Skip to content
Tweak Your Biz home.
MENUMENU
  • Home
  • Business
    • Business
    • Finance
    • Technology
    • Growth
    • Sales
    • Marketing
    • Management
  • Mind
  • Tools
  • About

How to Have Tough Conversations With Your Employees

By Libby Calaby Published October 21, 2019 Updated March 17, 2023
Tough Conversations With Your Employees

Every manager dreads it. The thought of it can be nausea-inducing. But, if you don’t do it, then your entire team could be at risk. I’m not talking about getting rid of Vicki’s breakfast kippers from the employee fridge (although that, too, can be disturbing). I’m talking about having a tough conversation with one or more of your employees.

Knowing the right time to put a stop to toxic behavior or poor performance is vital if you want to improve office life in general, and make things more comfortable for your wider team.

This is the time to push back the nagging apprehension and tackle the problem head-on before the problem gets out of hand.

According to a recent workplace trends study, managing conflict at work should be high on the HR agenda. The report states that conflict management needs to be seen as a high-value activity. Especially as line managers may lack the confidence to deal with the issue, and HR teams may be risk-averse.

Handling a tough workplace conversation, be it conflict or performance-based, requires a great deal of skill, especially as it’s typically against our natural instincts to get caught up in someone else’s issues. Get it wrong, and you could land yourself with a grievance, a much more complicated situation, or an employee that misinterprets your intentions. Get it right, however, and the situation should be steered towards a sensible and swift resolution.

Get in the right frame of mind

Before sitting down with the employee in question, be clear on your objective and question your own attitude to the situation. If you feel negatively towards this person, then your own perceptions may influence the conversation, and you could portray a condescending, rather than supportive attitude. If you feel positively towards them, you could end up skirting around the issue rather than confronting it, through fear of offending.

Before you have the conversation, it’s essential to get yourself in the right frame of mind. Remain rational and neutral; be prepared to be direct. If you waffle or deliver a muddled message, your intentions will be unclear, and you won’t be doing yourself, or your employee any favors.

It may help to mentally prepare for your conversation. Take ten minutes for yourself to do some breathing exercises or meditate. Get yourself in the right mindset and know the result that you want to achieve at the end of it all.

Set the objective

From the outset, you’ll need to acknowledge the problem at hand and how you plan to resolve it. It will help to jot down a list of your objectives and desired outcomes before the discussion, and mentally tick them off as each one is discussed.

For example, if the employee is underperforming, then talk through a plan of action to support their improved performance, and most importantly, what they should do to help themselves.

If the employee has behavioral issues in the workplace, then discuss how this might be overcome, while considering their point of view.

If the employee is taking too much time off work, then be sure to uncover the reason why. Once you’re armed with the right information, then the situation can dramatically improve. Most importantly, follow it all up in writing, so you both have a copy of the agreed action plan.

You’ll also need to prepare yourself for how the other person might react. Could they be emotional? Is the conversation likely to upset them? Do they often overreact? Do you think they may pay you lip service, agree with everything you say, and then carry on with their harmful behavior, regardless?

The more prepared you are, the better the conversation will be.

Remove the emotion

The workplace can be an emotional hazard, filled with multiple, complex personalities. During an awkward conversation with an employee, it’s essential to recognize your own emotions. Do you feel frustrated or annoyed at dealing with the situation in the first place? You’ll also need to recognize the feelings of your employees; do they feel threatened and defensive at being called up in front of the boss, or HR?

It’s important to prove to the employee that you have heard and taken on board their side of the story. Emotionally intelligent leaders listen to what their employees have to say and help them to re-centre by injecting positivity into the conversation — highlight why they’re good at their job and show compassion by asking how they’re feeling about their current situation.

There are, of course, situations that will never get better and that require an alternative approach. But a carefully considered and emotionally intelligent conversation to bring it all out in the open will help you better prepare for the next time.

Find the best place to talk

Chatting over a coffee in the employee lounge or local Starbucks is great for off-the-cuff conversations or quick catchups between colleagues. It’s not a great place, though, for a tough talk.

Choose your setting carefully and respect the privacy of the employee in question. Are there opportunities for other people to overhear? Is the environment too noisy or distracting? Is there any chance that the environment you’ve chosen will be uncomfortable for either of you?

When choosing where to talk, there are many factors to consider. Most importantly, you’ll need a safe, quiet space where the conversation can flow freely.

Follow up with a review

There is nothing worse than holding your employee to account and then never following up. That will just make them feel as if they’ve been criticized with no opportunity to show improvement. Be sure to close off the conversation with a set date in the diary for when you’ll meet again for the review.

Most importantly, when having a tough conversation with an employee, try to show empathy and understanding for their situation. This is not about apportioning blame or pointing fingers but about finding the right solution for them, you, your team and the wider business.

More on this topic

  • Sometimes Leaders Need To Be Dictators
  • Fratarcangeli Wealth Management Shares How High-Net-Worth Individuals Can Maximize End-of-Year Assets and Investments, While Navigating Uncertain Times
  • Why Most Digital Marketing Advice You Get Won’t Work for Your B2B Business
  • 7 Ways to Avoid a Terrible Hiring Choice
  • A Look at the Future of Wealth Management
  • 4 Ways to Inspire Employee Loyalty
Produced with AI assistance. Reviewed by the Tweak Your Biz editorial team before publication. See our editorial policy and about page.

About this article

This article is for general information and reflection. It is not professional advice. For your specific situation, consult a qualified professional. Editorial policy →

Posted in Management

Enjoy the article? Share it:

  • Share on Facebook
  • Share on X
  • Share on LinkedIn
  • Share on Email

Libby Calaby

Libby Calaby is a freelance writer, specialising in careers, self-development and entrepreneurship topics. She lives in the beautiful county of Shropshire in the UK and loves her dogs more than she loves most people. Connect with her on LinkedIn or Twitter.

Contact author via email

View all posts by Libby Calaby

Signup for the newsletter

Sign For Our Newsletter To Get Actionable Business Advice

* indicates required
Contents
Get in the right frame of mind
Set the objective
Remove the emotion
Find the best place to talk
Follow up with a review
More on this topic

Related Articles

Management

When Ed Catmull instituted the Braintrust at Pixar in the late 1990s, the rule was that the assembled directors could critique any film in development but had zero authority to mandate changes — Catmull argued that the moment feedback carried power, honest feedback would disappear from the room within one meeting

Tweak Your Biz Editorial Team June 30, 2026
Management

Andy Grove walked into Intel’s Santa Clara headquarters on a Monday morning in 1985 and asked co-founder Gordon Moore what a new CEO would do if they were brought in — Moore said exit the memory business — so Grove walked them both out the door and back in to do exactly that

Tweak Your Biz Editorial Team June 30, 2026
Management

Patagonia closed its headquarters and all 29 of its U.S. stores on Election Day 2016 and paid every one of its roughly 2,000 employees for the day off — then closed the company for every general election that followed, co-founded a coalition that now spans more than 2,000 employers, and in 2024 moved the closure to early-voting day

Tweak Your Biz Editorial Team June 24, 2026

Footer

Tweak Your Biz
Visit us on Facebook Visit us on X Visit us on LinkedIn

Company

  • Contact
  • Terms of Use
  • Privacy Policy
  • Accessibility Statement
  • Sitemap
  • Editorial Policy
  • Corrections

Signup for the newsletter

Sign For Our Newsletter To Get Actionable Business Advice

* indicates required

Copyright © 2026. All rights reserved. Tweak Your Biz.

Disclaimer: If you click on some of the links throughout our website and decide to make a purchase, Tweak Your Biz may receive compensation. These are products that we have used ourselves and recommend wholeheartedly. Please note that this site is for entertainment purposes only and is not intended to provide financial advice. You can read our complete disclosure statement regarding affiliates in our privacy policy. Cookie Policy.

Tweak Your Biz

Sign For Our Newsletter To Get Actionable Business Advice

johnsmith@example.com