Nice Work: Make it awkward—you’ll thank yourself later

Hey there,

Spring is almost here and we are ready to emerge from hibernation with our first big, public event of the year! It’s on April 10, and we’re calling it Make it awkward: Why saying hard things matters at work (and how to actually do it). A panel of product and design leaders from the Active Voice community will share how they learned to rock the boat without falling overboard—and how you can learn to do it too.

We’ve got all the event details below. But before I tell you about those, I want to share why this topic means so much to me.

I’ve always had a spidey-sense for disharmony. And friends, it’s intense.

I don’t just notice tension—I can feel it. Like a lump in my throat. Or a brief loss of air. When I catch a whiff, my body tenses like a taut rubber band—ready to jump in if and when the shit hits the fan. It’s like being one of those people who can smell spoiled milk days before the rest of us. Only my spoiled milk is bad vibes.

This is now one of my leadership superpowers—but first I had to learn how to wield it.

Early in my career, I considered it an invitation to rid the world of any kind of conflict. After all, shouldn’t the first person to smell smoke scream fire? I’d get the tingle and go into reaction mode. Fix it. Stop it. Distract it. Run away from it. And it wasn’t just to protect myself—it was to protect those around me who seemed to not be reading the room.

I was really, really proactive about diffusing friction. But because my definition of conflict essentially was “any interaction that created feelings other than joy,” I was putting in a lot of overtime. I thought it was worth the trouble… until it blew up in my face.

Here’s the situation I faced in my first official leadership role: I was given a team in a state of disarray, at least as far as my bosses were concerned. People aren’t stepping up. They’re missing the big picture. They’re too immature. They’re too unprofessional. Basically, my bosses hoped I would steer these folks out of the org so we could replace them with a “better” group.

As for my team? They had a lot of strong feelings about my bosses, like: I feel completely unappreciated. I don’t understand this direction at all. What a bunch of hypocrites—they should all step down.

Being in the middle was not a fun place. But I figured I could just be extra proactive with my fixing. I’d talk to one side, hear their concerns, validate those concerns, and try to explain what the other group was feeling. Then repeat with the other side.

I was playing conflict whack-a-mole, and it was exhausting. But I really thought I was doing the right thing. That as a leader, my job was to make everyone happy, squash disagreements, and help people understand each other. And that if I just worked harder at it, all our problems would be solved and we could get back to doing the work we all cared about.

But it didn’t work.

These conversations lowered the temperature a bit, but only temporarily. Embers still smoldered under that fragile peace, so it didn’t take much to reignite the tensions. Like one of the bosses catching a teammate make a mistake. Or a teammate feeling snubbed by a boss at a social event.

And then it got worse when both sides found a common enemy: ME.

I didn’t get a lot of direct feedback, but oh boy did it start filtering in over backchannels. From above, it was brutal. Basically, my bosses believed I was taking the magical thing they’d built and letting it rot. It wasn’t much better from below. I was too nice. I needed to fight harder. I needed to pick a side.

Conflict was scary enough for me when I was just in its vicinity. Now, as an official target, I was crushed.

And that’s when I found my voice and turned it all around…

Just kidding. I never turned it around. Instead, I resigned in shame.

I spent a lot of years reflecting on how things went so wrong—and what I’d do differently. This is what I realized:

Quieting conflict can turn into bypassing real fast.
Swooping in to save the day doesn’t make you a hero. I’m proof. Did I believe all my meddling and peacekeeping was for the greater good? Sure. But if I really get honest I see that I was mostly looking out for myself. Conflict made me stressed out, anxious, and sad, so I wanted it to go away. I didn’t care if the peace held or if the peace was deserved, so long as the noise stopped. But it always came back. I would’ve saved myself time, energy, and heartache by addressing what was going on instead of kicking that can down the road for a later date.

Backchanneling is a band-aid—not a solution.
If I could go back in time, I’d get everyone in a room and make us talk it out. What pressures were my bosses facing that made them come down so hard on us? What pressures were my team facing that made them so resistant to feedback? And what pressures was I facing in navigating these choppy waters—new to the role, new to leadership more generally, and stuck very much in the middle between both sides? I’d heard everyone’s sides, but it turned into a game of telephone. The team needed to hear from each other—not me. And while having those hard conversations might not have fixed everything, not having them was a disaster.

Friction can be a force for good.
Engaging in conflict means having the chance to make something better. Shutting down difficult conversations cuts you off from any possibility of positive change. Conflict is a vote of confidence—it means there’s hope that things can improve, and not just on the surface. It’s an act of optimism, when wielded with care. It says: I’m not giving up on you—or this. Even if it’s really freaking uncomfortable.

I have a lot of regrets about that time. I always will. But I’m grateful that the experience was so fucking excruciating that it cured me of my belief that stuffing down my feelings—or other people’s—will ever make anything better. Now, when I feel the temperature rise in a group, I try to tell myself: this is a good thing! The sooner we lay our cards on the table, the sooner relief and resolution can come. And then we can get back to spending time on the things we all care about.

If I can learn how to embrace friction, I know you can too. Because if you want true peace, you gotta make things awkward sometimes.

—Jen

Make it awkward

Why saying hard things matters at work (and how to actually do it)

Wednesday, April 10 from 12-1:30pm ET. A pay-what-you wish event.

At this event, we’ll be joined by a panel of leaders working in design and product who’ve all taken the plunge into having hard conversations—and found that life really is better on the other side. They’ll share:

• When and how they realized they needed to form better relationships at work

• The mindset shifts they needed to make to break through habits of avoidance

• Techniques for starting difficult conversations about expectations, boundaries, feedback, and conflict

• How they’ve learned to move through fear, get past the awkward part, and just say it

We’ll close with sharing a tool for starting hard conversations, and facilitating a self-reflective activity designed to help you transform what you heard into practical next steps for yourself.

EPISODE 18

Why does my manager keep doing that?

Undermining, nitpicking, and gaslighting, oh my!

On the list

Read: Women Talk Design’s new book Present Yourself
Women Talk Design has been helping to elevate women and gender non-binary speakers since 2017 through their workshops, training programs, and community events. We adore them—which means we’re SO excited that they just released a new book called Present Yourself. It pulls together all their wisdom on how to find your voice, speak up about the things you care about, and get your ideas out in the world. Even more exciting? Sara’s one of their featured contributors.

Attend: UX Copenhagen
Too many design conferences spend more time hyping the big company names in their speakers’ bios than speaking up about issues that actually matter. Not UX Copenhagen. On March 20-21, they’ll be exploring UX from a different lens—one that’s not about hypergrowth and billion-dollar exits, but instead dares to talk about intentional degrowth and moving away from consumerism. Join in-person or online—and use the code LASTMINUTE for 25% off!

Read: A survey of digital product teams reveals the value of content design
At a time when content designers feel like they get no respect, I loved seeing Indeed’s content team try something other than proving their value. Instead, they asked their product partners to explain it themselves! What’s going great? Collaborators feel they deliver higher quality solutions and experience higher morale when they partner with a content designer. Areas to improve? Availability and process.