Hard Conversations

Read time: 5 minutes

In this edition

They get easier to execute with experience, but they are never (and should never) be easy.

I’m talking about hard conversations, of course. Conversations where you are delivering news or feedback that is negative or difficult to share that will have a significant impact on a person’s employment.

Think performance improvement plans, employment termination, no budget for raises or promotions, or layoffs. Yuck.

It’s understandable why these conversations are hard. But the fact that they are hard should not be an excuse to avoid them. The chickens will inevitably come home to roost.

This week’s newsletter covers the challenges of having tough conversations. With thought and preparation, you can get through them.

Thanks as always for reading.

Hard Conversations


Personal Performance Flavor

These conversations involve discussing a team member’s failure to meet expectations, which can lead to warnings or even termination. They are uncomfortable but necessary for maintaining team performance and accountability.

Company Imposed Flavor

These conversations are about redundancies and layoffs, budget cuts affecting promotions or raises, and other organizational changes. They are driven by broader company decisions and can deeply affect morale.

Why Hard Conversations are Hard

In my own experience, and from coaching others to have hard conversations, I’ve come across three reasons why people struggle.

1. Hard conversations are power driven

Hard conversations are tough partly because of the inherent power dynamics. As a manager, you’re in a position of authority, which some people find uncomfortable, especially when delivering bad news. From the employee’s point of view, they are powerless to stop what’s happening.

2. Hard conversations are emotionally charged

Conveying failure or disappointment triggers physiological and neurological reactions in both parties, leading to feelings of vulnerability and defensiveness. When these feelings boil over (e.g., an employee who explodes in anger), the situation becomes even more threatening.

3. Hard conversations are uncommon

How often in your career might you have a hard conversation if you’re not in HR? They are infrequent, to say the least. Because they are unfamiliar territory, you might not know what to say or how to handle the situation effectively.

Preparing for Hard Conversations

Preparation is vital. There are a series of steps you should always undertake before having a hard conversation. These aren’t just to help you get through the situation. In cases where someone’s employment may be ending, they are for your security as well.

1. Ensure you clearly understand the situation and can easily summarize it

Before initiating a hard conversation, ensure you fully understand why the issue has arisen. Be prepared to explain this clearly and concisely to the other person.

2. Collect and review all documentation

Any time you are dealing with difficult situations, you should religiously document the actions that have been taken and why. This can be in the form of meeting notes, emails you have exchanged with others, or even notes to yourself. Documentation is crucial, especially for performance issues, as it becomes a verifiable history of events and prior conversations to support your decisions.

3. Plan what will happen after the hard discussion

Have a clear plan for what will happen after you have the conversation. If you are creating a performance improvement plan with an employee, that means setting expectations about what behavior will change and by when, and planning any future discussions. If a person’s employment is coming to an end, this includes any steps involving HR or IT, such as disabling systems or returning company equipment. Having a clear plan helps in managing the aftermath smoothly.

4. Create and practice a script

Yes, literally write a script. It should be very short, direct, and to the point. This ensures you cover all necessary points without rambling. Then practice it, literally, in front of a mirror or record it on your PC/phone. Nerves jangle even for the most experienced leader, so make sure you have a good flow. On the day of the meeting, bring bullet point notes to keep you on track.

5. Engage with HR

Consult your Human Resources team before the conversation for guidance and support. Their expertise can help steer the process and ensure it’s handled correctly.

Setting Up the Meeting

Don’t leave anything to chance. This includes even the process of setting up the meeting. Choose a day and time that gives you at least 30 minutes before and after the meeting to mentally prepare and debrief. You can either schedule a special meeting (sending the invite no more than 24 hours in advance) or use a pre-existing timeslot like a weekly 1-1.

If the conversation could end in termination, invite an HR representative (or an in-house lawyer) to be present. Their knowledge and experience will be helpful, and it will ensure the conversation remains on track.

Conducting the Meeting

The most nerve-wracking part of any hard conversation is the first couple of minutes. Do not be late. Be early. If you have invited a third party, make sure that person comes a few minutes early as well. The worst-case scenario is when you are late and the person with whom you’re having the hard conversation is already there and wondering why HR is also in attendance!

Opening the Conversation

No small talk. Start with a very short, very clear, very direct statement: “We are meeting today to talk about X. The situation has been Y. Because of this, we are now going to Z.” Then stop and let there be silence, no matter how uncomfortable it gets. You want to allow for a reaction.

Handling Reactions

In my experience, once I have finished speaking, the person will respond. However, if they haven’t, invite them to do so. (“Is there anything you would like to say?”)

One of three things will happen:

  • They will accept the situation more or less gracefully. While they may offer excuses or reasons for what happened, or not be in agreement, they will not freak out or get emotional.
  • They will not accept the situation gracefully and will freak out or get emotional, expressing either sadness (crying) or anger (yelling).
  • They will not say anything, in which case you move on.

Listen dispassionately; don’t respond with emotion. Your base response will be something along the lines of “Thank you for sharing that, but this is the decision.”

If the person becomes very emotional, acknowledge their feelings but reiterate the decision. (“I see you have strong feelings about this, however, this is the decision.”) If the emotions are so strong that it is proving impossible to continue, offer to pause the meeting and resume later in the day. (“It seems it is going to be difficult to continue at this point. Let’s come back together in an hour to continue the discussion.”)

Explaining Next Steps

Once the person has shared their thoughts (or not), detail what happens next. For example, if the person is placed on a performance improvement plan, explain what improvements need to be made and by when, and then set a follow-up meeting. If it’s an employment-ending event, the HR person should explain the off-boarding process.

Closing the Conversation

Ask if they have any questions. Provide answers if you can, or commit to getting back to them. Sum up any follow up actions. Then, end the conversation.

Post-Meeting Reflection

After the meeting, take time to reflect on the conversation. Do this in two ways. First, debrief the meeting with HR to share perspectives, gain support, and confirm any follow-ups. Then, reflect on your own feelings and observations. It’s natural to feel guilt or discomfort, even when you know it’s the right decision, and even if you’ve had many such conversations. This reflection helps in processing the experience and preparing for future conversations.

Finally, do not beat yourself up. This is part and parcel of the job. You won’t always have perfect situations. If that makes you reconsider the job, then have those thoughts, too. Use this reflection to contemplate how you avoid such situations in the future.

Keys to Success

To sum up, there are three keys to successfully navigating hard conversations:

  1. Preparation – Be mentally and practically prepared. Understanding the situation thoroughly, practice what you will say, and get all your ducks in a row.
  2. Courage – Be courageous and keep your message brief. This reduces the chances of getting sidetracked and ensures clarity.
  3. Reflection – Continuous reflection on these conversations and their causal situations will help you improve your approach, better handle such conversations, and perhaps even avoid their causal situations in the future.


Hard conversations are not easy, but they are an essential part of leadership. Handling them effectively requires preparation, a bit of courage, and some reflection. Leadership inherently involves making tough decisions and having tougher discussions, but with practice and the right approach, you can master this crucial skill.

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