Hint: Because You’re Trying Too Hard

Earlier this week I taught a course called “Is Management for Me.”

The class was full of about 35 adults who work in various parts of the Ontario Government. There were people who were a couple of years from retiring, and there were people who had only been there a year or two, and they all had one thing in common:

They wanted to know if they should even consider applying for a management job.

So I did my thing, and we talked about what it means to be a manager, a leader, and a leader-manager.

  • We talked about how transitioning to management means learning to let go of things you do now (even if you love doing them).
  • We talked about delegation, strategic thinking, transformation and process improvement, and coaching.
  • We talked about the good stuff: having impacts on people and teams, influencing direction, having more flexibility in approaches to work, and the feeling of achievement.
  • We talked about the hard stuff: longer hours, more complex expectations, the importance of optics, dealing with conflict and having difficult conversations.

That last one, “having difficult conversations,” was a doozy.

When I let people know that managers have to chat with their teams about their work AND about things like body odour, emotional outbursts, salaries, and a host of other awkward topics, the mood in the room changed.

At the end of the course I asked everyone to write their biggest fear on a post-it note, and then crumple it and throw it across the room.

Then everyone picked up a note that someone else threw, and read it out loud.

The number one fear of becoming a manager was that of having awkward conversations and “doing it wrong.”


How Do You Fail At Awkward Conversations?

Well the biggest way to fail is to not do it at all.

You have to tell someone that their interrupting and loud voice is impacting the team? You’d rather die than hurt someone’s feelings?

Well sure then, just don’t do it and everyone else will just have to get used to it.

Wrong.

Do it. Let the person know. Make the team function better. Help the person grow.

The next biggest way to fail is more like letting yourself and the person down by being half-assed about the whole thing.

You have to tell someone they have body odour, and again, you’d really rather not, so you leave a bar of soap on their desk.

Or you just call them into your office and say, “Dude, you stink.”

Or you have a group meeting about body odour and personal hygiene, and while you don’t single anyone out, that person (and everyone else) KNOWS it’s about them.

Or you call them into your office and have a roundabout conversation with little innuendos and never really say anything but try to but you can’t so you laugh about how people are so sensitive to perfume in the office and why is smell so hard for people and have you ever had to deal with a person with body odour I know it’s hard thank God we don’t have that problem here ok have a great day good talk.

Here’s Why Awkward Conversations Are So Hard

You’re trying too hard.

  • You’re trying to avoid the issue altogether.
  • You’re trying to avoid hurting feelings.

Guess what? The issue isn’t going to go away. And feelings are going to be hurt. And the conversation is going to be hard. And you’re going to blush or stammer or whatever you do when you’re nervous.


How To Make This Whole Thing Better

Two things you have to do:

First of all, be honest. 

You know how when you’re on a first date and you’re all nervous and the other person is all nervous and then finally someone says, “I’m so nervous” and the other person says “Me too!” and then everything settles down?

This is the same thing.

Open your conversation by letting the other person know it’s going to be difficult, or awkward, or embarrassing. Tell them that you’re nervous but this is important so you’re jumping in. Let them breathe a minute and realize the import of what you’re about to say.

It can sound like this:

“Hey Sam, thanks for coming.”

Sam sits down.

“Ok so I have something really awkward to talk about with you. It’s one of those conversations where we are both going to feel weird, so if my face gets red, that’s why.”

Sam looks at you with new intensity, feeling a little weird, but not afraid. He says, “okaaaay…” and waits for you to continue.

You take a deep breath and your face starts to get red.

“I’m just going to jump in then. I asked you to come in to talk about a hygeine issue. You have a body odour that is starting to impact the team, and I wondered if you were aware of it.”

That’s it. You said it. You stop. He turns red. You are already red. But now that it’s out there, you both can start to calm down and discuss it.

Starting out by admitting that it’s going to be hard or awkward or whatever, is the single biggest thing you can do to make it go as well as can be expected AND to preserve the other person’s dignity as well as you can.

The second thing you need to do is practice.

This technique can (and should) be used everywhere because it’s respectful, open, and honest. Start trying it now when the opportunity presents itself.

Hey neighbour, I have to talk to you about something a little awkward and I feel weird about it, but here goes…

Hey friend, I need to say something that will be a little awkward and I’m already nervous, but here goes…

So practice now.

And, practice before the actual event. Think about what you’re going to say and how that person may respond. What will you say to those remarks? What if the person with body odour says:

  • Yes I’m aware. I’m so sorry, I didn’t know it was that bad. I am taking new medication.
  • Yes I’m aware, but that’s who I am and I don’t believe in deodorant. People need to just deal.
  • No I wasn’t aware. OMG thank you for telling me. I am so embarrassed how will I go out there and face the team?

You need to plan for these responses (and others), and if you don’t know what you will say, then talk to an expert.

If you have an HR team, talk to them! What resources does the organization have to help people with medical issues? What are you able to say to people who refuse to address odours? What can you do to coach people who are embarrassed?


By being honest and prepared you can be an amazing leader-manager, and make your team feel great about coming to work each day.

Just stop trying so hard, and let people know the real you and how you’re feeling. It will take you far.

CLICK HERE to receive my free Coaching Conversations worksheet! This amazing tool includes instructions and a two-page worksheet to help you plan your next important conversation.

And follow the publication “At The Whiteboard” for more tips on how to “Crush It At Work!!!”

Ruth Henderson is co-owner of Whiteboard Consulting, and focuses on ways to make things better through a wide spectrum of business activities including sales, marketing, customer service, and financial operations, although her specialties are Coaching, Training, and Business Process Improvement. She’s a podcaster, blogger, process nerd, and loves to call Toronto her home.Find out more about her atwhiteboardconsulting.ca.
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Ruth Henderson is co-owner of Whiteboard Consulting, and focuses on ways to make things better through a wide spectrum of business activities including sales, marketing, customer service, and financial operations, although her specialties are Coaching, Training, and Business Process Improvement. She’s a podcaster, blogger, process nerd, and loves to call Toronto her home.Find out more about her atwhiteboardconsulting.ca.

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