Difficult conversations at work

Having a difficult conversation with your boss or employee is extremely daunting, but putting it off makes matters a lot worse. However bad the news or sensitive the problem, tackle it as early as possible.

Worry simply leads to stress and anxiety, which affect your leadership skills as a boss, and performance as an employee.

If you're a union member, a trained representative can accompany you to any formal meeting with your manager; or advise you on how to manage any such difficult conversation. To find out how an independent union can support you, why not look at Prospect or  visit workSMART.

Workplace situations in which a difficult conversation is necessary include:

Below are basic guidelines for employers and employees on how to request, manage and recover from a difficult conversation at work.

Difficult conversations with your staff

How should I initiate the conversation?

A direct approach lets the employee know a difficult conversation is coming up, and allows them time to mentally prepare.

I'd like to talk to you about a few issues we're having with missed deadlines. How about tomorrow at 10am?

A neutral location, ie not your office, is likely to make the employee feel less intimidated.


Ensure you talk to them promptly in light of a development or following the situation/behaviour that is subject of your concern (i.e. do not wait until the end of the month – or next review).

What tone should I take?

Don't waste time with small talk. Deliver bad news or raise the issue straightaway. In the case of redundancy, an emotional response is likely, so be empathetic.

Stay calm, clear and concise. Refer to 'the behaviour' or 'the situation' rather than the more accusatory 'you'.

Remain objective. An employee's unfavourable behaviour may stem from personal problems. Give them the opportunity to talk to you about this.

Discuss what you expect to change, setting objectives you would like to see achieved.

A magazine editor says:

The worst behavioural problems I've had to deal with are social media-related. Slagging off your boss or co-workers on Twitter or Facebook is incredibly stupid. I'm not good at confrontation and dislike having to pull people up on their actions, so I try to keep discussions as straightforward as possible. I make it very clear why I'm unhappy, and give them the benefit of the doubt. Of course if they continue to badmouth the company online, it's a different story.

Difficult conversations with your manager

Email or approach your manager in person, requesting a one-to-one (in a location of your choice, if you prefer) to discuss something that has been bothering you.

Make notes and try to stick to your objective - what outcome do you want from this meeting?

Try to state your concerns positively, rather than presenting a list of negatives.

After the meeting, document your discussion while it's fresh in your mind. This is essential if you feel your complaint or request has not been acted upon effectively and you need to take a more official route.

Ensure you access and are familiar with your company/organisation’s grievance or capability procedures.

Moving on from a difficult conversation

A senior manager at a gifts company says:

The most important thing I've learned when having tough conversations with my staff is to always ensure that once the conversation is finished, it is left inside that meeting room. I always acknowledge what's been discussed, what's been agreed and how we together can move it forward. No one likes being disciplined, but delivered in the right way it can provide a lot of positives.

Are there preventative measures I can take to avoid future confrontation?

As an employer, keep the lines of communication open to your team. Introduce regular, confidential catch-ups to allow staff to talk candidly about their jobs and air any grievances. Have quiet words with your employees at the first sign of poor performance or if you think someone seems unhappy.

Open lines of communication work in the employee’s favour, too. Remain on good terms with your manager, and allow yourself to be approachable. Letting a problem fester is counter-productive and will impact on how well you do your job. Any concerns or complaints should be raised with your boss at the earliest opportunity and, rather than being considered a nuisance, will more likely earn you their respect.

Further advice

It is best to seek expert advice, which can include a union, citizen advice or ACAS. For more information and support, visit workSMART.