A few years ago I switched teams inside of Microsoft and joined the Office 365 group inside of the Exchange team. I was jumping in mid-release and as a manager, so I had to get up to speed on my own responsibilities and that of my team. If you know me you’ll understand when I say that my first day was about creating lots of lists: who to talk to on my new team, documents to read, customers to talk to, etc. I love lists, and I love tasks. Since I was joining a big team with peers who had several directs themselves, I put together a big complicated list that mapped each of the PM’s in our larger team to their project and their manager. I found this helpful because I always like to ‘see the big picture’ visually. I shared it with my peers and my manager and asked them to update it since I had made guesses about some of the projects, telling them we could use it as a reference across the team. I didn’t get a response after a week and pinged them again. No response. Huh.

A few weeks later during a peer feedback session I got a response from a colleague that has stuck with me clearly ever since then: “I really enjoy working with Michael, but when he first joined the team he immediately tried to get us to use this complicated way of keeping track of our directs and their ownerships. I didn’t have a need for it and got annoyed that he kept pushing for it.”

Whoa. That wasn’t me. I wasn’t the guy who pissed people off while I was trying to help them. Or was I? What I realized was that sometimes my personal organization processes and styles need to be just that: personal. The point? Transitions are super tough and involve a million little things changing at once, and it’s easy to forgot areas of your personality that are already weaknesses when dealing with larger parts of the transition.

Now about this book. I feel the same way about self-help and self-training books that I do about the types of in-person training I’ve attended while working for big corporations: if I feel like at least 70% of the time I spent attending/reading was valuable then it wasn’t a total waste of time. That may be a cynical way to think about it, sure, but I’ve been burned in the past by overly-drawn three day training sessions where the entire time you’re wondering “WHAT IS GOING ON?!”, and then there have been rock-star ones like “Situational Leadership” that I still discuss and use almost every day in my job.

“The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter, Updated and Expanded” easily meets my 70% rule for being a great book and I believe can help with transitions in your career.

The first time I read it was when I left Microsoft in Fall 2013 and was on the recommendation of my best friend Vinny Pasceri, a fellow Microsoftie who knows a lot about transitions between startups and big companies. It was immensely helpful while I was making the transition to work at Contactive because of how well it structured the process of feeling like I had 9 million things to learn at once. Most importantly, it hammers home the idea of not making lots of quick, bad decisions because of lack of information that then inhibit your ability (and reputation) to do long-term good in the organization.

I re-read the book this January as we were going through the acquisition process with ThinkingPhones. It was faster the second time around and I was able to skim through parts that weren’t as relevant, but I found it a good refresher of some of those “blind spot” challenges that can be easy to hit in a new transition.

The book has a LOT of frameworks in it, and sometimes I feel like it tries to straddle the line too much between being a step-by-step training manual and a good reference of ways to approach situations. I tend to be very example-driven, so I wished it had more of the mini case studies to support the various frameworks. I stopped trying to fill out the (many) worksheets as I was reading it and instead allocated 30 minutes each week to pick a section and make actions items for myself based on it.

I didn’t find any framework or set of steps that was completely foreign to me. I did, however, find the single most useful outcome of reading the book to be getting way more honest about what my weakness are in times of transition, like trying to force old ways of work into the new one, and forcing me to write them down in order to be mindful of them.

The book is focused on senior-level management positions in large organizations making big transitions, and only really pays passing mention to startups. That’s not a blocker for making this a usable book by almost anyone making a transition in an information worker role, especially one in management, since the frameworks and methodologies are non-specific.

4/5 for me.

Thanks!

-m