Start with Why (and Why‑Not)

Clarify what 1‑on‑1s are not: they’re not a Jira stand‑up or an annual review wearing casual clothes. They are a safe space for feedback, career growth, and life‑stuff that influences work (hello, surprise daycare shutdowns).

Opening line that never fails:

“Thanks for making time—what would make this half hour valuable for you?”

Set the Logistics (aka “The Boring but Trust‑Building Part”)

There are a lot of logistical items that may seem boring to some, but end up being the foundation of a successful working relationship. Setting expectations upfront shows that you respect them and their time. The real secret here is remembering these expectations and being consistent with them.

A two‑minute discussion here prevents two years of calendar roulette.

Cadence

In my experience, how often you need to meet with people on your team (even with your own boss) will vary over the course of a given year. Some team members may need more attention for a period of time, others may either need less or already have a high level of touchpoints with you throughout the week.

Notes

It is very important to maintain a timeline of notes around your discussions. At a minimum, you should keep detailed notes of every 1-on-1 meeting. Ideally, this would be a shared document between you and your direct report. This allows both of you to add items at will, see the history of everything discussed, and maintain a shared understanding of what was discussed.

Most places I’ve worked have provided some web-based tool to track these types of notes, but I tend to always fall back on a shared Google Doc. Use what works for you and your team mate.

Location

For me, the ideal set up in a remote environment is a cameras-on, face-to-face virtual meeting (i.e. Zoom, Google Hangouts, etc). I’ve had peers espouse the benefits of a “walking 1-on-1”, which I think can work depending on the content of the meeting, which you may not know ahead of time. I’ve had everything from super casual 1-on-1 meetings where we ended up discussing our weekends the entire time to the entire time spent screensharing while debugging a tough coding issue (because that’s what would “make this half hour valuable” — so that’s what we did).

Mine for Motivation

Skip the corporate icebreakers and try these instead:

• “Tell me about a recent project that energized you—what made it fun?”
• “If you could hand‑wave one annoying task away forever, what disappears?”
• “Fast‑forward a year: what are you proud we accomplished together?”

Write answers down; future‑you will thank present‑you when building growth plans.

End with Action Items the Size of a Pushpin

Two bullets, max—one for you, one for them. Example:

• Manager (you): DM Staff Eng Kara to pair Alex on the new observability spike.
• IC (them): Draft questions before first on‑call shadow.

Small, immediate wins snowball into trust faster than swag hoodies (though, swag hoodies are typically pretty rad).

Common Pitfalls & How to Tumble Over Them Gracefully

Final Nudge

Pick one report, schedule a “reset” 1‑on‑1 using this structure, and let me know on LinkedIn how it felt. If it’s awkward, blame me publicly—I’ll own it and we’ll iterate together.