Being a Program Manager at Microsoft

My awesome friend Christopher also works at Microsoft, but his career and mine have taken different paths since we joined. Here we are together back in 2008, before either one of us worked at Microsoft. He’s the one not wearing a Manowar t-shirt.

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No, no, the other one.

Our backgrounds are remarkably similar. We each spent years before joining Microsoft as Microsoft Certified Trainers, with an emphasis on software development rather than systems administration. We each became involved in the MCT community, and in the broader technical community, and to one extent or another this helped us find our first positions at Microsoft.

These days Christopher is working with student developers – I’ve seen him tweeting a lot recently about Django on Twitch, which probably means that he’s still teaching people about software development… or may be watching Quentin Tarantino movies while drinking too much coffee. Honestly, either one is possible.

Anyway… Christopher reached out to me last month and asked if I’d be interested in talking to college students about to graduate about what it’s like being a program manager at Microsoft. I said yes[1], then I said this:

I’ll let the video speak for itself. I tell my story for the first 15 minutes or so, and around the 14:50 mark I talk with Will Thompson and Tessa Hurr from the Power BI team and ask them to share their experiences as well. But there are a few things that I want to add that didn’t really fit well into the video.

First of all, every team has a need for many types of program managers. I’ve blogged about diversity enough that you probably know how I feel about the value of diverse teams, and this applies to PM teams at Microsoft as well. Since this video is targeted at college students and recent college graduates, I’d like to focus briefly on the career diversity dimension.

What does “career diversity dimension” mean? Looking at most PM teams I see program managers falling into three broad groups:

  1. New to career – program managers who are starting their careers after college, or after switching from a non-IT discipline.[2]
  2. Industry hires – program managers who are new to Microsoft, but who have an established career in a related field.[3] This is often someone who has been a consultant, developer or administrator who works hands-on with Microsoft or competitive tools and technologies.
  3. Veterans – program managers who have been at Microsoft long enough to succeed a few times, fail a few times, and understand what PM success can look like on multiple teams.[4]

Reading this list it may be easy to think that there is a progression of value implied, but this is not the case. A successful team will find ways to get from each group the things that only they can contribute. A PM in one group will be able to see things and do things that a PM in other groups will not, and an experienced team leader will be able to direct each PM to the problems that they are best suited to solve, and can add the most value.

The second thing I wanted to add to the video is that each team is different. I said this in the video, but I want to elaborate here. Each team will have its own culture, and some teams will be a better fit than others for a given PM. I’ve worked on multiple teams where I didn’t think I was contributing effectively, or where I felt that my contributions weren’t valued[5]. At one point this culture mismatch almost led me to leave Microsoft, but with the support of my manager at the time I instead found another team in another org where I could thrive.

And this leads me to the the final point I wanted to add: Microsoft is huge. I’ve been a PM at Microsoft since October 2008, but I’ve had 4 or 5 major career changes since then, with very different responsibilities after each change, requiring very different contributions from me.

When I was interviewing for my first position in 2008, the hiring manager asked me why I wanted to work for Microsoft. I already had a successful career as a data warehousing and ETL consultant, and becoming a Microsoft employee would include a reduction in income, at least in the short term. Why give up what I’d built?

I hadn’t expected this question, and my answer was authentic and unscripted, and I’ve thought a lot about it over the past 11+ years. I told him that I wanted to join Microsoft because Microsoft had bigger and more challenging problems to solve than I would ever see as a consultant, and would never run out of new problems for me to help solve. If I joined Microsoft, I would never be bored.

I wanted to join Microsoft because Microsoft had bigger and more challenging problems to solve than I would ever see as a consultant, and would never run out of new problems for me to help solve. If I joined Microsoft, I would never be bored.

And I was right.

If you’re a PM at Microsoft, please share your thoughts and experiences.

If you’re thinking about becoming a PM at Microsoft, please share your questions.

If you’ve joined Microsoft as a PM after watching this video and reading this blog, please send me an email, because I would love to say hi.


[1] It’s a good thing he asked when he did. I haven’t had a haircut since late February, and I don’t know when I’ll let anyone point a camera at my head again…

[2] This was kind of me when I first applied for a position at Microsoft in the 90s, although I already had a few years’ experience. I was not hired.

[3] This was me in 2008 when I was hired.

[4] This is me in 2020. I tend to talk about the successes more, but it’s the failures I think about the most, and where I learned the most along the way. Success is awesome, but it’s a lousy teacher.

[5] Yes, this sucked as much as you could imagine.

Tough love in the data culture

When I shared on Twitter the most recent installment in the BI Polar “data culture” series, BI developer Chuy Varela replied to agree with some key points from the video on executive sponsorship… and to share some of his frustrations as well[1].

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Chuy’s comments made me think of advice that I received a few years back from my manager at the time. She told me:

Letting others fail is a Principal-level behavior.

Before I tie this tough love into the context of a data culture and executive sponsorship, I’d like to share the context in which the advice was given.

At the time I had just finished a few 80-hour work weeks, including working 12+ hour days through a long holiday weekend. Much of that time was spent performing tasks that weren’t my responsibility – another member of the extended team was dropping the ball, and with a big customer-facing milestone coming up I wanted to make everything as close to perfect as possible.

Once the milestone had been met, my manager pulled me aside and let me know how unhappy she was that I had been making myself ill to deliver on someone else’s commitments[4]. She went on to elaborate that because of my well-intentioned extra effort, there were two negative consequences:

  1. The extended team member would not learn from the experience, so future teams were more likely to have the same challenges.
  2. The executive sponsors for the current effort would believe that the current level of funding and support was enough to produce the high quality and timely deliverables that actually required extra and unsustainable work.

She was right, of course, I’ve added two phrases to my professional vocabulary because of her advice.

The first phrase[5] gets used when someone is asking me to do work:

That sounds very important, and I hope you find the right folks to get it done. It sounds too important for me to take on, because I don’t have the bandwidth to do it right, and it needs to be done right.

The second phrase gets used when I need to stop working on something:

After this transition I will no longer be performing this work. If the work is still important to you, we’ll need to identify and train someone to replace me. If the work is no longer important, no action is required and the work will no longer be done.

Now let’s think about data culture and executive sponsorship in a bottom-up organization. How does a sponsor – or potential sponsor – react when a BI developer or analyst is delivering amazing insights when it’s not really their job?

If the sponsor is bought in to the value of a data culture, their reaction is like to include making it their job, and ensuring that the analyst gets the support and resources to make this happen. This can take many different forms[6], but should always include an explicit recognition of the work and the value it delivers.

And what if the analyst who has enabled more data-driven decisions is ready to move on to new challenges? What happens to the solutions they’ve built and the processes that rely on their work? What then?

Again, if the sponsor is committed to a data culture, then their reaction will involve making sure that it becomes someone’s responsibility to move the analyst’s work forward. They will assign the necessary resources – data resources, human resources, financial resources – to ensure that the data-driven insights continue.

If you’re working on helping to build a data culture from the bottom up, there are a few opportunities to apply this advice to that end. Please understand that there is risk involved in some of these approaches, so be certain to take the full context into consideration before taking action.

  1. Work with your immediate manager(s) to amplify awareness of your efforts. If your managers believe in the work that you’re doing, they should be willing to help increase visibility.
  2. Ensure that everyone understands that your work needs support to be sustained. You’ve done something because it was the right thing to do, but for you to keep doing it, but you can’t keep doing it with all of your other responsibilities.
  3. When it comes time to change roles, ask who will be taking over the solutions you’ve built in your current role, and how you can transition responsibility to them.

Each of these potential actions is the first step down a more complicated path, and the organization’s response[7] will tell you a lot about the current state of the data culture.

For the first potential course of action, managerial support in communicating the value and impact of current efforts can demonstrate the art of the possible[8] to a potential executive sponsor who may not be fully engaged. If you can do this for your current team or department, imagine what a few more empowered folks could do for the business unit! You see where I’m going…

If this first course of action is the carrot, the other two might be the stick. Not everyone will respond the way we might like to our efforts. If you’re building these solutions today without any additional funding or support, why would I give you more resources? Right? In these cases, the withdrawal or removal of existing capabilities may be what’s necessary to communicate the value of work that’s already been completed.

Wow, this post ended up being much longer than planned. I’ll stop now. Please let me know what you think!


[1] I don’t actually believe in New Years resolutions, but I am now retroactively adding “start a blog post with a sentence that contains six[2] or more hyperlinks to my goals for 2020[3].

[2] Yes, I had to go back to count them.

[3] Nested footnotes achievement unlocked!

[4] If your reaction at this point is “what sort of manager would yell at you for doing extra work?” the answer is “an awesome manager.” This may have been the best advice I ever received.

[5] I’ve probably never said either phrase exactly like this, but the sentiment is there.

[6] Including promotion, transfer to a new role, and/or adding capacity to the analyst’s team so the analyst can focus more on the new BI work.

[7] Remember that a culture is what people do, not what people say – have I mentioned that before?

[8] The art of the possible is likely to warrant its own post and video before too long, so I won’t go into too much depth here.

Never stop asking “stupid” questions

When I joined Microsoft, the team running my NEO[1] session shared a piece of advice with my “class” of fresh-faced new hires:

“Think of your first year as a grace period where you can ask any question you want, without anyone thinking it’s a stupid question for which you should already know the answer.”

This sounded like empowering wisdom at the time, but the unspoken side of it was damaging. Between the lines, I heard this message as well, and it was this part that stuck with me:

“You’ve got one year to figure things out, and after that you’d better have your act together and know everything – because if you keep asking stupid questions we’ll know that we made a mistake hiring you.”

I hope it’s obvious that this wasn’t the intent of the advice, but I’ve spoken to enough people over the years to know that I’m far from the only one to take it this way.

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How Matthew pictures everyone reacting when he asks questions.

In retrospect, I believe that I should have known better, but I let this unspoken message find a home in my brain, and I listened to it. I remained quiet – and remained ignorant – when I should have been asking questions.

Over the past few years[2], I have finally broken this self-limiting habit. Day after day, and meeting after meeting, I’m the guy asking the questions that others are thinking, and wishing they could ask, but don’t feel comfortable or confident enough to speak up. I’m the guy asking “why” again and again until I actually understand. And people are noticing.

How do I know that others want to ask the same questions?

I know because they tell me. Sometimes they say thank you in the meetings, and sometimes ask their own follow-up questions. Sometimes they stop me in the hall after the meeting to say thank you. And on a few occasions people have set up 1:1 meetings with me to ask about what I do, and how they can learn to do the same.

How do I know that people are noticing?

A few of the people I’ve interrupted to ask “why” have also set up time with me to discuss how they can better communicate and prepare to have more useful and productive meetings.[3] These are generally more experienced team members who appreciate that my questions are highlighting unstated assumptions, or helped them identify areas where they needed a clearer story to communicate complex topics.

I’ve been with Microsoft since October 2008 – a little over 11 years. I’ve been working in the industry since the mid 90s. At this point in my career it’s easy for me to ask “stupid” questions because the people I work with know that I’m not stupid.[4][5]

This isn’t true for everyone. If you’re younger, new to role or new to career, or from an underrepresented group[6], you may not have the position of relative safety that I have today. My simple strategy of “asking lots of questions in large groups” may not work for you, and I don’t have tested advice for what will.

My suggestion is to ask those questions in small groups or 1:1 situations where the risk is likely to be lower, and use this experience to better understand your team culture… but I would love to hear your experience and advice no matter what you do. Just as your questions will be different from mine while still being useful, your experience and advice will be different, and will be useful and helpful in different ways.

Whatever approach you take, don’t be quiet. Don’t stop asking questions.

Especially the stupid questions.

Those are the best ones.

 

P.S. While this post has been scheduled and waiting to go live, there have been two new articles that showed up on my radar that feel very relevant to this topic:

  1. The Harvard Business Review posted on Cracking the Code of Sustained Collaboration and how leaders can build and encourage cultures where these behaviors are rewarded.
  2. Ex-Microsoftie James Whittaker posted on Speaking Truth to Power, which presents critical observations of three eras of Microsoft, with examples of how different generations of leaders have affected the corporate culture.

These are very different articles, but they’re both fascinating, and well worth the time to read.


[1] New Employee Orientation. Sadly not anything to do with Keanu Reeves.

[2] I wish I could say that this was a deliberate strategic move on my part, but it was more reactive. Credit goes to the rapid pace of change and my inability to even pretend I could keep up.

[3] Yes, that means meetings where fewer people interrupt to ask “why.”

[4] I’m waiting for the flood of snarky comments from my teammates on this one…

[5] Or in any event, my asking questions is unlikely to change any minds on this particular point.

[6] If you’re not a middle-aged, white, cisgender man…