Why a Stint at a Large Tech Firm Can Make You a Better Startup Exec (from my time @ Microsoft)

What are the traits of a successful startup executive?


Here are my top picks:

  1. Bold. Adaptable. Lifelong learners.
  2. Culture builders. Great Executers. Great Hirers. Superb Firers.
  3. Passionate. Great Communicators. Team Builders.


1, 2, or 3, or all of them combined?


Whichever road you choose, the next question will always be the same: how do you become one?


It’s the question that a lot of younglings (graduates), new entrepreneurs, and people planning to become startup executives ask themselves, and experienced and successful startup executives. The answers can be divided into two primary camps:


  1. Joining a startup, and wading through birthing hell to understand the problems and realize opportunities firsthand
  2. Joining a large tech firm and gaining experience and building connections in its talent’ network pool


Andy Rachleff informs us of a mid path. He literally advises the younglings to join mid-sized private companies. However, I will not be going in that direction. And though I’d rather not conclude so early, I do believe that one should not learn how a startup culture is built by being part of a startup. It be learned, but it’s too formulaic. It curses one, forevermore, to finding the right formula for success instead of consistently evolving and testing and rebuilding the business model and organizational structure as they progress ahead.


On the other hand, I believe that a stint at a large, established firm is sure to bring you face to face with the reality of how to handle the top end — managing people, allocating talent, boosting morale, staying abreast of market changes, and keeping teams together. I believe “culture” will always remain something that you will have to found again at every new startup.


So without further ado, here’ what I had learned at my stint at Microsoft, and how it has shaped my executive career ever since.


It taught me to take action without discussions


The first aspect of management I learned was a lesson in management hierarchy. I found that involving others is not always the best job. I saw people and teams get stuck into what I’d call the think-tank loop. Everybody pitches in an idea and everyone wants to find the problem with it, you know, “be sure” that it is the perfect idea for the business.


It’s overly cautious, and it gets you nowhere.


You’ll always be taking a pilgrimage around the team leads, the department head, and other managers to get the big O.K.


If you really want to do something, then you have to take the action, believing that it is the right thing to do. I mean if you don’t make a complete ass of yourself from time to time, you’re either not doing anything or doing something seriously wrong. In hindsight, I realize how each of those teams (those that progressed and those that died out) was nothing less than a startup in their own right. I have already written on building startups for scaling, where I consider each team as a small startup, and now I caution people to be cautious of this attitude.


At a large firm, you have more leverage for taking bold (albeit thoughtful and reasonably calculated) decisions. Given that these firms are highly dependent on innovation, you have a higher chance of breaking through the chaos and leading something with backing of the entire structure. All the more training to work on the model and build a team to pad your decisions.


Allow, Nay! Value Screw Ups


The next lesson I learned was how to react to screw ups. I saw people getting worked up over small things and as a result made everyone in their team cautious. In hindsight, I see that many of those “mistakes” had no bearing in the next 5 years. It taught me to separate the things I don’t need to care about and the things that really need my attention.


I mean, unless employees are breaking things, or trying to bend the rules, how do you expect them to back your strategic and risk-laden decisions? How will they grow? How will the company grow if everyone would just stick to what they know?


It taught me to know when it was time to leave a big firm. Let me share it with you too: If the place where you’re working with has pin drop silence in meetings; if everyone is afraid making mistakes, and If the manager is too focused to bring your smallest of transgressions in your performance review, leave. Leave and find a different firm for your stint.


Being Proactively Engaged



You have to gain the trust and respect of your team. But how do you measure it? By your level of engagement.


Look for people who are seeking you out.


If they are not doing so constantly — ranging from discussing problem and ideas, or seeking things from you — then something’s a miss. The corollary from this is that you need to be engaged in all key aspects — ranging from checking mailing lists, the latest builds, and more.


You have to be proactive, because unless you’re plugged in, or turn away people seeking you out, don’t expect to be involved when the key decisions are being made. One way of being proactive is through part timing.




One of the best things about the culture at Microsoft was that one could try doing a different job for a while, all the time. It was quite easy to be a part-time Program Manager, or a part-time developer. People always love all the help you can give them.


Executives need to realize that the best way of tapping into someone’s potential is by letting them give a try to something they want to do. That they believe they want to do. Give them chances, yes multiple times. Give them some leverage, allow them to build onto their skills. Shooting them from the first miss-go will not only re-enact the cautious atmosphere in the office, it will also demoralize your resource pool.


Keep Trying Out Stuff


The tech industry is one that changes every few years or so. Hence, the worst thing an executive can do is to not keep up with the latest changes and let themselves stagnate.


I’m not saying you need to have your smartphone buzzing with apps, or have profiles on every new social networking site. I’m saying that you should be playing with whatever is receiving attention and is popular. Get the gist of it. Discuss possibilities for its use, and the like.



Let People Know


Executives have consistently underestimated the value of letting someone know that you appreciate what they’ve done. Praise them in public, and in case you have an issue with someone’s attitude and performance, have the conversation behind closed doors.


A little email goes a long way in making everyone happy, and a Public Display of Disappointment (PDD, for humor’s sake) can sink your talent pool like a flush tank.



In Conclusion — Don’t expect everyone to be passionate about the Organizational Goals


Executives are tasked with leading the company, strategically. That means they always have to see ahead (the bigger picture). It’s like dreaming; new possibilities may arise and appear, and causing waves of enthusiasm, which coincidently and unfortunately cannot be all shared with everyone else. And everyone else (the majority) is most likely to have other priorities from life — other than creating a better product or putting in the extra effort to eke out that small flourish in the product.

In the end, your career at a startup comes down to you knowing, working with, and dealing with the right people. Because remember, you have to scale the startup into a growth company, and that won’t happen if you have no idea, or have never experienced the culture and lifestyle of a company in its post-scaled years looks like, how to work with people in those circumstances, and how to lead them.