having successful difficult conversations means taking the time to listen and to be vulnerable. And that's freaking scary.

The scary thing that makes a good workplace great

A little while back I wrote about the one thing that can make a good workplace great, the tolerance for taking risks and making mistakes.

If I were to pick another Big Scary Audacious Goal (which is a more unfortunate acronym than Big Hairy Audacious Goal..?), it would be the ability to have difficult conversations. Even more than tolerating mistakes, this is by far the most difficult skill I’ve had to work on in my career, and I’m not even close to perfection.

having successful difficult conversations means taking the time to listen and to be vulnerable. And that's freaking scary. Screwing up the courage to face a difficult situation head-on by having a tough conversation is something that could make any relationship go either way: it can lead to working better and becoming closer to the other person, or it could lead to a separation (if you’re lucky, a separation that leaves both people with positive feelings towards each other).

Having successful difficult conversations means taking the time to listen, and to be vulnerable.

And that’s freaking scary.

In fact, both these shifts that can change a workplace culture into a great one have that one thing in common: a willingness to show vulnerability.

I believe the more people talk about those difficult conversations they’ve had, the more acceptable it will be to have more of them. And I believe it’s the role of communication professionals to encourage more intentional, face-to-face communication skills among those we advise. The most useful professional development event I attended last spring was from IABC-BC — Speak Up: Important Conversations. All the speakers were amazing, but Tracey Wimperly’s talk really resonated with me:

“We do business with people, not entities…Conversation between people is where the magic happens … We are coaches and convenors of conscious interpersonal communications … Talking points are great for content, but do our leaders know how to really listen? Do they demonstrate empathy? The soft skills are really the hard stuff … Are our leaders comfortable with the soft skills?” – Tracey Wimperly

People, particularly those in leadership positions, need to signal loud and clear that they are open to having the difficult conversations, by their words and their actions. They need to be vulnerable in order to encourage their employees to feel supported enough to take risks and contribute the whole of their talents and skills.

I was reminded of that again when I listened to Brett Gajda’s podcast, Where There’s Smoke; the episode Be Seen (Vulnerability), with Bobby Umar. Brett practices what he preaches – my partner and I saw him speak at an event the other night, and I envy the people who get to work with him. In the Be Seen episode he gives an example that is so raw and compelling, I choked up thinking of similar examples from my own career.

Here’s one leader who also certainly fits the bill: Dan Pontrefact (you lucky Telus employees, having him on your leadership team!), who has embraced the Working Out Loud movement (Yay!) and wrote a pretty raw piece on why his next book is postponed.

In fact, if I’m ever asked again in an interview what I consider my biggest weakness, I’d probably have to be honest and say: “I find it extraordinarily stressful to have the difficult conversations that must sometimes happen in a professional situation. And I’m working hard on getting better at it, because if you can have difficult conversations where the other person feels valued and respected, even if you have to part ways in the end, you have a stronger relationship because of it.”

Here’s Tracey’s entire talk. It’s well worth eight minutes of your time, especially if you are, like me, a communications professional:

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