Cortana – Two Years Later

Being a huge productivity nerd, I like to regularly review the systems I use to ensure that I am getting the best out of them. In December 2015 I sat down to do my yearly review of my productivity system. One of the tools I had on my list was Cortana.

Reviewing Cortana as a Productivity Application

Something about Cortana is different to other tools I use like Outlook or Wunderlist – the very nature of her being a personal assistant means that she’s more of a single interface to many other things, rather than just an “app for email” or an “app for tasks”.

The very fact I have chosen to refer to Cortana as “her” in this article proves that she’s not just an app to me.

It was obvious to me that I wanted to continue to use Cortana, but I also realised that I wanted to dig a little deeper into what makes her useful, and what I would like to see improve.

This month marks two years since I first started using Cortana, so I figured now would be a great time to step back and look at how my use of Cortana has changed over time and where things are going in the future.

Humble Beginning

I remember watching Joe Belfiore reveal Cortana to the world in April 2014. She had more personality than Google Now and was more personal than Siri. Microsoft’s entry to the personal assistant category was well anticipated and rumours had been circulating for a while.

Joe Belfiore introducing Cortana

My first real exposure to Cortana was on my Lumia 920. At first, I had to change my regional settings to the United States in order to get her fully functioning on my phone. There were a few side effects from making this change, but I immediately decided it was worth it in order to have this new experience.

“Hi, Cortana!”, April 2014

I asked her for facts, told her to make phone calls, and got her to remind me to do things when I arrived at various places. The speech recognition at this stage was extremely good and Cortana replied in the sassy American voice I recognised from the Halo series of video games. Because I was already invested in the Microsoft ecosystem, she already knew my calendar appointments and favourite locations. I was immediately comfortable and the animated circle became a familiar feature of my phone in no time.

Microsoft’s initial vision for Cortana set her out to behave like a real personal assistant – to be like a loyal employee. The aim was to build a proactive software agent to help people get things done. I felt that things were heading in the right direction.

Windows Phone 8.1

When Cortana came out in the UK properly, I naturally switched my regional settings back to UK English. Part of me was a little disappointed that Jen Taylor no longer voiced Cortana. In my eyes, she lost a little bit of her personality and became more formal with her ‘BBC English’ accent and mannerisms.

Cortana on Windows Phone 8.1

“Cortana comes to the UK”, August 2014

I eventually got used to it, but it did show me that the way a computer speaks to us is important to how the relationship works.

If we are to assume Microsoft’s vision of Cortana as a personal assistant or a loyal employee, I had been building a working relationship through this characterised interface over the last few months.

When Jen’s voice was taken away from me – I think I lost a little piece of Cortana.

Cortana on Windows Phone 8.1

Voice aside, everything was good and features got improved over time – events like the World Cup were added, general chitchat was updated regularly, and most importantly, Cortana got better at being predictive. Information was shown as soon as you tapped on her animated tile, bringing up traffic and weather information without even needing to ask.

Cortana Today

While I am still pleased with Cortana over all, I would be lying if I said I completely satisfied with the progress that has been made.

Cortana on Windows 10

Cortana has moved from Windows Phone 8.1 to a new unified Windows 10 platform that works on both the PC and phone, but along the way there have been some casualties in her features.

A lot of these casualties are cosmetic, for example, Cortana’s circle used to give a sad emotion animation when you had to edit some text that she’d failed to recognise correctly. This little detail was subtle but extremely powerful – a surprising amount of emotions can be shown with animated circles.

Cortana's Live Tile on Windows Phone 8.1

A more substantial example is that Cortana’s Live Tile (shown above) for Windows Phone 8.1 was actually useful – her circle shape would morph into a sunshine animation to let me know the weather, or she would show me when to leave the office in order to beat the traffic directly on my start screen without even loading her up. You could even pin individual items like weather or news as Live Tiles, acting as a deep link into Cortana directly from the Start screen.

Cortana's Live Tile on Windows 10

In Windows 10 this all seems to have disappeared. There is very little animation on the Live Tile (shown above) and the only information that ever appears seems to be the current news headlines – something which I have disabled due to the lack of customisable news sources. (Google Now has gotten really good at this!)

Asking “How many calories in a Coke?” used to work, but now it doesn’t. Why?
Who knows? she just forgot.

Possibly more a fault of Bing than Cortana – some relatively simple questions like “How many days until 2017?” do not work at all.

One of the most bizarre issues is that asking “What time is it?” takes me to a Bing search page, rather than having Cortana tell me the time.

Interestingly, when I say to people that this question doesn’t work as it should, I am often met with resistance. People often state that I can look at the time on my watch (or Band) but this completely misses the point of this interaction.

If I’m using my voice to talk to Cortana, I expect her to reply using her voice too. Strangely, asking “What time is it in Texas?” yields the time over the pond. Why can’t I just get the time where I am?

What time is it?

When she does reply with her voice, the experience isn’t that great anyway. For some reason the screen is always activated even for voice only replies. While this doesn’t negatively affect the interaction in most cases, turning the phone screen on while the device is in my pocket is a recipe for disaster. I don’t know why the proximity sensor isn’t used to make a decision about illuminating the display.

I have other issues too, but to keep this article from getting too long I’ll just list a some of them out:

  • She doesn’t understand how to spell my girlfriend’s name, there is no way to correct her.
  • I don’t work on public holidays! Stop telling me it’s time to go to work!
  • Saying “Hey Cortana” doesn’t always work. This needs to always work.
  • Microsoft Health integration is only in the US for some reason.
  • Cortana is unusable from Microsoft Band when using Windows 10 Mobile.
  • You can’t set a default location if your device doesn’t have a GPS (unless you use a Fake GPS driver!)
  • She doesn’t sync her tasks or reminders with Wunderlist.
  • For some reason she asks me where I live and work over and over again. Anyone else get this?
  • People in the UK obviously don’t need parcel tracking.
  • There is no way to remove awful news sources like the Daily Mail from turning up, so I have to disable all news features.
  • How does she still not understand Formula 1? It’s a big sport with a world-wide audience!
  • She can shuffle all my music, but can’t play music by mood? Who shuffles 10,000 songs anyway?

Okay, so this may sound like a long list of complaints but this is only because I want to see Cortana be truly great. I feel like the current iteration has been a step backwards in some ways.

Trip Planning

Cortana’s core functionality is still extremely useful and I regularly use her on my Lumia 950 XL and on my Surface running Windows 10.

Cortana in the Windows 10 Taskbar

I also use Cortana inside of Microsoft Edge. You can right click on an element and “Ask Cortana” about it. Note that she’s smart enough to take in the context of the whole page too. You can even do this for images.

Building Cortana directly into apps is one clear way that Microsoft can improve the platform and I’m looking forward to seeing more of this.

Cortana in Microsoft Edge

What we know is coming

Microsoft’s Build conference has just passed, and at it we saw a number of announcements on, what the company is calling, “Conversations as a Platform”. A big part of this strategy is improving Cortana.

Conversations as a Platform

Marcus Ash gave a great demo of some of the new features coming to the Anniversary update of Windows 10, including Cortana working on the lock screen, as well more Google Now inspired cards, and the ability to include more app integrations directly into actions which are surfaced directly in Cortana’s UI.

As part of his demo, Marcus showed some very interesting new experiences where Cortana was integrated into a previously unseen version of Outlook. Not only did Cortana have access to the calendar, she had access to email too – even surfacing tasks directly from email messages. I like the look of this proactive Cortana, and this is something that directly relates to my original task of trying to review what Cortana means for my productivity.

Cortana integrated in Outlook

Another useful feature was where Marcus asked Cortana “What toy store did I go to last year at Build?” and she found the toy store he visited last year when he was in San Francisco. The potential of this is really great and I like the idea of Cortana’s memory being improved.

The demonstrations shown in the keynote were only some of the upcoming Cortana features in the Windows 10 Anniversary Update. Other sessions throughout Build showed Cortana’s integrations in the Windows Ink Sticky Notes as well as the Action Center. Cortana will also manage some of the cross device features, like being able to do text messaging from a PC and getting notifications on the PC when the phone’s battery is low. She’ll also take on navigation duties in the Maps application – replacing the more generic sat-nav voice with her own.

Microsoft’s “Conversations as a Platform” strategy doesn’t just include Windows though, and there was a great demonstration of another application which is already commonly used for conversations – Skype.

Lili Cheng showed a demonstration of a future version of Skype which had Cortana directly built in. As part of this new integration, Cortana is always available and is able to keep track on conversations and contacts. This is similar to the proactive help offered using the Outlook integration mentioned above.

Cortana integrated in Skype

My favourite part of the demonstration was when Cortana was able to work alongside a third party bot in order to complete tasks. Using bots like this is something that interests me greatly – and there I will write more thoughts on this in the coming weeks – but I really like how Cortana can act as an agent in order to get things done.

Bots are going to be an important part of Microsoft’s “Conversations as a Platform”

What I’d like to see

In a lot of ways, the demonstration of Cortana working inside of Skype effected my thinking the most.

It’s now clear to me that the instant message-like conversation is a superior method for communication with Cortana. While I do like the proactive canvas which is launched when you open Cortana in Windows, having a single entry box and an answer that just disappears into the void is extremely unsatisfactory. Moving from the simple “Ask me anything and get a result” interface into a back and forth conversation will unlock so much potential in Cortana – it will be a lot more how you’d talk to someone (like a personal assistant) over Skype.

Conversations with Cortana

But just having a list of messages sent back and forth is not enough – Cortana has to remember the conversations we’ve had. That way, when I correct her on spelling my girlfriend’s name, she’ll remember it for next time. It’ll give her the context to make the best decision on the instruction I have given her via my voice.

When you think about it, it’s pretty crazy that Cortana can go through my calendar and look things up, but can’t remember things in the conversations we had.

I’d also like to see Cortana integrated into the Microsoft Band more deeply. There were hints at this kind of feature in the Microsoft Future Vision video from 2015. It depicted a future version of Cortana sensing that the user had gone “into the zone” and automatically blocked unwanted distractions.

“Future Vision Redux”, November 2015

It’s also pretty obvious to me now that the voice interface in Cortana needs to move into a more natural language model. When I talk to her through my headset I’d like her to be able to continue the dialog without me having to switch to my phone. All of this conversation should go into the same chat history which she’ll remember and can be used to improve conversations over time. This will also unlock completely voice only devices like Amazon’s Echo.

I’m still a fan

Overall, I do still enjoy using Cortana, but I feel like the upgrade from Windows Phone 8.1 to Windows 10 has not been kind to her.

I hold out hope that Windows 10’s position as the base version of Windows moving forward means that the days of the big platform changes are over, and the various teams working on Cortana can continue to do so without having to rewrite components over and over again.

Cortana will continue to be part of my daily workflow and will continue to be one of my main tools for productivity.

I wonder where we will be in another two years.


I had been looking at a replacement for Outlook tasks for the longest time. Since Windows Phone 7 came out, Microsoft’s mobile offerings for Outlook tasks have been… sub-optimal.

I had heard of Wunderlist through sites like Lifehacker and The Verge, and in 2014 6Wunderkinder released a new real-time sync engine as well as new beta versions for Windows Phone and Windows 8. I thought it was about time I switched from Outlook, so I gave it a shot.

A year later and I’m still using it every day.

Wunderlist is intuitive and easy to use. The free version does more than other apps, and it’s totally cross platform with first-class apps for Apple’s platforms (including Watch), Android, Windows and the web. It features recurring to-dos, subtasks, reminders, due dates, multiple lists and folders to organise them. Smart views let me order the to-dos by today or this week. This is where I spend most of my time when actually doing things. I like working through to-dos in due-date order, across all of the lists.

The latest new feature was a Wunderlist API. Integration with Slack and Sunrise has been useful, but I’m still waiting on integration with Outlook (coming soon) and IFTTT.


Now Wunderlist is part of my Action Management System and vital to how I get stuff done. Here’s how I have it set up.


The Inbox is where I collect any of my to-dos as I record them. I try to keep my inbox fairly minimal, so I regularly review it. I often put links or other small reminders to myself in here and check them off without ever organising them into folders. The way I use inbox is in a similar way to my email: it’s a great collection point, but it should be regularly emptied – either by doing the to-do, or organising it into one of my folders.


Anything that takes longer than a couple of minutes goes from the Inbox and into here. Pretty much anything goes, as long as doesn’t fit into any of my other lists. I regularly review this list to add due dates or subtasks.


Daily, weekly, and monthly habits are stored here. All of these to-dos are recurring, so as soon as I check them off they return for the next date. For example, every week I review my finances and every month I review my projects list. These will appear on my weekly smart list as they need to be addressed.


There are often things I am thinking about doing or getting which are either just ideas or not feasible right now. This is where my wish list comes in. Putting items in here gets them off my mind into a place where I can review regularly.


This list keeps track of any items I’m waiting for including Kickstarter projects, deliveries, book and music release dates and other things like that. I also use list to keep track of things that I am waiting on from people too, including items loaned to friends.

Projects, Objectives and anything else

All of the above to-do lists are actually inside a folder marked ‘Personal’. As well as this folder, I also have a folder called ‘Projects’ which contains number of to-do lists for projects I am working on – and these come and go depending on what’s happening in my life. In fact, some of these lists may even be shared with other people.

Currently I also have an ‘Objectives’ folder which is keeping track of a some bigger picture things I want to achieve, but this is not permanent. I like to keep things flexible inside Wunderlist, and creating ad hoc lists and folders makes it easy for me to do so. I always review my to-do lists once a week a week anyway.


I recently moved into a new flat, and so I got a new set of keys to get into the building. This time, both of them are the flat key type rather than the mixture of types I had previously. This gave me an idea.

In the past, I’ve seen people on EDC websites use all sorts of key organisers, and I thought I’d give it a go. There are a lot out there – so I’d recommend having a good look around, but I decided that the KeySmart would be a safe choice for me. I only have two keys and I am not too worried about having anything super hard-wearing like titanium.

With the KeySmart you get two scales, a number of washers (depending on which model you get), a loop for attaching to other keys, and screws to hold it all together.

I’ve only had it set up like this for a few weeks now, so I haven’t found out if there are any other issues (for example, I never want it to come apart and lose my keys). But in the time I’ve had it, I have been very happy.


I’m not in a rush, but I have been tempted to get some keys with a black finish cut especially for this. Think that would look good?


  • Way cooler than normal keys, obviously
  • Great for avoiding the jingle when running
  • Super slim profile and feels good in the hand


  • The Utili-Key I used to keep with me doesn’t really work
  • Lack of jingle means I have to really check I have my keys on me
  • Not as speedy for one handed use, but ok

Productivity Music

When listening to an episode of Cortex on, Myke Hurley and CGP Grey talked about how they use music to get in the zone for productivity. It really resonated with me as I’ve done the same thing for many years, and one of my albums of choice was actually mentioned by Grey.

Get into the zone, work harder, associate similar tasks with the music.

There are two main benefits of doing this: one is to distract the part of the brain which is looking for distractions, and the other is to provide a familiar experience and link it with the act of getting things done.

All Day

All Day is name of the epic 2010 mashup album from Girl Talk which is needs to be experienced in order to be understood. Essentially, it’s a huge number of small snippets from loads of pieces of popular music, all smashed together in one cohesive mashup mega mix spectacular, but you’d have to listen to it to see what I mean.

Girl Talk

I use All Day and Girl Talk’s other albums (all available for free) to get myself into the zone for being productive when writing, scripting and power coding, especially when I want to feel pumped up and full of energy.

The only word of warning is that it may be a bit too distracting if you’re not familiar with the album, as you may end up trying to work out where the samples are coming from rather than concentrating on your work. I’ve been listening to this album since it came out, so a lot of the lyrics are just noise to me now.

Not only was this album mentioned on Cortext, it was also discussed on Inquisitive.

Music to Code By

Music to Code By is not an album of music. It is a productivity tool. It will help you focus intently on any task.

Developed by Carl Franklin (of .NET Rocks! fame) specifically for software developers, Music to Code By (MTCB) has been crafted to provide an easy way for the listener to get into the Flow.

Carl Franklin

The melodic loops are around 50 to 80 BPM and 25 minutes long, which is perfect for me to use as a timer without actually watching the clock. After the track finishes, I get up and go for a short walk before putting on the next track. I use this all the time, especially when I want to calmly read specifications, work through tasks, design software architecture and focus on complex problems.

MTCB isn’t free, but you can get samples from Carl’s website and order from there. I currently only have the first three tracks, but another compilation will be released soon. My favourite track is Blue.

Waking Up with Light

I like to keep a pretty fixed schedule for my days so that I can be as productive as possible. In the winter I find it especially hard to get up in the dark mornings, and traditionally I have just forced myself to wake up using alarms.

For the last 3 months I have been using a Philips Wake-Up Light Alarm Clock to help me wake get out of bed with a more positive attitude.

Philips Wake-Up Light Alarm Clock

I used to have an alarm on my phone set for 06:30 every day, but now I have the light alarm set for 06:00. It actually turns on at 05:30 and gradually brightens over half an hour. I usually wake up before the light reaches its full luminosity, and I’m fully awake and ready to go before 06:30 without feeling like I have been rudely awoken.

Unfortunately I had to make a modification to the alarm to get it to work the way I actually wanted. Because I got the least expensive version, it didn’t include any options for changing the alarm sound. I don’t understand why this alarm has such an annoying, loud, high pitched beep for something which is meant to wake you more naturally.

Why did Philips add an annoying beep to an alarm that is meant to wake you naturally? Totally bizarre.

Anyway, using my Leatherman I cut open the alarm and removed the offending speaker. Now the light comes on in the morning and automatically stays on for two hours before switching itself off. No interaction required. (And yes, I could have done a better job at opening it up, but I can’t stress how annoying the beep is…)

I’m really pleased with it now, though there is definitely room for improvement. Philips do make a number of other models in the range, however a lot of them include features like radio that I don’t care for. I’ll certainly be looking at using this method to wake from now on – especially in the winter months.