A Question of Entrepreneurship

I recently met a lawyer/entrepreneur who has developed a communications training model based around the notion of questioning. As a litigator, his specialty was in preparing, examining and cross-examining expert witnesses, and so over the years he became, what can only be described as, an expert questionner.

Prior to meeting him, I hadn’t specifically thought about either entrepreneurship or leadership in those terms, but since meeting him, I’ve started to realize that the key to most understanding and development lies in uncovering the right questions to ask. And as I look around me, I see that questions are a common theme for entrepreneurs as we get 2010 off to an entrepreneurial start.

Getting Started

For new or prospective entrepreneurs — especially those who know they want to start their own business but who have not yet figured out what that could or should be — StartupNation offers a list of questions to ask yourself to find your passion.

Passion is a favorite topic among entrepreneurs, and for good reason: starting your own business takes a lot of time, energy and sacrifice. Loving what you are doing, believing in the value you are providing, and finding meaning in your goals can sometimes make all the difference between doing what needs to be done, or going out and getting a job at Starbucks just to have health insurance again.

Never underestimate the importance of passion. It’s not something you can fake. And being passionate about what you are doing is how you find the mentors, partners, collaborators and customers who are going to be necessary for you to grow your business — because people want to be inspired and motivated, and that can only happen when someone is passionate.

Building Your Business

If you’ve got a startup that’s still getting underway, VentureBeat has a list of questions for entrepreneurs to ask to help get through the difficult early stages of a new business. With a focus on the types of things that new businesses, new teams and new products need to keep in mind, VentureBeat’s list focuses on getting your venture out of the crib and up on its feet.

Growing Your Business

For those who have been running a business for a while, Business Know-How identifies the questions that are cricital for any leader to ask themselves. Think of these questions like hitting the ‘reset button’ and clearing the decks. They are designed to help you stop, think, remember and evaluate where you are, how you got there and what you need to do to change course based on updated input.

One of the hardest things for human beings to do is change habits. Yet, as entrepreneurs, sometimes our habits can kill our business. It’s often too easy to forget that what worked yesterday may not work today, and probably won’t work tomorrow. Often times, the entrepreneur is so used to handling day-in/day-out activity of the business that they lose sight of the forest for the trees.

Stopping, asking these questions, reconsidering your previous assumptions and then examining what has changed around you are all important steps for an entrepreneur to take to make sure that both you and your business remain relevant and competitive.

In reality, of course, no matter what stage your business is in, each set of these questions has value. After all, over time it’s not just our business, competitive landscape or customer base that can change — but our passion and interest as well. One of the hardest questions of all for an entrepreneur to answer may simply be, “Is this the business I want to be in anymore?”

Either way, the real lesson in all of these questions is: Never assume. Always ask. And start with yourself.

Alora Chistiakoff is an entrepreneur, content strategist and project manager who has been developing online business and technology for startups for more than a decade.  She co-owns The Indigo Heron Group, Inc., a content strategy firm in Austin, Texas