How to have a difficult conversation with employees?

coffee meeting for having a difficult conversation with employees

What is your process for having a difficult conversation with employees? What is your style?

There are a few elements that make up a one on one discussion:

  • You (the messenger)
  • The employee (the recipient)
  • The message
  • The context, and
  • Ambience (the setting for the meeting)

Each of these influences the outcome of the meeting. The recipient and the context are mostly out of your control when you need to have a difficult conversation with employees.

The other three elements are within your purview. You can control them, influence them.

You – the messenger

How you plan for the meeting. How good are you at listening to the employee? Are you willing to acknowledge the recipient’s perspective and arguments? Are you compassionate and empathetic? Do you have a solution ready? Can you guide the employee to reflect and learn?

The message

Keep the facts ready. Avoid both overprocessing and under processing information. The communication style should suit the recipient’s persona. Some like to be straightforward. If so, do not beat around the bush. Some like extra cushioning. They need to be told everything will be okay. It is critical you understand your audience. Prepare the tone and phrasing of the message.

The ambience

Where do you plan to have the meeting? Today, we will talk about the ambience – the setting of the meeting to have a difficult conversation with employees.

How does ambience play a role when delivering messages or news to employees?

Especially the not so pleasant messages. Denying a raise, not approving a leave request, reprimanding for a failure, counselling for better behavior at work etc. are some usual manager – employee conversations.

My first “difficult conversation”

This was early in my career. I had been working with the company for a little more than a year when my supervisor took four of us out for a drink.

Nothing unusual here. We were in the same age group. We frequently went out for drinks and dinner. This time though he had something else on his agenda.

He is a very unassuming leader. His reactions are measured. He has this unique skill of talking less and yet communicating more.

Coming back to the context of the meeting – ours was one of the best teams at work. The message here was not the usual tough talk. This was a career counselling session.

How did he plan and conduct the meeting?

He planned to make the four of us realize what each one was capable of. He did not want us squander opportunities of growth. It was simple – “Fellas, it’s time to move your asses.

He realized his best employees were in a comfort zone. They needed some kicking in the butt.

After a few drinks, he transitioned well to the agenda. He had the message worked out. He addressed us as a team but effortlessly managed to communicate one on one at the same time.

This conversation would not have accomplished the results in a closed room inside the office. That was not his style. We were more friends than his DRs.

He planned the meeting well. He worked on the message to appeal to each of us. The ambience was appropriate for the meeting agenda.

Remember the famous CCD tag line – “a lot can happen over coffee”.

They certainly were bang on. A lot can happen over coffee, tea, beer.

coffee meeting to have a difficult conversation with employees
Coffee Meeting with the Boss

Why out of office meetings are effective in having a difficult conversation with employees?

It has a lot to do with the employee’s frame of mind. A person is more relaxed, at ease and open to receive messages in a café than a 4 by 4 monochrome meeting room. Okay, modern office meeting rooms are colorful. I get it. But I’d rather meet in a café 😊

In an outside setting, the manager can wear more hats – a friend, a confidante, a counsellor.

The unknown place and faces around give the recipient more freedom to react. The employee does not have to worry about menacing coworker stares after the meeting ends. Ever been the focus of a penetrating gaze from coworkers as you stepped out of a meeting room?

It does not have to be a café or a restaurant. A walk outside the office building is a great setting too.

I have, I must say, overused the “Walk the Talk” philosophy. The results have been promising to say the least.

I have had retention discussions during walks. I had to change the approach when employees on notice period preempted the agenda as I asked them to accompany me for an after-lunch walk.

The setting of the meeting depends on the employee’s comfort and equation with the manager. Avoid any awkwardness. The idea is to break the “formal, tense” mould of the meeting.

The tea vendor outside the office, a walk near the premises, a coffee shop, restaurant, the local diner – choose what works best for the person and the context of the meeting.

You need to connect with the “person” and not the “employee”. Break the mould. Step out.

Got any tips or stories to share? Please reply in the comments section or tweet me your reply.


use popular opinion by tricking employees to agree to your viewpoint
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Leaders cannot duck or bury their faces in the mud when making tough calls at work. Leadership is tested when selling unpopular decisions to the team. How do you do that? “My way or the highway” does not work. It gets you obedience, not acceptance. Do you use popular opinion as a work around? Can you?

By Nitesh Verma

Founder - Business Management Blog. I am an independent business strategy consultant, helping companies take data driven business decisions. My mission is to find and implement simple solutions for complex business problems.

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