Lesson Learned #4 – Schedule 1v1s

I know that in 2024 the hot topic is “Remote” working – back in 2015 it wasn’t. In 2015, I transitioned from being an onsite / in person employee in Redmond, WA for Microsoft to being a fully remote employee living in East Tennessee.

One major lesson that was highlighted for me in that transition from in-person to remote work was that I needed to create a rhythm of 1-on-1 meeting cadences, usually 30min, with specific people to ensure that my team and I were ultimately successful in what we set out to accomplish.

I needed to meet with my direct manager regularly. I had people reporting to me that I need to meet with regularly. There were collaborators in Ireland, India, and Australia that I needed to keep in sync with.

Each of those relationships required different and specific upkeep.

• For my manager, maybe meeting every two weeks or so worked just fine.
• For my team members, some required weekly syncs while others were fine with monthly.
• For people across different geographies, sometimes those required every two weeks or so.

Those would be what I’d call “tactical” 1v1’s. People you interact with on a regular basis to keep up to date and work through any applicable problems that may come up. Think of these as “doing my job” type 1v1’s.

Then there are some more “strategic” 1v1’s – these I usually have monthly (or so) and typically tend to be 1-1.5hrs in duration depending on what all is going on. Think of these as “intentionally growing” type 1v1’s.

• Who are you being mentored by? Could be a leader you look up to, an advisor, a parent figure.
• Who are you mentoring? Who are you teaching what you already know and pouring into?
• Who are you seeking out to learn more from or intentionally broaden your horizons?
• How often do you meet with your skip-level boss to get a broader view of the org and how you can provide the most value? (quarterly maybe?)

Lastly, always try to add value to the 1v1s you’re a part of. Simply ask them how you can best help them or add value to them. Always be thinking about how you can bring value to that person or help that person with what they’re working on or the tactic at hand.