3 Ways to Make the Most of Business Coaching

Today, Evan Williams is an entrepreneurial inspiration for his work as co-founder and CEO of Twitter. But in 2005 he was running Odeo, the company that would develop and spin out the social network a year later—and not everyone thought he was doing a good job of it.

“He got a lot of flak for not making decisions fast enough [and] not being assertive enough,” recalls Tony Stubblebine, who worked for Williams at the time. “He was hiring people and really hoping they would solve a lot of the cultural problems of the company.” A decade later, Williams is the CEO of online publishing platform Medium, which Stubblebine describes as “one of the most innovative, well-run companies that I’ve ever run into.” Williams is also a good friend of Stubblebine’s, and an investor in Coach.me, the company Stubblebine founded in 2011.

Williams’ transformation from so-so manager to culture-defining leader is a good example of the power of coaching, says Stubblebine. “One of the things that a coach can help you do is help you define who you are and who you want to be as a leader, and then put that into practice,” he says. “I’m really proud of this entrepreneur, who you would consider to be a top performer—he’s a billionaire because of Twitter, he started two or three companies that people think of as major startups—but [who] keeps investing in his own performance.”

Stubblebine’s own experience with an executive advisor is what caused him to start Coach.me, which he believes solves two of the big problems with coaching: geography and price. Rather than rely on the best tutor you can find within a reasonable driving distance of your location, Coach.me connects users to coaches virtually. And while Stubblebine usually pays $600 per hour to work with his advisor, Coach.me’s tutoring rates start in the low tens of dollars. Feedback, self-accountability and monitoring are vital when it comes to self-help type initiatives, so there’s also a free app to let users track their progress towards their goals.

Here are three things Stubblebine says you should understand about working with a coach to become a better entrepreneur and leader.

Collaboration is key

A coach can’t help you get to your goals without your cooperation. “They don’t just come in and fix you—you have to work on it together and you have to be ready to work on yourself,” says Stubblebine.

It’s also not enough to spend an hour in your coach’s office each week and then go about business as usual for the other 167. So Coach.me focuses on “checking-in every day and making daily progress and improvement to your business or whatever you’re working on.”

Why stick to one?

The world of business is becoming ever-more complicated, and no one guru can possibly teach you everything you need to learn to be a better leader. “Think of coaches sometimes as specialists,” suggests Stubblebine. “When you’re working with the coach, there’s one thing at a time that you’re going to work on.”

Don’t just engage the first coach in the phonebook with expertise in that area either. “Now that you have access to so many different coaches and it’s so easy to vet who’s good and who’s not, you can just kind of go piece by piece and level-up all of these different characteristics of yourself,” says Stubblebine. “Cycle through coaches as you improve various parts of your life. You can always go back to a coach that you liked or if you feel like you need a refresher in some area of what you’re working on.”

It’s worth it

Time and money are the two things every entrepreneur could do with more of, and coaching expends both. But Stubblebine points to Warren Buffet to show why a tutor is worth making space in your schedule for. “His autobiography is called Snowball, and the metaphor there is: start with a small snowball and you roll it down a steep hill and it gathers momentum, and by the bottom of the hill it’s just this massive, multi-billion dollar enterprise,” Stubblebine says.”