5 Min reading time

DevOps, human bottlenecks and favourite mistakes with Sasha Rosenbaum

08. 12. 2019

DevOps is all about collaboration, maximizing value for end users and removing bottlenecks. Sasha shares that the biggest lesson she has learned is that blindly deferring to people based on their experience and seniority isn’t a good idea. With a corollary that we must stay humble as we progress in our careers.


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I have been following Sasha’s work for some time now and have finally e-met her after binge-watching several of her talks. Particularly interesting are her experiences in introducing DevOps culture while transforming the way Microsoft works internally. She currently works as Sr. Program Manager on a product called Azure DevOps that supports the complete product delivery lifecycle.

Sasha, thank you for this talk!

Ivan: Sasha, you have started your journey as a developer. What made you think about DevOps? Was there a specific situation or a project that shifted your mindset to DevOps and made you never look back?

Sasha: I have to start by saying that I love coding. It’s always been incredible to me that I could create a tangible application providing value to people in just a few hours. To me, writing code is like writing a poem – structured, yet creative. It is one of those things that easily get me into the state of “flow”.

In 2011, I joined a small consulting company that was helping clients deploy applications in Azure cloud. We were using the early versions of “platform as a service” cloud services, and hence managing the infrastructure, as well as the application. It gradually became clear to me that there is a host of unsolved problems in this space, and that there is a community developing around helping people solve these problems. Years later, I feel like we are just getting started!


Ivan: You’re also one of the organizers of devopsdays Chicago. Organizing a conference is never easy. What gets you going?

Sasha: The DevOps/DevOpsDays community has been incredibly impactful in my life, and I continue to see it helping people around the globe. We are all too busy, which often precludes us from taking on “more work”. Yet, helping people is tremendously empowering. The work we do pays back a 100-fold!


Ivan: Your talk about people being a single point of failure is 5-6 years old but sadly still relevant in some organizations. Sooner or later we all stumble upon that one irreplaceable person that cannot take a vacation. How do you cope with that situation in your team and what is your favorite action to start fixing it (or preventing it)? In fact, have you ever been “that person”?

Sasha: I believe that we’ve all been there at this point or another because we are all guilty of thinking “it is easier for me to do this than explain it to someone”. However, it becomes a systemic issue in two cases – either the organizational culture rewards the wrong type of behavior, or a particular individual believes that withholding information and/or autonomy from other folks would further their agenda or career.

There are no easy answers as to how to change the culture. If people are well-meaning, you could try to get to the bottom of their trust issues and alleviate them. If people are intentionally toxic, you are better off without them.


Ivan: Microsoft has strongly shifted its focus from providing offline products to providing SaaS solutions. This year in Kyiv you had an insightful talk about what Microsoft is doing internally to support such transformation. What do you see as the biggest obstacles that truly large enterprises face during transformation and how are you overcoming those in Microsoft?

Sasha: The biggest problem of any successful company is the conflict between execution and evolution. To achieve success, a company must be really good at executing a certain strategy, delivering a set of products, and operating under a set of assumptions. However, as the marketplace evolves, the existing strategy inevitably becomes obsolete, and the existing products get disrupted. How do you continue executing on a profitable strategy, while simultaneously creating a new mindset that is a better fit for the new reality?

Microsoft has been really good at reinventing itself, but there are only a few examples of companies successfully navigating this conflict for more than a couple of decades.

Sasha Rosenbaum

Ivan: Are you still getting your “hands dirty” in the code?

Sasha: Not as much as I would like to. It always makes me happy to work on a code project that goes beyond a demo. Although, as I get rusty, merging to production becomes more and more stressful!


Ivan: Looking back, what was your favorite mistake that taught you so much that you would never want to “roll it back”?

Sasha: The mistakes I’ve learned the most from involved human interactions, rather than technology. The biggest lesson I’ve learned is that blindly deferring to people based on their experience and seniority isn’t a good idea. With a corollary that you must stay humble as you progress in your career.


Ivan: You have written a book on serverless computing in Azure with .NET. What are the concepts and keywords that you would bet on to fill our Twitter feeds in the following year(s)?

Sasha: I am betting on ML becoming more and more pervasive in everything we do, and hence expect more tools and products to develop in this space. I also believe that shifting left on security is a necessity and that cyber-attacks will continue to intensify.

I am probably more concerned with the problem of how we remain ethical and avoid hurting humans or our environment, than with how we can create new technologies faster. To quote Max Tegmark,(Life 3.0) “This brief century of ours is arguably the most significant one in the history of our universe. We’ll have the technology either to self-destruct or [to] seed our cosmos with life.”


Ivan: Can you share with us what are you reading these days and who are the people you follow that make you think differently and do better? I know for a fact that you’re reading at least one great book these days.

Sasha: People to follow: Ian Coldwater @IanColdwater, Jabe Bloom @cyetain, Bridget Kromhout @bridgetkromhout

It is so difficult to recommend a single book! I will go with “Fierce Conversations” by Susan Scott.

Also please check out this new conference DELIVERY|CONF 2020!

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