Four Tendencies in Remote Work
Managing internal and external expectations in a remote world
I’m an obliger. In Gretchen Rubin’s Four Tendencies framework, that means that I tend to meet outer expectations, but resist inner expectations. Basically, if someone asks me to do something, I’m more likely to do it, but I often struggle with sticking to commitments on my own.
Some ways this shows up for me:
I often put others’ needs before my own, and it requires concerted effort to carve out space for myself
If I externalize my goals, I am much more likely to stick to them. This might look like announcing online that I’m participating in the #100dayproject, or just taping a piece of paper on a wall that has my daily goal of writing morning pages, that I can check off daily.
Gretchen Rubin’s framework describes patterns of The Obliger, The Upholder, The Questioner, and The Rebel.
The last few months, in my many conversations with friends and teammates, I’ve been pondering, how do these tendencies show up, especially in the new-ish world of remote work? How can we leverage our understanding of these tendencies to help people thrive in a remote work setting? Of course, remote work is not for everyone, but given my network and industry, my conversations have been fairly limited to remote work.
Here are some thoughts for each tendency.
You can count on me, and I’m counting on you to count on me
This is the tendency that I’ve thought the most about, both because it is me, and also because I think it is one that’s very impacted by remote work.
Office environments provide a lot of external expectations at every level — the social expectation that you’ll show up to work around a certain time (before your standup perhaps) which influences your alarm and morning routine. The implicit expectation of an open office that at most times, you’ll be at your desk focused on work, except during lunch and meetings.
Socially accepted breaks are built in — the post-lunch coffee run, a short conversation when you grab a snack, the moments before and after meetings.
In a remote world, in the absence of those external expectations, obligers are left sorting out how to structure their remote work routines.
For obligers who are parents, or have other timely obligations, the externally imposed morning structure of getting ready for and dropping kids off at school on time provides some much needed structure around the day.
For obligers who don’t have externally imposed schedules, they may struggle to take breaks or make consistent progress on their work.
External structures might look like a scheduled morning check-in with a teammate, accountability check-ins during 1:1s, publishing weekly commitments, or blocking out clear start and end times on Google Calendar.
Questions for obligers:
What structures or expectations would be helpful to thrive in a remote setting? (May be helpful to think back on past experiences where you’ve thrived)
What do you need external accountability around? Maybe setting a goal for yourself and sharing it with your team in a slack channel may make a world of difference.
What deadlines, commitments, or dates do you want to set for yourself (if you have none externally imposed), and what sort of external accountability do you need?
I’ll comply, if you convince me why
The questioner meets internal expectations, but resists external expectations — that is, until they are internalized. This might look like someone who always asks why, who wants to know the full context behind a project before they can really get started on the work in a meaningful way. This can be frustrating if you don’t understand this tendency — WHY is this person asking so many questions, and is the whole process of working with this person going to be like this?? But once they have internalized why something has to be done (and it makes sense to them), they’ll move swiftly.
In an office setting, questioners generally get a ton of ambient context about the company direction, their team’s goals, and how their work may fit in. Gaps in communication can be filled with quick questions in the hallway, or when overhearing a conversation. Office paraphernalia like walls, whiteboards, or displays with metrics, designs, company values, and roadmaps all add to the filling in of WHY.
In a remote workplace, if a team is not intentional about filling in these gaps, a questioner will struggle to understand the impact of their projects, and thus struggle to make progress on them. They might pick up other projects that feel more clear, while primary projects linger on.
In a remote setting, a high level of context is possible, and when done well and intentionally, context is shared more widely and accessibly. When the why behind goals and roadmaps is written up in a shared doc, broadcast by email, shared to slack channels, pulled up in Zoom meetings, searchable in remote tools — all that context is reliably and explicitly available, not just to someone who happens to walk by the CEO and product manager chatting in the hallway at the right time.
While the downside of questioners not understanding the why is more pronounced (their productivity will tank), they’re a great sensor for the team or organization — and filling those gaps in a systematic way will benefit others as well. If they don’t have that context, many others on the teams also don’t, but may just be chugging along busily (see obligers) doing what they’re told.
Consider using templates so that all product specs and tech specs for projects clearly communicate the problem statement, how it relates to team or company goals, why the proposed solution was chosen, and anything important about how the work should be done (timeline, scope, etc).
Questions for questioners:
What context are you missing? How can you get this context (as a one-off and also consistently?)
Who can you ask for support? If you’re aware that you’re a questioner, rather than asking a string of questions until you’re satisfied, it may make sense to share more openly with your manager / tech lead / functional lead. You can share the framework (or this post!), or just say, “In general, I find it’s much easier and faster for me to execute once I fully understand the why behind an initiative. Can you help me with that?”
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Discipline is my freedom
Upholders meet both external and internal expectations. They find it easy to do what needs to be done, cranking through to-do lists and delivering project on schedule.
In an office setting, upholders may get more nudges that redirect them if the direction they’re sprinting towards isn’t quite right. Maybe overhearing a conversation gives them pause about the necessity of what they’re working on that moment, or someone sees them at their desk and is reminded to pop over and say, “Hey did you start that yet? Can you hold off — I need to get some clarity around priorities.”
And given how easily they meet any internal or external expectations, they may also struggle to understand other tendencies’ needs for additional structure, accountability or context, especially in a remote setting.
Taking a moment each week to share their top priorities can help ensure that as they execute on their to-do lists, they’re also working on the right things.
Questions for upholders:
Are you working on the the most important thing?
If you’re struggling with teammates, how might their working style or tendency be different from your own? How might that knowledge help the team be more effective?
You can’t make me, and neither can I
Rebels resist all expectations, preferring not to be tied down to commitments. Gretchen Rubin shares that many of the strategies that work for other tendencies don’t work on rebels. But rebels do like to do things differently, when they want it, and on their own time. Rebels can be incredible in a work setting if they decide to take on a challenge and given the autonomy to do it their way. Of course, it’s a manager’s role here to nudge them towards a challenge that is a stretch but not something completely out of their wheelhouse.
I’m actually not too sure how rebels differ in in-office and remote work settings, but what comes to mind is that remote work and flexible schedules can better support a rebel’s life, rather than conforming to a 9-to-5 office schedule. A manager who can find ways to support a rebel’s interests that may not fit in a standard schedule, while also making sure the team and company get what they need, can really bring the best out of a rebel.
Coaching is a particularly powerful tool for rebels — taking the time to build a strong relationship, one where you don’t just dispense best practices and advice, but take the time to understand, who is this person? What’s important to them? How can they get what they want out of their time in a role?
Questions for rebels:
What are you looking for more of? How can you get that need fulfilled either at work or outside of work?
A note to managers
Maybe you’re wondering if the teammate who’s struggling is an obliger and needs more structure and accountability. Or maybe it explains why someone else asks so many questions!
I encourage you to open up a conversation with your team. Share this post, or drop the Four Tendencies Quiz in a slack channel. Bring it up in your 1:1s. People (including yourself) may not know what tendency they are, and talking about what you’re learning about yourself openly encourages others to do the same.
This may open up conversations about people’s remote work routines and challenges, different time they’ve felt like they were thriving at work, how they want to be supported, and more.
Feel free to modify and use the questions under each tendency.
And let me know how it goes! I read every response I get (either in comments or email replies) and love to hear how these ideas are landing with the community.
This feels like an incredibly rich area for more ideas, content, guides, etc. — I’m happy to compile stories and share insights, patterns, success stories (and failure stories).
Lead Time Chats
I love a well-facilitated meeting, so I was really excited to chat about this topic with Douglas Ferguson, founder of Voltage Control. Specifically, we chatted about facilitating large meetings (you know, the 50+ meetings…) — whether they should be that large at all, how to structure them to be engaging and inclusive, and how to be the one who inspires meeting culture change at your organization.
Thing I’ve been enjoying
Emerging from pandemic fog - we’ve had a few weekends with a good mix of family time, solo time, and social time. I had forgotten that was possible. I’m excited for the continuing evolution of how I spend my time, all while trying to stay vigilant about COVID and other sicknesses.
Weekday dinners - Years ago, when my kids were toddlers or babies, I remember listening to an Edit Your Life episode where the co-hosts Asha and Christine talked about the new milestone of being able to have friends over spontaneously for a casual weekday dinner. We’re at this milestone! We’ve had casual weekday last-minute dinners a few times, and it provides a welcome change to the weekday routines.
Summer weather AND air conditioning - The Bay Area has been experiencing a heatwave. It is mind-blowing to me that it could be 98 degrees in Berkeley, and I can drive half an hour to Ocean Beach where is it 65 degrees, and I can also drive half an hour to Walnut Creek where it is over 110 degrees. Thankfully, our beloved portable air-conditioning unit (purchased after a heatwave two years ago) has been doing a great job, which has allowed us to actually enjoy the warm weather.