Before I get into this, I need to address something from my last post. I used the word "terrified" to describe my career experiences with hard conversations, and that was the wrong word. What I meant was: those situations were really personally challenging for me. Anxiety-inducing and uncomfortable in ways that touched on my own internal stuff.
But, terrified? No. I'm incredibly lucky and privileged in so many ways. There is a lot happening in the world right now that is genuinely terrifying, to people who are experiencing things I can't even comprehend. So I'm not going to use that word for career discomfort anymore. Those experiences were just scary for me, for personal reasons. Maybe that's TMI, but I'm trying to be real here.
In my last post, I talked about what makes a dream team for me: honesty, trust, the ability to disagree loudly while fully committing. But I kept it all pretty abstract, so here's a follow-up post on what I actually try to do to help create the conditions where that kind of team can grow.
I'm intentional about how I communicate. I try to assume good intent from the people I'm working with. When I catch myself reacting defensively to something, I try to step outside the situation and be a little more objective about it - what context might I be missing? What story am I telling myself and how do I know that it's true? I've learned that responding from a place of curiosity instead of reactivity can change the entire dynamic of a conversation.
I make it ok to make mistakes. When something goes wrong I keep the focus on what we can learn (it’s easier to do with other folks’ mistakes than my own 🙃). When people see that mistakes are learning opportunities, they're more willing to try hard things. That’s why I share (loudly) when I've screwed up and what I learned from it.
I make it ok not to know something. Not only do I share what I’ve learned after mistakes - I share what I'm learning, period. When I was more junior, this meant sharing what I learned with folks who might not have the same information. As I grew, it became more formal mentorship. Now it's also about enabling others to do this by building a culture where learning out loud is normal. And the business case: It makes the team faster because we don't waste time hiding problems or pretending we know things we don't.
I try to help us understand how our work affects each other. Not in the "let's demo what we're working on" way (though that's important too). I mean the “how does my work impact the people I'm working with?” way.
People tend to have a good sense of this within their immediate teams because work is usually clearly connected. But when you have an engineering team supporting, say, a sales team or support team, and you're making changes to processes or tools - if you're five degrees of separation away and you don't have context about how your work might impact them, you can't imagine what your changes might mean for other people. Without that context, you can't see how decisions ripple outward and something that feels small from one angle can create real friction from another.
I'm really intentional about connection. On remote teams especially I actively look for ways to let each other know what's going on in our lives and share more about who we are as people (reasonably, not forced, respecting everyone's boundaries).
There are so many ways to approach this - sharing "manual of me" or "working with me" docs (I wrote about this here). Starting team meetings with a quick icebreaker that's not about work. Doing things like Fun Thing Friday (a new coworker brought Fun Shirt Friday over from his last gig, and since I don't have fun shirts, I do Fun Earring Friday instead).
We all have real lives and interests outside of what we do at work. Keeping that visible helps us remember we're all human when things get tense. And things always get tense eventually.
I try to live by two personal principles I’ve gotten clearer about over the last few years, even though I’ve been operating by them for much longer without having good language for it.
- Do what’s best for the collective, even - maybe especially - when it’s uncomfortable for me personally
- Don't let fear of failure or embarrassment be the *only* reason I don't do something
These principles show up everywhere in my life and at work they push me to do things like naming uncomfortable dynamics out loud, giving feedback that would be easier to avoid, and pushing back on behavior that undermines the culture I want to be part of.
Those conversations are hard! They’re even harder when the person on the other side is more senior than you. And I want to be clear: it’s not always safe or appropriate to have them - power dynamics and psychological safety matter. When I can, though, I push myself to have them, because avoiding hard conversations almost always makes things worse in the long run.
Look, I want to be real here: I fail at these things. I don't meet my own bar regularly (even recently 🫠). Sometimes not even close! But I want to work with dream teams enough that I’m willing to do the uncomfortable work that helps create the conditions where they can grow.