Reflections on Leadership Learnings...

Today, May 10th 2019, marks my last day at Microsoft. After over 12 years of an amazing ride, both professionally and personally, I’ve decided to try something new, learn something else, go outside the Microsoft bubble and make myself uncomfortable and vulnerable. We’ll see how it goes, and I’m both nervous and anxious. This post, though, is about looking back, and reflecting on my Microsoft journey. This particular one focuses on the people, organization, leadership side of things – if folks find value, I’ll do separate posts on Product and Process as well.

No, I’m not the first or the last to join or leave Microsoft, nor am I unique in spending a few years here (lots more people have spent a lot longer!), but I feel enough people have asked me about my journey, and I think there might be little bits of information for someone else to look at and use as perspective as they reflect on their own professional journey.

Note: the thoughts expressed in this article are solely my own and not representative of Microsoft.

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12 Years, 12 Key Learnings – A Summary:

• It’s all about People, Product, Process – backed by your Perspective (it can change how you look at the other 3 pivots)
• A career in computer science is about Life Long Learning – and there’s lots to learn in big corporate product companies (as well as startups) and people to learn from (mentors, coaches)
• Find your motivation – and get beyond the narrow mindset around corporate ladders, and money
• Prioritization is a very important skill – especially in leadership (learn quickly how/when to say NO)
• Congruence in decision making is the key – and consensus will rarely happen especially in engineering. Bias for action and fail fast as needed
• Communication helps solve many leadership/organizational problems – when done clearly, honestly, transparently
• Empathy is your friend – irrespective of who you are and what role you’re in (assume good intent always!)
• If you want something, ensure it is known you want it ?? – and don’t leave it to Karma or someone else to figure it out
• Challenge the norm – and if it’s uncomfortable or you feel vulnerable, you’re on the right track
• Leaders are just one of you – and they are human, they make mistakes and are often as seemingly clueless as the rest of us
• People and relationships are more important than you think – and its been proven quantitatively and qualitatively that they’re critical to success (organizational & personal)
• Enjoy the journey, try not to stress yourself too much – and when it’s all said and done, how would you want to be remembered?

And above all, Invest aggressively in your career – explore, try, fail, try again, know what you like or don’t like and build your plans for your profession as you learn more. This is yours to manage and yours alone.

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12 Years - The Journey

Microsoft – An interesting beginning

For me, joining Microsoft was not what I had planned for the beginning of my “official” professional career. This was late 2006 – prior to that, I had learnt the ropes of building products and services from my father, co-working in a startup with him and my brother, and I was loving it. So much to learn, both from an industry veteran, as well as in doing all possible jobs for your customers and products. But then we felt that I needed some big company exposure to enhance my learning of scale, and how enterprise works. So I started looking for big company jobs, and was all set to join Yahoo! in India, when a chance Microsoft recruiter call to my now wife (she gave up her slot so I could go interview - I love her!) turned into an impromptu recruiting event for me followed by a late December interview at Microsoft campus resulting in a job offer and role that made me leave the Yahoo offer and take up a career in MSFT.

For me, my professional choices at that time were all about the product, and nothing else mattered. I still remember a CVP asking me in my as-appropriate interview if given a choice between products whether I’d choose to work on Education, Gaming or Communication products. My answer was clear!

“Of course, I’ll work on Gaming!” (P.S. It was all about the product for me back then)

I’d grown up building games while studying computer science. Whether it was a simple game of snake, or battleship or a complex logic based game of chess, or the more graphically intricate 3D world based role play games, this was a common hobby while studying.

So that’s how began my stint in gaming. First product was re-building out the game of Bridge (on a multi-player web platform) where apparently Bill Gates was a frequent player, and we had a very obsessed set of fans who wanted the game and the multi-player lobbies to continue to function, so we spent a good chunk of time making Bridge work for Bill and our soccer moms ??Lots of fun & learning with a newly formed product team in India, working remotely with teams in the USA – my first exposure to both Microsoft scale and Microsoft product development coupled with remote development, and cross-continent, cross-culture teams. It was here I started learning about importance of people in teams, culture being important for an organization as well as how to manage large cross-function, cross-region teams. It was also my first exposure to understanding process and how product development is managed in large companies and why it’s critical to project manage a product.

From a motivation standpoint, It was all about soaking in the big company culture, and because I didn’t know any better, I figured it’d be in my best interest to push myself to climb the corporate ladder at Microsoft. I set a goal for myself – to get to principal band before I hit 30. and there began my quest to go from my level at hire to principal band in less than 7 years. I don’t know why I chose it, It just felt like a goal I could measure, it was aggressive and something that had some form of longevity associated to it so I could plan and focus around it. In hindsight, not the best of motivations to run after, but I really didn’t know any better at that time. What it did help with, was that it was clear and measurable, and I let my management know that’s what I was focused on.

The Move to USA, and subsequent international teams & roles

Bridge shipped. Ship parties became the norm. Our team started to work on MSN games & Messenger games, which our Redmond teams also worked on. At some point (about 12-18 months into my role) our leadership decided to co-locate all of our teams in Redmond, and most of our team moved to the USA, to continue working in their respective roles. For someone like me, this was awesome but we also had folks who moved with their families to a new country exploring the new world of opportunities Microsoft offered here.

Breaking the chronological order a bit, We’ve had the pleasure of working in and with teams that have spanned various aspects of the globe. We worked in the India team, and then the Redmond team. We ran teams in Slovakia/China/Canada, worked closely with teams in Paris/Israel/Boston, recruited in many countries including UAE/Middle East/Brazil, and partnered with folks in locations pretty much all over the map (shipping Microsoft store to over 100+ countries and many regional teams was a massive exercise). In my mind, this is one of the BIG advantages of working in a large corporate company – you get exposed to so many perspectives and cultures by working with so many talented people all over the world, and you also get the pleasure (and responsibility) of growing that culture by hiring from across the world as well. For me, this exposure was invaluable and taught me the value of differing perspectives, understanding local vs global thoughts and variances, as well as taught me to value people and relationships in a professional setting, and how to manage that well when your teams are geographically spread across the world map. It also taught me that the world is a small place, and people are super talented and motivated everywhere, so leverage and learn from the best ?? Last but not least, this experience also helped me understand the value and importance of clear, crisp communication since you can’t meet everyone in-person every day so that crisp communication and expectation setting becomes a lot more important.

The Layoffs

Back to gaming and just having moved to the USA – the first few months were focused on learning (you’ll notice a pattern here ??) – learning the product better, learning the people better, learning the culture and everything else that changed with the move. This was also the time I learnt (with the help of some amazing managers and mentors) how and when to say No. I understood that Work-Life balance was what I made of it, and it was purely and solely in my control to define which way I moved that dial. Also, making sure that of the work we did sign up for, we prioritized appropriately based on customer impact and business need.

Just when I thought I had this figured out on how to survive and succeed – came the ill-fated day - 22nd of January 2009. The first ever layoffs in MSFT’s 34 year history, at the worst economical time in the US. I can never forget that day in my life – seeing very close friends and co-workers lose their livelihood, our teams getting affected very badly, me losing everyone on my team and a few layers of management (I don’t know how/why I survived) and having to restart from scratch from all aspects – team, role, people – everything.

This really hit me hard and taught me the realities and frailties of the tech world and the corporate industry, where this can happen, and you have to pick yourself up and others around you, and move on to do bigger, better things. It also taught me this concept of detachment, where yes you should be passionate about what you do, but try to have some detachment from your professional life even though you will get emotionally attached to it no matter how hard you try.

I also learnt about valuing people and relationships, and ensuring you can cherish them while they last, because who knows when they’ll end. So if you have praise or appreciation to give to someone, give it now. If you want someone to reflect on something for improvement, say it now because there is no better time.

This was also the first real example I saw of the fact that leaders are one of you – nobody in my leadership chain knew anything about this, and were as un-informed as I was. So all my perceptions of “My <leader> knows what’s happening and probably is controlling it” were shattered pretty quickly and I learnt to empathize with leadership even though there will always be chatter of us vs them (for employees vs leaders). I saw many other practical examples of this fact as I worked over the years here, and have the firm belief that not only do I think it’s true, I also think that if you believe in it, you’ll have a healthier relationship between leadership and the team.

Xbox: We have fans, not customers. The real customer connect!

The layoffs and subsequent re-alignments to the teams made me focus on a couple more additional things – one, I wanted to understand a broader perspective of the product beyond my team’s areas so I could learn how to build a product from scratch (or extend an existing one). And two, my focus became clearer on people – both customers and employees. On the customer side, I got to experience firsthand how to be truly customer obsessed in Team Xbox, starting with Avatars. I started working on Avatars, with our teams spread across Redmond and Slovakia, and I learnt about engagement as a success metric. Not just engagement in terms of customers coming back or not, or time spent – this was engagement in terms of “does it bring a smile to my face”, or “am I immersed in the experience” or “did I enjoy the experience”. These are much harder to measure but are the key metrics for success in an entertainment world. Functionality was important but immersion was even more important.

I also learnt about the passion of our customers, so much so that we always referred to them as fans. And they truly indeed were fans. Every small change was noticed, there was a clear customer connect both ways in terms of things we did they liked vs things they didn’t. and there was a clear, fairly direct feedback loop that led to Xbox features being delightful to the fans.

I learnt 3D programming again (CG 101 revisited and more ??), and we also explored cross-platform development across Xbox, iOS/Android & Windows. This was the time when Microsoft was embracing open source a lot more than before, and I truly loved the mix of technology and the customer connect.

This experience led us to working on SmartGlass (second-screen experiences) for Xbox (both 360 and One) – again cross-platform, again customer connect being critical, and on a super tight timeline. From the time of the E3 announcements and SmartGlass becoming the hotness, to delivering it on both 360 and Xbox One in short amount of time was nothing short of miraculous. Xbox One shipped – with all launch titles with SmartGlass companions, and we had managed to ship a 10 year product roadmap in a 1 year time-frame ??

I always found Team Xbox to be run in a very start-up-ish fashion – being super fan-obsessed, getting to faster/quicker releases, focusing on MVP and iterating with fan-feedback, and a tight-knit team. And this was all I had seen so far in a big corporate like Microsoft. I was loving it.

Also, right around Xbox One Ship was when my previously stated objective was achieved – I did manage to hit principal band when I was 29, only to realize that it didn’t feel any different, that many other folks had done it “better/faster” and that I was running with a very narrow mindset of climbing the corporate ladder and it isn’t what would give me eventual satisfaction. Reading the book “What got you here won’t get you there” by Marshall Goldsmith (and attending his session), and attending Pathwise (leadership coaching focused on psychological analysis) also gave me new perspective on how to broaden my mindset.

Commerce: Why it matters

Just after Xbox One ship, it was time for a change, so I decided to move to the commerce focused teams, completely switching focus, product philosophy and customer outlook. Xbox was all about engagement and fun, Commerce was all about reliability, availability and getting functionality right, and then optimizing the minutest of detail to optimize for conversion. It started with working on commerce for Xbox, expanded to commerce for Microsoft (all Microsoft stores), and eventually to Dynamics Retail (selling a commerce platform to 3rd parties). Commerce was definitely becoming the hot space then (still is now ??) with Amazon starting to dominate, and other retailers starting to innovate to stay in the race, and I learnt a lot about how commerce works technologically and from a business perspective, and how to survive and succeed as an organization. It gave me lots of perspective around global reach (most retailers are in multiple markets and business strategies vary widely by geo) and managing scale based on events/times (Black Friday traffic in US are orders of magnitude higher than rest of the year but retailers don’t want to pay infra cost for the whole year). There was plenty of opportunity for what the industry calls Digital Transformation both for Microsoft and for retailers/commerce providers.

My first product here taught me how to manage a product completely on your own – almost full autonomy, control over the backlog and the technology stack, direct relationship and accountability to partners, results drove funding for team etc. It was a small product, our team was small but focused and hungry, and we managed our own processes so we learnt from our mistakes and functioned as a self-learning, self-managing unit that delivered great results. One of the best combinations of people, product, process I saw in my time at Microsoft. This was another proof of the usual stats you see in articles that a high-powered, well-functioning, inclusive (where everyone felt heard) team can drive much more productivity than when the team isn’t functioning well together. Only caveat worth mentioning here, is that to do this in a large corporate, you need top-level leadership buy-in and support, and thankfully we had that!

Our scope and team expanded significantly, and over time we built commerce and web platforms for various parts of the company supporting a multitude of scenarios, and it exposed me to the real breadth of Microsoft as a company, and the varying perspectives it brings with it. I worked on a number of platform teams, driving adoption of those by a number of enterprises big and small. Top learning here was that irrespective of how technically good your solution/platform is, it is imperative to get customer buy-in and have an effective sell-pitch and vision to customers, and keeping on with that constant customer engagement and satisfaction is critical for any platform’s success.

As the team grew, we saw the implications of larger teams – decision making became more interesting as when you put X engineers in a room and try to take an architectural decision, it is rare to have all of them agree on the same approach, thus the learning around congruence in decision making and consensus being rare. We also saw that clear/precise communication became a lot more critical as the team size grew since it became harder and harder to keep everyone in the loop. This is also where I got to leverage my learning in Pathwise, and practice empathy a lot – always assuming good intent. Bigger teams, more people, more opinions can lead to more mis-communications, more mis-expectations and it’s very easy to get into blame mode, or “it’s not me” mode, but if you assume good intent, you’ll notice many issues stem from purely mis-communication or lack of appropriately set expectations.

During my time here, we exercised prioritization and macro-planning at large scale for large teams, and it was amazing to see teams getting better and better at being able to relatively accurately macro-plan for longer periods of time, and being able to surface scope, time or resourcing issues earlier than before.

This was another example where I got to see the aspect of “Leaders are just one of you” again – often times, when discussing scope, time or resourcing issues – leaders would have very similar thoughts, constraints and ideas as the rest of the team, and clear, transparent communication between the team and the leaders often led to decisions that were congruent to both sides and prevented the festering of us vs them feelings between the team and the leadership. A better aligned leadership + product team always results in a healthier, more productive & happier team, a better product and more effective outcomes.

Lastly, while working in this area, I also continued to practice detachment – it was a concept introduced to me formally by Pathwise (as suspension of attention) but my interpretation of it took it a bit further and it allowed me to find peace in my passion, it allowed me to focus on what I was passionate about, but also have a sense of detachment from it, so if it didn’t work out as planned, or other circumstances led to the dissolving of the idea, team, product, or something else, that you could find learning from it and move on.

Thank You!

I’ve had an incredible time at Microsoft. Some folks asked me why I was leaving, and also why now – I do believe Microsoft has tremendous opportunity both as a company, and personally for me as well. I could continue to work at the company for years to come and not get bored, tired or non-productive. For me, it was more of an opportunity that opened up by circumstance, and something that I think will give me new learning from a different perspective – a new viewpoint, a new culture, and a new set of people. Essentially, I’m changing (for myself) the people, the product and the process all over again. And it’s both exciting and nerve-wracking. That feeling of vulnerability was what I was after.

I have to end by thanking the incredible set of people I’ve worked with over the years – my teams, my peers, my partners, my managers, my mentors, and my leaders. I’ve learnt so much from my experience in this big corporate company and I’ve grown so much personally and professionally that I can’t find enough words for, but can only be grateful for the time here.

A quick note about mentors – I’ve leveraged mentors quite heavily in my time at Microsoft, and found it incredibly rewarding. In my mind, it’s another advantage of working in a big tech company – there are so many incredibly talented people you can learn from! Definitely a target rich environment, should you choose to engage in it. My only suggestion about mentoring would be – as a mentee, find what you want to learn, and then look for the appropriate mentor based on that. Keep it focused on learning, keep it time bound, and know that the learning is on both sides, but you need to drive the relationship.

Special shout-out to my wife for supporting me through my madness at work (she works at Microsoft as well and does an amazing job managing work-life with 2 kids now!), and my parents (I've learnt most things in life from them!) and brother (I've always wanted to follow and emulate what my brother does!) for supporting me through life!

A big THANK YOU! to everyone – thanks for the memories and the adventures!