You Gotta Have a Plan.... Or Do You?

Christian and I go back and forth a lot about planning. He is an uber-planner; me, not so much. I prefer to let things happen organically—when things happen you didn’t expect, that makes it even better to me. I’ve been able to get through life so far pretty well this way, but being married to someone who feels the opposite, this has at time caused “strain” on us. With him being gone this fall, I’ve really managed to keep myself busy with lots of plans, so perhaps I’m not as organic as I think. We’ve had a few longer-ranging plans come from when he and I take trips together (ie, the "Bermuda Plan" called for settling down a bit with a dog/SUV/computer, the "Idaho Plan" called for C going to grad school in CA and the "Africa Plan" calls for kids in the next 5 years…) but other than that, I don’t know how much long term planning I really do.

I was lucky enough last week to be invited to attend a lunch with Jerry Yang, one of the original founders of Yahoo! He’s been pretty much a celebrity since he and David Filo famously created the company in trailers on the Stanford campus, on the covers of many, many magazines, and worth well over (yes, say it like Dr Evil), 1 BILLION dollars. The employees of Yahoo! are known as Yahoos, and his title is Chief Yahoo.

So after the company started growing so fast and he stopped knowing everyone’s names, he started this program called “Chat and Chow”, where two dozen or so people get invited to come and have lunch with him in one of the classrooms on campus. We were informed in the email invite that the format is intended to be very open and casual, but you never know how these things are going to go. How many times have all of us been to “informal” events with company leaders that are little more than meet and greets where afterwards mgmt crosses “Employee Engagement” off the to-do list until next quarter.

Happily, it ended up being a really interesting session. There were about 20 people there, all from the UED (User Experience & Design) team, from varying levels of background and experience. The session started with each person saying who they were, what they did, how long they have been with Y!, a cool innovation that they’ve seen at Y! or outside, and a question for Jerry.

It was a neat way to start off the meeting, as the wildly varying degree of innovations that each person saw was really cool. It ranged from a baby book to the Yahoo! Answers product to a new screwdriver design. The questions were also interesting—many centered around the new brand advertising Yahoo! launched this week (see the adverts here—I like the HOUSE one, but the car one is pretty lame to me) to how the different orgs in the company could be more nimble to enabling an environment that encourages more innovation.

Jerry proved to be as humble and down to earth as the press reports him to be. He was almost an awkward speaker, looking at the floor a lot, but still had a lot of good insights to share and was very open with us. He talked about the organizational difficulties of comparing ourselves to start-ups, which are often competitors in certain areas, how the UED organization needs to continue to be stronger, and other interesting tidbits from someone with his level of access. The session was fairly interactive, mostly engaging, and I think most of the group enjoyed it.

He actually closed the session with my question – “Where do you see Y! in 5 years, and how accurate were you in your predicition about what we’d be doing 5 years ago now?” He chuckled and said “not really that close” and went on to talk about the rapid acceleration of social media and other factors that didn’t seem as close in 2001. He postulated a bit about life for Yahoo in 2011 and some things we should focus on, but openly said that even with the maturing of the internet space, its still really hard to know.

So what does all this mean? Is it better to develop a plan and stick to it? Or is it better to just figure it out as you go? I think, as with most things, the right answer is somewhere in the middle. It's important to have an idea of where you want to be, but also be flexible enough to adjust as things happen in life and business. Not a bad message to take away from meeting with one of the biggest celebrities in Silicon Valley.