to reflect.

Being aggressive or sarcastic will only cause the other person to become defensive or react in kind, at which point neither of you are listening.

Focus on the issue not the person

Whatever you do, don’t make it personal. You risk causing long-term harm to the relationship if the conversation descends into adversarial, tit-for-tat mudslinging, so focus on the problem rather than the personality.

Stay professional and present, even if the way the person works and thinks is totally different to yours. Share specific examples and facts, and propose constructive solutions or alternatives.

This is where keeping accurate records can provide evidence rather than simply comparing opinions. A digital platform can make this much easier: MyHR’s smart notes feature lets you record and collate events and observations as they occur, so you have a rich picture of employee performance and conduct, and can easily reference this with your employee weeks or even months after the event in question has taken place.

Say your piece

Get your points across clearly using simple, neutral language. Use “I” statements, e.g. “I’ve observed that… I was uncomfortable with the way this was handled…”

Apologize if you feel you have done something wrong but don’t blame the other person or try to play the victim by asking them to have sympathy for you.

Be curious and compassionate

Our different ways of thinking and being creative are what make a strong team, if we can work together cohesively and with respect.

So try to understand the situation from the other person’s perspective; be curious about their ideas and understand where the differences are. Ask questions to make sure you have it clear: “Let me play that back to you… Is there anything I’ve missed or that I don’t understand?”

If the other person senses you don’t respect them, they’re likely to focus on defending their dignity rather than working constructively.

Listen to understand

We all like to feel heard. Give the other person plenty of space to explain their side of the story and actively listen. Again, ask questions rather than making assumptions or jumping to conclusions.

Keeping the pace of the conversation slow will also help you find the right words and it lets the other person know you’re listening.

Look for mutually-beneficial outcomes

Mutual purpose is going to be way more beneficial than each person fighting to be “in the right”.

Discuss the outcomes that you both want to achieve and how you could both work towards them. You want to both feel like you have had real input, which will mean you’re more invested in actually making it happen.

Also decide on how you will measure success and plan to meet again to review progress.

Tips for initiating the conversation

When it comes to having a difficult conversation or giving constructive feedback, starting it right can be the difference between a great talk and an unproductive conversation. Here are a few ways to start the conversation without putting people on the defensive:

  • "I wanted to set aside some time to check in with you. There are a few things I’ve observed recently that I think are important for us to talk through together…"
  • "I’d like to talk with you about something that’s come up. It’s a bit of a sensitive topic, but it’s important that we address it honestly and professionally…"
  • "I wanted to speak with you privately about something that’s been brought to my attention. My goal is to understand your perspective and talk through what’s going on..."
  • "I’d like to talk about some upcoming changes and how they may affect your current role. I know change can be challenging, and I want to walk through it with you…"

What if things blow up?

If the conversation isn’t going well, you feel you’re getting wound up, or the other person isn’t being constructive, take a break. Despite our best intentions, these conversations don’t always go to plan or have a happy ending.

You might agree to come back and revisit the matter when things have cooled down. Inviting an impartial third party to join you can lower tensions and encourage both parties to try and reach a viable outcome.

After the conversation

After a tough conversation, allow some time to “come down” and process what happened. Have a cup of tea or go for a walk.

Reflecting on what went well, what you might have said differently, and how you reacted will help you get better at handling these situations in the future. 

Write down on any agreed actions or plans and share them with the other person. Then work on doing the things and book a check-in to revisit if you need to.

Creating a culture of safeness and openness

Collaboration is integral to the success of any organization, and employees should be encouraged to have open, honest conversations without fear of being shut down or singled out.

Most of us have never been taught the skills to address difficult situations in a way that creates productive dialogue (the CMI study reported 80% of workers had no formal training in handling difficult conversations), so look to offer skills training to all employees.

As a leader or manager, you also need to model the behavior you want to see, in how you address problems, verbalize concerns, treat people, and support them to speak up.

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