When privacy and entitlement collide in the work calendar

Taj Moore
7 min readJun 10, 2020

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An intersection is blocked by emergency vehicles and surrounded by traffic
Photo by Kevin LEE on Unsplash

It started with a seemingly simple request: we should all open our Outlook calendar privacy setting so that we can figure out when people are available to meet. Currently, everyone’s calendars show an ocean of “Busy” because Outlook doesn’t differentiate between a committed “yes” and a “maybe” or non-response.

What I heard was a desire to ensure that colleagues can request appointment times from each other with as little friction as a possible.

I also noticed the request came with an insidious imperative … should. If you want to get my attention and raise my hackles, tell me what I should be doing as if you have it all figured out. I don’t want anyone “shoulding” on me or anyone else. (Full disclosure: I’m a hypocrite — I do this myself.) That word got me thinking and pointed the way to some invisible assumptions that obscure how complicated things truly are.

Assumption of matching values

What may seem normal, reasonable, or common sense to one person may seem imposing, unreasonable, or out-of-bounds to another. Different values can create tension. That tension can be creative or destructive, depending on how great the tension is. Not everyone has the same values, even if we are subject to the same incentives, conditioning, or controls within a (corporate) culture.

Assumption of entitlement to time

Many people operate with the assumption that unstructured time in someone else’s calendar are free to be booked. (I default to this assumption, myself.) Taken to its extreme, however, this assumption can create a sense of entitlement to other people’s time. When someone has a lot of unstructured time, an hour might not feel like much. To someone whose every minute is accounted for, an hour can be precious, even priceless. The marginal value of an hour depends on the recipient of a schedule request, not the person making the request.

To further complicate matters, some people already have more more time pressure than shows up on the calendars. Parents have carry an load with home life (especially now that parents are all at home with their children). The lion’s share of unaccounted parental duties fall to women. Underrepresented minorities also end up with a lot of extra uncounted time devoted to “second-shift” duties, emotional labor, and all the heavy lifting that comes from having less privilege in the working world. Even when people with extra work aren’t physically occupied with that work, there is always an extra cognitive load that can affect every waking moment.

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Personally, my day sometimes includes time answering questions from my child, feeding him, or generally making sure things are happening the way they need to on the home front. Any time I don’t spend doing all of this falls to his mother, because his needs don’t diminish … they actually increase. (Truth be told, most of the time it falls to his mother, which is problematic on a number of levels.) I don’t schedule this time because family needs don’t arise on a schedule.

Also consider that people need time to think. The CEO of Salesforce schedules two hours every day for deep work. That sounds like a luxury to me. I’m glad he’s setting the tone, but I find it hard to imagine people further below him able to command their time so publicly. For those of us that might schedule time to think, it can be helpful to keep that private so that we don’t receive requests from people who don’t value that time the same way. It can be hard to say no to requests for our time; it requires willpower; and studies show that willpower runs out.

Assumption of self-determined privacy

A woman’s hands type on a laptop computer
Photo by Kaitlyn Baker on Unsplash

If you want to maintain privacy on the internet, you don’t achieve it solely by using a VPN and some anonymous browser like Tor. You gain privacy by blending in. Even with the above methods, you still need to leave a digital signature that doesn’t stand out. If you stand out you become traceable, which removes some of the privacy you were after. And even though you might have nothing nefarious to hide, there can be a presumption of guilt. Calendars are not so different. If private calendars are normal, then private calendars don’t stand out. If open calendars are the established norm, then private calendars can raise questions.

Some people feel relatively secure in how they spend their time: they might not have family concerns impinging on their schedule, no particular needs for self-care, nor any other considerations that take them away from work during typical working hours. Other people have myriad things vying for their time during the day, some of which need to be added to the schedule and yet need to be private. Some of those people already face extra scrutiny, for reasons such as gender, race, ethnicity, religion, or stigmatized physical and mental health conditions.

For many, these are not issues that can be discussed with one’s team, manager, or HR department. It not only takes trust to have the psychological safety to discuss parts of one’s life, it takes evidence that it’s actually safe. That team, manager, or HR department might very well be the people they feel the least safe with. I have had experiences where I felt hesitant to reveal myself in my work; when I did finally find enough trust to reveal myself, I experienced negative repercussions. At the same time I have also experienced hardship from not being more revealed and therefore not getting the help I needed.

The stress of a double-bind like this becomes a problem unto itself. It’s a problem for underrepresented minorities of all kinds, out of fear that it can validate the biases, assumptions, and stereotypes that other people might have. It’s even a problem for White men, who may have been raised to keep emotions hidden when the opposite is needed. It only takes one moment of vulnerability and feeling betrayed to have permanent effects on psychological safety.

If we are to work against the other people’s presumed entitlement to our time, we need privacy. And if we are truly to have privacy, we need others to regard privacy as normal.

(I should mention that keeping personal appointments on a separate calendar is not an option because there would be nothing to prevent that time slot from being double-booked, unless it were also kept on the work calendar.)

A narrative user story

I am hopeful. Because this is work related, and because I practice product management for a living, I look at this through a product lens. I want to solve problems in fundamental ways, first by making sure we frame the problem, and then by identifying what “good” and “done” looks like. The following is the user story I would use to solve the calendar problem.

People walk along a plaza decorated with a massive calendar
Photo by Curtis MacNewton on Unsplash

Why

Everyone on a team is using Outlook to schedule time with each other. Everyone receives numerous calendar invitations that they don’t always have time or inclination to respond to — many calendars are filled with committed and uncommitted invites. But when people’s calendar visibility is set to private, Outlook shows any event that hasn’t been declined as “Busy.” At the same time, systemic biases find their way into business culture and leave many team members feeling greater scrutiny than their more privileged counterparts about how they spend their time, leaving them inclined to keep their schedules private. And, those same people may face a double-bind if they become the only category of people to keep their calendars or appointments on their calendars private. Therefore…

As a work team member
I want a way to find available times on people’s calendars
So that I can book time with colleagues to meet

Acceptance criteria

Scenario: Looking for a common time

Given a colleague’s calendar is private AND includes invitations that are rsvp’d yes AND some invitations are rsvp’d maybe OR some invitations have no response
When someone looks for an available time to invite that colleague
Then they can see which times are committed to other appointments AND which times have been requested but not committed

Scenario: Requesting a common time

Given a calendar includes few blocks of available time AND the calendar is set to private
When someone is unable to see a common time when their calendar request may fit a colleague’s schedule
Then they have a way to reach out to ask if there is a good time for that colleague to meet

Scenario: Rethinking privacy

Given some colleagues have calendars that are open AND some colleagues have calendars are private
When someone encounters a calendar that is set to private
Then it is considered normal, professional behavior

Note

The desired outcome is booking an appointment. One output is a system request for time, but the outcome might not be available until having a conversation. A request for time that looks available does not guarantee a “yes.”

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Taj Moore
Taj Moore

Written by Taj Moore

Writer and advisor with expertise in product leadership, organizational transformation, design, and tech.

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