Having Awkward Conversations at Work

I remember when I first started working in a professional office environment; I could hardly stand having awkward conversations. Even asking for things was awkward for me. Putting myself out there enough to ask my boss whether I could have the last hour of the day off (unpaid!) for a dentist appointment could give me cold sweats. Every time I had to own up to a mistake or bring an issue to somebody, I would have an internal meltdown.

I’ve become much better at having these conversations, mainly because of my job. 80% of the conversations I have as part of my position are awkward conversations, and I’m constantly having to tell people bad news.



I had one colleague who had a knack for articulating bad news and having awkward, uncomfortable situations with people in a positive and collected way. I noticed a stark contrast between my awkward, jolted speeches filled with “like”, and “um”, and her smooth, thoughtful way of speaking.

I approached her one day to hopefully glean some of her wisdom, but she had few answers for me. Rarely will a person be able to tell you how they do something well. It’s then up to you to watch them in action.

First, I reflected on these conversations after I’d had them myself. I’d consider what made me feel awkward about it; was it the situation or how the person was taking it? If it was how the person was taking it, were they taking it poorly because I wasn’t delivering the message well? Did I say a word repeatedly? Did I feel that I got the message across? Did I ask the questions that would deliver the answers I needed?

After I did this exercise a few times, I set out to observe my colleague when she had these types of conversations. How did her mannerisms and speaking style differ from mine? What did I really like that she did, compared to what I was doing? How could I incorporate this without giving up my own authenticity?


One thing I noticed almost immediately after having gone through this exercise was that when she – and other people I’d observed speaking well – spoke, she didn’t use filler words. If she got to a point in the conversation when she’d lose her words, or need to come up with an answer or a though on the spot, she didn’t try to fill silences. She just thought.

This sounds intuitive, but it’s not used as often as you might think. Many of us feel the need to fill those silences with words, whether or not they are contributing to the conversation. The words “just”, “like”, and “um/uh/hmm” do not contribute to the conversation. They are fillers. It’s difficult, but try to cut these out by filling those moments with silence and thought. This will also help you say what you want to say better; nobody can think properly when they are talking.


Going into a conversation that you believe to be difficult unprepared can be detrimental. You don’t have to sound rehearsed, but reviewing what you need to say and what the purpose of the conversation is before you go into it will make it go much more smoothly. Consider what action you hope to get from the conversation; how you want to sound, what questions you want to ask, and what the relationship between yourself and the other person is like. You also should consider their personality and how they will react to different ways of delivering your message.

You likely won’t sound rehearsed anyway, because conversations can go any number of ways depend on the reaction of the other party, however, running through it a few times as if you were speaking to the person will really help.


If you feel the need to have a conversation in the heat of a moment, try to remove yourself from the situation and come back to it the next day. Even if the conversation is one that you must have, it will go over more smoothly when you’ve cooled down a bit and emotions aren’t running high on the other individual’s part, as well.


Being successful in these types of situations can be a hit or miss. As you continue to do them, you'll get more comfortable with them and they'll come easier.



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10 thoughts on “Having Awkward Conversations at Work

  1. Ooh, good tips. Learning to be comfortable with silence (and thus avoiding the urge to fill the void) is a really powerful thing.

  2. This is great advice. I took a class in University called "Management Skills Development" which really should have been called "How to talk to people". It basically centred around all of this stuff, how to have productive problem solving conversations at work in a way that leaves everyone feeling positive about the interaction. We did a lot of role playing and I've found it to be extremely beneficial.

    Covering tough topics at work can suck, but with a little deliberate preparation, it doesn't have to be so bad!

  3. I find its helpful to be forthright with bad news rather than trying to sugar coat it. These are very good life skills that everybody should have.

  4. In the therapy world we call what you described in "think" as "sitting with silence". If things feel awkward or weird, sit with it for a minute. Don't try to fill in the space to avoid those awkward feelings. It takes a lot of practice, but once you get good you can use the silence to think or reflect, or make the other person speak (they will feel weird and fill in the silence). Good tips.

  5. I used to have awkward conversations with my boss when I was working at college. I eventually learned through time how to deal with it. I usually organize first in my mind what and how am I going to say what I have to say before I approach my boss.

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  7. Tahnya Kristina

    Oh I am so over chit chatting with people at my work. Being social at work only gets us in trouble and hurts our career. If you don't talk with anyone, just polietly smile, there will be no awkward conversations. 🙂 Just saying.

  8. Love these tips! As a manager or leader in an org, it's so important to be able to deliver all kinds of news with tact and grace. Thanks for the tips!

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