Guide for Difficult Conversations: 4 Reasons to Embrace the Awkward
In 2024, Chantilly Mediation and Facilitation began holding Executive Roundtable discussions exclusively for nonprofit leaders. It was through this program that Gina met Roopal Mehta Sarah, Executive Director of the English Empowerment Center. After experiencing a shortened form of our signature training Curiosity, Conflict, Communication, Roopal requested more information about handling specific scenarios. This post is the third and final installment, and it takes a big of a different approach than parts 1 and 2.
I remember the moment clearly, despite it happening over a decade ago.
I was leaning against a grey cubicle desk (I hated those grey cubes), chatting with my intern - a young and very smart person who worked hard and asked questions. She was excellent. We were working at Planned Parenthood affiliate, and a portion of her internship hours included talking with patients in the waiting room about our legislative advocacy work.
I remember the hesitance in her voice as she struggled to find the right words, just between her and me, to state what was bothering her.
“It’s just… It’s a bit… awkward? Do you have any advice for how to make it less… awkward?”
I think I remember this moment because, at first, I had no idea what to say. Yes!! It is awkward! Is what I was thinking. There was definitely a moment of silence before I responded, and it was one of those times where I didn’t think through very much what came out of my mouth - I just had to be honest.
(TBH with you, reader, right now - while I am willing to swear that the above questions from my intern are precisely how she stated them, I am not 100% certain this 👇🏻 is precisely the wording I used…)
“It is awkward, I know. We do it anyway because it’s important. You just, like, have to let it be awkward, do you know what I mean?”
She replied, “So you’re telling me to embrace the awkward?”
“Yes. Embrace the awkward.”
Embracing the awkward, I’ve since decided, is absolutely excellent advice, for many situations in life.
When I had to tell a loved one that I didn’t want their racist partner around my toddler, for example - didn’t want to have that conversation, felt awkward, it was important, did it anyway.
When I had to tell an intern (a different intern) that they shouldn’t show up to our office job looking unkempt - didn’t want to do it, felt awkward, did it anyway.
When I did exactly what the intern in the above story did - talking to patients waiting to see a medical professional about legislative advocacy, sometimes not directly related to why they were there, like signatures to get a sex ed program into schools - I didn’t really want to do this either, despite it being a program I had created. An award-winning program, in fact. It was awkward! And important. So I did it anyway.
Embrace the awkward.
Let’s be real: In the workplace, we can all find ourselves in some terribly awkward situations.
New mom returns to work and is leaking milk through her shirt.
Your coworker says something racist, and seems genuinely unaware they’ve said anything wrong.
Someone else takes credit for your work, and when you confront them they seem to think it was their idea first, really.
You overhear a volunteer giving completely false information to guests at an event, and you have to find a way to gently correct the volunteer and provide accurate info to the guests.
In all of these cases, very few of us would ever actually WANT to be the person speaking up to tell someone the truth. Yet, in all of these cases, doing so improves the situation - whether for you speaking up, for the person you’re speaking to, or for others who work with you or are your clients.
No, Really: Embrace the Awkward… Difficult Management Conversations
If you’re leading people, it’s likely one of the reasons you avoid difficult conversations is because they feel so uncomfortable - so very awkward!
Yet speaking up when someone is missing the mark is just as important as speaking up when someone is doing amazing, wonderful, really great things.
It’s just as important of letting the new mom know she needs to change her shirt.
It’s just as important as telling a coworker that what they’ve just said is offensive.
It’s just as important as getting credit for your own work.
It’s just as important as correcting falsehoods.
It’s as important - and as kind - and as vital - as any other management conversation you could have. One-on-ones? Promotion potential? Disciplinary actions? On-the-spot bonuses? Onboarding?
Some of these may feel like the difficult, awkward conversations I’ve been talking about, and some may not. But all of them are the responsibility of the people manager. It doesn’t matter if you’re a first-line manager, a mid-manager, or the Executive Director who only oversees a handful of senior staff who in turn oversee others who oversee others.
So here, finally, are the …
4 Reasons to Embrace the Awkward
There is a greater good. (Example: My story with the intern. We had a larger advocacy goal and it was equitable to include patients as a piece of our advocacy network, rather than only work with people who were not and possibly had never been patients.)
It’s the kind thing to do. (Example: The new mom who needs to change her shirt… and possibly go pump.)
It’s the right thing to do. (Examples: Speaking up when someone makes a racist comment. Telling a supervisee they are not hitting the mark if they want a raise.)
It will make it easier next time.
Yes, really! The more you practice embracing the awkward, the easier it will be to speak up in uncomfortable situations. Many of us have never been expected to correct others, or point out something uncomfortable. It’s a difficult position to be in. And yet, it’s important to - yes - embrace the awkward, and speak up.
Say it with me now: Embrace the Awkward. Add it to your mindset tools to prepare for difficult conversations.
Still Feeling Uncertain?
That’s the point: Embrace the uncertainty - embrace the awkward.
Also: sometimes it’s helpful to acknowledge it. Here are some phrases you can use:
I feel a bit awkward about this, but I have to say something.
I wish I didn’t need to address this, but I know it’ll help you to have this information in the long run.
This is awkward for us both, but you should be aware…
Try them out in your next awkward conversation.