Handling tough conversations at work

Handling tough conversations at work
Conveying hard news doesn't have to be a PR disaster.

"If you're on this call, you're part of the unlucky group being laid off," said Vishal Garg, ex-CEO of the mortgage giant Better.com.

The video where Better.com laid off more than 900 folks later went viral on social media, and Vishal had to “take time off” immediately after the incident.

But having tough conversations doesn’t have to be akin to walking on a field full of landmines. Many business leaders delivered news of layoffs, business closures, etc., with dignity and grace.

Learning to have difficult conversations is one of the biggest challenges for a leader to master, and it becomes crucial for them to address issues head-on with finesse.

In this article, let us talk about something that we at Peakperformer encounter a lot – having difficult conversations at work.

Why do people traditionally opt for conflict avoidance?

Conflict avoidance is a common phenomenon in the business world since most people would rather be liked by their colleagues than argue, disagree, and make things harder at work. And there are several cultures, especially Asian ones, that frown upon tough conversations and prefer to soften the blow when conveying the news.

But beating around the bush will backfire more often than not. Not only does being indirect cause frustration, a break of future communication channels, it also erodes the trust factor and takes your relationship to the point of no return.

Importance of feedback

  • Feedback enables every one of us to grow as a person, personally and professionally, by understanding and self-reflecting on the crucial things that ought to matter.
  • Feedback also enables us to grow as individuals by incorporating feedback into our daily habits.

No matter how intelligent folks are, it is impossible to develop self-awareness without listening to feedback from others, no matter how critical it is.

Tips on handling conversations

Pen down your goals

Noting down your goals before the session is a good practice.

The goals may be anything ranging from:

  1. Be it onboarding team members effectively and correcting their habits.
  2. Ensuring that employees perform at their best.
  3. Denying a promotion to a hardworking employee due to unavailability of funds.
  4. Or any of the 100 other scenarios where it is no longer feasible to push the can down the road.

In addition to goals, it is also crucial you note down the outcome that you can realistically achieve from the session. Do not make the result personal and avoid whining, arguing, or making the other stakeholder a “bad person” when the conversation goes south.

Be Empathetic

Having empathy at the core of difficult conversations is probably the #1 thing you ought to have in mind. Conveying bad news can have real-life consequences that are out of your control.

Manzoni had to say this on HBR, “Experience tells us that these kinds of conversations often lead to [strained] working relationships, which can be painful.”

Suppose you are looking to salvage the relationship. In that case, it is especially crucial to understand the other person’s viewpoint and take actions to rectify the situation at hand from a common point of view that both stakeholders can agree on. Empathy is essential not to take the “my way or the highway approach.”

Be present personally

If there’s one thing to learn from Uber, Better.com, and Bird’s fiascos, it is not to do an impersonal mass layoff or have a manager/leader who had nothing to do with the individual deliver the unpleasant news.

Not only does the absence of the immediate manager sound robotic when conveying huge decisions, but it also leads to a backlash, as evident when Bird’s Glassdoor rating tanked after mass layoffs, and even customers took to uninstalling the app.

Also, avoid emails and prefer in-person conversations as much as possible. As a servant leader, you must connect with an individual and deliver the news personally.

There are several examples of conversations where the management went the extra mile to ensure that it cushioned the decision’s impact. Your employees and customers will remember you for how you handled it and thank you for it.

Don’t be a narcissist.

The worst thing you can do is ask your counterpart to sympathize with you. Avoid saying phrases such as “I feel so bad about saying this,’ or ‘This is hard for me to do.”

Phrases such as these are offputting, and it is imperative not to consider yourself a victim because you are not. Playing a victim will only backfire on you since you aren’t the topic of the conversation.

Slow down and listen if the conversation gets hot

Most folks are terrible listeners. When discussing, don’t spend all your time thinking about what to say next, and instead focus on listening to the other stakeholder.

Try to understand their point of view, probe if needed, and understand how the discussion makes them feel. Also, check if your bias is hindering you from listening to the viewpoint of others.

You may learn something about them that you didn’t know or see the situation differently. If they see that you’re switched on and engaged with them, they're more likely to do the same for you.

Slowing down your train of thought will also help you find the right words and make the entire discussion as neutral as possible without getting emotions to get in the way.

But be direct and specific

Many folks refuse to be straightforward since they believe being “polite” might cushion the news and sometimes even blame themselves in front of the other stakeholder.

But doing this will also aggravate the problem and increase the issue at hand. While taking notes on what points to address can help, don’t expect the conversation to play out the way you want.

Your counterpart may not necessarily be in the same bandwidth as you, especially if emotions are involved. So, be flexible, and keep the language clear, neutral, and direct.

Offer a solution

As a business leader, if you deliver a critique, it is also crucial that you provide genuine suggestions to improve the situation.

Let us say, you want to explain why a specific individual is not getting a raise. Not only does offering suggestions improve their future performance, but it is also the right thing to do and improves your relationship with the other stakeholder.

Even if you are about to fire someone, explaining the issue will help the other person improve their performance in the next job.

Some Do’s and Dont’s


  • Take regular breaks during the day; It is crucial that you remain calm and composed.
  • Be constructive rather than being pessimistic.


  • Envision the conversation to play out the way you want to. Be open and flexible to the idea of improvisation.
  • Neglect the viewpoint of the other stakeholders. Make sure that you can look for common ground in your perspectives.

Get advice from leadership coaches on handling tough conversations

At Peakperformer, we provide personalized leadership coaching and help executives resolve their day-to-day challenges.

Our digital leadership coaching platform is currently used by tech behemoths such as CRED, Groww, MPL, Bizongo, etc.

We help people leaders transform employees into global leaders in a practical, scalable, and measurable way.

If you have read this far, do check us out!

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