Current email, calendar and task list setup

I use a few tools to help me keep on top of my email, calendar and task list. These are in addition to the basic Gmail and Google Calendar services.

Airmail – I’ve always preferred having my email in a client rather than in the browser and the cleaner and simpler the better. Airmail does the job very nicely if you’re a Mac user.

Sanebox – the filters/tabs for ‘promotions’ and so on in Gmail don’t really cut the mustard for my inbox – I need something that can spot just the important messages and filter out the rest. I also like to be able to have a set up where I only look at unimportant messages once a day. Sanebox does all of that and has some great other features too.

TextExpander – part of my job involves saying the same thing to lots of different people and so saving snippets in TextExpander saves me a lot of time. You soon remember the keyboard shortcuts to paste whole messages and then tweak before sending.

Motion – I’ve found that the best way for me to manage my task list is to allocate time for things directly on my calendar. Motion is the most intelligent way of doing that I’ve come across. You add things to the task list and then it automatically allocates them to a free slot in your calendar and updates as things change. Really helpful for less urgent but important recurring tasks.

HubSpot – we use Hubspot for a lot of things at work and I prefer their meeting booking experience over the other options I’ve tried. It means you can send a link to people for them to choose a time for a call.

I recommend all of them but also keen to hear if there’s anything else I should be trying!

Chasing Andrew

Adventures with my AI personal assistant

I signed up to the waiting list about a year ago. I was visiting Craig and Kanyi at the Collaborative Fund in New York and Craig had simply copied ‘Amy’ into our emails to sort out the details. I noticed the strange email address straight away and did some digging. Amy it turned out was an artificial assistant created by New York based company The process worked without a hitch and I remember thinking how unremarkable the whole experience was.

Even though I knew Amy was an AI, I remember feeling that I should be polite to her. I generally make a point of thanking all the PAs who arrange meetings with other people for me and treat them in the way I would treat the person I’m meeting. It was hard to shake that habit.

Fast forward nine months and I got the email saying that I could now use Amy too as the beta trial grew. I’d actually forgotten I’d signed up (nobody else I’d met had been using in the period between), but I quickly clicked on the link and went through the very simple setup process of sharing calendars and answering some basic questions about common types of meeting (how long they should be, favourite locations etc). I also got to choose whether I wanted Amy or Andrew and decided on Andrew.

Then I got a bit stuck. It was not so much that I’d never had an AI personal assistant before — I’d never had a personal assistant at all.

Before trying it out on others I felt I needed to give it a quick test so sent my colleague Vicky at BGV an email suggesting we go for a coffee and that Andrew (cc’d) could arrange a time. Now Vicky in a past life used to be an executive assistant so I thought she might be intrigued. In fact she was just rude and deliberately awkward making Andrew’s task all the more difficult by changing her mind and suggesting venues that she knew wouldn’t work. Andrew gave up and politely ‘reverted this one back to me’.

Next I tried letting him organise a few phone calls that weren’t time sensitive and Andrew did fine. Then a few coffees, which also went fine. I didn’t ever use it for my social life — that would seem a bit weird to me — and if it was a really important meeting I still did it myself.

I did a bit of maths and realised scheduling takes about 5-10% of my working day so anything that can reduce that is very valuable. It’s also a real drag — even the PAs I know would rather do more valuable things if they could so my feeling at the moment is that is creating job displacement rather than job replacement.

Most people I meet who have interacted with Andrew want to talk about it and they usually only have positive things to say. A couple of people didn’t notice that he’s an AI at all and a lot of people have asked if I can get them bumped up the waiting list (I can’t).

I’m not sure whether I’ll go all in and let Andrew organise all my meetings. It’s going to take a bit of getting used to but the barriers are more human and social (what other people think) than technological. It’s not quite ‘Her’ or ‘Ex Machina’ but it does feel like the future, albeit in a very mundane way.