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Fortnightly gripes and hacks: 'deep work on the team level' edition

Christine P. Dela Rosa

In this edition of 'fortnightly gripes and hacks,' I want to hear from y'all on how your teams come together to accomplish deep work.

question Thought starters if you need some inspiration

Does your team even come together to do deep work as a team? Why or why not?
Is there a blocker to working as a team when on distributed teams?
What are examples of how your team can take chunks of time to actually collaborate together (and here's the twist) not async?

*Please note: I'm hoping these fortnightly gripes and hack posts facilitate sharing across the group. Maybe we have a hack that others would benefit from. Maybe we have gripes that others can help improve. Who knows? If you have a gripe or hack off topic, start a new discussion. This is the group to engage with!

Comments

Christine P. Dela Rosa

Hacks

At Atlassian, we have quarterly hackathons that last for 24 hours. They're called "ShipIt" (featured within this article), where we can work on whatever and with whomever to accomplish something with. The reason why I think this hackathon format works, is because the entire company is focused on this quick burst of innovation, or at the very least, aware that others will be participating in it.
Besides the team offsite, we also have something called a "spike," which is like an offsite but can take place in an office or entirely remotely. It has a structured agenda to accomplish very specific objectives. You're not supposed to work on anything else but the team goal and it's nice to feel like the whole team can spend be thoughtful about a big chunk of work rather than starting and stopping over and over across a long period of time.

Gripes

When there are so many personalities and workstyle preferences, it's tough to accomodate everyone's needs. For example, I find it hard to create an experience where everyone is brainstorming on the fly because many (including myself) like to thoughtfully ideate by themselves vs in front of a group. Turning my camera off or telling a team to take 10 minutes and then come back are helpful hacks. But that's just one example. People who feed off of live collaboration want something else. So I guess the challenge I have is when facilitators plan for just one type and not a diverse group of individuals.
Another gripe I have is that I often can't pause my other work while doing deep work with a team. So one way I combat that is knowing waaaaay in advance when I'm going to do deep work as a team. That way, I can set an expectation for my other projects that they won't be tended to for a period of time. Of course, the gripe is that you can't always plan ahead for deep work as a team, especially when there's a sudden opportunity when you need to drop everything.

Dave LIAO

If you have the luxury of time, it's useful to figure out when your teammates function best - "morning people", for example - so you can block time when they're most effective.

I wonder what other dimensions there are besides ideation style and our best times of the day?(It's definitely not my time of the day right now so I'm drawing a blank... ha!)

Nic Brough -Adaptavist-

I like @Dave LIAO point about time. I'm a night-owl but some of my team are morning-larks. We can't change that, but being aware of it means we can be more productive together if we plan the closer working to fall between 10am and 4pm

But I wanted to talk a bit more about something @Christine P. Dela Rosa mentioned - types of communication.

Make a bit of time to work out how people communicate best and what suits each member of the team, find a happy medium that works well for everyone on the team and look at how to cope with the outliers who don't fit, rather than try to wedge them in. I'll use our sales team as an example - one of them is a complete all-rounder - she doesn't care how people talk to her, meetings (real life or zoom), chat, email, phone call, helpdesk requests, they all get the same response. At the other end of the scale, a salesman has made it clear that he's only paying any attention if it arrives via Slack, or you're in a a real-time room with him (VR, office or pub basically).

You don't need to pander/adapt to every style, but do pay attention to what works best across the team, and expect to have to nudge outliers towards the main group.

You can have people with absolutely superb ideas, but if they're only talking on Slack and the rest of the team is buried in Confluence docs, you're going to miss out.

Christine P. Dela Rosa

You're bringing up the old "working agreements" alignment, @Dave LIAO. I'd not only +1 your response but go as far to say that these are not a luxury practice but a required practice for teams to make inclusive decisions about the way they work together.

Besides time of day to meet, here are a few I like to throw in as part of working agreement discussions:

When to async collaborate vs when there needs to be live meeting collaboration.
How often to provide project or status updates and via what method (standup, status reports, usage of tools for reporting, etc).
How does the team like to spar and consume lots of new information? Maybe it's through async content reviews and then live feedbacking. Maybe it's through regular spars where teammates rotate their updates. Maybe it's about sharing chunks of info over fully polished info to cut down on the amount of time consuming info at once. Lots of options here.

Would be curious to hear what else folks establish as part of their working norms. Especially as it relates to this larger discussion in terms of deep work as a team.

Christine P. Dela Rosa

Communication isn't one-size-fits-all, @Nic Brough -Adaptavist- . I couldn't agree more.

And thank you for the specific examples you provided. Helps illustrate your point!

Paul Stallworth

What is "deep work" in this context and what's the goal of it? Are we talking about the book definition of "activities performed in a state of distraction-free concentration that push your cognitive capabilities to their limits"? Or are we talking about some other definition more associated with collaborative, creative, brainstorming?

Either way, I regularly go back to a takeaway from one of Dom's talks at a previous Summit describing the difference between outputs and outcomes. Is it necessary to focus on what I'd consider the output (live brainstorming, a curated one-page memo, etc.) or is there instead an outcome we can point to that people can work towards regardless of how they get there.

Christine P. Dela Rosa

@Paul Stallworth , good question. What I mean by “deep work” is collaborating as a team where your output is a rich amount of outputs. In theory, your outputs could serve one or a limited amount of outcomes, but they may not. You mention distraction-free stretches—that’s one approach to deep work as a team. You mention live brainstorming—that’s another approach via a collaborative document (e.g. Confluence) or even meetings. In any of these examples, see work is producing more than quick answers that might by generated via one asynchronous ping.

My discussion question centers on what teams are doing to accomplish such rich collaboration. What’s working and what’s not?

Esme Crutchley

My VA and I work at the same time, for an hour at a time (or two depending on the task), then have an hour off. By always working at the same time, we're both around if the other ones get stuck, needs to ask a question or needs support. Sometimes we're working on the same task, or the same project, but sometimes we're working on totally different things to keep ourselves fresh and keep different things moving. We have a daily sit down and work out what we're both going to be working on that day and when and try to align each other's task to best support the other person. I might be working on a proposal and my VA could be working on my calendar or task list, we do it this way to complement each other and to be able to work together, but separately, in order to best serve our clients and ourselves. This means that I can focus on what I can do to move the needle most in the business and my VA can do what they do best to push us towards the same goal.

Christine P. Dela Rosa

Interesting! Sounds like y'all get on the same schedule, regardless of being in the same physical location or not. I like that! And don't usually do this with my team, but in retrospect I think we get more work done when that happens.

PS - What does VA stand for, @Esme Crutchley ?

Walter Buggenhout

We do have an annual ShipIt at our company too. But apart from that, deep work as a team to a large extent depends on the team you are working in / with.

I find myself doing most of the deep work as a team with customer teams I work with as a consultant.

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