Friday Q&A: When is it okay to be a jerk?

When is it okay to be a jerk?
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Every Friday, we’re answering your questions about business, startups, customer success and more.

Happy Friday!

This week’s question comes via comment from Casey Tibbs:

One of my favorite clips from Silicon Valley is Erlich’s rant on “knowing how and when to be an asshole.”

Warning: Not office-friendly language, obviously.

It’s a trope in business that in order to be an effective leader, you have to know how and when to be an asshole.

I don’t think it’s entirely wrong, but I do think it’s misguided.

It’s not about being an asshole. It’s about being having enough empathy to understand what the most effective approach will be in a particular interaction.

Some people will respond best to a softer approach (e.g., “Could you please do X?”)

Some respond better to an approach that puts them in the driver’s seat (e.g., “I think we should do X. What do you think?”).

Others respond best to a direct approach (e.g., “Do X.”)

You can weed this out by asking job candidates “how do you prefer to be managed?”

You can do it by testing different approaching, and paying close attention to how the counterparty reacts.

You can also do it simply by asking vendors and people you’re negotiating with “what would make you happy in this situation?”

(Note: we do have some great tips on building empathy over on our support blog)

In Casey’s case, the counterparty has pretty much given him the answer on a silver platter by saying that “the squeaky wheel gets the grease.”

So here, the next step? Be the squeaky wheel.

And by the way, you can be a firm but respectful squeaky wheel without being an asshole 🙂

Alex Turnbull
Alex Turnbull Alex is the CEO & Founder of Groove. He loves to help other entrepreneurs build startups by sharing his own experiences from the trenches.