Dec 08, 2022

How to have a difficult conversation with employees

Is it you or is it them? Who’s right and who’s wrong? In reality, difficult conversations have nothing to do with facts. They are a clash of perspectives, beliefs and values. Yes, you can learn some techniques to overcome this. Nevertheless, the most important part of learning how to have a difficult conversation with employees is to get to know your emotions and your intentions.

Difficult conversations or the art of empathy?

Do you avoid difficult employee conversations? Does the mere thought of tough conversations fill you with dread? Deep down, do you feel like giving up? 

The challenge when learning how to have a difficult conversation is that we hold onto the belief that we are right. We see the world and difficult situations through our personal filters and worldviews. These block us from truly understanding the other person and their motivations.

Without empathy, we approach tough conversations almost as if we are forcing our opinion. This can come from very good intentions. After all, if only that manager could soften her approach, she’d get buy-in from her peers. Generally, as leaders, we want to help our team members but without empathy and self-awareness, we create friction. 

For example, if you approach giving negative feedback by telling someone they need to increase their sales numbers, you’re more likely to stress them and decrease their productivity. Instead, connect with empathy and curiosity to understand what’s going on in their reality. They are then more likely to come up with a way to let you help unblock them. 

Empathy isn’t easy especially when we have our own pressures to perform. As this paper on “empathy is hard work” describes, it takes effort, and we don’t always see the immediate outcomes. This puts us off. Nevertheless, without empathy, you can’t create a psychologically safe space for open reflection that encourages change. Moreover, you get frustrated, emotions escalate, and no one wins.

Partnering with a coach to learn how to have a difficult conversation with employees will open up your approach:

One of the most effective ways to develop your empathy is to work with a leadership coach. They’ll also challenge you to improve your self-awareness and to practice reframing situations from different viewpoints. As we’ll see below in the process, you’ll then learn that a performance issue can be a transformational moment rather than a painful telling-off.

  • Letting go of the need to be right. This is probably the hardest first step that a coach will support you with. Being right only puts people on the defensive such that they withdraw. Besides, there is never a right or wrong but simply a different perspective.
  • Discover your inner motivation. We all like to feel more knowledgeable but this intention again shuts down the other person. It also blinds you to your biases whereas a coach will get you to work through those so you can be more open to your team members’ realities and problems
  • Accept people for who they are. Often, subconsciously, feedback is about wanting others to be like us with the same approach and style. You counteract this by looking for their strengths and where they can actually make a difference. 

5 steps to managing a difficult conversation with employees

As the Harvard Negotiation Project team explains in their book Difficult Conversations, how to handle difficult situations means uncovering what’s being left unsaid. We all have feelings and assumptions that we don’t necessarily surface. 

The ability to have a difficult conversation means moving from a transactional, or telling approach, to a transformational one. In the latter, Judith E. Glaser, explains in her framework on conversational intelligence, you ask questions to challenge your own assumptions and uncover those feelings. Glaser’s framework:

  1. Set the scene: To have tough conversations with employees, you need to be fully present. You need to feel comfortable with no distractions such that you are emotionally calm. This will create a more peaceful space for the other person. It may also be a good idea to step away from the workplace and go for a cup of coffee. 
  2. Discovery: This step is about leaving your assumptions behind. Usually, most of us go into tough performance reviews with the goal to change the other person. This only creates resistance. Instead, master how to have a difficult conversation with employees by focusing on transformation. You do this by encouraging employees to discover their own need for change. In short, be curious and ask open questions to enable your employees to change their point of view
  3. Exploration: As you explore, rather than berate, your employees’ feelings are more likely to come up. They might even talk about why they are struggling. A good way to get them to accept their struggle is to focus on facts. This means talking about actions rather than judging behaviors. You might say to someone, “I noticed you were late to work that morning” and not “you’re always late for work and it’s affecting your performance.” This is you jumping to conclusions. 
  4. Co-creation: When you handle difficult conversations, aim to co-create the solution. After you’ve raised awareness by asking open questions, get your employees to come up with how they want to change. A great question to ask, for example, is “how do others see you and how does that match up with what you aim for?” Once they’ve spotted the gap, all you need to do is to listen as they work through it. In fact, a fundamental technique for how to have a difficult conversation is active listening. Make it a habit in your everyday life and challenging conversations will get easier. 
  5.  Follow up: Tough conversations with employees are coaching opportunities. The work has only just begun at this first conversation and it’s critical to follow up. Agree with each other on the cadence of your follow-ups. Then, remember you’re not providing solutions but only flexing your management coaching style.

Apply this approach to these common examples:

  • Denying a promotion request – remember the skill in this one is to get them to suggest they are not ready rather than just telling them. 
  • Performance review disagreement – again, ask questions for them to show you the required evidence for the review.

And adapt the process for these two examples:

  • Misconduct 
  • Termination 

It’s worth noting that when facing more final situations, such as the two listed above, and assuming you’ve already tried the co-creation approach, these processes may not work. This is sadly an inevitable part of any manager’s role but you still need empathy.

In summary, for those extreme cases, you want to be fact-based and to the point. It’s also usually advisable to have an HR representative in the conference room with you.

Never give up practicing how to have a difficult conversation with employees

Challenging conversations arise because of mismatched expectations and beliefs. Moreover, we all have decades of ingrained patterns of thinking that bias our views. 

Rather than get stuck in a clash of opinions, the art of how to have a difficult conversation with employees is to develop empathy. By listening, asking open questions and being curious, you create a safe space for others to discover their own shortcomings. Then they can develop their solutions for creating the required change. 

In essence, you’ve leveraged a tough moment and turned it into a coaching opportunity for personal transformation. Finally, be patient because all change takes time along with continuous follow-ups. It’s all about showing empathy and understanding. 

Or as the authors from Difficult Conversations state, “people never change without first being understood.”


Coaching, Communication, Company Culture, L&D, Leadership, People, Skills-Based Coaching

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