Life as a Lead at Microsoft


Last September, our Development Lead and all-around great guy Charles left the Windows Live Writer team for the greener pastures of venture capitalism. (In Microsoft parlance, Development Leads manage developers, while Development Managers manage development leads.) With mixed feelings, I stepped into his role—my first time being a manager, not counting a few ill-fated months in 2001 that I’d rather forget.

I couldn’t have been happier as a developer on Writer. There’s something simple and pure about creating features, fixing bugs, and solving customer problems. A good day meant that when I went home, Writer did something cool that it didn’t do when I had arrived in the morning.

Being a lead, so far, has been anything but simple, even though I’m only managing two developers. I’m finding it much harder to measure my contribution or to even know what’s the most important thing to work on at any given moment. “Time management” for me used to mean making sure I don’t spend too much time on YouTube or TechMeme. Now it means having 12 hours a day worth of work each day I could be doing, and deciding what subset of it I’m actually going to spend time on. It means deciding which of the three meetings I have scheduled for 1PM I will actually go to. All the while knowing that things I’m leaving undone, and the meetings that I’m deciding are not as important, all have the potential to bite me in the back down the road.

And that work, and those meetings, are not always clear and simple like building a feature or fixing a bug. I spend a lot of time these days just “getting on the same page” as people. Having arguments without reaching clear resolution. Planning to plan. How do you measure whether you’ve been successful at these kind of things? How do you determine the impact on the product, on your users?


That all being said, I’m glad to have this opportunity. Going up the steep part of any learning curve is by definition both challenging and rewarding. To be honest, it’s been a while since I’ve hit any really steep learning curves as a developer. And even after this short time, I’m starting to get comfortable in the role and learn how to find real satisfaction in what I’m doing.

Over the past few months I’ve gotten some great management advice from some great managers. I’ve also had some thoughts percolating for some time, that being a lead has helped crystallize. I hope to blog as I learn, partly to give some food for thought for other new managers out there, but mostly as a journal I can look back on after a few years, and wonder at how naïve I was.


15 Responses to “Life as a Lead at Microsoft”

  1. You’ll do a good job, for sure 😉

  2. Congratulations, Joe. I was always afraid of the prospect of management while I was employed as a developer. But now that I’m running my own business I feel like it would have been valuable to have the experience within another company.

    Kick butt! I hope you get to squeeze some coding time into those long days!

  3. Joe,

    Congratulations on becoming Development Lead! Do you still write code, or development leads only manages projects?

  4. Congratulations on your promotion. 🙂

  5. 5 Dipinder

    Great post Joe ! Do you miss coding ?

  6. Ah, I should’ve clarified. Development leads at Microsoft are supposed to spend some proportion of their time also being a developer. Since I only have two developers, I’m expected to do at least 50% of a Senior Developer’s job in addition to my lead duties. On the other hand, leads that have, say, eight developers are not expected to do much coding at all.

  7. 7 Scott

    Nice one Joe, you kept that quiet 🙂

  8. Congratulations Joe!

  9. 9 Bonnie

    Go, Joe, Go! And to think I knew you back when you had to share an office…

  10. Hey Joe,

    I highly (and seriously) recommend, Dogbert’s Top Secret guide to Management

    When you first read it, you will think, these are all of the things that I should not do! Knowing what I should not do must be half the battle, so receiving the recommendation for this book was a big help. 🙂

    Then after a while you will think, these are the things I should do, because the system of a large company is so screwy that this is the only way things can actually work. Its wrong, but we are talking survival here. It is a recession afterall! I’m really thankful someone recommended this book! 🙂 🙂

    Then some more time will pass, and as you reflect on this book, you will come to recognize that even though the book is written with humor, it actually channels many of the teachings of Confucious. Before you realize it, employing the techniques and strategies mentioned has you fast tracking your way to the top and weirdly enough ‘Getting Things Done’. After you get your next promotion or two, you will be really happy someone recommended this book, but you won’t remember who it was so to make up for that slight oversight you will start recommending it to all of the managers that are now working for you and promoting those that quote it will giving lower marks to people that quote books like Who stole my cheese. 🙂 🙂 🙂

    Then one day about 10 – 20 years from now, you will find yourself making so much money that you are a burden on the corporation and the potential for a stock holder return on investment. You will have a few too many gray hairs and might be somewhere in your 40’s or 50’s. You’ll accept an early retirement package and semi-retire to Idaho or maybe at that time, Arkansas which will be billed as the new Idaho. You’ll have dreams of picking up some work as a part time developer and double dipping an extra salary to go with your early retirement package. That won’t pan out quite like you expected, and before you know it, you’ll be hustling for any dev job you can find, interviewing with people that fear you because you are 5 times more qualified than they are to do their job let alone the job they are interviewing you for at 1/4th the starting salary you received out of college. It will be right about at that point, where you will realize that whom ever recommended this book, was just crazy and probably laid some sort of trap for you. You will curse the day you read the boook and make it a point to comb your old files to find the crazy person who ‘did you wrong’.

    Amid your plans to plot and exact your revenge on them, some copies of your notes will be hacked and spread virally around the internet. You will simultaneously receive a $1 trillion movie rights contract offer from Hollywood for your story and an indictment from the Arkansas Grand Inquisitor of Future Crimes.

    The indictment will go to trial and that will cause Hollywood to quadruple their offer, hoping for you to sign before a conviction. The AGIFC will offer to settle with you for $3 trillion, and at that moment you will remember that I offered this comment of forgiveness and full waiver against the plot so that you can tell the AGIFC to go stuff it, and pocket the $4 trillion, which regrettably will be worth about $2,500 in today’s dollars, but in a world with free universal health care, free transportation, free room and board, and basically free everything that is tangible, your only expenses will be those products you can buy online and $2500 will cover those expenses for about a year. So you will be happy, and have enjoyed a full life and career and even an extra 15 minutes of fame at the end.


  11. @brettbum I am way ahead of you, a friend gave me that book as a high school graduation gift (I actually majored in Management Science in college). I am currently on a trajectory towards the “making so much money that you are a burden on the corporation” phase. Muhahaha.

  12. LOL 🙂

  13. 13 Anne-Marie

    Hello Joe,
    Management is another ballgame. Used to be a management consultant..OY!

    Sorry to bother you sbout an old program of yours: Onfolio. Yeah…it’s a headache…and i am trying to move out of it. My problem is my largest and most important collection seems to have been corrupted. I keep getting a “not a valid Onfolio collection file.” Yes, it was!
    Anyhow, I tried with cfs2xml and got a JIT error. I am not a techy or a programmer and this is really depressing.
    Is there any way you can help me please? Or suggest someone who could recover my file?

  14. Anne-Marie, please e-mail me at joe.cheng *AT* Thanks.

  15. 15 Ray

    Thanks Joe. I know you wrote this 3 years ago but it has been very useful to me. I am currently a Software Dev at Expedia and have been given the same oppurtunity as you did and worried i woukd not cope with it. Knowing there was someone in the same situation is great. I hope whatever you are doing now you are enjoying

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