How to have difficult conversations at work

Madlen Popignatova 17
Article by: Sophie Poulsen
How to have difficult conversations at work

For any employee at any organization, difficult conversations are unavoidable. Whether it’s addressing poor performance, terminating an employee’s contract, or asking for a promotion, leaders will also have to face tough conversations.

We spoke to three THNK Faculty members – Bernice Feller-Thijm, Rosalie Puiman, and Ien van Duijnhoven – to get a few tips on how to have difficult conversations at work.

What Are Difficult Conversations?

A difficult conversation is exactly what it sounds like. It’s a conversation or topic that you find hard to talk about. We tend to avoid difficult conversations because they are awkward and uncomfortable. We fear confrontation. We worry about being disliked. We worry about the other person’s reaction.

Bernice says, “A difficult conversation is always something that has a personal impact. For example, when you have to tell someone they did or said something that you don’t like or they’ve rubbed you the wrong way. Those types of conversations are always very difficult.”

While this article focuses on examples of difficult conversations in the workplace, you might find that you can also apply the tips below to the tough conversations in your personal life.

Examples of Difficult Conversations -

Types of difficult conversations at work include:

  • Turning down an employee’s idea.
  • Encouraging an employee to improve their performance.
  • Resolving conflict between team members.
  • Terminating a position.
  • Asking for a raise or promotion.
  • Reporting bad behavior, like abuse or sexual harassment.
  • Giving negative feedback.
  • (Re)establishing boundaries.
  • Admitting a (big) mistake.

Tips on Handling Tough Conversations -

Based on input from experienced THNK Faculty members, here are 10 tips to handle tough conversations like the ones listed above.

  1. Be Prepared –

As with most professional conversations, it’s important to be prepared. Some things you can do to prepare for an upcoming difficult conversation include:

  • Reflecting on the purpose of the conversation.
  • Identifying what emotions are connected to this conversation.
  • Thinking about the best way to approach the conversation.
  • Reviewing the facts of the situation.
  1. Give Context –

At the beginning of your tough conversation, it’s important to explain the context to the other person. Bernice advises, “Express things that are objective: something that another person could have observed. Don’t make it too vague.”

Giving context and background to why you’re having a conversation can help get everyone aligned. As Bernice puts it, “Make sure that you’re in the same conversation. Ask the other person if they recognize this before you continue. Make sure that the other person knows what you’re talking about.”

  1. Listen!

Listening might be one of the most valuable things you can do in a difficult conversation. Unfortunately, it also might be the most difficult. “That’s always the problem when it comes to difficult conversations: that we are not able to listen to each other and to really hear each other,” Ien says.

Rosalie adds, “If you can listen to the other person with real curiosity and real honesty and speak with sincerity – truly speaking your truth, not covering up, not faking things – then the other person has no other option than to come with you in that sincerity.”

At THNK, deep listening is a part of almost every leadership program we offer. Listening helps to build trust, resolve conflict, encourage empathy, increase productivity, and deepen relationships.

  1. Don’t Try to “Win” The Conversation –

“Often what we find in a difficult conversation is that we disagree with someone and we go into the conversation to try to persuade the other person and make them see our point of view,” Rosalie explains. “The thing is that makes it a difficult conversation. Going into it wanting to ‘win’ makes it a difficult conversation.”

Trying to “win” a conversation will not bring you success. In fact, it will also diminish trust between you and the other person.

To avoid trying to win a conversation, adopt the “And Stance” – taking control of the conversation by using “and.” Rosalie explains, “Knowing that you can be right AND the other person can be right at the same time will lead you to not necessarily win the argument, but you will find that you can come to a way forward that works for everyone.”

  1. Try To Understand The Other Person’s Perspective –

For Bernice, “it all comes down to trying to understand the perspective of the other. What we forget, especially when we’re hurt, is that we want to be right. In a difficult conversation, it’s not about being right. It’s about understanding each other’s perspectives.”

This doesn’t mean you have to reach a point of agreement. Even if you get to a point where you understand each other but don’t agree, that’s also a successful result.

On a related note, don’t make it about you. Ien says, “The hardest part is to allow yourself to hear new things and not only the things that confirm your beliefs.”

  1. Focus On Your Commonalities –

In any type of difficult conversation, it always helps to return to what you share with the other person. What are your shared values and goals? Why are you in this together?

Ien tells us, “When people have been working with each other for a long time, they have more assumptions – but that’s part of the pattern.” Becoming aware of your assumptions and behavioral patterns is the first step to finding common ground with the other person.

  1. Be Present –

Rosalie emphasizes “the power of mindfulness in difficult conversations.” Fun fact: Rosalie even wrote a book called “The Mindful Guide to Conflict Resolution.”

She says, “Very simply, you need to be present. Thinking about what you’re going to say next is very counterproductive.”

A classic mindfulness approach is adopting the “Beginner’s Mind.” In a difficult conversation, this means stepping back, looking at the facts, postponing judgment, and examining what is going on in the present. Understandably, this is easier said than done, but it can be very helpful to do during a tough conversation.

  1. Don’t Enter the Conversation With The Desired Outcome –

Perhaps the most ineffective thing you can do is enter a difficult conversation with a solution in mind. “We are all solutions-driven. We want to solve the problem,” Ien admits. But it’s important to “keep an open mind and an open heart,” Ien puts beautifully.

“If you go into a difficult conversation wanting to get to point B specifically, you make it a lot harder for yourself,” Rosalie adds. “It’s the winning paradox: you’re so focused on reaching that one point, you lose track of what’s actually going on.”

When you go into a conversation with an open, curious mindset, oftentimes you’ll find that new solutions arise that you didn’t even think of.

  1. Break Up The Conversation Into Stages –

If the conversation isn’t going well, it might be better to revisit the topic at a later time. “Sometimes it’s best to just put it aside and revisit it in a few days,” Rosalie says. “Cutting it in stages can be very helpful.”

Even if the issue you’d like to discuss is urgent, it’s not an emergency. “It’s very important not to go straight into defense or offense,” Bernice urges. When you are calm and level-headed, you’re less likely to be offensive or defensive.

  1. Make Your Next Steps Concrete –

If your difficult conversation has gone well (hurray!), “make it concrete how you move forward,” Bernice suggests. “If you want to work together moving forward, make that tangible.”

Bernice also emphasizes the importance of letting go. “People are very resentful and they don’t let it go,” she says. “If you had a really good conversation, let it go.” If it happens again – whatever the issue may be – make concrete steps on how you will both resolve it next time.

Develop Your Leadership -

Difficult conversations can bring up a lot of emotions in everyone – whether they bring up past issues or make you feel vulnerable and out of your depth. By using essential leadership skills like deep listening, empathy, and an open mindset, you will surely become more comfortable in having those tough conversations.

Learn To Lead Difficult Conversations At Work

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We have leadership programs for three career levels.