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Roger Sherwood’s iPad Pro and iPhone setup

Every week, we post a new interview with someone about what software they use on their Mac, iPhone, or iPad. We do these interviews because not only are they fun, but a glimpse into what tools someone uses and how they use those tools can spark our imagination and give us an idea or insight into how we can do things better.

New setup interviews are posted every Monday; follow us on RSS or Twitter to stay up to date.


Who are you and what do you do?

My name is Roger Sherwood, and I work at Cisco Systems in the sales group as a global industry lead. I live in the Bay Area and work from home when not traveling to customer and company meetings.

What is your current setup?

Roger Sherwood's desk

I move between my home office and our guest room depending on the time of year (downstairs home office when the kids are out of school). I’m on the distraction-free band wagon and most of my work time is spent on the iPad in Do Not Disturb mode. I have a 2015 12” MacBook that sleeps a lot and an iPhone X that does allow people to disturb me. I retired the Airport Time Capsule and went with Ubiquiti’s Amplifi Mesh Wi-Fi System as the replacement. Also close by are a pair of B&O H6 headphones and a remote for a pair of Teenage Engineering OD-11 speakers.

Which iPad do you have?

Roger Sherwood's iPad Pro

I have the silver iPad Pro 10.5”, 512GB, Wi-Fi+Cellular paired with the Magic Keyboard and Pencil. The iPad sits in a Yohann stand (hat-tip Ben Brooks) when I’m in the home office and I travel with the Smart Keyboard and leather case.

Where can we find your wallpaper online?

It’s the default iOS 12 wallpaper from whatever the latest beta is.

How are you using your iPad on a daily basis?

For almost everything! Cisco has had a BYOD (Bring-Your-Own-Device) policy for several years and there are only a couple of things that I need a traditional laptop for now. The combination of iPad Pro and iOS 11 really enabled the transition away from the MacBook for work — in particular, the Files app, customizable Share Sheets, and the Multitasking functions. It meant letting go of old workflows and learning some new ones, but to me the iPad is such a rewarding and fun device to use. And I’m still discovering new things! The ability to minimize emails rather than saving as a draft every time I want to do something else in the Mail app is something I stumbled upon recently…iCloud takes care of backups and syncing.

What apps do you use the most, and why?

For work, it’s the standard enterprise apps — Mail, Calendar, Contacts, etc — in addition to a couple of company collaboration tools, like Webex and Teams. Box is the Cisco corporate standard for file-sharing. I use the iOS Microsoft Office suite for document and presentation creation/review.

I’m a big believer in the power of the narrative memo and the articulations of ideas and proposals in written form; Ben Thompson referred to it as getting “in between the bullet points.” Ulysses has become my go to for writing. I am in no way a power user, but most of my ideas, multi-line emails, company blog posts, proposal documents, and team memos start in some form in Ulysses.

Which app could you not live without?

It’s got to be Messages. Every other app could be replaced with something else, but that’s the one where I can’t think of a suitable replacement. I don’t use social messaging apps, so staying in (non-verbal) touch with family, friends, and colleagues happens exclusively with Messages. It’s taken for granted just how easy it is to share anything from almost any app into Messages without any setup, and it’s probably the most secure mass-market messaging solution at this point.

How would your ideal setup look and function?

It’s pretty close today, but I would love to be iOS-only and I’m hoping the MacBook is the last laptop I own. There’s only two things I use MacOS for now: 1) music library management and 2) Powerpoint presentation creation.

My music library is over 100GB, which includes rips of my own CD collection and downloads from online sources. I’ve spent many hours curating it and the last time (2015) I tried to use iCloud Music Library, a significant amount of that curation was seriously messed with. I have not dared try it again since. So I’m manually syncing my iOS devices with iTunes every month or so, and while not a major hassle, I do wish Apple would allow for import into the iOS Music app without iTunes.

Powerpoint and Keynote on the iPad are still tough to use compared to their desktop versions, especially when creating from scratch or compiling a deck from several other sources. I don’t know what the solution is here given the medium other than to continue to try and get the corporate world to move away from Powerpoint!


What iPhone do you have?

Roger Sherwood's iPhone X

The iPhone X, 256GB in silver. Wrapped in the Grainy case from Hard Graft and charging wirelessly via Drop from Native Union.

Where can we find your wallpaper online?

That’s a wife and daughter selfie from a few months ago.

What apps do you use the most, and why?

Similar to the iPad setup with a few mobile additions. Castro has been my favorite podcast player since it was first released. I’m on a masters rowing team and we’re gearing up for our biggest race of the year. It’s a critical period in terms of preparation and the team is using TrainingPeaks to manage/monitor workouts, weight, and fatigue. ErgData connects wirelessly to the Concept2 rowing machine and logs a lot of the data that gets exported to TrainingPeaks.

Which app could you not live without?

Messages and Music.


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