If you've ever passed through a great books class or Western Civilization 101 while at university, you've probably encountered the Socratic Method. Perhaps you hazily remember it has something to do with asking questions, but being a busy business owner, you can be forgiven for not spending too much time thinking about ancient philosophy since your undergrad days.

But if you're keen to become a better mentor to employees and other young entrepreneurs, perhaps it's time to dig into those memory banks, successful venture capitalist Brad Feld recently suggested on the Unreasonable Institute blog. A co-founder of the accelerator Techstars, Feld uses the kickoff of the latest Techstars Boulder program as the launching point into a thoughtful discussion of what makes a great mentor.

Promising much more on the topic in the future (18 items to be discussed, he says), Feld writes that asking question is fundamental to the Techstars approach to mentorship. But not just any questions. "It's how you ask questions, what you try to accomplish with the questions, and what your responses to the answers are," he says. And if you want to craft truly excellent questions, brushing up on the specifics of the Socratic Method can help.

Talk to Your Mentor Like a Peer

The first principle of great questions, according to Feld, is to avoid coming across as a remote, all-knowing expert. "As a mentor, it's easy to establish a one-up-one-down relationship with the entrepreneurs you are talking to," he writes. "However, your goal should be to create a peer relationship, where the mentee learns from the mentor and the mentor learns from the mentee. As a result, tone matters. A lot."

Admit What You Don't Know

If you want to talk to your mentee at eye level rather than from up on a pedestal, it's key to acknowledge the limits of your knowledge. "If you--as the mentor--don't understand something, ask a question. You don't have to show the mentee that you are smarter than her. You don't have to establish your credibility--you already have it," Feld reminds mentors.

Use Questions Like Experiments

Great mentors don't supply answers; they support their mentees in discovering their own. The way to do this is to treat a conversation less like an exercise in brain mining, and more like a group thought experiment. "Use your questions to guide the discussion, presumably toward testing hypotheses you might be developing in real time. Be explicit about these hypotheses as you are testing them, and try to show your thought process through the questioning. This can be subtle, where you just guide things along, or it can be explicit, where you state your hypothesis and then start asking questions," he writes.

Bad Answer? Respond With Why

If a mentee's response to one of your questions wasn't exactly what you were looking for, resist the urge to supply your own thoughts or make the person feel bad in any way. Instead, just dig deeper with "why?"

"The corollary to 'there are no stupid questions' is 'there are no stupid answers,'" Feld reminds would-be mentors. "When a person hasn't thought deeply about the answer to a question or hears a question for the first time, the response often doesn't really address the question. When this happens, just ask, 'Why?'" (If you're not familiar with "Five Whys," Feld suggests you read up.)

The Goal Is More Questions

As an entrepreneur you probably have already figured out that struggles, problems, and questions never cease no matter how long you've been in business. And what's true of entrepreneurship in general, is true of the mentorship process in particular. You'll never be totally "done," so don't try to come to some complete and definitive answer.

"The goal is not to end up with the definitive answer to the questions. Rather, you are trying to use the questions to set up a new set of hypotheses to go test. You are at the beginning of a long arc of inquisition," concludes Feld.

Published on: Jul 22, 2014