Everything I learned in 30 years at Microsoft Part V

Don't choke people you work with

Like everything else in Bentonridge, Arkansas, the airport feels off. It’s too big for the town — walking down the long concourse, each gate is abandoned save mine.

Bentonridge is a company town — everyone works for Valumart or something Valumart adjacent. Every restaurant and hotel is a chain, arrayed in mini-malls like decorative charms along the fringes of the sprawling corporate campus.

My flight is delayed.

It’s getting late in the empty airport, and now I’m squirreled away at a table at the back of the one open bar, nursing a beer while I half listen to teammates relive the few dramatic highlights from the earlier customer workshop.

I have to go back to Seattle for more meetings before I can go home. I bring another guy out with me — Brad — but he catches the early flight, escaping before we finish the workshop.

Brad posing before things go sideways.

Valumart is a longshot. The competition has them locked up, but then, opportunity knocks. An executive I know from General Electric jumps ship, taking a high level IT position in Valumart.

I need someone from our side at the same level to match up. My big boss — the guy who runs our entire org — picks Brad as that guy, our executive sponsor for Valumart.

Brad is one of our Directors of Product Management and he’s ready for a fight. If he can win Valumart, land the white whale, a promotion is waiting.

Brad’s a big guy and he carries big guy energy. While he’s a recent addition to the org, he’s a 10 year Microsoft veteran with a proven track record. He may be a little rough around the edges when it comes to customer conversations, but he’s smart and quick on his feet.

Once I bring him in to talk with a different customer that matches Brad’s energy. He gives Brad a hard time, calling our product crap. He stands up, Brad does too and in a second their two sweaty faces are inches apart, pointing and yelling.

I call the meeting, walk Brad out to cool him off and head back for damage control. It wasn’t the last time I’d do that.

Back at Valumart, first thing in the morning, Brad and I get 20 minutes with the new, ex-GE executive. Brad shakes his hand and launches into his pitch.

The Valumart executive is polite but unexcited.

Afterwards, Brad and I, along with some of his team, lead a workshop. Valumart lists off requirements. Brad promises dates that aren’t on our roadmap. I raise my eyebrows.

I look over at Brad and he’s furiously typing into a screen of chats lighting up his laptop. When we take a break, Brad heads outside, pacing, talking on the phone.

Brad leaves after lunch, catching an early flight back to Seattle.

Me, I get in at 1AM.

The next day, I sit in the monthly leadership review trying to stay awake. My big boss — the one who anointed Brad as my exec-sponsor buddy — sits on the other side of the big table. No one sits next to him, because he flails his arms about wildly, yelling when he gets mad. This happens a lot and no one will sit in the blast radius.

Big boss makes an offhand comment about how one of our directors is no longer with the company after a physical altercation with another director.

I jolt out of my stupor. What?

And just like that, Brad’s gone.

I immediately know who the other director is — Simon. Simon is the big boss’s heir apparent. While Brad and Simon are peers, Brad doesn’t have the same big boss history.

Simon is intimidating in an entirely different way. Gaunt, bald, albino-esque pale, he never smiles. Think Voldemort. He intentionally speaks in a low whisper, forcing everyone to lean in and listen carefully.

If Brad is a frenzy of blustery chaos, Simon is a composed assassin.

Brad knows Simon is his competition. Simon sits on the same floor as the big boss; they have lunch together. Brad gets an office a couple floors down in the middle of coding crew chaos.

Brad falls into Simon’s trap. He heads straight from the airport back to the office, full of ideas to land Valumart. He gets time with the big boss. Simon lays in wait, already sitting in the conference room. Systematically, he forces Brad to rewind every commitment: we need headcount, Legal has to bless it, Security won’t sign off. He dismantles it all and Brad snaps.

Create a pressure cooker; people snap.

You know that saying — keep your head down, stay out of office politics and you’ll do fine? That’s not possible. You can’t untangle the real work from personality and politics. Have strong opinions, speak out, push back, be convicted.

Just don’t choke anyone.

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Afterword: What happened next

Brad gets another gig nearby and I run into him a few times. Simon leaves Microsoft, leveraging a promotion right before the big boss retires, landing an executive role at a smaller company.