My iPad Pro homescreen

A week with the iPad Pro as a startup CEO

I first switched to Apple products in 2007. I had just purchased the original iPhone and after using the awful Windows Vista for a period, decided I wanted the same quality experience on my desktop as I had on my I phone. So I switched to OS X.

In 2010 I purchased the first iPad. It was great for video and reading but although I periodically attempted to switch all my computing to it, I always went back to the Mac. My iPad Mini broke about 18 months ago and I didn’t replace it. My iPhone 6 was big enough to watch video whilst travelling and I couldn’t justify the cost of a new iPad.

However, since the release of iPad Pro 12.9" last year, I have been considering whether it may be time to try things again. However, the size was putting me off. Similar to my MacBook Pro (13"), it felt like I’d just be switching the form factor for the sake of it. I’d been a MacBook Air user since the original because I loved the lightweight compact size but my last purchase was a MacBook Pro for the performance.

So when Apple announced the iPad Pro 9.7" last month, I decided it was the perfect opportunity to give it another go. For just over a week now I have been trying to use it as my primary device, and this is a report on how it’s going. I didn’t get the Apple Pencil (I never draw and haven’t decided if it’s worth it for handwriting notes) but did get the Apple Smart Keyboard.

Since there are plenty of great reviews (Om Malik) about the hardware and the form factor itself, I will stick to the key things that mean the most to me.

CEO use case

I used to spend most of my time coding for Server Density, but now that’s a tiny part of my job. Instead I spend most of my time on a few particular activities:

  • Working on documents. Product specs, internal planning, content for our blog/website/newsletter.
  • E-mail. I try and keep to inbox zero and use my inbox almost like a todo list. I regularly experiment with tweaking notifications, automated inbox categorisation, scheduling/read later and filtering to find the right balance of interruptions vs work.
  • Chat. Server Density has a London office but most of the team work remotely, so we make extensive use of Slack and Google+ internally.
  • Meetings. Management meetings, one to ones, customer calls, marketing idea generation, engineering planning.

What works well?

Generally speaking I am enjoying this form factor. I’m a big fan of the portability and screen size for most tasks because it forces me to focus on a single task.

That said, I make extensive use of the Split Screen feature of iOS 9 and typically have Slack open in a small window with the main app taking up the remaining 3/4. Working between two apps is actually quite a regular thing, particularly when moving data between apps or taking notes from the web.

Being able to take advantage of running iOS on both your iPhone and iPad as a primary device is an interesting change. I now notice the utility of many of the built in iOS features much more when I’m using the device for hours instead of many short interactions throughout the day.

  • Night shift and the new True Tone display are very subtle but having used Flux on OS X for years, it’s really noticeable when you disable them.
  • Touch ID for authenticating with locked notes and in particular, 1Password logins saves me a significant amount of time.
  • Using Handoff to answer the phone. For some reason I stopped using it on my Mac even though I continued to use SMSs through Messages. But I’ve now found I use my phone less and less when I’m at home or at the office because everything comes through my iPad.
  • Battery life is amazing. I recently purchased the Apple Battery case for my iPhone and it’s making up for the dying battery that comes with having an older iPhone (but not wanting to buy a new 6S when the 7 will be out in a few months)! I have been able to use the iPad Pro on wifi, playing music and doing multiple calls for a full day 8am to 6pm going from 100% down to 20% battery.


I’ve used most e-mail apps out there and usually come back to Apple Mail. It’s what I use on my Mac, but on mobile I’ve found it lacking. It’s not that it’s poorly designed but it just seems unreliable. In particular, notifications for GMail aren’t real time and there are often sync issues with messages showing in the Inbox that have already been archived or read.

It also lacks features like scheduling and smart categorisation for notifications – it’s either all messages, none, or I have to maintain a manual list of VIPs.

As such, I’ve been using Outlook on my iPhone for months and it’s great to now have that as my primary mail client on iPad. Notifications for Focused Inbox means I get notified about the right messages. On my iPhone I have sounds disabled so I don’t get interrupted when I’m out but the categorisation is so accurate that’s fully enabled on my iPad.

I have considered GMail Priority Inbox but it lacks scheduling, and the UI for Inbox by GMail is too jarring on iOS. I recently tried it on iPhone and desktop but dropped it because of bugs and the UI dissonance.


Server Density uses Google Apps and I’ve been using Google Docs & Spreadsheet for years. They are incredibly powerful tools, particularly for sharing and collaboration with a remote team, and it’s only this year that some more complex financial models needed me to purchase Excel.

Excel on iOS is really very good – much better than on OS X where it feels like it’s running in some kind of emulator. Apple’s Pages and Numbers are also well designed apps. I use them for simple, personal work but they’re not powerful enough even for basic modelling and lack all but the basic sharing functionality.

Working with Google Drive and iCloud Drive is better than I expected and even when you “download” files from the web, you can save them directly to either. You can also attach files from iCloud Drive in Apple Mail (but not in Outlook).

Google Drive itself supports split view, but for some reason no other Google apps do!

Other apps

I was expecting to have to be spending a lot of time in Safari. Every product Server Density uses to run the business is SaaS but I was pleasantly surprised to find that almost everything now has a native app. This ranges from banking (Barclays), to social (Buffer), to Google Analytics, to customer support (Zendesk).

The only ones missing are accounting (Xero), engineering management (JIRA) and a few other minor tools. And it doesn’t matter since they all work fine in Safari.

I have also been enjoying dropping iTunes and using the much better designed Music app for iOS and having Apple Notes sync across all my devices is convenient.

It’s definitely a much more convenient device to take notes in meetings, and it has replaced my paper notebook for that. This is the only use case I’ve been considering the Apple Pencil for, but Apple Notes doesn’t seem like a great app for it. According to a recent roundup, GoodNotes 4 with handwriting search indexing is the best choice.

Of course, our recent Cloud Status App supports the iPad layout.

What doesn’t work well?

Of course, nothing is perfect.

  • Keyboard shortcuts and split screen are great, but they have to be supported by the apps you’re using. Most apps have implemented proper support by now but the major exception is Google. Not supporting split screen is very jarring and really hurts my workflow.
  • Missing keyboard shortcuts are annoying but even more so is when shortcuts differ for the same thing across apps. The one that gets me most is the shortcut for sending an email in Outlook is Cmd+Return but in Apple Mail it’s Cmd+Shift+D. And GMail doesn’t implement it at all.
  • Inconsistent OS level functionality. I’ve used iCloud Drive on OS X since it was released because I trust Apple’s stance on privacy more than Google[1] and Dropbox. The iCloud Drive app on iOS means I can access all my files as normal. In Apple Mail on iPad I can long press a file attachment and save it to iCloud Drive but other apps often don’t implement this. It’s not possible in Outlook, for example. And even in some iOS apps, the “Share” sheet lets you copy a file to every other app except iCloud Drive!
  • I’m switching between 3 different mail apps for specific tasks. The GMail app still has the best search and is the only one to implement “Mark as Spam”. Apple Mail has the best mail viewing and editing e.g. Quoting replies and viewing properly formatted messages but Outlook is the best general purpose client with a good Calendar[2], scheduling mail (e.g. Hide until this afternoon) and the best Focused Inbox.
  • Google’s iOS apps are quite poor in general. GMail still feels like it’s just a web view and most of them implement Google’s design guidelines, which are very un-iOS like. It makes them feel like non-native and lower quality. Docs and Spreadsheets would be fine, if they supported split view and shortcuts! This is a good example of Microsoft executing well on its cross platform strategy whereas Google is still in a muddle of favouring Android and web.
  • It feels like Siri’s potential has been limited. There’s no shortcut button for dictation when the Smart Keyboard is attached and even though I use it occasionally for reminders or checking my calendar, I feel like dictation is a great use case. Using “Hey Siri” can be a problem because it often triggers my iPhone as well!
  • Switching between the keyboard and having to use touch is sometimes annoying. For example the speed of being able to authenticate with 1Password using TouchID is offset by the fact I have to use the Actions Sheet then tap 1Password in Safari, rather than the keyboard shortcut I’m used to on OS X. This is particularly the case with scrolling — different apps implement this in different ways for using the keyboard arrows and/or space bar. The Twitter app doesn’t implement either!
  • I’m unsure whether the home screen is the best way to launch apps. You can use the global Cmd+Space shortcut to access Spotlight Search but there is an animation delay which means you can’t start typing right away, even with the reduce motion accessibility option set.

What do I still need to use my Mac for?

I’d say that the iPad has been able to replace about 75% of my work on my Mac. Most days during the week I can go into the office with a small bag and just my iPad. However, I have found myself still using the Mac for some tasks.

  • There are no good encryption apps for iOS. All my sensitive work files are GPG encrypted and we regularly send GPG encrypted emails internally for sensitive topics, typically around finance. This means I still have to use Mac Mail with GPG Tools, and decrypt documents locally on my Mac when I want to edit them. I’m hoping Keybase will soon be releasing their mobile apps they have supposedly been working on.
  • The iPad Pro is only 9.7"! Of course, this is by design and one of the reasons why I bought it. But it makes working with large financial models quite difficult. I have spreadsheets covering up to 18 months of numbers and for these I really need my 30" Cinema Display. I can certainly make specific, small edits on my iPad and double check figures but for the couple of times a month I need to work on them, I have to go back to my Mac.
  • Coding and code review is still best done on a big display. I recently switched to using Cloud9 IDE because of the nice VM based isolation between projects, but that isn’t supported on iOS. Navigating through code diffs and pull requests in Github is also not so great unless you have a big display and room for multiple windows.
  • Google Hangouts work fine through the Hangouts app but screen sharing is not supported, which I use for displaying documents during meetings, particularly board meetings. It also has no way to join Hangouts from a calendar link. I have to go to GCal on the web, force desktop mode, then fiddle with tapping the link from the designed-for-desktop UI. Only then does it launch Hangouts. On iPhone I can use the link in the GCal native app, but that isn’t optimised for iPad. Hangouts also really drain the battery, compared to FaceTime, Skype or even Slack Voice. We use Hangouts extensively through Google Apps and the Chromebox for Meetings in the office.
  • Copy and paste works very well with shortcuts but selecting text using touch is very tedious! Writing is fine but editing less so.


I am enjoying using the iPad Pro. Every time I have tried to do this in the past I’ve gone back to my Mac within a few days. So far I’m sticking with it. It feels like this is the future direction for Apple products and the advances in iOS are more frequent and more impactful than recent improvements on OS X.

I really like using a single device in multiple “modes”. This might be sitting at my desk in the office, at home on the sofa, on the train or even outside. It’s a very versatile device and is truly “mobile”.

I’m particularly excited to try it out when travelling and out of the office. I did a lot of travelling last year and have stayed put in London for all of 2016 so far. I purchased the wifi+cellular iPad and am looking forward to trying the Apple SIM functionality abroad.

It now feels strange when I switch back to my MacBook with its “big” keyboard and “different” UI. I can’t switch 100% but a large part of my workflow is now iPad based.

And yes, I wrote this on the iPad, in the Medium app!


[1] We still use Google Apps for Server Density primarily because of the hassle of moving everyone’s email, docs, sharing, hangouts, etc to new platforms. However, as a paying customer we also get better privacy guarantees.

[2] I mostly use Calendar in read only mode since the majority of my meetings externally are scheduled for me by, which is working very well.

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