How to Handle Awkward Conversations at Work (Without the Stress)

Few things make managers uncomfortable quite like having to tackle an awkward conversation. Whether it’s about performance, attitude, timekeeping or a personal matter, these chats can stir up anxiety for everyone involved.

Avoiding these conversations rarely helps - in fact, small issues left unspoken can quietly grow until they cause bigger problems down the line. Handled with empathy and care, difficult conversations can actually build stronger working relationships. They show honesty, courage and a genuine desire to make things better. These are qualities that help shape a healthy, open workplace culture.

So, if your stomach knots at the thought of ‘having a word’, here’s how to make it a more positive and productive experience for both sides.

Prepare With Empathy

The best conversations start before you even open your mouth. Take time to prepare. It’s not just what you’ll say, but how you’ll say it.

Think about your intent. What’s the goal of this chat? What outcome would be helpful for both you and them? Planning your key points helps to keep the conversation focused, but approach it with genuine curiosity rather than judgement.

Empathy is key here. Ask yourself how might this person feel hearing what you’re about to say? If it were you, what would make the conversation easier to receive?

Frame things around facts and impact, not character. For example: '“I’ve noticed the reports have been late and it’s delaying client responses” is constructive. “You’re not reliable” is personal and unhelpful.

Pick The Right Time and Place

The setting makes a big difference. Choose a quiet, private space where you won’t be interrupted. Whether that’s a small meeting room, a walk outside or a video call at a calm point in the day.

Try to avoid ‘corridor conversations’ or raising issues on the spot, especially in front of others. It can make people feel exposed and defensive.

Timing matters, too. Don’t jump in when emotions are running high or someone’s under visible stress. Sometimes it’s better to wait until everyone’s calmer and can think clearly.

A calm, private space shows respect and sets the tone for a more constructive conversation.

Be Clear and Kind

It’s completely possible to be both - in fact, the best managers are. Being clear doesn’t mean being harsh. It means being honest, direct and respectful.

When you dance around the issue, people can leave the chat confused or unaware there was even a problem. On the other hand, if you deliver your message bluntly, they may shut down emotionally. The best place is somewhere in between.

Start with why you’re having the conversation, then describe what you’ve noticed and how it’s impacting others or the business. Keep your tone calm, steady and supportive. The mix of clarity and care invites collaboration instead of confrontation.

Listen - Really Listen

It’s tempting to rush through a difficult conversation to get it over with, but one of the most powerful things you can do is simply stop and listen.

Give the other person the space to share their perspective. You might learn that something outside of work is affecting them, or that there’s been a misunderstanding or lack of support.

Active listening doesn’t mean agreeing with everything said, it means showing respect and understanding. Usually, once people feel heard, they’re far more open to finding a solution together.

You don’t have to fix everything in that moment. Sometimes being a calm, steady listener is enough to start turning things around.

End With A Forward Focus

A good conversation always ends with a plan. Summarise what you’ve both discussed, agree on what happens next and set a date to follow up. This helps to avoid any confusion and shows your genuine commitment to helping them improve.

Following up keeps accountability ongoing and proves that the conversation wasn’t just a one-time ’telling off’. It’s about progress, not punishment.

Need a hand?

Awkward conversations may never be anyone’s favourite part of the job, but they can be some of the most meaningful. When handled with honesty, empathy and integrity, they can transform tension into trust, confusion into clarity, and mistakes into opportunities to learn.

If you’d like support handling tricky conversations or helping your managers grow in confidence with people issues, BloomHR can help. We offer supportive, practical guidance to make those difficult chats a little easier for everyone involved.