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What to do after a difficult work conversation

What to do after a difficult work conversation
Marie Ryan

Marie Ryan


Congratulations for having the difficult conversation at work that you’ve been putting off. Regardless of the outcome, it’s over, you did it. For it to stick, your next steps are important. If there’s no follow up, it may as well not have happened. Here’s what to do after a difficult conversation. 


Praise yourself

It’s not easy having difficult conversations, especially if you’re new to it. Take a few minutes to praise yourself for rising to the challenge. 

Take a break

If you read the earlier articles, you scheduled time for yourself to wind down after the meeting. Go for a walk, get a coffee, surf the web or meditate. 

This is your chance to process your thoughts and get back to normal. You don’t want people to see you looking flustered or stressed, so leave the office. If asked, you can say you took an early lunch or decided to try the new coffee shop.

Provided you are cool, calm and collected when you get back to the office, people won’t notice a difference. 

Phone a friend

Speak to someone outside of the company. You can talk about the conversation you just had, or something completely different. They are outside the company, they won’t repeat anything you said to colleagues. It’s an opportunity to get it out before you go back into the office. You could speak to your spouse, a friend, or a family member. Anyone you’ve chosen in advance and let them know to expect your call. 

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Reflect and learn

This is the part you don’t want to do but will get the most out of. Later in the evening, when you’re home, reflect on the conversation. By examining it and being honest, you’ll improve your performance for the next time and the next time. Here are good questions to ask:

  • How did it go overall?
  • What went well in the meeting?
  • What didn’t go well?
  • What could you have done better?
  • How will you use that to do better next time?
  • What questions should you have asked?
  • What was the outcome?
  • Did you get the outcome you expected?
  • Why or why not?
  • How did the person react?
  • Why did they react like that?
  • How will you do better next time?
  • What did you learn from this experience?

You don’t want to do this. I know you don’t want to do this. If you do it anyway, it will stand to you the next time you have a similar experience. 

Follow up


If there’s anyone you need to speak to in the office, speak to them and tell them what happened. 

For everyone else, keep it private. There are always rubberneckers who’ll ask “What was that about?” Have a stock answer prepared. E.g. “Oh nothing, We were discussing holiday leave or training opportunities.” If you repeat it enough, they will believe you. If they don’t, who cares?


On the day

I suggest keeping it casual after the meeting. Send a short email such as “Thanks for the meeting earlier. I’ll send you a follow-up email tomorrow.”

The email

The follow-up email is important, so take your time writing it. 

Thank them for their time. Mention anything positive that they said in the meeting. If they didn’t say anything positive, then thank them for showing up!

Give a synopsis of the meeting along with action items, next steps and anything else you need to include. Write the email but don’t send it until the next day. When you’ve had time to reflect and a night’s sleep, you might have a different perspective the following day. 

It gives the employee the chance to reflect on it too. They will be less defensive about the email the following day. 

Before you send it, ask someone else to read it. It could be a trusted colleague that knew about the meeting or the person you spoke to after the meeting. This is important as they will be objective. They will spot any veiled criticisms or jabs against the employee, intended or not. 

Discuss next steps in the email

If there are action items how will they be evaluated? Do you need a follow-up meeting?

Will the follow-up be in their next monthly or performance review?

Who will be monitoring them, you, their line manager?

Make it clear in the email. 

How can they contact you?

The nature of the conversation, in severity or complexity, affects the method of communication after. If it’s serious, email only. If it’s less serious, let them know they can drop by your desk or send a chat or email. 

Hold yourself accountable

If you said you’d do anything for them, do it. You need to hold yourself accountable before you can expect it from anyone else. If you promised new equipment, organise it. Did you discuss training options? Make sure it happens. 

Do you need to take it further?

If the conversation was unsuccessful, what are the next steps? Do you need a mediator or a senior manager? Make it clear in the email. 

Other sources

Is there anyone else the employee can speak to? If the issue is one that can be solved by someone else in the company, offer an introduction. 

E.g. “Keith is great at Excel. If you like I could organise a training session.”


Follow these steps after a difficult conversation, to ensure a successful outcome, build better relationships and maintain your reputation. 

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