“Nourish beginnings, let us nourish beginnings.” —Muriel Rukeyser, from her poem “Elegy in Joy”
Do you remember your first job? Or maybe that first step into a role that you hoped would become a career?
Think back to what it felt like to be new. Not just new to the job, but new to working.
What would have helped you feel more comfortable?
Recently, I had a conversation with a past client who manages a fully remote team. She noticed that some of the early careerists on her team—smart, capable people—would sometimes get deep into the weeds without recognizing they were stuck. They didn’t always know when to ask for help, what questions to ask, or how to navigate their way out of a challenging situation.
That conversation highlighted something we can easily forget after we’ve been working for a long time. Early careerists are learning two things at once:
➡️ How to do the job
➡️ How to navigate the workplace
Those are two distinct kinds of learning—and we tend to provide far more support for the first.
Besides figuring out what’s expected in their role and how to do the job itself, early careerists are also learning how to communicate with a manager, ask questions without feeling foolish, advocate for themselves, interpret feedback, navigate ambiguity, admit when they don’t understand something, and recover when they make a mistake.
That’s a lot to learn at once.
Onboarding Alone Isn’t Enough
Over time, we accumulate all sorts of knowledge we may not even realize we have. Some of it is practical—like knowing who should be copied on an email. Some of it is more nuanced: when to ask for help, when to push back, how long to try solving something on your own before bringing it to a manager, or how to tell when a problem needs to be escalated.
Much of that judgment comes from experience. These aren’t things employees learn from onboarding alone.
A new employee can be taught the company’s systems, policies, and expectations for their role and still have very little experience navigating these situations.
What does this mean for team leaders?
It means leaders have an opportunity to make some of that invisible workplace knowledge more visible, as early careerists are still developing the judgment and confidence they’ll eventually need to navigate those situations on their own.
There are many ways to create opportunities for that type of learning. One of the simplest is something I call the 5-minute vibe check.
The 5-Minute Vibe Check
Most work conversations center on what you’re working on. There’s nothing wrong with that, but we also need conversations about how we’re working together. That’s what the 5-minute vibe check is for.
It’s easiest to add this step to the end of your existing 1:1 meetings. Leave 5 minutes at the end of the meeting to ask:
“What could I be doing more of, less of, start doing, or stop doing that might be helpful for you?”
This question creates room for an honest conversation on things that may never come up in discussions about deadlines and deliverables. It gives young employees an opportunity to think about what they need—and to practice articulating it.
Some alternative ‘vibe check’ questions you can ask are:
- Where are you getting stuck right now?
- Is there something you haven’t asked me because you weren’t sure whether or how to ask?
- Am I giving you the right amount of direction, or would more or less be helpful?
- What’s one thing I could do differently that would make our 1:1s more useful?
You don’t have to agree with every suggestion or change the way you manage based on every answer. But you do need to listen, thank them for their feedback, ask questions if you don’t understand, and consider what you’re hearing.
These conversations give early careerists practice asking for what they need, recognizing when they’re stuck, communicating openly, and navigating situations that once felt unfamiliar.
And eventually, the things they need help navigating now will become things they know how to navigate on their own.
