How to Handle and Prepare for Difficult Conversations at Work

conversations, workplace, preparation

A few years back, I had talked myself into a bad situation at work. I was unhappy in a vital role, so I told my boss. They listened to me and moved me into a different role – a role I thought I would really like. Unfortunately, the economy was tough at the time and my new role wasn’t vital to the company. I wasn’t performing at my best because I didn’t feel like I was making a difference.

I saw the writing on the wall, but I failed to find a new job in time. Even though I wasn’t ready to move on, I was ready for the conversation that every employee dreads – the layoff with my manager and the HR director. I was ready for that conversation because I had rehearsed it in my head a dozen times. So when the time came, there was no acrimony – there were no hurt feelings. I knew that it was no one’s fault I was being downsized and laid off, at least, it was as least as much my fault as anyone’s.

My first piece of advice is obvious. It was stupid of me not to do everything in my power to find a new job. If you suspect you’re on the way out – find a new job first! But that’s not why I’m writing today. I want to share the skill I learned through this experience – rehearsal.

How to Handle and Prepare for Difficult Conversations at Work 

It’s never helpful to dwell on difficult experiences, but sometimes we know or suspect something unpleasant is going to happen. If a project is going down the tubes and everyone is unhappy about it, what are you going to say when your manager asks you about it? If a co-worker is unhappy and continually complains to you about his or her situation, how are you going to react? You have to rehearse these conversations in your head so you won’t blurt out something stupid when the time comes. Think about the following things before you rehearse the conversation:

1.)    What is your part in the situation?

Before you can talk honestly about the situation, you have to understand the part you played. What mistakes did you make? What did you say that you shouldn’t have said? Decide what those things are and own up to them right away. (Even better- if you’ve identified these things, make them right before someone asks you into their office.) You have to own the problem.

2.)    How are you going to speak the truth without burning bridges?

It’s a very appealing notion to speak your mind when the chips are down: “I never take crap from anyone.” You know what I call people who never take crap from anyone? Poor people. If you’re working with an impossible co-worker who is always blaming, or heaven forbid, a boss who mistreats you, it’s very important to speak truthfully and honestly about the situation, but it’s also important to be diplomatic. How are you going to discuss the situation truthfully without assigning blame? It sounds impossible, but with enough practice beforehand, you can do it.

3.)    How are you going to solve the problem?

Never go into an unpleasant meeting without a plan for how you’re going to come out of it. Be ready to propose a solution, apologize, or accept a reprimand, or worse, a layoff, graciously. Getting angry and storming out of a meeting only reduces your influence and confirms any negative beliefs about you.

Prepare Yourself for Difficult Conversations No Matter the Situation

Once you’ve thought about these things, it’s time to rehearse the difficult conversation. First, here’s some hard advice nobody wants: Even if you work for the greatest company in the world, you love your boss, and your co-workers like you, you need to pay attention to the way the winds are blowing. If the company has fallen on hard times, profits are down, consultants are swarming the office, executives are shuffling, or management is behaving strangely, you MUST rehearse a layoff meeting. Picture yourself going into the room, seeing an HR rep and your manager, and hearing what you never want to hear. What are you going to say? Be ready to ask about severance pay, to ask for references, and for professional outplacement services. And just as important: You’re going to feel stressed, angry, and sad. Be prepared for these feelings and be ready to depart graciously.

But even if you never get laid off or impacting by downsizing, you need to be ready for other difficult conversations. What are you going to say to a difficult co-worker who is always blaming? What about when your boss calls you on the carpet for a mistake that wasn’t your fault? (Or one that was your fault?) What about a meeting to discuss a project that’s going down the toilet? Finally, how are you going to act when you get blindsided with a difficult situation that you never saw coming?

For all of these situations, you need to literally close your eyes and walk through the conversation. What is your co-worker going to say? How are you going to respond? These difficult situations can make or break your career. If you want to be a calm, cool, and collected professional who your coworkers respect, be ready. Difficult conversations will come – but they don’t have to come as a surprise. Rehearse them in your head beforehand. Your career will be better for it.

Dan Lovejoy

Dan Lovejoy is a User Interface & Experience Architect at OG&E and a self-admitted adorable curmudgeon. The opinions here are his own and not his employer — in case you were wondering.

Reader Interactions


  1. Pam Constantino says

    Hi Pam,
    I thought you might like to read this article. Smart Briefs is an excellent resource for information on many topics. It is free to subscribe. I find it very useful as they find excellent articles on the topics that you sign up for them to reach.

    If the sign up isn’t included in this email and you’re interested, go to and pick out the topics that you want them to send you.


  2. Mary Ann Schell says

    I agree with this article 100%. If you are aware and see the larger picture of how your job role fits within the company you can be prepared to either move within if that is your goal or find another position outside of the company. Either way, when you are prepared a difficult conversation is not horribly difficult. Take care of your physical self as well, as this will keep your emotions (male or female) professional.



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