Biz Features

12 Questions Every Entrepreneur Needs To Ask Themselves — That We Rarely Do

by . March 5th, 2016

A little introspection can make or break your startup.

You’ve already asked yourself the obvious things. What are my strengths? What do I need to learn? Who am I selling to? How much operating capital do I need?

Here we lay out some of the less obvious questions all startup entreps and small business owners need to ask themselves.

12.) Who can help me if I asked?

You need at least a healthy ego to even consider creating a startup. But many of us have way too much of it to consider even getting help from others, even when we need it. Many current and future problems in most new startups can be avoided simply by asking the right people.

Will we be relevant in five or ten years?

If the answer is “no”, it doesn’t necessarily mean that you have to stop what you’ve started. Businesses all have a lifecycle. Only in exceptional cases will a business last longer than a lifetime.

Regardless of the projected lifespan of an enterprise, it’s always best to the have a grounded exit strategy in place. This is only possible if you likewise have realistic  idea of the outcomes of your business in the near future.

11.) Am I tolerable to work with… or work for?

Contrary to popular belief, business always contains personal elements. If your personality stinks, you might find it far more difficult to keep the people you need.

Retaining key partners and employees is especially critical in the first few years of your business. Continually retraining and reorienting personnel in important positions can be a huge drain on time and other resources.

10.) What values won’t I compromise?

In my limited experience most brands don’t really give much more than lip service to values. And it’s a shame. Values aren’t just important for giving you and your startup a definite direction, they are also important for your brand as well.

You want you and your brand to be trusted, and that trust doesn’t come easy at all.  Knowing what you stand for and sticking to it is the only real way to earn this trust, as well as delight customers in these cynical times.

9.) How will I develop our employees?

If you want people who can think to stay with you, money will only do so much before they get bored. If you’re running a new startup, chances are good your partners and employees are all wearing multiple hats, and while that almost always leads them to learning things they might not otherwise have, it may not necessarily be the best thing for them. They may not have the desire or aptitude for those skills or they may want to learn more in another field.  Accounting for this almost always allows key employees to become valuable force multipliers in your enterprise over time.

8.) Would I act differently if my accomplishments remained anonymous?

How much is ego affecting your decisions? If you’re like most people, probably a lot more than you admit.Understanding your own true motivations and how they are affected by other people can not only help you manage your business better, it can help you understand yourself.

7.) What are unexpected ways our product has been used?

Products are often used in unexpected ways. Bubble wrap for instance, was intended to be used as a type of insulated wall surface. The now unusual archaic swing-top bottles used by Grolsch have in recent generations become popular among guitar players for their rubber washers — handy for securing straps to instruments. Apple actually developed the iPad before the iPhone — Steve Jobs thought the technology would be a game changer for mobile phones.

If your product is similar to others in the market, try to see how else your competitor’s customers use them. If a certain application is not being adequately served, it may very well represent a valuable opportunity for your startup.

6.) Can I keep up with the pace of change in the world?

It’s common for projects to be unnecessary by the time they’re finished or even for entire business models to become obsolete overnight. That’s just the way things are. Stability remains important, but never at the expense of adaptability. Frankly, not everyone could handle constant change. At least, not by themselves.

5.) What do I wish I did differently five years ago?

Popular wisdom might tell you not to regret anything. Regret however, is a useful emotion. Without a healthy amount of it, you will be hard pressed to find areas to improve on.

4.) How can I keep healthy?

Maintaining a healthy lifestyle doesn’t just help you feel and look great — it can also help you make better conditions. Fewer sick days also means more time that you’re actually productive.


Working Out Means Working Smart – Why Entrepreneurs Need To Seriously Address Their Health Issues

3.) How much sleep can I lose?

If you create a new venture, you will lose sleep over it. Which kind of puts you in a quandary because sleep is essential to productivity. A lack of sleep can easily snowball into an avalanche of bad decisions that could hurt your business, and shorten your lifespan.


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2.) Where else can I improve?

Even if you find yourself building the proverbial “better mousetrap”, there is always some way you can improve nearly anything. Enterprises should be iterative. Even if one cannot improve or change the actual physical product or service, there are always processes in production, distribution, management, marketing, sales, and everywhere else that could be improved, however incrementally.

1.) Does my market need me? If not, how can I make it?

Sometimes we’re so in love with our ideas we don’t bother to stop for a few minutes to consider if anyone else believes in them. The common reasons for this are either the central premise of your concept is flawed, or that your audience does not understand what the heck it means to them.

If it’s the former, it’s usually time to either redevelop your concept or find a completely new one. If it’s the latter, it’s time to invest in some marketing or find a different audience. In many cases, a little of both may be warranted.

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Arthur Piccio manages YouTheEntrepreneur and has managed content for major players in the online printing industry. He was previously BizSugar's contributor of the week. His work has appeared multiple times on The New York Times' You're the Boss Small Business Blog. He enjoys guitar maintenance and reading up on history and psychology in his spare time.