Starting a business? 20 questions to ask yourself

Dustin Johnson
By Dustin Johnson

Do you think you’re ready to own your own business? Having a great business idea and being prepared to execute it are different. If you believe you have the next market disruptor, take a few moments to ask yourself the right questions. 

These questions should accomplish two things for you:

  1. Challenge you to think outside yourself and consider every angle before jumping into business ownership
  2. Ask questions whose answers will empower you to start your own business with confidence and clarity

Business ownership is a huge commitment. If you aren’t taking that lightly, read, ponder, and even print off these questions.

Marketing questions to ask yourself

Who are my competitors?

Rarely will you find a business idea that has zero competition. If money is to be made, then you can rest assured that other people will be in it. Competition isn’t bad, as it signifies demand for your offering.

So you’ve identified your competition. What do you do with that information?

First, determine what they’re doing that is working. There’s never a need to reinvent the wheel. Second, what are they doing that you can improve?

How is the market currently and in the future?

Where is the market heading, and does this tell you whether going into business is a good idea? Will you need to pivot in a few years, and will market demand disappear?

How is my solution different from my competitors?

As we said, entrepreneurs follow the money, so if you have a lot of competition, you need to determine what you’ll do differently.

Here are some ideas:

  • Location: Offer the same thing but in a different location or tailored more for consumers in a specific location.
  • Price: Offer a lower price for the same or similar solution.
  • Delivery: Offer the same or similar solution, but deliver it quicker.
  • Customer Service: Provide a better customer experience than your competition.
  • Individuality: Offer one specific solution to one highly targeted type of person and build a tribe around that.

Who is my ideal customer?

Many new business owners waste time figuring out the hard way that not everybody is their ideal customer. The sooner you can hone in on your target market, the better. 

How will I market?

There are hundreds of ways to market a business, but what is the best way to market YOUR business? Certain products and markets respond better to certain marketing methods. 

The best marketing strategies for your business will be a combination of two things. The strategies that your market responds to the best and the strategies you have the resources (time, money, and knowledge) to deploy.

Financial questions to ask yourself

How will I fund my business?

Funding is the #1 barrier to entry for aspiring business owners. Luckily there are many options, from loans, friends, family, and grants, if you can’t fund your startup personally. The amount of available funding will affect how your business starts and what risks you can take.

When will my business become profitable?

Even if you secure customers right out of the gate, your business likely won’t become profitable until some time later. Low profitability, in the beginning, is acceptable to ensure market share, customers, and feedback. However, eventually, your business needs to reach profitability. 

How will I price my offer?

The right pricing strategy is essential to stay competitive. And yes, we said “pricing strategy” because that’s precisely what it is. Pricing will affect your revenue, growth potential, customer satisfaction, and more.

How much will I pay myself? And when?

Are you going into business with the priority of paying yourself as soon as possible? Or can you wait to pay yourself instead of investing profits into your business? When you decide to pay yourself, how much money can you take out of the business to maintain the delicate balance between business and personal?

Legal questions to ask yourself

How will I structure my business?

For your business to be recognized as a legal business, you need to choose a structure. The structure you choose will determine how you pay taxes, where you can do business, and what legal protections you have. You can choose a sole proprietorship, partnership, LLC, or corporation. 

How will I prepare and pay taxes?

Two things are guaranteed in life; death and taxes. Your taxes will be based on your legal structure, location, profit, and expenses. You want a plan in place for your business to pay taxes, so you don’t incur unnecessary penalties.

What kind of insurance do I need?

Not all businesses require insurance, but having it protects against unforeseen circumstances. Insurance can protect yourself, your employees, your property, and even your customers.

What kind of licenses do I need?

Some businesses are required to have licenses to operate. If that’s the case with your niche, then ask how much the licensing costs, the requirements and how long it will take to get licensed. Nothing will slow your business down like being unable to work or sell because of licensure.

Mindset questions to ask yourself

Why start a business?

Are you starting your business for the right reasons? Ask yourself why you want to go into business. Then, ask yourself if those reasons are strong enough to stick out the inevitable tough times. You can make money in tons of ways, so why does it need to be as a business owner? 

How will I define success?

Your business doesn’t need to have an end goal, but eventually, you should reach what you deem success. Is that a certain amount of money? Is that a certain lifestyle? An achievement?

How committed are you?

Are you quitting your job to go all in on your business, or are you starting out as a part-time entrepreneur? There’s no right answer to this question. 

Support/family questions you should ask yourself

Who will you work with?

No great entrepreneur is a success on their own. Even if you don’t have a co-founder or employees to start out, we suggest finding people who can advise and support you in your business journey.

Do you have the time?

Earlier, we asked how committed you are to see if you’ll be a full-time or part-time entrepreneur. Not all businesses can thrive with a part-time owner, so consider how much time your business will require from you.

What will my day-to-day look like?

Depending on how you set up your business and the industry you go into, it can consume your life or give you time freedom. Consider how your day-to-day will change compared to now as an employee or in your current situation. Is this a favorable change, or do you need to make some changes before starting your business?

Is my family on board?

Family is supposed to have your back when starting a business. Hopefully, that’s the case, then ask why that’s the case. If you can do nothing about it, you’re better off knowing sooner rather than later. On the flip side, starting a business with family can be an exciting venture if you plan correctly. 

Start your business off on the right foot

There are tons of questions you need to ask when starting a business, but these are the most important ones. This may seem daunting, but if starting a business was easy, everyone would do it! One tip we can share when starting your business is to find support in any way you can. When it comes to paying taxes, there’s no better business sidekick than ComplYant

Dustin Johnson
By Dustin Johnson
Dustin Johnson is a Senior Tax Research Specialist at ComplYant. Prior to joining ComplYant, he spent over eleven years performing tax research at the world’s largest tax preparation company. Dustin holds a Bachelor of Business Administration and a Juris Doctor. Outside of work, Dustin enjoys biking and spending time with his family.

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