Being a Manager at Microsoft: 1. Becoming a Manager

Recently I had the good fortune of becoming my team’s first-line manager (M1). I’m starting a series to document the challenges and lessons I run into along the way, partly so I can look back and reflect on them later, and partly in the hope of sharing them with more people. Comments welcome!

How I Got This Opportunity

In one sentence: my boss left, and the manager seat opened up.

As one of the most senior people on the team, I was naturally a possible successor. In fact, my boss (M1) proactively recommended me to his boss (M2) to inherit his kingdom. But things were nowhere near that smooth or simple — what followed was two to three weeks of conversations and interview screening.

Of course, I had always been preparing to become a manager. Before joining Microsoft, I’d already been a tech lead twice at startups, leading teams of 6–10 people (granted, a startup tech lead and a manager at a big company — especially Microsoft — are very different beasts). After joining Microsoft, I told every single one of my bosses that I wanted to be their backup. Add to that the fact that I was outstanding (okay, a relentless overachiever), and every boss gave me opportunities to match: taking part in the team’s process of scoping and green-lighting requirements, leading a small group to build a specific feature, and overseeing and coaching the team to take customer incident postmortems seriously. I worked for my most recent boss for three years. Especially in the last year, as the areas and headcount under him grew, I became the squad lead (dotted-line leadership) of a four-person sub-team, fully responsible for maintaining one area: managing the incidents (customer-impacting issues) and bugs in that area, keeping the number of unresolved incidents and bugs within a reasonable range, and making sure customers’ reasonable requests (incidents, bugs, and email threads) were addressed within a certain time frame (otherwise customers might get unhappy and escalate to leadership).

How I Handled My Boss Leaving

Once my boss had decided to leave, he told his boss (M2) and very soon told me as well. My first reaction was shock, but I quickly realized this was both a challenge and an opportunity for me. I could try to follow him out the door; I could look for a new opportunity elsewhere (after all, the boss who trusted me most was leaving, and if someone got parachuted in, I’d have to spend time and energy rebuilding trust from scratch); or I could stay and wait for the new boss — since I had the most reputation/influence on the team, the new boss would definitely lean on me for help. At that point I didn’t think I had a shot at replacing him, for two reasons:

My level was Senior, not Principal, and our broader org had just gone through a reorg in the past six months that required every manager to have at least 7 direct reports; some managers with smaller teams had been turned back into ICs (individual contributors). Compared with my boss, my level and management experience normally wouldn’t allow me to manage that many people — at the time our team had 11 people, including one or two colleagues at a higher level than me.
On my team and our sibling teams, there were quite a few Principals who had been around for 5 – 10 years or even longer and had been managers before. So what I was actually thinking at the time was whether I should vote for colleague L or colleague B as our new boss.

Two days later, my boss came to talk to me with an idea and asked whether I wanted to take over as the boss. By then I’d already been thinking about going for it, so I said yes. He then showed me a draft email — a gift he had prepared for me. In it, he proposed which areas our team could keep owning and which could be handed off to sibling teams, so that I’d manage fewer people (especially senior-level colleagues) and own fewer areas. With that plan, he recommended me to his boss as his successor. Looking back, it still gives me a warm feeling — it says a lot about how much my boss trusted me.

Coincidentally, around that time I had just attended a talk on networking organized by Kedaibiao Lizheng (a Chinese online content creator) and given by Howie Xu (a paid talk, 149 USD). A TED talk about how meritocracy actually works inside organizations also inspired me a lot (Carla Harris: How to find the person who can help you get ahead at work | TED Talk). After my boss told me he was leaving and wanted to recommend me as his successor, I used that as a conversation starter and started networking like crazy. I chatted with colleagues on my team about the boss’s departure to test the waters, and also talked to my former manager (an M2), the M2 of the neighboring org, the head PM of my own team, M1s on sibling teams, and so on.

One colleague messaged me directly in the middle of the very meeting where my boss announced his departure to the team: “if you get opportunity accept it” (if you get the chance to take over as our boss, take it). Later, when I chatted with other colleagues, many of them also volunteered that they’d fully support me if I got the chance. I joked that, unfortunately, “You do not have power to decide or even vote”.

My former manager (the M2) told me to be blunt: Just tell your M2 that you want to become the manager. Of course, we also went deeper. He asked me questions about my determination and confidence to help me confirm whether I was ready to throw myself fully into being a manager (see — the most important thing about being a boss is commitment), and we talked about my then-M2’s style (my former manager and my M2 were good friends). Later, when he had a meal with my M2 in person, he brought me up (and surely put in a good word for me). He even told my M2, half-jokingly and half-seriously, that if he didn’t make me the manager, he’d come poach me for his new team.

My former manager was also honest enough to tell me that back when he was the M2 of this team, his backup pick for this team’s manager wasn’t me, but another colleague, B, who had been an M1 before (yes, the very person I’d been considering voting for as my new boss) and was now an IC on a sibling team. His reasoning was that I was still too green — both my level and my experience had room to grow. Right after the first half of that sentence, he said “I’m not sure if I should tell you”, and I immediately replied “of course please be direct to me”. He was probably worried it would knock my confidence, but it didn’t; I didn’t dwell on any of that. Funnily enough, colleague B did end up competing with me this time — and, of course, I made it through the final interview round and became the new boss.

An M1 on a sibling team told me that the most important thing was to show M2 that I had a strong desire (willing / passion) to become the manager and plenty of confidence that I could run the team well. One key indicator: M2 needed to believe that if he handed this team to me, he could sleep soundly at night.

The M2 of the neighboring org has been a manager for 19 years (he became an M1 at Microsoft in 2005). He taught me some of the most important traits of a good manager: doing three things well — model, coach and care — and to always bring clarity, and so on. Finally, at my request, he agreed that whether or not I succeeded this time, he would keep mentoring me for a while to help me grow into a good manager.

My chat with the head PM was rather rushed, but it had two goals: first, to introduce myself (we hadn’t talked much before), and second, to learn from her the team’s short-term product direction and plans (public information) and why those decisions were made (private information). Rushed as it was, it also helped in my final interview: when I talked product with M3, I discussed the product direction the head PM had shared with me and my own thinking on it, showing that I was a leader who cared about the big product picture rather than an IC with my head down in the work.

In the end, I went to my M2 with all this homework done, told him about my determination and confidence to be the manager, and briefly shared my thoughts on the team. Backed by my boss’s (and my former manager’s) recommendations, my M2 told me I was his number 1 choice. However, he couldn’t just handpick me on his own, mainly because a reorg was underway at the time. Specifically, under our M3 there was a China-based team being moved wholesale to the US and merged with us, and they had more managers than ICs coming over. M3 asked why not simply bring one of their managers in, since their management ability had been proven, whereas I was an unproven manager. It would also spare M3 the awkwardness of one of his managers becoming an IC while I, an IC, became a manager at the same time (especially since moving the China team to the US was already a major change for them, and M3 wanted to secure some opportunities for them). So M2 said we might need an interview process so it would be a fair competition. Of course, he sincerely hoped I’d win, because he also wanted the team’s opportunities to go to internal candidates rather than parachuted-in outsiders — that way everyone would feel that working hard here actually pays off.

How I Prepared for the Interview Questions

So M2 sent out an email recruiting for the manager role to all Senior-and-above employees in North America in our broader org (about 500 people in total, of whom roughly 50 – 100 met the criteria), and then shortlisted 9 colleagues for interviews. The three interviewers were my M2, a senior engineer responsible for customer relationships (reporting directly to my M3, at the same level as my M2), and my M3. After the first two rounds, the 9 were narrowed down to 3, who went on to a final interview with M3.

My departing M1 and my M2 each coached me for the interviews, and I think that played a big part in my success.

My boss mainly shared two things with me:

The STAR (Situation, Task, Action, Result) method for answering behavioral questions. Link: Amri Celeste – Interview Coach – YouTube.
Microsoft’s internal sample questions on company culture/behavioral interviews. Since these are confidential, fellow Microsofties can search for “Focus areas interview questions printout” on the internal SharePoint.

So I quickly studied the STAR method from that YouTuber and prepared my answers to the sample questions. The main thing was to prepare some representative stories from work — many stories can be reused across different questions — and to make sure all three of my interviewers would immediately understand what challenge I had been facing.

My M2, on the other hand, treated his formal interview with me as a mock interview (well, I was his number 1 choice, after all. There’s a slight whiff of a foregone conclusion on my M2’s part here, but I think it’s fair enough — whoever got picked would report directly to him in a manager role, so having a preference is understandable and acceptable). He asked me some important questions, and afterward gave me feedback on which answers weren’t the perfect answer, along with his suggestions.

For example, on my strengths as a manager, I answered that I’d grown up along with this team, knew its product and people, was the most influential member of the team (based on past performance), and was already fully owning an area — so compared with anyone else, I was the person best positioned to keep the team running smoothly. He said that wasn’t a good answer: star employees aren’t necessarily suited to be managers, and sometimes bringing new talent onto a team to drive change isn’t a bad thing. He said this point was my differentiator, and that he could play that card but I shouldn’t (He can play this card for me but I should not). He said my strengths were the passion, the drive, the diligence and customer obsession, and so on; he believed I had those mindsets and hoped I’d answer the question by showing the qualities a manager needs.

Finally, here are some of the questions I was asked:

Why do you want to become a manager? What’s your passion?
What do you see as your strengths and weaknesses as a manager? What’s your strength? Weakness?
What’s the biggest problem your team is facing right now? What ideas do you have? Why haven’t you pushed those ideas forward as an IC? Why do you need to be the manager to tackle these challenges? (This actually relates to a classic interview question: Influence without authority, but the question I got was more like its flip side: with authority, what can you achieve more?)
Tell me how you handle conflict. How to resolve conflicts?
Of the following, you may choose two to sacrifice — which two would you pick? Work life balance, Rewards, etc. (I forget the other options; I chose these two as my answer and explained why.)
If, in the future, a junior employee on your team reports that working with a certain senior employee makes them very uncomfortable (e.g., they feel they aren’t valued or respected in the collaboration), how would you handle it?
If you become the manager, what are your plans for the team’s future?
If you don’t become the manager, how will you handle it? (Honestly, I hadn’t thought about what I’d do if I failed — shying away from hard things just isn’t my style — so I improvised on the spot. I said I’d do a retrospective to find my gaps, and borrowed a story my M2 had told me: as an M1, he once competed for an M2 role and lost, then learned a lot from the leader who was brought in instead, and when another opportunity came up six months later, he became an M2. I then said I’d wait for the next opportunity and grab it with both hands.)

What I Got Right Throughout the Process

If you want to be a manager someday, tell your boss and your boss’s boss early (just like I told my bosses I wanted to be their backup), and look for chances to start building leadership and management skills, so that when the opportunity comes, your bosses will actually consider you.
Day to day, focus on building your reputation and on networking: the essence of meritocracy (see the TED talk) is that people with power recommend people to move up. You need not only solid, real ability, but also to be known by people with power — in other words, you need to find sponsors. In my story, I was the team’s star (high performance ratings year after year), and my boss and my former manager were my direct sponsors. Later, my M2 was won over by my passion and saw me quickly reaching out in all directions to prepare for the role (for example, both my former manager and the head PM had confirmed to my M2 in their day-to-day conversations that we’d talked), so he became my sponsor in front of M3 (he made it clear that I was his number 1 choice).
I prepared thoroughly for the interview questions. With coaching from my M1 and M2 (which, of course, I asked for myself), my answers were clearly structured, and after the interview my M3 told me I had fantastic communication skills. The stories I prepared were also fairly persuasive: beyond showcasing my strong qualities, they were tailored to each of the three interviewers (for example, as my M2 stressed to me, in the interview with M3 I emphasized my focus on the product and customers rather than on the team). Each interviewer fully understood the story I was telling / the problem I had solved, and recognized both my approach and the qualities it reflected.

Looking Ahead

The interviews are behind me, and while my memory is still fresh, I’ve written down the key points of the whole process, hoping they’ll help my future self and others. There will surely be more to share as I step on more landmines along the way — in fact, I already ran into several challenges in my very first week as a manager. To be continued.