A ‘Tough Messages’ To-Do List

Eight tips for difficult conversations.

Effective leaders are expected to deliver difficult messages with just the right mix of empathy, firmness, and professionalism. It isn’t in the job description, but it is definitely part of the job.

And at times these conversations can be as stressful and draining for the person delivering the message as they are for the individual hearing it. Dealing with mistakes, disappointment, and negative feedback is rarely easy, and many executives point to these exchanges as one of their most demanding responsibilities.

So how can we organise for these inevitable discussions? What are the best practices to follow when a difficult conversation is on the horizon?

While there is no single formula for success, the suggestions that follow will help you communicate authentically and professionally when the time comes to deliver that tough message.

Prepare thoroughly. Don’t hold these conversations until you have done your preparation. You owe it to the other person and to yourself, so invest time and thought in getting ready. One of the best ways to reduce stress and increase the odds of a fruitful conversation is to prepare in a consistent way, so you will know you have ‘done your homework’. You will be prepared, and more to the point, you will feel prepared.

Be timely. This is difficult for many people given the inclination to put off an awkward or painful conversation. Don’t procrastinate, especially if you need to deliver negative feedback or disappointing news. Delay will make it more stressful for you and for the recipient, so make prompt feedback a habit.

Focus on the issue or behaviour, not on the person. This is crucial: tough conversations can easily go awry if people feel they are being criticised at a personal level. Talk about the work or the behaviour, not the individual. Be fact-based and objective, not emotional or judgmental. Concentrate on one issue so the person doesn’t feel overwhelmed. Try to empathise: if you were receiving this message, how would you want it to be delivered?

Allow time to recover. This is a personal kindness. Schedule tough conversations so people have time to absorb the impact and recover their poise before facing colleagues or customers again. You as the ‘leader’ may prefer to deliver a tough message early in the day to get it done, but the person receiving that news will almost certainly prefer to hear it at the end of the day or perhaps just before lunch, allowing time to recover his or her composure. Try to anticipate what will be best for the person receiving the message.

Logistics of the conversation. Think carefully about the setting and circumstances. There are many variables to consider: Where you will meet to ensure privacy and discretion? You might want to avoid speaking in the canteen or in a glass-walled meeting room. How much time will you allot for the conversation? What steps should you take to avoid interruptions? Have you turned off your phone? These details matter, and can be managed if you anticipate them.

At a more formal level, should there be another person present for moral support, documentation, or perhaps as a legal witness? If so, how will this be organised and explained? What seating arrangements will you have, and what message will those convey? For example, sitting behind a desk while delivering feedback sends a different message than sitting together at a table.

There are many such details that can be anticipated and handled in a thoughtful way. This demonstrates professionalism and will help a difficult conversation proceed more smoothly.

Non-verbal communication. Pay attention to body language and non-verbal expression. Only ten percent of our communication is in the words we speak: the remaining 90 percent or so of our ‘message’ is non-verbal. So be sensitive to the other person’s body language and non-verbal communication as well as to your own.

Possible follow-up or support. Think about questions they may ask and requests they could make. Will they ask for documentation or data? Might they request coaching or remedial training? Will they ask for your advice? Anticipate and have your answers ready.

Be authentic. At the end of the day this is going to be a challenging conversation for both of you. Be your authentic self, conveying firmness and empathy in a way that demonstrates professionalism and your respect for the dignity of the other person.

Tough conversations are never easy — hence the adjective — but these suggestions will help you be more comfortable and effective regardless of the circumstances. This is an unavoidable aspect of our leadership role, so we need to perform it as well as we can. Remember: empathy, firmness, and professionalism.

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