“Every time someone steps into a new role, they’ve been trained to do a previous task and they’ve been promoted because they’ve been a manager really well, a director really well. And so the previous habits that they had which is having lots of meetings, or being able to figure out goals, or being able to be tactical, all of those habits need to be untrained,” said Elaine Wherry, Cofounder and Chief Experience Officer of Meebo which was purchased by Google just a few months ago. “It takes everybody about 6 to 12 months to be able to get there, but knowing the missteps you’re likely to make along the way will really help.”
Wherry led a truly standing room only session at the 2012 Silicon Valley Code Camp entitled “The 100 Mistakes You’ll Make from Contributor to CTO.”
Wherry’s first piece of advice as you level up to the first two positions, manager and director, is to have a clear vision. Communicate clearly. A common mistake is to get into the minutia. Instead, you should just be describing one goal over and over again, in different ways to your different audiences. Say it multiple times so everyone knows the story from their aspect. Don’t get hung up in the details.
When Wherry’s became VP her biggest surprise was that she needed a plan B. While VPs are required to track metrics and performance goals, you’ll still be surprised. Excuses are not an option when you become VP. You will need to be able to deliver no matter what happens. So Wherry recommends that you always have a plan B, and probably a plan C as well.
When you get to the level of CTO, you’ll be responsible for hiring VPs and that’s really difficult, said Wherry, as you’re probably already going to know the person you’re going to hire or at least know of them. You’ll have a sense of whether they can do the job as there are a lot of people you can call as references. But there are going to be lots of discussions and debates and you’ll have a very dynamic relationship. Still, whatever happens you need to respect each other’s roles and decision making.
“When you’re a C and you’re hiring for a VP, saying, ‘Hey, yes, they can do the job, but do we have the same values?’ is a totally different conversation,” said Wherry.