27 September 2023

Four steps for easing into a tough conversation

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Ashley Stahl* has advice for the nervous new manager about to have their first difficult conversation with an under-performing employee.


Your heart rate is accelerated, your palms are sweating and you are full of nerves.

Today is one of those days at work that you need to get your hands dirty and dive into the trenches of leadership — you’re going to have a tough conversation.

Tough conversations are delicate.

Masterful communicators learn to inspire their employees through tough conversations.

Struggling communicators leave their employees feeling discouraged, unmotivated and less loyal.

More than one-third of managers shy away from having a difficult conversation about poor employee performance or feedback.

Millennials are stepping up in the career ranks, growing quickly in their leadership and management roles.

Learning how to deal with difficult conversations is something many of my clients come to me for guidance on.

I keep hearing the question: “How do I tell someone they might not have a job anymore unless things change? It is so hard knowing I might have to fire them.”

When an employee isn’t meeting expectations, it can be tough to step in as a manager and raise awareness.

However, if you prepare correctly, the talk will be easier than you think and the outcome more positive.

Here are four tips to prepare for that next challenging conversation.

Put yourself in the other person’s shoes

There are two sides to every story, and the sooner you can see both, the smoother the conversation can unfold.

This means going into the conversation with a desire to understand the other person, not to judge them.

When you are able to practice empathy and feel the connection to their viewpoint, communication and collaboration improves.

Sadly, empathy levels have declined over the past decade, with 40 per cent of graduates expressing less empathy than those before them.

The good news is that empathy is a skill that can be learned and improved.

Before approaching the issue with your employee, consider spending intervals in silence, quieting your chattering brain.

Then consider the employee’s background, job history, and how possible external factors may be contributing to their lower success.

Physically walk in their shoes.

If they work in a laboratory, warehouse or office, go there and walk the layout.

Perhaps you will discover one of the culprits to their poor performance.

During the conversation, practice active listening.

So often we consider listening to someone the act of waiting our turn to speak, when it should be an active process of hearing what the other person is saying.

Pay attention to the employee’s words, not your thoughts, do not interrupt them and when they are done speaking paraphrase back what they said to ensure you fully understand.

Begin the reply starting with: “So you are saying…” or “to clarify, you think…”

Perception checking is a powerful tool to help you understand others better, as opposed to jumping to a conclusion.

When you practice empathy through reflection and active listening, the employee will feel respected and more willing to communicate about the issue at hand.

Use role play and practice to prepare

Find a trusted peer or contact that is willing to role-play with you as you practice what may be said.

If you would prefer to keep this between you and the employee, practice it alone, but be sure to say the words out loud.

Don’t be afraid to stand in front of the mirror and practice what you need to say.

Start with outlining the facts, then lead into the outcome these facts have been making and next inquire with them for their perception of the situation.

Compile examples and lead with facts

Facts don’t lie.

Spend time prior to the meeting to create a list of facts that support the intention of meeting with them.

If you are discussing the need to put an employee on a performance improvement plan, have documented examples of areas where they need improvement.

Print out emails where they didn’t speak appropriately or missed deadlines.

Use this information as an insightful tool to help show them areas that can easily be improved.

If client complaints were filed against them, be sure you have them listed and ready for review.

Having this data prepared beforehand will make the conversation easier to support and back up if they become defensive or combative.

Get your mindset in a good place

Walk into the conversation with calm and positive energy.

Remember that this conversation doesn’t have to be adversarial.

In fact, it could be an opportunity to bond and better nurture your employee.

Studies have revealed that visualising actions is as powerful as actually doing them.

Give it a try and sit at your desk before the meeting to visualise how you want the conversation to go and what you want the outcome to be.

Take a few calming breaths before the meeting, and during the conversation do not raise your voice, even if they do.

As a leader, you hold the energy of the room.

If things continue to escalate on their end, you can always offer to complete the discussion at a later time when things have settled down.

Having to review someone’s performance or job future isn’t ideal, but it’s a true opportunity for a manager to step into leadership.

Leadership isn’t what happens when you have a corner desk or a high salary; it’s what happens in the uncomfortable conversations, the delivery of bad news and the growth that teams embody as a result.

*Ashley Stahl is a career coach, keynote speaker, podcast host and author. In a previous life she was award-winning counter-terrorism professional. She can be contacted at ashleystahl.com.

This article first appeared at Forbes.com.

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