The Right Questions To Ask As An Entrepreneur

Business questions are common to me. As the owner of a few businesses, co-host of a TV show called “The Small Business Show” and a live YouTube broadcast called SBCN TV, an author, a mentor, and the sponsor of a well-established business network, I deal in questions about small business practically all day long.

What I’ve noticed is that they tend to fall into 2 distinct categories — one that puts more work on your plate and one that can eliminate much of your overwhelm and help you take big strides forward.

The most common kind of question business owners ask is: “How do I…?”

How do I create a sales funnel? How do I get my work in front of more of the right people? How do I develop an online course? How do I grow my email list? How do I create a Facebook ad campaign?

These aren’t bad questions. They might be exactly what you need to know right now. But… 9 times out of 10, when we ask these questions, they’re more of a stab in the dark or a reaction to someone else’s marketing efforts than they are a reflection of deep intention or considered strategy.

This kind of question creates more work. These questions are the reason that small business owners with mediocre results have so much on their to-do lists. They’re the reason you’re constantly juggling conflicting priorities and competing tasks.

On the other hand… The other kind of question,  the questions that aren’t asked nearly often enough,  are “what if” and “why” questions. They’re the kind of questions that lead to creative thinking, productive focus, and strategic decisions.

They type of questions help to eliminate all but the most important “How do I…?” questions so that task lists get smaller, results get stronger, and prosperity (profit, time, and well-being) flourishes.

Of course, when you’re smack dab in the middle of a “Now what?” phase of your business, it’s easy to fall back on learning how to do new things. After all, when you’re learning how to set up a automation sequence in your email provider or host online workshops or run a Facebook ad campaign, it can seem like you’re moving in the right direction and making progress.

But, more often than not, learning how to do new things keeps you spinning your wheels instead of making real forward progress. With each new how-to you learn, you’re back to “Now what?” because you still haven’t spent time deciding on and designing the next phase of your business.

You don’t really know where you’re headed and you fill up your time with “how to” questions instead of making the space to make bigger plans.

And I get it…

It’s easy to get caught up in “How do I…?” when you’re less than confident about your skills as an entrepreneur. It seems like the answer to a mysterious “how to” question could solve all your problems. But, if you’ve gotten this far with your business, you know — deep down — that’s just not true.

You can learn all the how-tos in the world and still fail to put them together in a meaningful, strategic way.

That’s why I’m so passionate about helping small business owners spend time in uncomfortable spaces where most questions start with “what if” and “why?” There’s more power in asking a “What if?” question than in asking a “How do you?” question. There’s more potential in asking a “Why?” question than in asking a “What?” question.

I like to say to my staff “Don’t come to me with a question. Come to me with a question and your proposed solution.” Status quo for business owners. In other words, give it some thought, do you research and develop a proposed solution. Otherwise any advice you receive probably cannot be implemented successfully by you.

That’s not to say there isn’t a time and place for discovering new tactics and techniques. Of course there is! But one of the reasons we get so overwhelmed and the juggle of entrepreneurship gets so punishing is that… we start drowning in all the how-to questions before we’ve figured out which of those questions actually matter.

The challenge is that making the biggest progress on your business starts with clearing time to just ask open-ended questions, consider the possible answers, and discuss them with peers and mentors.

It feels like you’re sitting still — even though what you’re really doing is fuelling up for a huge surge ahead.

Most entrepreneurs don’t clear this space, make the time, or allow them to just think about what might come next. That means they end up spinning their wheels in endless “how to” questions, overwhelming to-do lists, and mediocre results.

I help small business owners create that space and nurture the conditions for wrestling with the bigger questions. It’s a deep dive into thinking about your business. The best part is that it requires a commitment to active participation. Instead of passively considering your options, and getting sucked back into the status quo, it’s an opportunity to get down and dirty with the tough stuff. Allow others to challenge and expand your thinking, and make concrete decisions about how you want to move forward.

It helps entrepreneurs to get uncomfortable and explore the still-dark possibilities for their businesses so that they can come out the other side armed with some strategic choices about what’s next for them. It shortens the amount of time they spend wandering alone in the “Now what?” phase of business and gets them to the land of “I’ve got this” as quickly as possible.

Wrestling with these bigger questions is the key to becoming a more resilient, independent, and confident business owner. And, it helps you to win back your time, your energy, and your forward momentum, too!

Make the time. Regardless of what you think you’re seeking right now, whether you’re aware that answering a big question will put your on the right track or you’re overwhelmed more “how to” questions than you can count, carve out the time soon to ask — and finally answer — a new set of questions about your business so you can focus on what counts, eliminate what’s unnecessary, and move forward with phenomenal results. That’s the right way in Keeping Life Current.