And How to Fix Them
The 3 AM anxiety isn't about the email itself—it's about not knowing whether your boss expects an immediate response or is just working on their own schedule.
Your boss sends an email at 11:07 PM. You see the notification. Your mind starts racing: Does she expect a response? Should I answer now? Will she think I'm not committed if I wait until morning? You lie awake wondering what she expects, when the real problem is: you're both operating on different unspoken assumptions.
The NYC Expectation Reality Check
As a New Yorker, I expect people to walk on the right side of the sidewalk. I expect someone to say thank you when I hold a door open. I expect people to throw their trash in an actual trash can instead of dropping it on the sidewalk.
But here's what living in NYC teaches you faster than anywhere else: not everyone shares your expectations. The tourist stops dead in the middle of the sidewalk. The person you held the door for walks through without a glance. Your expectations meet reality, and reality wins.
The same thing happens at work, except the stakes are higher and the confusion lasts longer.
Why We Assume (and Why It Fails)
We build expectations based on past experiences. If your last boss expected instant responses, you assume this one does too. If your previous team always debated decisions openly, you expect that here. The problem isn't that you're wrong—it's that you're operating on data from a different context, applying it to people who never agreed to those rules.
The Conversation That Changed Everything
Early in my last role, I had a conversation with my boss that saved both of us countless hours of unnecessary stress. We talked about expectations explicitly: anything urgent outside normal business hours would be marked as such. Otherwise, he was just working late on his own schedule. I never had to guess again. He never had to wonder if I saw his message. One conversation eliminated months of potential anxiety.
Six Questions to Make Expectations Visible
Your team is already operating on expectations—they're just unspoken, misaligned, and causing quiet friction. Here are six questions that force expectations into the open:
1. Work Scope & Ownership
"What types of work do you expect from each role, and where do responsibilities overlap?"
2. Values in Action
"What behaviors do we expect when our stated values are tested?" (Because everyone says they value "collaboration" until it slows down a decision)
3. Time Boundaries
"What do we expect regarding response times, availability, and after-hours communication?"
4. Communication Norms
"How do we expect people to communicate disagreement, uncertainty, or problems?"
5. Conflict Navigation
"What do we expect when two people or teams have competing priorities?"
6. Decision Authority
"Who do we expect to make which decisions, and when do we expect others to be involved?"
Why This Conversation Rarely Happens
Most teams skip this conversation because it feels obvious. "Of course people should respond quickly." "Obviously we value collaboration." But "quickly" means different things to different people, and "collaboration" can mean everything from "tell me before you act" to "keep me informed after."
The teams that thrive aren't the ones with perfect expectations—they're the ones who've made their expectations explicit.
Take this leadership team we worked with. Three hours uncovered that psychological safety, candor, and rigor were all valued—but in completely contradictory ways. The CEO rejected the solution everyone else wanted. The workshop "failed" by traditional measures.
But here's what actually happened: expectations became crystal clear. No more guessing. No more false hope. People could finally make informed decisions about whether to stay or go.
Even if you don't like the expectation, clarity trumps guessing every time. At least you know and can act from there.
Your team is already operating on unspoken expectations. They're just not the same ones.
Having this conversation well requires more than just asking questions—it requires creating the safety for honest answers and the structure to turn insights into agreements. We help teams have the conversations that matter, using our team.build() approach to surface what's really expected and turn that into workable agreements.
Ready to surface what's actually expected? Get in touch and let's talk about what your team needs.
