It’s never too late to start connecting with your team

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A senior manager and peer of mine (from another organization) wanted to know how to start having one-on-one meetings with his direct reports despite having never had them before.

His team wasn’t that big and his direct reports were managers. Even though they had been on his team for years, he had not had a single one-on-one with any of them.

Their communication was limited to meetings for projects, emails, technical documents, and so forth, as well as asking for updates on Slack. The only time performance or careers were discussed was in December for the company’s year-end reviews.


Snooze Slack and plan ahead

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You can run meaningful 1-on-1 meetings with members of your team, even when you’re remote.

Remote meetings come with a ton of challenges, from technology, timing, digital distractions, and more. Mastering 1-on-1s with your direct reports is also key to being a great manager and leading productive teams.

Nothing beats being face-to-face with a team member, but even when remote there are many steps you can take to run better 1-on-1s. Here are five ways to make that happen.

1. Meet at Least Once a Week

One-on-one meetings must be at least weekly, depending on how much your direct report is responsible for, maybe even more often.

Inventing a commute can help you transition between work-life and home-life

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When my team transitioned from commuting on the subway to commuting from their bedrooms to living rooms, context-switching became tough.

From day one, I had trouble getting a feel for when work was genuinely over. Was I watching Netflix to unwind? Or was I still working and it was just on in the background? It was too easy to just keep working.

I realized quickly that my commute was actually an important ritual in my day. In the morning, it gave me time to go through emails, read books, and mentally simulate meetings that may happen in the hours to…

Just because your commute has stopped, doesn’t mean your career has to

A foot with a sock on it raised up balancing a stack of books and a beverage.
A foot with a sock on it raised up balancing a stack of books and a beverage.
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You are working from home, which seems awesome. No commute and fewer interruptions. Your cat curls up by your side and the kettle comes to a whistle. This is how work was meant to be.

Time passes and your one-on-ones start to feel repetitive and rushed, your tickets are for work that you often do solo, and it takes days for you to get any eyes on your pull requests.

You thought this would be a dream, but you have suddenly lost the visibility that came default with being in an office.

Now is the time for you to level-up…

You can innovate, but can you deliver?

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Your team moves fast! My team does too. You work on a number of large production systems, and deviating from the process can be a source of innovation.

When starting something new or experimental it is helpful to break out a team and hack. Amazing and innovative work comes from the teams closest to the ground when they come together to solve problems.

Too often though, once the magic has been revealed, it becomes imperative to launch those tools and products to the world.

But how can something built in a day be ready for production?

How can one engineer’s…

Lift yourself up by supporting those around you

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I knew what the meeting was about.

Ali had called me aside, and I had a feeling it was to complain. We grabbed the nearest cork-covered conference room that was open, pried back the tabs on some seltzer, and sat down.

He looked over at me and started: "You need to calm way down. I see you freaking out about the site outage and how there is nothing you or anyone can do. But your panicking is making you look foolish."

We were rivals. We competed over the same raises and promotions. And I had handed him the perfect moment…

How to approach an international, multi-lingual company culture

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“Should we require foreign offices to always speak English? Even when not on a call with HQ?”

A new mentee was seeking advice on how his company should approach culture in their overseas offices. The HQ was in the U.S. and the first international office was about to open in France.

It took me a moment to process the question.

Communication is the most valuable and most difficult part of work. When you have an international company with multiple languages you need to have a common way to communicate, but does that mean standardizing all communication and all documentation in…

Establishing a “Team OS” to encourage process problem solving

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The product owner canceled the team’s retrospective for the third time in a row. My mind was blown. How could the team change and improve if they didn’t take time to look back at what was working and what wasn’t.

I approached him to ask why and was shocked to find that retrospectives were the main item the team brought up to stop the last time they met.

The Team Retro

If you aren’t familiar with a team retro (short for retrospective), it’s one of the many meetings in scrum that bring the team together. The general format is to have three columns…

If you think your team needs retraining, you don’t have a skills problem, you have a culture problem.

A hallway with slightly open doors of different muted colors where the paint is chipping on the walls.
A hallway with slightly open doors of different muted colors where the paint is chipping on the walls.
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Having gone through a cloud migration for one of the world’s top 100 websites, there were a couple of ways it could’ve unfolded. The first was making choices based on old thinking, and sticking to what we knew.

The other way, the way that it happened, was for everyone to learn what was needed and step into new, evolving roles.

Engineers doing Ops, Ops doing Dev, Networking specialists writing YAML... all well known signs of the end of times.

How did so many people put aside their hangups, work cross-discipline, manage-up to multiple bosses and get all the work done?

Create A Workplace That Allows For Thinking

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Andy’s head was kicked back as she stared at the ceiling. With a quick swing, her eyes refocused on the computer monitor in front of her as I walked by.

“Is everything alright?”

“Totally, I just needed to sort out how I wanted to connect these services together.”


We spend a lot of time at work either doing or talking. The chat Andy and I had afterward was about thinking. When I was an individual contributor, I would hit roadblocks all the time, either in code or in architecture, and there were many problems that completely escaped me.


William Anderson

VP, Engineering @ Forbes | Technical Leadership | Tech Strategy | Stegosaurus

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