Doug Winnie On Productivity And Writing

How can you combine working as a software product manager, university lecturer and author and not go completely insane? Lifehacker sat down with Doug Winnie, Adobe's product manager for Adobe Flash Catalyst, Flash Platform Workflow and WorkflowLab, at the recent MAX conference in Los Angeles to find out how he organises his life and how he manages the process of writing a book.

Lifehacker: You wear a lot of hats. You've co-authored books, you teach at university, and you have a full-time day job. What technologies do you rely on to keep yourself organised?

Doug Winnie: In Myers-Briggs terms, I am an ENTP, which means I like to make a list, and then I throw the list away. I like to have at least some planned idea of what I'm going to do, but then I will always go off track, though I will always eventually get it back. I've played with so many different things in terms of to-do list managers. I've worked with getting things done and OmniFocus and other kinds of approaches, but I'm a simple man (laughs). I tend to just like basic to-do lists.

If I am doing something that is much more project-focused -- as a product manager there obviously are budget-related things -- in that case I will create myself a punch list in some sort of form, usually Excel or Word or something pretty basic, and just make sure that I hit everything. I have certain people who will get upset if I might miss a deadline -- not that I ever do! I'm pretty basic in terms of all that though. If I can write the list down and get it in my head, it's conscious. I find that there's a lot of consciousness that has to happen because if I haven't actually written it out it doesn't exist sometimes.

LH: What's your preferred smart phone?

DW: I have the Galaxy S. I got this phone for two things. I watch lots of movies and TV, usually when I'm at the gym, and I don't necessarily want to take a tablet to the gym, because then I'll just look odd. I love this phone because it has probably the best screen that I have ever seen. It hasn't done an OTA update with Froyo yet so I'm still waiting for that, but I love it because of the media support.

In productivity terms, there are a couple of things. Probably what I use the most on here are social network tools. I'm a big FourSquare user and always on Facebook and I tweet quite a bit. Having all the widgets is helpful for me, because that way I get to see what's going on without having to actually go into an app. I really like the New York Times app for Android too -- I think it's really slick.

LH: How did you go about co-ordinating the challenges involved in co-authoring a book?

DW: James, Aaron and I worked together for several years before I came to Adobe. We all had worked together on a lot of projects with a lot of intensity, so we all knew how each other worked. When we approached the book we first did our outline which was the first requirement for the publisher. I have the design background, Aaron has the development background and James has the quality engineering background. We divided the book up into categories and chose which author would be the right person to do each section.

The introduction chapter we authored that together, collaboratively. It was also good to get in sync with tone and style. Each of us write in a different way but when we read the book the voice is very consistent so that was a good exercise to do in the beginning. We did a writing retreat where the three of us left the Bay Area and went to Sacramento and locked ourselves in a room and just locked ourselves in a room and wrote the introduction together over a weekend. And we came out alive at the end! After that, we basically knew how each person wrote and then we would do a chapter and send it to the other two co-authors to edit, and then we'd review the edit and then we'd send each chapter off to the publisher. It was very collaborative and I think it worked out really well.

LH: Did you ever have writer's block?

DW: The biggest struggle was when I needed to write a chapter referring to content in a co-author's chapter. That was when having the outline helped, but I would leave a blank area in some chapters and then eventually fill that in. The struggle wasn't writer's block, the struggle was that I had too much stuff in my head. I've been using Adobe products for over 10 years, so I know all these products inside and out and I wanted to put lots more information in there but we only had a certain page count. We tried our best to provide more of a workflow best practice than necessarily information on how to use the products. That was the biggest struggle, with all these things that all three of us knew that we wanted to put in the book.

LH: How do you balance writing, product management and teaching?

DW: Each piece that I do has some sort of interaction with each other. I've recommended to a lot of new product managers that work with software to try and do some teaching and do some training, especially if you're working on a product that has maturity. It's difficult to get a good sense to how new people learn your product. A lot of the writing and the videos that I do is based on what I've learned during the development of the product, so other people don't have to go through a painful process to also learn that.


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