No more guessing games

We check in on projects and progress, but how often do we talk about our work relationships themselves? Not enough — and that’s a problem.

Early in my career, I worked closely with a more senior colleague. They were smart, experienced, and took no shit. I looked up to them. I learned from them. More than anything, I wanted to impress them.

There was just one problem: I was never quite sure where I stood with them. “Is this what they had in mind?” I’d ask myself after sending a document their way. “How did they think that went?” I’d wonder after running a workshop.

I didn’t actually ask them those questions, though. I didn’t tell them when I needed more information, or when I wasn’t sure what they had meant. I was afraid that if I did, they’d think I was insecure, too needy. I was afraid they’d stop trusting my work. I was afraid they’d like me less.

So instead, I tried to play sleuth: What’s behind that facial expression? Why are they being distant? How can I make them happy? And I spent a lot of time quietly hoping I’d never disappoint them.

Then one day, I did.

Suddenly, all that communication I’d wished for came flooding in. They told me just how badly I’d screwed up. That I should have realized much sooner that things were going off the rails. That I’d been out of line and unprofessional. It was incredibly painful, and I walked away brimming with shame. Our relationship never recovered.

Years later, though, I can see that the problem started so much earlier than that awful moment. Our working relationship failed because we had never truly communicated: They’d said very little, and I’d pretended not to need more.

Honestly, it was the same way I’d handled dating as a young person: Fish around for clues about what the other party was thinking. Drop subtle hints. Over-analyze every sentence. But never, ever talk to them about the relationship outright.

It didn’t work when I was dating, and it certainly didn’t work with this colleague. But I can also see now why it felt so normal to me. It’s how I grew up — always on uncertain footing, scared of upsetting someone. I was so used to feeling unsafe that I didn’t even realize that’s what I was feeling. This was just what relationships were like.

I know I’m not alone in this. So many people I work with in my coaching practice tell me how nervous they feel asking for their needs to be met at work. They’re scared that they’ll lose credibility if they have too many questions, that they’ll be perceived as “difficult” if they set boundaries. That if they aren’t perfect all the time, they’ll be rejected.

And sometimes? They’re right. If they’re not working in a safe environment, they’re not wrong to try and protect themselves.

But what I wish someone had told me long ago is this: If you can’t safely express your needs in a relationship, that’s not a problem with your needs. That’s a problem with the relationship. Suppressing your feelings while guessing at theirs will never fix it — no matter how good you get at it.

If you’re in a leadership position in your organization, I hope you’re reading this carefully. While healthy communication relies on both parties being present and honest with one another, the stakes aren’t equal for everyone involved. The less power someone has, the riskier it is for them to be direct about their needs and boundaries.

The converse is also true: the more power you have, the greater your responsibility to start and steward these conversations.

So if you’re a leader looking to make it safer and easier to talk about hard things, where do you start? It’s actually quite simple: normalize talking about your working relationship. Not just checking in on projects and progress, but the relationship itself.

Here are a few topics I recommend:

• What would a thriving work relationship look like to each of you? What’s a definition of thriving that you can both agree on?
• What’s working well right now in your relationship, and what’s getting in the way of thriving?
• What’s been left unsaid recently? What do they need to feel more comfortable saying those things?
• What behaviors make them feel seen, understood, and respected? What behaviors do the opposite?
• What topics are difficult for each of you to discuss? How will you let one another know when something’s uncomfortable? How will you work through it?
• How do you want to treat one another when things are difficult? Which behaviors will help you work through rough patches, and which ones will make things worse?

If you’re anything like me, these kinds of conversations might feel weird at first. Actually, scratch that: they’ll feel downright bizarre. That’s not because they’re wrong or bad, though. It’s because a lot of us never learned to communicate about our needs and expectations. Instead, we’ve often learned to do what I did back in the day: guess, assume, and hope it works out.

Changing this habit isn’t easy. It triggers discomfort for a lot of people. But leaders, I say this with love: It’s time for us to work through that squirm. Because the alternative is exhausting for everyone.

If your team has to guess at what you’ve left unsaid, they’ll need constant vigilance — and they’ll still get it wrong sometimes. If they don’t feel safe sharing their needs with you directly, they’ll waste time hinting around — and you’ll still miss their signals sometimes.

This is a lot of extra work even in the best of times, but let’s be real: We are not in the best of times. Pretty much everyone I know already feels frayed — whether they’re grieving for Ukraine or Uvalde, worrying about inflation or abortion rights, trying to protect trans kids or avoid catching COVID. The last thing anyone needs right now is a workplace that leaves them feeling even more uncertain and anxious.

So if you want to lead in a way that respects your team’s humanity and eases their burden in hard times, I hope you’ll think about your own communication habits. What difficult conversations do you avoid? When do you stick to talking about the work when you really need to talk about the working relationship? What do you need to work through to change those habits? I promise I’ll keep doing the same — and sharing what I learn as I go.

This post originally appeared in the June 8, 2022, edition of our newsletter, Nice Work. Subscribe here.