I had breakfast with one of our CEOs this morning. It’s a great way to talk about the company, and his career progression, in a relaxed environment.

One thing he has done is brought on some CEO mentors to the Board. I’m a big fan of bringing “CEO coaches” to a Board, as I think Boards dominated by VCs is a bad thing. I also think CEOs need “safe” conversations with a sounding board, someone who is not a double agent for the VC.

We talked about some other candidates that could be helpful and talked about the pros and cons of various individuals. Finally, I told him this: “Pick someone whose life you can imagine living when you’re that person’s age.”

I didn’t author that line. I don’t know who told it to me when I was early in my business career. But, honestly, it has been a “true north” principle in my work life. It has encouraged me to stay at some jobs and to leave others, all with a clear conscience.

Saying you can imagine living that person’s life one day forces you to answer whether the following about that person jives with you:

• Day to day tasks of the job
• Personal growth potential
• Income potential
• Work-life balance
• Values
• Industry focus
• Functional expertise
• Hobbies
• How they treat their family
• How they treat junior staff
• How they spend their money
• Etc.

I’ve found it to be a powerful question: can I live that person’s life? If yes, continue the relationship. Perhaps, even, you’ve found a mentor. If no, get out and move on.