At a certain point in the development of my first business, I realized that my personal development was a limiting factor on the company’s growth. I wanted to stay ahead of that. So when I met Jeff Ward at a holiday party and he said he did coaching, I seized the opportunity. Maybe it was the spiked egg nog, I don’t know.

I learned a lot from Jeff over my two years of coaching.* Two messaging tips he taught me have been particularly helpful. They’ve spared me a ton of drama in both my work and personal life.

The first is super-easy. Just ask:

I notice you [blank]. Help me understand….

Those three words help me understand are magical. They’re magical because they force you to seek understanding before reacting. It’s like saying Wait, before I get angry let’s understand what’s really going on. The result, for me, is that I’m much less reactive than I used to be. It puts into...

I saved my most provocative question for the end. I was at a strategy session with the executive team of a $100m B2B media business. The company was growing, but they were looking for ways to expand digital revenues. I was invited to provide a fresh perspective.

“How many of you have experience in programming, interaction design, or product management?” I asked. One out of the 12 executives raised his hand, the CTO. The rest looked at me cross-eyed. “There’s your problem,” I thought. I didn’t need to say it.

With the explosion of digital devices and technologies, it’s remarkable how lacking most media businesses are in product management. Most executives I talk to recognize the need for digital product development — revamping the website, creating an iPad or iPhone app, making their emails responsive, launching new data products, etc. They know what needs to be done, they just don’t...

I never realized how often I said “should” until a friend pointed it out. We were at a sidewalk cafe having a conversation about life decisions. It was the kind of mini counseling session uniquely suited for long-time friends who’ve seen each other through break-ups, professional ups and downs, and three-martini nights.

“The question isn’t what you ‘should’ want, but what do you actually want, Jeff.”

His comment seemed esoteric at the time. But I observed my language and thoughts afterwards and realized he was right. I was much more in touch with what I should want than with what I actually want. And yet I considered myself so independent and free… ha!

This set me off on a journey not unlike Jim Carrey in “Yes Man.” What do I really want? Do I really want to go out Friday night or just be a homebody and order pizza? Do I really want to build a billion-dollar company or a highly...