Clockwise is okay automated calendar wrangling

The main thing I remember about having an EA for a year was the way my calendar became less a miserable time-sink with the stink of guilt and more a magical, ever-updating guidepost for the day.

The EA and I established a few ground rules: At least 30 minutes for lunch, please never move a 1:1 with one of my direct reports, and please herd things toward the morning where possible. Those understandings in place, it just became my job to go where I was supposed to be.

It has been a few years, and I still feel that loss pretty acutely. Putting together a meeting can take a lot of time, and there’s a tendency to just pick the time everyone’s available, which means that your meetings are creeping earlier and earlier, or people are just helping themselves to half your lunch.

The other problem you end up with is that you have all these extraneous 30 minute blocks that you delude yourself into believing can be productive time. But by the time your last meeting ran over, you’ve sent out notes on the meeting or followed up on something that came out of it, and get a glass of water, you’re just in time to start your next meeting. So the “real work” gets pushed into lunch, or after normal work hours, or in little slices here and there, and then it’s not really quality work because it feels like it’s “extra.”

I’ve tried, a few times, to go straighten out my calendar by consolidating as much time as possible for focused work, but that is laborious and sort of fragile: I invariably book over an odd monthly 1:1 because I didn’t check the time far enough ahead, or don’t notice the other person has a can’t-miss every other week.

I’ve also tried a few iOS apps meant to help with the problem of calendar fragmentation, but they weren’t super smart and were tied into the Apple ecosystem in a way that made me suspicious of them because I am suspicious of how well Apple’s Google Calendar integration works and mistrustful of it working well enough to turn my back on it.

Recently, though, I was trying to find time with a colleague and she said “feel free to book into my focus times … I have an app that puts them there for me,” and that’s how I learned about Clockwise, which is, at root, automated defragmentation of your Google Calendar. After three weeks, I’m a pretty happy user and I’m willing to recommend it to other people, even if just to find some fatal flaw I have not yet found.

The core concept behind Clockwise is that fragmented calendars kill productivity because they don’t allow for uninterrupted deep focus. Clockwise at its most basic is just a tool that goes out once a day, looks ahead at your calendar, and tries to find ways to consolidate all those 30-minute blocks into a longer, more meaningful chunk of focus time. When everything lines up, it shifts calendar items around then protects the focus time it has found for you.

I would be pretty happy with it if all it did was moving meetings around behind the scenes, but there are ways to imbue it with a little more intelligence:

  • You can tell it your meeting hours by day. Since the R&D org I work in has a “no meeting Friday afternoon” policy, I can tell it not to book anything after 12 on Fridays.
  • You can tell it the time range in which you’d like lunch to fall, how long lunch can be, and the shortest acceptable amount of time lunch can fall back to. For instance, I have it set up to consider 11a to 1:30p to be acceptable lunch times, that I don’t mind going as long as 45 minutes, and am also fine if it’s as short as half an hour.
  • You can tell it which meetings are okay to put on “Autopilot,” and which are not. That’s great for two reasons: I prefer to keep 1:1s with my directs or mentees relatively sacred, because I want people to feel like that time is truly their time for them. Second, people have to plan to do work for some meetings, and it can feel disruptive to plan out your work in anticipation of meeting at one time, only to have it shift.
  • You can feed it a few other parameters, such as when you prefer to have focus time (morning, afternoon), how much you’re okay with it moving a given meeting, and whether it should hold travel time.

In addition to those extra smarts, it can do things like color code your meeting types (1:1s, team meetings, one-offs, external attendees), and you can connect your personal calendar to it so that you don’t have to do double-entry for personal appointments: It just blocks them as “busy” so that the time is protected, as is your privacy.

It also shows you the occasional bit of data: How much focus time it found for you, which meetings it moved and why, and who else in your org is using it. One thing I appreciate about it is that it seems to think in terms of finding focus time for other people, too. So the notice I just got telling me that it had moved a meeting explained that it was looking for focus time for me, and also found a time more convenient for the other person, too.

Some caveats and attendant best practices

There’s a certain kind of corporate citizen who is pretty good at optimizing their own life, is blithely indifferent to the suffering that may cause for others, and can even become tetchy or hostile if you do anything that breaks whatever brittle life hack they’ve discovered. Clockwise could be terrible in the hands of these people, and could, worse, sort of paint you to be that kind of person without you even realizing it. During my three weeks of use, I’ve thought about a few ways to use it and how to establish norms around it if a group of people are using it:

  1. It will offer to book all your time for you if you let it, but it will also ask for a max amount of focus time. I do not ask it to book every spare minute so I can balance my need for interrupted “flow” time with other peoples’ need to talk to me outside scheduled meetings. If your goal is a more networked, less hierarchical organization, you should make it easier to communicate outside of a rigid meeting framework, not harder.

  2. You can tell it which meetings can be on “Autopilot” and which should not be. As I mentioned earlier, there are certain kinds of meetings where, if you’re the person with the power, you should consider signifying the importance of that time by not giving it over to a robot to manage. Some people, in my experience, also look to the weekly 1:1 with their manager or mentor like an oasis; or they gauge their emotional energy for dealing with some frustration or setback by how long it’ll be until they can get some help from their manager without going outside the 1:1 cadence.

  3. It’s good to communicate to people that those focus blocks are important to you, but not necessarily inviolate. For my department’s “No meeting Friday afternoons,” for instance, I put this message in my calendar:

“The R&D organization observes a ‘no meeting Friday’ on Friday afternoons. We get that folks from other groups might need to schedule during that time, so please do check in via email or Slack if you need to book into this time.”

Clockwise doesn’t have a way to add a message to focus time events, which is unfortunate because I’d like to be able to just set that norm/expectation automatically. I guess I’ll go find the feature request form. In the mean time, Clockwise does allow you to toggle whether those focus blocks are marked as “busy/unavailable” or “free to book.” Once a group had adequate norms around what “focus time” means to each other, that toggle might be enough.

Final words

At our last 1:1, my boss asked “how’s your battery?” As I thought about my answer, something that kept popping into my head was that recently I’d felt like I’d been getting a lot more done, and so my battery felt pretty good. Like, definitely tired at the end of the day, and definitely going pretty fast on some stuff, but there’s the kind of tired you can get from just knocking stuff down and the tired you can get from feeling like there’s a lot of heat loss, and I reported I was definitely feeling the former.

As I thought about why, I realized it was because for the past several weeks, Clockwise had been finding me these two hour blocks and I was taking advantage of them. Most of them. The first one it found, I actually decided to take a breather and went to the lounge chair I keep in the corner of my office and I fell asleep. After that, I’ve gotten better at just doing a lap around the house, making a cup of tea or grabbing some water, reading the headlines or triaging mail while I waited for the tea to steep, and then spinning up for a good 45-minute block before taking a midpoint break for a few minutes.

The kind of work I was doing in those protected spaces felt better, too. I needed to review some work from someone doing that kind of work for the first time, and I felt more patient and able to just share notes and feedback instead of battling myself over whether to just do it. When I got stopped because I needed to ask a question or do some research, I was able to ask more thoughtful questions. When asked for thoughts, even outside of that focus time, it was easier to slow down and answer them because, I think, having those uninterrupted blocks has an effect on your overall rhythm and cadence. Maybe it’s just knowing that by having a two hour block coming up, you don’t have to ruthlessly optimize every second of your day.

So … several weeks of Clockwise use has been a good experience for me. I definitely recommend it for individual use provided people follow some of those best practices I mentioned, or at least agree to norms around it.

I also see people around me beginning to use it, and see that it has some team-based functionality I haven’t even tapped. The individual use experience has been so good, I’d love to experiment with it managing the meetings of a defined group.

Copying Excel formulas I can never remember into gists: Management apotheosis complete.

Some Notes on How to Listen to People

Last year I was asked to put down some thoughts about how to have an active listening practice as a manager or leader. This has been knocking around as a Google Doc for a while because after the talk I meant to get back to it as a bigger project. Until I can get my thoughts in order on that, I’m going to just put this on the public web.

People deserve to know their choices. Focus on that instead of fixing things. 

Nobody likes it when people who do good work leave, and some people don’t even like it when people who do mediocre work leave. During a time when there’s a lot of focus on attrition or concern about morale, people will sometimes soft-pedal bad news, avoid making hard decisions, or try to defer unpleasant or hard conversations to keep everybody happy. 

When you do that, though, you’re just kicking the can down the road and possibly withholding what people who are genuinely unhappy need to get “escape velocity,” make a decision, and move on. 

Don’t withhold in the hopes they’ll just calm down for a while. If they’re faced with a situation that simply isn’t going to change, they should know that, whether it’s “that’s not how we work here anymore,” or “we’ve made that decision and aren’t revisiting it.” 

Anything less is just allowing them to stay in a state where they think something will change that won’t, and it’s keeping them from making a better decision than “hang around until the thing I hate goes away.” 

You’re having these conversations because there are strains in relationships, and you should be working to make those relationships whole again

People will always need someone to talk to, but the list of people you’re talking to at any given moment will change. 

Ideally, you’re giving them someone to talk to, and encouraging them to take their problems to the person best equipped to solve them as they’re able to get enough perspective to do so. You engage in constrained and discrete action or intervention as a last resort. 

In other words, the interactions you’re having with any given person aren’t the desired end-state: It’s an interim situation. 

Some rules

You have to sit and listen

It’s tempting to come to think of yourself as a fixer, whether it’s of a broken manager/report relationship, a system or process, or even just someone’s faulty perspective. 

When someone first agrees to sit down with you and tell you what’s going on, though, the thing they’ve asked you to do in that moment is listen. They might ultimately want you to fix something, and the hope that you’ll fix something is probably part of why they’re sitting there talking to you, but in that moment the thing they want you to do is listen. Their problem probably feels unique to them, in the particulars if not as a general kind of problem. Something about it feels like it’s outside their experience or ability to handle, or they’re simply not sure what their expectations should be. 

Just listening can be pretty hard. You might have some idea of what their problem is before they even begin to speak. You might be able to see where they’re going before they get very far in to what they have to say. It’s important to let them talk it out: They need to talk through their feelings and they’ve asked you to help them do that. Sometimes they’ll even talk themselves into a solution or end up better understanding what they want to ask for. 

You don’t always have an answer, and you need to admit to that

Sometimes you don’t know. It’s okay to say you don’t know and need to go learn more. 

You have to learn how to find the balance between acknowledging their feelings and being part of a management team

Sometimes, you’ll believe another manager made a mistake in their handling of a situation. The times that’s obvious and clear-cut are pretty few. More often, there are a bunch of perspectives on the problem. In some ways, it just doesn’t matter: Your primary function in the moment someone has brought a problem to you is to listen. (If they’re reporting unsafe behavior or a violation of policy, you definitely need to escalate.)

It’s still possible to show empathy and kindness without making comment on a colleague’s decisions: 

“How did you feel when they said that?”

“How do you feel now?”

“I understand that didn’t feel great. Looking at it from your perspective, I’m not sure I’d like that either.” 

You can’t ambush your colleagues with the things you learn

To most good managers, having a good understanding of the dynamics on their team and the state of the people on the team is essential to their professional self-respect. When it turns out they’ve missed a situation, or the fact that one of their folks is having problems, it can be embarrassing. 

One way to make sure people are in a good place to take in what you’ve learned about a situation on their team is to share it with them discreetly, not around a meeting table where they’re hearing about a problem at the same time as everybody else. If you use information you have about their team dynamics or one of their employees to show them up or contradict them, all you’re doing is creating resistance to finding a solution. 

You’re listening to everybody, but you have a network and need to acknowledge that

Even if you’re touching base with a lot of people, you probably have a few people you talk to most. They’ve got a particular perspective and while they may be pretty key and influential people, it’s still just their perspective you’re hearing. 

When asked “what’s going on on the floor,” acknowledge that: “The folks I’m closest to are saying this but I’ve also heard that.” 

A Workflow

When someone needs to talk, there are a few things you have to do: 


Just listen. Try not to say much outside the usual “active listening” stuff:

“What did you do next?”

“What went through your head when you heard that?”

Stay off your phone and stay out of your laptop, or set an expectation (e.g. “my son needs to call me from school this afternoon so I’ll have to pick up my phone when I get a notification.”)

Play it back

Once they’ve told their story, playing it back to them in a few sentences shows them you were listening and helps ensure that you’ve actually spotted the issue. You may have missed it, especially if you went into the interaction thinking you already knew what the problem was. 

Just play it all back in a few sentences, and make sure you got it all:

“What I heard was a, b, and c. Did I miss something in there?” 

Keep your own emotion out of it

Sometimes people bring some stuff that’s frustrating to hear. A lot of strong emotion from an authority figure can put people on high alert, or cause them to shut down. They’re often afraid they’re going to trigger some sort of reaction out of proportion to what they were hoping for. It’s not wrong to show empathy, or say “I can see how that would be upsetting,” (or frustrating, frightening, etc.) but don’t take on their emotions (that’s bad for you) and don’t make a big display of your own anger or frustration (they’re there for help, not to watch you process your own emotion). 

Let them know what they can expect

Our open door guides tell managers that they have a few obligations to people who escalate an issue to them. I generally relate the important ones or encourage the employee to review them so they can have an idea of how I’ll behave. 

I always make clear their story stays with me unless there’s a policy, legal, or safety issue. Some managers don’t like that, but it’s one way to insulate the person doing the listening from being turned into a back channel: If the employee was hoping for that back channel, they know they won’t get it. 

Call it out when what they saw was wrong or unusual

Sometimes, you’ll learn of things that are plainly unprofessional or inappropriate. It’s not wrong to offer an opinion. Just make clear that it’s your opinion. 

I once dealt with an employee whose manager a. claimed that there were secret criteria for being promoted that he couldn’t tell her and she hadn’t met; and b. told her teammates she wasn’t mature enough for promotion. 

I called those things out as a. untrue and b. inappropriate. I made clear that she had an expectation of confidentiality around performance conversations, and that the behavior wasn’t normal for managers at Puppet. 

Ask for permission to raise the issue with people who can fix it

Our open door guides make clear that this is a core expectation on managers. Again, we don’t want to be used as back channels for manipulation, and it also reassures people there asking for help with problems they can’t resolve that they won’t get someone in trouble or “call down the thunder” when they aren’t even sure there’s really a problem. 

Set expectations

Tell them:

  • Who you’ll talk to, if they’re okay with that
  • What you propose as a next step
  • What you’ll do next
  • When they can expect to hear from you

Follow up right away

Let them know once you know something useful, whether that’s “this is fixed,” or “I can’t do much more here, but here’s who probably could …”