Thank You, Greg Winston

If you live long enough and lead a certain sort of life, you end up writing a lot of correspondence that you don’t really want to write when you start writing it.  If you’re lucky enough, more of those missives relate to happy things happening in peoples’ lives than sad things.  If you’re not wanting to congratulate someone on a happy thing, chances are you’re being selfish.

Greg Winston has been my Senior Director – my “grandboss”, as I like to call him, my boss’s boss – since I hired into the SQL Server Center of Excellence way back in 2006.  Greg is great guy and a great grandboss (not to be confused with a greatgrandboss; I have one of those and she’s a wonder as well, but that’s another post), an adept manager of technical people who was – and still is – a technical person himself.  He’s never lost that geek’s fire in the eye that we (and our loved ones) know so well.  His background is primarily in networking and Exchange, but he is fully capable of carrying on deep conversations about SQL Server, and generally tends to mirror my kid-in-a-candy-store vibe whenever he ventures into T-SQL.

Did you catch that?  A Senior Director who still spins code?  In other than his “native tongue”?  Wow!

You know almost all you need to know about Greg.  To an extent unprecedented in my career, Greg runs a family-oriented business (could it possibly have something to do with the seven kids he and Shelby have at home?).  There are managers at Microsoft who “talk the talk” when it comes to work/life balance, only to send their teams on monthly marriage-straining death marches against ridiculous goals.  Greg, on the other hand, gets actively angry if he catches one of his charges prioritizing work over family.

He takes it personally.  Asks how he’s failed us.  And then repeats that he doesn’t want us putting anything before family, never mind work.

He means it.  And it shows.

It’s a sufficiently inspirational environment that more than one of us call him Dad, even though he’s younger than most of us (including yours truly, the resident greybeard).  He is quite simply the most approachable and grounded person I’ve ever seen at his level of the food chain.

While I was in Barcelona last week, Greg scheduled a 1:1 meeting with me this past Monday which I had to cancel in order to go to the doctor and find my voice.  The news he so desperately wanted to deliver to me in private was announced in our staff meeting later in the afternoon: Greg wants to get back to the technical front lines again, either as an individual contributor or as a manager of technical people.  He doesn’t want to manage managers anymore.

As my numbness and shock faded, I started to type.  With Greg’s permission, I’m happy to share what ended up being, by the time I was done writing it, an email I was happy to send.

Don’t fear for our team.  Greg has already identified his successor, and we’re in good hands.  Dad wouldn’t have it any other way.

If you are lucky enough to work for someone like Greg, don’t ever take your good fortune for granted.  And most of all, tell the good managers everywhere in your food chain how you treasure them.  The more they inspire you to reach out to them this way, the more both of you probably need it..

Dear Dad..

I really appreciate the effort you took to get in touch with me before your public announcement, and I’m sorry that the doctor’s appointment got in the way.  Knowing you the way I do, though, I know you’d prefer I went to the doctor.

That’s just the kind of guy you are.

See, I totally get it.  I totally understand where you are.  And the reason I know..  I know.. that this is going to work out for you, is that in 2006, I was where you are now.  And in 2006, you were there for me when I decided to be intentional about my career.  The laws of karma simply require that somebody be there for you when you’re at the point of being intentional about yours.

Make no mistake – you twice saved my career at Microsoft (I know that’s a heavy burden).  You showed me that enlightened, family-oriented, respectful-of-one’s-expertise management didn’t just exist at Microsoft, but that a team could kick ass while operating by those values.  Then, when I needed to make a change for my family which it took me a year to sell to my direct manager, you were bought in before the end of a half hour meeting.  Your respect for and confidence in your team is obvious, and really is truly inspirational.

Whatever you decide to do, I know it will be the right thing.  That’s just the kind of guy you are.  For whatever it’s worth, though, I find you to be a singular leader of technical people.  While I recognize the costs that these gifts impose upon you and your family, I hope you’ll find a place where you can continue to leverage those talents to the benefit of the new family you’d be sure to build around you.

Be a dev lead. *g*  Then you can have it all..

I dearly hope that we will be friends for a long time.  I appreciate everything you’ve done for my family and me more than words can say, and I’m really thrilled that you’re doing something for you and your family.  Please let me know if there’s ever anything I can do to help in your journey.

I will always appreciate the confidence and respect you have shown me.  And I will selfishly miss you, even as I’m thrilled and inspired that you’ve got the guts to follow your heart into a new adventure.

Leading by example, yet again.

Thanks, Dad, for everything.  Godspeed on your journey.


Comments (3)

  1. Anonymous says:

    UPDATED 20 Dec 2008 to fix links It’s that time of year again, when I disappear from the blogosphere

  2. Steve Patrick ( SPatDSG) says:

    Hear hear. I worked with Greg years ago when he was in CPR and always had great respect for him, then and now. He is an amazing example of someone who has effected more people than I think he knows about. I wish him all the best.


  3. Jimmy May, Aspiring Geek says:

    Over the course of my career I’ve had some great managers–& I’ve had some not-so-great ones.  

    I’ve always felt me career was MY responsibility.  Yet there’s no doubt that a competant manager can lubricate the engines of productivity.

    I’ve never met Greg, and your frank testimony is poignant & moving.

    Congrats to you both for building such a productive relationship, setting the standard toward which we can all aspire.

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