Remote One-on-One Checklist

4 minutes, 4 links


Updated March 23, 2023

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Over time, I’ve learned that getting some particular data during an initial one-on-one can be really helpful, as I can refer back to the answers as I need to give a person feedback, recognize them, and find creative ways to support them.Lara Hogan, management coach; co-founder, Wherewithall*

To ensure one-on-one effectiveness, it’s helpful to make sure you are:

  • Managing time well. We recommend meeting for one hour, every week.

    • It’s best to skew timezones in favor of the direct report, and to optimize for the time of day that is comfortable for them to share more easily, where possible.

    • Keeping the full amount of meeting time signals how much you value these meetings.

    • Don’t reschedule or cancel: signal how important this time is by showing up.

  • Having the right environment. This means using video calls, not just audio calls. You want as much information as you can get, including body language and facial expression.

    • For more effective meetings, both people should use headphones and be in a quiet place.
  • Starting with a baseline. For the first one-on-one, you’ll want to establish a baseline understanding of how your direct report works. Lara Hogan routinely asks the same set of questions in every first one-on-one. (If you’ve already been doing one-on-ones, but not to this degree, you can still do this now!)

    • For subsequent one-on-ones, the direct report can prepare an agenda ahead of time and share it.
  • Documenting your meetings. It’s wise to use a shared document that you both have access to.

    • As the manager, you will want to take your own notes in an additional private document. It’s most effective to keep key information about what’s important to them and what they have going on in their private lives (family news, hobbies, pets, future plans) at the top of your private document.
  • Being prepared. Before the meeting, it helps to scan over your private and shared notes from the previous week so you can follow up. This includes:

    • Having some questions ready to ask your direct report if the agenda is short.

    • Mapping out career goals and progress every six weeks (twice per quarter).

  • Being present. Pay attention! 80% of people admit to surfing the internet or doing unrelated tasks during video calls. Respecting your direct report’s time helps ensure that the one-on-ones don’t become a waste for both of you.

  • Leaving time at the end. You can use this time to prompt your direct report to share anything they may have been avoiding—good or bad; work-related or not—by asking, “Is there anything else at all that’s been on your mind?”

Litmus Test of A Successful Remote Manager

Relationships don’t have easy metrics to measure, but there are questions that can help managers gauge the depth of understanding they have reached with their direct reports:

  • Do you know what irritates your direct report?

  • With whom do they like working the most? And the least?

  • What are they fundamentally responsible for—what is the point of their role?

  • How does your direct report like to celebrate wins?

  • What’s their “tell”—the way you can see that something is wrong?

  • What are the names and occupations of the people closest to them in life? Can you draw any insights about their values or passions from this information?

  • What are their core values in life? (Here’s a list you can pull from if you’re not sure where to start.)

This level of managerial relationship on a remote team is the bar that to aim for. As a manager, it is your job to become an expert in knowing who your direct reports are, how they work, and what you can do to create the optimal environment for them to succeed.

One-on-One Questions for Remote Managers to Ask

It’s helpful to have a well of options you can turn to regularly to keep your one-on-ones fresh and find new ways to prompt interesting or useful answers from your team. Asking deeper questions leads to greater trust and intimacy than small talk does; a key pattern to foster in developing close relationships is “sustained, escalating, reciprocal personalistic self-disclosure.”*

Rather than ending a one-on-one early when an agenda is light, you can ask your direct report one or two of these questions, ideally getting more personal and reflective over time.

Productivity and Career

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