This Week
A VP of Product, six months into a new role, told me something that surprised her.
She had weekly 1:1s with her boss. Never missed one.
She came prepared every week: updates, risks, questions. She assumed the relationship was solid.
Then a reorg was announced.
A peer got the expanded scope she had assumed would naturally come to her.
When she asked her boss about it, he looked confused. "I wasn't sure you wanted it," he said.
She’d never said she didn’t want it. But she’d also never said she did.
In six months of weekly meetings, they’d never once talked about where she was headed, what she was building toward, or how he actually saw her.
She’d been present in the meetings.
But absent from the relationship.
The Problem
Most leaders believe that having a regular 1:1 means they have a relationship.
They don’t. They have a reporting cadence.
Status updates are transactional. You share what’s happening. Your boss asks questions. You answer. The meeting ends.
When you operate this way, you become a function.
Your boss knows exactly what you are doing, but they don’t know how you think.
They see your output, but they don't see your potential for wider scope.
This isn’t about doing more. It’s about changing what your boss learns about you in the time you already have.
What Actually Works
Go beyond status updates.
There are 5 conversations you need to have with your boss.
These aren't necessarily 5 separate meetings, but 5 threads you need to weave into your regular check-ins.
1. The Situation Conversation (Alignment)
Don't just report on the work. Report on your diagnosis of the environment.
"Here is my read on the landscape. The core structural issue looks like [X], so I am prioritizing [Y]. Does that align with what you’re seeing?”
Early disagreement is a planning conversation. Late disagreement is a performance problem.
2. The Expectations Conversation (Their Own Success Criteria)
Forget the HR job description. You need to know what creates political capital for your boss.
"Beyond the KPIs, what would be a strategic win for you this year?"
The goal is to ensure you aren't winning a battle that your boss doesn't care about.
3. The Style Conversation (How You Operate)
Don't ask for permission to be you.
State your default operating mode and align on information flow.
"I bias toward early signaling on risks - I’d rather you know before I have the full fix. Does that match how you prefer to intake bad news, or do you want the solution before I bring it to you?"
The goal is to avoid the slow erosion of trust that happens when working styles clash and no one names it.
4. The Resources Conversation (Trade-offs)
Executives don't complain about being busy; they negotiate trade-offs.
“We’re currently under-resourced to hit [Target X] by Q3. My recommendation is to hold the timeline and defer [Scope Y]. That protects the launch date.”
The goal here is to stop pretending you can just "try harder" to fix a resource gap. Get them to agree on the math.
5. The Horizon Conversation (Trajectory)
This isn't about asking for a promotion. It's about aligning your scope with the organization's future needs.
"I’m focused on Q1 execution right now. But looking at the 12-month view, where do you see the biggest gap in the organization that lacks a clear owner?”
If you don't define your trajectory, they will assume you are content where you are.
Don’t schedule 5 new meetings. That feels formal and heavy.
Instead, weave these into your regular 1:1s. Protect the last ten minutes of every check-in to move from tactics to alignment.
"Before we wrap up, I want to check with you..."
Results demonstrate competence, but these conversations demonstrate value.
Have these conversations early.
Before you find out you were absent from a relationship you thought you had.