On leadership: the boor and the chairman

It was 2006. Ontela had existed for the better part of a year, and I’d been fundraising and networking my little heart out. People kept saying I should be sure to meet this guy Tom Huseby, but it never seemed to happen.

My cofounder, Brian Schultz, and I had wrangled our way in to the exclusive Lehman Brothers party at the 3GSM conference in Barcelona.  Even attending was a strain on young Ontela’s finances, but we had decided that we’d leave no stone unturned in our search for funding. It was fertile hunting ground for cofounders hunting for VCs to invest in a wireless startup.

From across the room, we heard a hearty laugh, and saw someone who looked like a cross between Kenny Rogers and the Gorton’s Fisherman.  His nametag read “Tom Huseby”.  We sauntered over and joined a group of spanish and french executives who were listening rapturously as he told a convoluted joke making fun of their nationalities, cuisine, and military history.  More uproarious laughter followed, and the night rolled onward.  Some time later we slipped in the Ontela pitch, and made plans to meet back in Seattle at Tom’s office – three blocks from ours.

This post isn’t about how you have to go to Spain to get a meeting with a VC who goes to the same coffee shop you do.  It’s not even about that joke, or many others Tom’s told in the four years I’ve had the privilege of working with him as Ontela’s Chairman of the Board.

You see, I was at a conference recently when a different VC of my acquaintance joined the conversation.  To punctuate a point, he cracked a joke about engineers who hail from a particular country.  There was a few polite smiles.  Someone left, I later found out, terribly offended. No deals were made, friendships sealed, or positive vibes sent.  It was actually pretty horrible.

In business, you get a lot of advice.  “Stand strong in the negotiation.”  “Empathize with him; put your arm around his shoulder and tell him it’s going to be alright.”  “Just tell her directly; don’t dance around the subject.”  Most of this advice is very, very bad.

It’s bad not because it doesn’t work well, but because it works well depending entirely on where you stand.  An executive who has an open and forthcoming relationship with their employees needs to share news as soon as it happens lest they be seen as untrustworthy.  A less communicative executive who lets the engineering team focus on engineering, by comparison, may scare the pants off them when they casually drop business news in the hallway.  Tom can crack a joke and make a stinging criticism feel like a welcome word of friendly advice, while someone, somewhere convinced the aforementioned anonymous VC friend that he was a comedian.  Neither one is right, and advice from one will lead the other to ruin and despair.

What you have to realize in business is that in some things you’re the Chairman, and in some you’re the boor.  Jokes work for Tom.  Not so much so my other VC friend.  I know brilliant leaders who inspire their team with generalities and don’t waste time on the details.  I know from experience that when I try to skip over the details with my team, I look and feel like Richard Nixon.

That’s why I’ve taken to qualifying any advice I receive… is this good advice for a Chairman, or for a boor?  And which one am I today?

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