Fond farewell to Microsoft

This is not my last Hard Code column, but it is my last as a Microsoft insider. After 25 years at Microsoft and 40 years working as a professional software engineer, I’m leaving Microsoft and my role as a software developer. My life circumstances have shifted. It’s time to change gears and give back more while working a little less. I’ve started a career coaching company with an emphasis on underrepresented, midcareer software professionals.

I’m sad to leave Microsoft. I will miss the excitement, passion, and exhilarating pace. I’ve had the privilege to contribute to almost every major Microsoft product: Visual Studio, Office, Windows Server, Xbox, Windows, Azure DevOps, Dynamics, and most recently Azure (plus stints with Research and Corporate). It’s been an incredible experience working for a company I truly love.

As I wrote in Fixing five fundamental flaws, Microsoft has its issues. In the seven years since I wrote that column, a few of those issues have improved, some still remain, and new issues have arisen. While I’ve never been bashful in this column, now you can be assured that I’m not concerned about what my management thinks. It’s time to discuss what’s going well, the work remaining, fun farewell facts, and where we go from here.

I love this company

Microsoft may not be as dominant as it once was, but arguably it’s never been stronger. The stock has reached all-time highs, reflecting the strength of our products, the value of our services, the trust of our brand, and the growth of our culture. Microsoft remains a fantastic place to work (like many tech companies) due to talented employees empowered and authorized to innovate (like some tech companies) with our focus on customers instead of advertisers (like fewer tech companies) to empower every person and organization on the planet to achieve more (like no one else).

The five fundamental flaws I wrote about years ago were being top-heavy, being overstaffed and overfunded, having a broken rewards system, disregarding past experience, and replicating our infrastructure. We’re still top-heavy, overstaffed, and overfunded. Our reward system has gotten much better, but arguably it is still broken (read the flaws column for details). We still disregard past experience, which is such a waste. However, we’ve vastly reduced our replicated infrastructure, and that trend is only accelerating.

Based on my experience, the most impactful things that have improved at Microsoft in the past 25 years are our software development cycle and our culture.

• Microsoft was practicing continuous integration when I joined in 1995. We’ve since added agile and lean project management, continuous delivery, and DevOps. These changes have been difficult, yet have dramatically impacted our responsiveness to changing markets, technology, and customer requirements. Every Microsoft product and service, even Windows, has adopted these new approaches. There are still vestiges of waterfall or Scrummerfall and teams that struggle to achieve DevOps, but the direction is clear.
• Microsoft culture used to be about trouncing our competition inside and outside the company. Type-A personalities were the norm. I.M. Wright was modeled after dev leaders from the late 1990s. Today, Microsoft is about inclusion, growth mindset, collaboration, and customer obsession. Longtime readers often mention how I.M. Wright has gone from being combative to being understanding, optimistic, and hopefully instructive. The writing isn’t as edgy (or perhaps as entertaining), but it’s more inclusive and better reflects the author’s personality (though my wife might disagree).

That’s a problem

Aside from improving talent management (which covers the first four fundamental flaws), I’d say the two biggest remaining issues for Microsoft are the continued prevalence of authoritarian leadership and the wasteful practice of subtractive planning.

As I covered in What’s my motivation? and The good stuff, “transformational leaders” who provide supportive coaching and an inspiring vision are twice as likely to exceed business and operational performance goals. (Implementing lean project management and continuous delivery is also necessary, but Microsoft already embraces those practices.) Yet Microsoft still retains people in positions of authority who lead through fear and intimidation. We should expect better from our leaders and hold them accountable to model the inclusion, coaching, and caring that our culture aspires us to embody.

In subtractive planning, leaders force their staff to plan for and commit every minute available. As new requirements arise and plans change, people must work harder or subtract planned and partially completed work to make room for new commitments. The result is wasted effort, inferior quality, and overworked staff. In contrast, additive planning only commits to delivering a few things well, with all other work added as opportunities arise. Teams end up delivering more than expected out of pride and the desire to please customers. It’s easy to adjust to new requirements because the team is not overcommitted. Less time is wasted on planning, implementing, and validating work that ends up being cut.

Authoritarian leaders love subtractive planning because it feeds their aggressive nature and drives their staffs to work harder out of fear of missing commitments. Microsoft needs to cleanse itself of these bullies and focus on the few key deliverables our customers and business depend upon, allowing our amazing engineering staff to fill the rest of their time with innovations, reduced technical debt, and rapid response to changing customer needs.

Now you know

Time for some fun farewell facts. These are common questions asked of I.M. Wright. Feel free to skip this section if you’re not interested.

• What does your manager think of your column? I never write about my manager, since I know that’s problematic. Out of the 10 managers I’ve had for extended periods while writing Hard Code, two never read it, one stopped reading it while I reported to him, one believed I was writing about him (I wasn’t) and was furious with me, and the other six were avid readers and loved it.
• Which column is your favorite? There are many that delight me, but if I had to choose one, I’d say Life isn’t fair. It nicely mixes career development, spotting opportunities, the review model, and understanding our business and customers. It’s also got some funny characters and wordplay. My most important column is probably I can manage, my most popular column is Level up, and the best overview of my recommendations is The good stuff.
• How did you learn to write the way you do? Mostly, I learned to write from reading. My early columns steal their style and even some of their expressions from my favorite columnists at the time. Like most skills, you get better with practice. I also have peers review my columns in advance, have a professional proofreader edit them, and then read them aloud. Those reviews catch most issues and provide substantial polish.
• What’s your most regrettable moment? I’ve had plenty of unfortunate moments, including having native code I maintained displayed to thousands of Windows developers as an example of a security vulnerability. However, my most regrettable moment has to be when my team was responsible for Office clipart, and we released a photo of a young couple sitting on the monkey bars. When you searched for “monkey,” you saw pictures of primates alongside the photo of the young black couple. We found and corrected the mistake, but too late to avoid Microsoft being sued.
• What’s your proudest moment? I’m proud to have contributed to many great accomplishments, such as releasing the first web service for Office, getting remote desktop terminals in every lobby, coaching half the dev managers at Microsoft, and launching Xbox One. The one moment that stands out is when Microsoft announced coverage for autism therapy. We were the first major corporation to do so, designing the benefit from scratch. I still can’t believe a group of parents made that happen, and how caring and devoted Microsoft Benefits folks were in breaking through all the barriers to help our children thrive. Empowering every person to achieve more—it’s beyond a slogan.

What’s next?

For all its flaws, Microsoft is still an incredible place to work. Yes, talent management could improve substantially, leadership could remove bullies from its ranks, and planning could focus on delivering a few things well while allowing our great engineers to be responsive to day-to-day needs. I’d still easily choose Microsoft over any other company.

As for me, I’ll be working part-time as a career coach. If you’d like my advice about your situation, feel free to reach out. My focus will be on underrepresented, midcareer software professionals, but I have a soft spot for Microsofties. You can find out more at Ally for Onlys in Tech. I established this business back in April, but the recent racial strife has only accelerated my desire to put my values into action.

Last but not least, I’d like to thank each of you for reading my columns, providing your unfiltered feedback, and generally making my Microsoft experience so memorable. If you’d like to continue reading my column, you can click the blue “Follow” button on the Hard Code homepage or follow me on LinkedIn. To leave me a message, add a comment to this column or send me your thoughts on LinkedIn.

Thank you, thank you, thank you.