Better time-leverage

I’ve started using Calendly to help manage my calendar & appointments. Right now, I’m using it bare-bones at the moment, to see if it works for me, because of a singular problem with all of these calendaring-automation tools that I haven’t figured out yet:

It feels dangerously self-important to ask people to schedule their own appointments with me.

I’ve always prided myself on my “human connection” skills within the tech industry, and the UI for all of the various calendaring apps still, in my opinion, feel like bots, not like assistants. Additionally, many feel like they want me to run my calendar in their UI, not work alongside my existing workflow.

Anyway — that’s just really an aside about the point of this post. Being a one-man-shop freelancer/consultant, time management is super-important. I’m also hyper-aware of how easy it is for a single meeting to run roughshod over an entire day’s worth of tasks, depending on its cognitive or emotional load. And so, when I book a meeting, I often then look to be most efficient by having other, adjacent meetings — a day of meetings feels productive. A day with a meeting, then an hour of heads-down time, then another meeting often feels like it was totally wasted.

Calendly, which offers a “buffer” around meetings, which is great — but doesn’t appear to offer any location data — which is important to me because I often (and indeed, usually prefer) in-person meetings. Which involves travel. So, if when booking an appointment, Calendly could ask for a where, then use my office location to calculate travel times, add that to *my* calendar time and buffer around that meeting, it would become vastly more useful.

But once I’m in a location, it would be great if I could schedule other meetings nearby:

  • On a hyper-local level, if I’m having a coffee meeting in Gastown, it would awesome if Calendly connected to my CRM of choice, and see which contacts are near my scheduled meeting (ie, also in Gastown), that I haven’t seen in a while, and send me a note letting me know it might be a good idea to try to connect with them.
  • On a regional/travel level, if I’ve got an upcoming calendar trip to, say, Toronto, check my CRM to see who might be available while I’m there to meet with, and suggest it to me. (next level: find people I don’t know, but suggest I should try to meet them)
  • aside: this is a problem with calendaring I don’t have a good answer for: When I’m away, I generally mark that time in my calendar as “busy”, because I don’t want anyone here to book time with me. but, I might totally want to book time with people there. I want a “busy-in-location” marker, or a “location change” marker to connote travel vs just being busy.

I recognize there’s a lot of data mining/analysis going on there. And, most likely, that’s a service that shouldn’t be provided by Calendly, but rather integrate via API (although, I do think not supporting location/travel time is a big problem for Calendly at the moment). And possibly there’s already services that sit between these data-stores to do just this task that I’m unaware of. And that’s also, personally, an area of interest — software tools that work with existing data-stores for people to help tie them together in interesting ways, and surface helpful things for you, so I think a lot about pulling data out of silos and tying it together.

Gearing up, gearing down

Extroverting while introverted

It took me a really long time — well into my twenties, maybe even early thirties, to learn to respect my need for downtime, both before and after social interactions. It took nearly 7 years of working with the same team for me to feel comfortable telling them of those groundrules for me. Of course, when I told them — they all already knew this about me, I just didn’t know how to tell them. But what was amazing was that by taking the time I really needed, the overall energy and effort these events take out of me has greatly decreased. It just took really looking into who I am and what I needed to function, and then adjusting my expectations for myself and others to accommodate that.

I recently tweeted about my experience participating in a round-table discussion:

And then afterwards, I started to think about why I find these so hard (apart from the obvious “because I’m an introvert”), and how I handle these intensely social interactions — and thought this might be helpful for someone else out there.


Names & Faces: When I know I have an upcoming social event, I try really hard to find out who’ll be there. This isn’t so much about learning things about people, but often just as basic as a list of names, and hopefully photos. This is primarily because my anxiety levels are at the highest when I first enter a room, and thus my ability to remember names & faces at the lowest. If I can do that work beforehand, I’m much more relaxed during that first interaction, and that can set a better tone for all that follows. I’ll often quickly flip through a list of them on my way to the event. Linkedin, facebook, etc — all great tools!

If I can’t get names and faces before an event (as was the case this past Tuesday — I went in totally blind as to whom I’d be meeting), I have a slightly different approach — I try hard not to panic all the way there. This is sometimes successful, but I’ve also been know to take an extra walk around the block now and then too.

Talking Points: If I have names & faces, I often go one step further and try to learn something about the person — not personally, but some sort of professional note. LinkedIn is actually really helpful for this: What does this person do, what’re their skills, where to do they volunteer. Where any of these meet with the circle of my interests, skills, experience, I get a Venn-diagram of conversational-comfort.

I also try hard to quickly scan recent news/media/pop-culture for 15 minutes. Twitter + trends is super-useful for this — I only need to be conversant so that when someone, inevitably, says “hey, did you see/hear/know — “ I might actually, which again — more conversational comfort.

Be Still My Beating Heart: as I approach the event, I almost invariably can feel my heart-rate rising. Calming my thumping heart is a critical thing. For me, quick meditative process works great. I’m really good a quickly quieting, if not completely emptying my mind. My favourite tool for this is music. Headphones on, eyes-closed, listen intently to the song, let the world disappear. Often, one song is all it takes, but it’s incredibly helpful. The takeaway here is that you likely need to find what tools help you quiet the mind, focus yourself, and move on the quickest way possible. Permanent Bliss isn’t the goal here — short-term calm is.


Listen: I used to get really stressed out about this habit, but now, I’ve come to embrace it: When I first get somewhere where I’m going to be dealing with a bunch of people, I just listen at first. If it’s a crowded room — a party, networking event, I’ll get a drink and wander through listening in lightly here and there, using the excuse of my drink to not participate much. If it’s an event like a meeting, panel discussion — I let the other people talk first. If I’m leading something — a seminar, presentation, this clearly doesn’t work, before I’m set to start, I’ll just sit quietly and soak in what’s going on.

I’ve been told that I can be hard to read, intimidating to some — and I think my need to listen quietly, to calibrate is in large part responsible — I’m often fairly stone-faced at this time. So — if you see me, do know that I’m listening and absorbing — I’m just not necessarily ready to contribute yet.

Engage: Once I’ve got a read of the room, it’s time to actually participate. I, oddly, can’t speak about this too directly because I often feel I step “outside” myself, and watch myself participate in ways that I find surprising in retrospect. But, some things I do while present in a social settings:

  • Measure how much everyone (including yourself) is participating. Don’t dominate a conversation. Conversely, don’t stay silent.
  • Look, and call for, unheard voices — This is a “abuse-my-white-male-privilege-for-good” tactic: particularly at business meetings, there’s always someone, usually a man, who’ll just blather self-importantly (make sure that’s not me!). Say something, and pointedly ask someone who’s being ignored to answer.
  • Stay engaged. When topics move on past what I’m interested, I’m prone to zoning out/disengaging, only to find a lot of time has passed and I’m lost. Or, I haven’t participated in a while. Staying present, engaged is a super-important piece of actually being in a social setting.
  • When you’re overwhelmed, take a break: go to the bathroom. Get a drink. Switch groups. Take a 30-second mental time-out. This is directly opposed to the above, but, in short bursts, they help each other.
  • Don’t waste time on people you don’t like. Don’t discount them — that person who just grates on your nerves may actually have useful contributions. But you don’t generally need to waste time engaging with them directly — or minimize where possible.


After an event, I’m invariably wiped out. A day at a conference? No, I’ll skip dinner with everyone & just go for a long walk for an hour, then go to the party. Otherwise, I’m just a mess. After the round-table I participated in on Tuesday, despite the cold rain, I walked home for 45 minutes to try and clear my head. Basically, when I’m done these social events, I need to be alone. I’m no good to anyone, so I try to never continue on to the next event, the after-party, what-have-you, unless I’m feeling really good. For me, even close friends often need to be ignored for a little while — your mileage may vary of course.

For work purposes, this can cause real problems. On Friday, I had a critical conference call, where I had to be on for 90 minutes. The call was at 11:30. It wasn’t until 2pm that I felt recovered enough to get back to work. & that’s totally normal. For me, morning social events are terrible because they often cost me my entire day’s work. A one-on-one coffee in the AM is ok — but I know that I’m going to need an hour or so. But conference calls, round-tables, seminars, presentations, etc? If I know I have one of these in the morning, I try really hard to do one of two things:

  1. Don’t plan on getting anything else done that day afterwards. Or, do only light, mostly mindless work. Chores, etc.
  2. Plan back-to-back socially-heavy things, but treat them mentally as one. A day of 4 conference calls is ok, I just know that’s all I’m doing that day. And don’t plan to get anything done in between.

The baseline: Once you’ve got something social done, take time for yourself, and take all the time you really need, not just what you think is acceptable.

All in all

These tactics/tips may, of course, not work for you. You’re not me. But maybe you’re likewise introverted with a dose of social anxiety on top — and this might help. Or maybe you know someone who is — and you’ve never really got them: I know when I’ve explained some of this to my more extroverted friends, they look horrified at how complicated interacting with the world seems to be for me, versus their own experience, but really, it’s not so bad. It’s just work.

Creating a win

In my job, I do a mix of project work (larger bits, building sites, etc), tickets (service requests from clients) & management (running a company). Historically, I would spend my mornings doing the latter two tasks – they’re all piecemeal items that take anywhere from 5 minutes to 2 hours to complete, then I’d switch over to project work in the afternoon before wrapping up with a little management action – mostly status updates from staff/contractors.

This was ok, except that it really left only 3-4 hours a day to do project work, and in the afternoons which have *always* been less productive than mornings & evenings for me. I felt like I always had a huge pile of tickets and wasn’t keeping up with project work. Partially because we’re so busy, but partially just a sense because with such a short timeframe, I often wasn’t reaching a milestone within a day. And I like checking things off my to-do list.

So earlier this year, I started to push things around, and watch how things fell out. I don’t work fridays, and I don’t launch projects on thursdays (because I don’t work fridays), so I tried to do tickets & non-daily management tasks on Thursdays. This worked out ok for me, but less so for clients – they wanted tickets done before thursdays so that they could review them too. So now I’ve moved my “tickets” day to Mondays. And this has been an epic win.

I discovered that no one minded if I told them that their request would be completed the following Monday – even though they minded when I used to say Thursdays. I think that’s because mentally, Mondays are the start of something, even if it’s the next something, whereas Thursdays are near the end, so people are feeling rushed to finish before the end of the week. And because I’m not in the office on Fridays, there was always an extra dose of staff management, partner meetings & ticket requests to deal with anyways.

So now on Mondays I do tickets, I buy supplies, I check on staff, I check in on clients. I spend all day doing little 5 minute-1 hour tasks. By the end of the day, generally, my to-dos for the week have dropped to only the projects I’m working on and 1 or 2 others. And, rather than feeling stressed because I’m already behind after 1 day, I instead feel accomplished because I’ve cleared my slate and now have 3 solid days of “real” development ahead of me. Days with few interruptions where I can knock off milestones and get that satisfying tick on my to do list.

So I’m not doing any less work, or any different work. But just by examining how I worked, and looking at what clients were expecting, I’ve been able to shift my week around to be, on the whole, markedly more productive than it was prior to my making this shift. I’ve created a win for myself where previously there was generally only failure and “close”. This month we’re experimenting by putting everyone on this schedule. We now have enough staff that every day but Friday has 1 staff member knocking out service requests, freeing the rest of us to just to project work the rest of the week. I’m hoping that we’ll not only maintain our current turn-around-times for service requests, but potentially actually get a little faster with this system, even though each staff is spending only 1 day a week, rather than little bits of everyday.


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