Here’s an anecdote from a woman named Elle Luna:

I was using Uber all the time in San Francisco, even though I hated the design. And then I went to the Crunchies awards ceremony and at a post-ceremony event, where I was in a ball gown, I saw the CEO of Uber, Travis Kalanick, sitting at the bar. I was three whiskeys deep at this point and I walked up to him and said, “I use Uber all the time and I absolutely hate the app. I think you should bring me in to fix it.” He replied, “Oh, yeah? What are the three things you’d fix about it?” I said, “I’d redo the logo, redo the entire app, and change the rating system.” I think there was something about being in a dress that empowered me to say such things (laughing). And do you know what he said? He said, “Be at the Uber office at 9am on Monday.” I told him I couldn’t do it alone and he said he’d have a team for me.

I thought the offer was bogus, but I went to Uber’s office on Monday at 9am, laughing to myself, and Travis led me back to a project room with two other designers—they were from outside of Uber and he had flown them in from New York! That is the magic of CEOs who get shit done. We took on the Uber app and redesigned it in three weeks. In fact, one of the guys he flew in from New York, Shalin Amin, ended up staying on full-time. The app is gorgeous and last night it won the Fast Company 2013 Innovation By Design Awards for the transportation category, beating out Mars Rover and Tesla.

I read it on a site where people celebrated her having the guts to seize the opportunity. Without intending to diminish that perspective, I couldn’t help but look at things from the CEO’s perspective as well. When you think like a leader you can’t help it. I commented as follows:

Everybody so far is commenting on the woman who approached the CEO. Let’s not forget the CEO, who committed and risked resources on a hunch or instinct or who-knows-what. If I had to pick one of the two to ask how they had the nerve to act and to learn from, I’d pick him. (Of course I’d prefer both and not to belittle her gumption and skills to back it up).

• What did he see to suggest risking those resources? … To create a team of outsiders to work on the core app?
• How likely did he expect things to work out?
• How did he explain the expenditure of flying the others in to the CFO or whomever?
• Or did he make a unilateral decision without asking others?
• Did he just get lucky?
• Had he done things like this before and succeeded? Failed?
• Was he worried about making waves in his organization? Did he?

Plenty more questions pop up.

It’s not obvious the CEO acted effectively or even responsibly, even though things worked out for them. The ends don’t justify the means in general, even if they work out. But he knew more than we do, so he may have had great justification that Ms. Luna didn’t know and therefore couldn’t tell us.

Still, we can learn a lot from either person’s actions.

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