Tips for Uncomfortable Conversations

How To Face Difficult Conversations

In my years of management and HR, I’ve had my fair share of uncomfortable conversations.  From telling an employee they are showing their nipples to telling my boss they’re under investigation for physical assault – there’s never a lack of them.  Each conversation creates butterflies, demands preparation, and I’ve never been thrilled to do any of them.  They are a necessity.  An uncomfortable necessity.

Many managers tend to want to “hide things under the rug.” If it doesn’t get talked about, it isn’t a problem, right?  I can’t think of a stupider way to face any difficult situation than to think that “ostriching” is the best course of action.  Managers dilute themselves into thinking  “it’s not that big of a deal” or “it will work itself out” and I can tell you that it rarely ever does.

Up front one-on-one communication always trumps any type of insinuations,  innuendos, or distance notifications (e-mails, memos, etc.)  When there’s bad news to be given, or even just uncomfortable news, there’s no better way to tackle it than to sit down, knee to knee, eye to eye to a person and lay it out to them in a respectful and caring manner.

That being said, here’s some…

Tips for Uncomfortable Conversations 

The Golden Rule.  No matter how you feel about this person personally, maybe they’re The Guffaw Laughter Lady or The Evil Retractable Pen Clicker Dude, don’t be rude.  Don’t be mean. Treat them as you would want to be treated.  Practice some empathy and ask yourself, “If I were in their shoes, how would I want this information delivered?”

Preparation.  I rarely “wing” serious or semi-serious conversations.  Whether they’re planned out in my head or outlined on some notes.  Going into an uncomfortable conversation can be nerve racking and confusing, bring a list of topics to discuss so you don’t get off topic or say something you didn’t mean to say.

Be Specific. Pull out surveillance video of them taking the last of the coffee and not refilling, reference the emails that show they have issues sounding “abrupt” – when you can, site specific instances.  Avoid generalizations, avoid sugar-coating, and especially avoid diplomatic jargon that gets confusing and garbled.

Don’t cave. Along the same lines of specificity, don’t allow yourself to shrug it off when things get really uncomfortable.  There’s a tendency to make light of things when it gets more uncomfortable.  While that sexist cat meme was funny – it still needs to be addressed.  There’s always the urge to hurry things up and make light of it all, resist the temptation.  Stick to the reality of the issue.

Have a goal.  In combination with preparing for the conversation, there should be a reason or specific outcome you’re looking for from this conversation.  Otherwise, why are you having it?  If  the employee is performing above standards but comes in late by 15 minutes every morning  ask yourself is it really necessary to talk about this?  Once you’ve identified the goal or outcome needed, state it.  The traditional method is “Going forward, I need you to ______ from now on, agreed?”

Once the conversation winds down be sure to ask them for their thoughts/opinions/reactions and truly LISTEN. At this point if they have any needs (within reason) to help towards the wanted outcome, see what you can do. Thank them for their time and be sincere about it.  Keep in mind that they were just as uncomfortable as you. Then, follow up.  If you promised to “look into something” or “we can talk about this again in a month” – mark it on your calendar and make it a point to follow through.  Don’t dump the bad news and leave them hanging. And lastly, be nice to your HR department – document it. You never know when the “Please stop calling everyone ‘boobie'” conversation will turn into the “We’ve had a complaint” conversation. True story.

Most uncomfortable conversation…?

What’s your experience with uncomfortable conversations? Have you ever had to deliver not so pleasing news to a co-worker?

Posted in

Christine Assaf

Christine Assaf is an experienced HR Professional with a passion for Social Media. Blogging for over three years Christine started, a professional blog, that talks about all these HR related – both from the manager and employee perspective. You will often find her on twitter exchanging HR wisdom from "behind the scenes." A conference speaking veteran, Christine enjoys helping job seekers with skills assessment, resume review, and mock interviews and coaching executives on best strategies. She is also an active participant in Toastmasters, plays Dungeons & Dragons, loves football and running. Christine’s wit and charm light up the “internet” with the perfect combo of HR knowledge and snark. You can connect with Christine on LinkedIn.

Reader Interactions


  1. Jason says

    By far – the 3 WORST discussions I have had and all were in Call Center Management:

    1) The male that was in an outbound call center was dialing 900 numbers and pleasuring himself under his desk and
    2) the male who was leaving on vacation – went to the bathroom and clipped off some of his pubic hair to give to a female colleague…. he was afraid she would “miss him” so wanted to leave something behind to remind her….
    3) the female that had split personality disorder. Some days she would come in her wheel chair van and other days she would ride her bike. One day when it was raining she rode her bike – and in the middle of the call center floor decided she was cold and needed to change her shirt…. and did so right there in front of everyone.

    2 of 3 ended in termination….

  2. Nick says

    Disagree with one point: don’t treat them as you would want to be treated treat them as they would want to be treated

  3. Marissa@Equibbly says

    Christine, your insights make a lot of sense. I guess, the most uncomfortable conversation for me is how to tell your colleague that you don’t really think his/her idea is good ( or how bad it really is ). People do get offended easily when you tell them their suggestions are bad – like it’s some kind of a personal attack. So, you have to find ways to make sure that you are pointing at the proposal; not the person. To deal, we have an internal dispute resolution process aimed to make the workplace.. a better, happier, conflict-free place. The last thing you want is for someone to post a rant that goes viral on the Web. Yes, it can happen and we’ve seen it in the news a couple of times. Here’s where I will say that ‘prevention is better than a cure’. Cheers!

  4. Christine Assaf says

    I whole heartily agree with the “prevention is better than a cure” theory. Being open and honest always trumps subversion or avoidance. I think if a relationship has been developed between the colleagues it also makes it much easier to talk about ideas/opinions. When there’s not a solid foundation of trust and camaraderie, it can get misconstrued.

  5. Demetri Ross says

    What about situations / conversations that are thrust upon you? People giving you too much information or something you just don’t want to hear because it makes you uncomfortable. Trying to avoid colleagues to keep from engaging them personally is not realistic. You don’t want to be rude because you have to work with them but you also don’t want to be drawn in.


Pin It on Pinterest