25 Hard Questions Entrepreneurs Must Ask


Entrepreneurs are dreamers turned doers. We understand that it takes risks to unlock life’s rewards. We are optimistic beings who push beyond our fears every day in pursuit of our goals. While we are fueled by our optimism, there are times when a dose of reality is just what we need to keep our priorities in check and our businesses on the right path. While ignorance is bliss, it does not pay the bills. Do not be afraid to ask the hard questions in order to reach your business goals.

Successful businesses are built by entrepreneurs who aren’t afraid to ask and answer the tough questions. By considering the hard questions, you gain valuable insight, which allows you to retool your strategy and create a stronger plan for achieving the success you desire.

Here are 25 hard questions all entrepreneurs must ask themselves…

1. What am I willing to sacrifice? In order to achieve your goals, you have to make sacrifices.  Knowing in advance what you are willing to do – and not do can keep you on track when you are faced with tough decisions. -Clifford A. Bailey, TechSoft Systems

2. How will I get the phone to ring? It’s easy to launch a business, but how will you get the phone to ring? Do you have a plan? And, if your initial plan doesn’t work, what’s your backup plan? -Dr. Deb Brown, South Florida Business Coach

3. Is my brand sending the right messages about my business? The marketing materials you use to represent your business tell a story about who you are and what you have to offer. If you are trying to convey professionalism, trust, and high quality service, then your marketing materials and brand assets need to be professionally done and of high-quality. Make sure you’re sending clear brand messages, so your potential customers won’t have to question your authenticity or your ability to meet their needs. -Tia Jackson, The BrandMakers

4. What skills am I lacking? Most entrepreneurs think they can do it all themselves. This is not true. Time is a currency and must be spent leveraging strengths.  -Barb Girson, My Sales Tactics

5. How many hours a day am I willing to spend dedicated to my business? This is an especially hard question if you work from a home office. The challenge for entrepreneurs can go two ways. Since there is no commute, you have the ability to spend 24 hours a day in the comfort of your home working on your business. This can lead to burn out if appropriate breaks aren’t scheduled in to re-energize. On the other hand, with the flexibility of working for yourself, you may become easily distracted by personal commitments. -Eileen Schlesier, SleeveShirt Consulting LLC

6. What is the best way to achieve my goals? It is important to keep asking that question. Keeping open-mindedness, willingness, and focus is the best way to achieve your goals. -Anand Bhatt, Sonic Wave International

7. Who should be on my team? Even if you’re a sole proprietor, you will benefit from having a business coach, an accountant, an attorney, and an IT professional (website designer, SEO expert, etc.) on your team. You’ll also be forming relationships with referral sources, vendors, and other professionals in the community. No business owner succeeds alone! -Dr. Deb Brown, South Florida Business Coach

8. Am I really prepared to be solely responsible for my own wealth and well being? As an entrepeneur, you are really the only person you can count on. Sure, you hold the key to future success but you also hold the burden of failure. Your family is completely dependent on the decisions you make - and that can be really frightening and stressful. -Brina Bujkovsky, The Younique Boutique

9. Does my time allocation accurately reflect my priorities? The biggest hurdle in entrepreneurship is usually time management.  You need to clearly define your priorities, especially if you have a family. The support of your family could be the biggest contributor to your success, so it’s critical that you learn to allocate your time in a way that minimizes disruption to your family life. -Clifford A. Bailey, TechSoft Systems

10. Am I willing to cause strife in my family (where spouse or close relatives don’t believe the risk/sacrifice you’re taking is worth it to the family)? It’s important to keep your family first (helps you to keep perspective and walk away from tempting, but negative opportunities). -Selena Cuffe, Heritage Link Brands

11. What can I say NO to? Entrepreneurs have many choices on how to market: social media and networking to name a few. They must have a clear idea on what they will eliminate or reject in order to succeed.  -Barb Girson, My Sales Tactics

12. Am I living a balanced life? Do you still find time to enjoy your family, have a hobby, exercise and engage in a spiritual walk? Can you see the day coming when you will be able to do these things? All of this is why you’re in business in the first place, isn’t it? Do you own a business, or does the business own you? Seriously think about it. -Sue Porter, Accidental Leader

13. How much will I pay myself? How much you will take out as “owner’s draw” or do you plan on no salary indefinitely? Paying yourself is very important. -Denise Beeson, DeniseBeeson.com

14. Why is my product/service better than the others? This answer always opens the Pandora’s box about how everyone could use their product/service and so on, which immediately tells me they have not done their primary research or basic SWOT analysis. Do your research and understand your strengths. -Michael C. Newhouse, WCN Group

15. What are the standards terms and pricing for similar products/services in the marketplace? Not pricing your product/service correctly and offering them with the terms expected by the marketplace can be a disaster. -Denise Beeson, DeniseBeeson.com

16. Do my customers want what I want? How do we balance our vision for the company with needs and requests from customers? Are we listening to them? -Nick Francis, Helpscout

17. Am I willing to stick to my values, even if it means walking away from a lucrative - but ultimately negative - deal? Hone your ability to trust your instinct (helps you to not sacrifice the perfect for the good). -Selena Cuffe, Heritage Link Brands

18. Can I work when I don’t feel like working? Entrepreneurs must push through the tough times even when they don’t feel like it, if they want to succeed. -Barb Girson, My Sales Tactics

19. Am I willing to fire someone? It’s never easy to face someone and tell them they are fired. It’s really hard to fire someone when you made the mistake and hired the wrong person, and they are nice people, but you can’t let the situation continue. -Cynthia Kocialski, CynthiaKocialski.com

20. Are my expenditures moving me forward? Too many companies spend money on things they think they need (like offices or unnecessary infrastructure) and not on things (like staff) that can advance their mission much faster. -Jeff Kear, My Wedding Workbook

21. How do I figure out what is essential and critical to do first? Whenever we consider starting something new we are understandably excited. The ideas flow fast and furious. We ask, What would happen if we didn’’t do/use/implement X?” If the answer is, the whole thing collapses then” we have a good candidate for something worth doing. The hard part is to have the discipline to not do the nonessential things just because we are enamored with them. -Kenneth Vogt, CroonerLabs

22. What is the most high impact item I can be working on today? Entrepreneurs must constantly challenge themselves to focus on revenue-generating activities.-Barb Girson, My Sales Tactics

23. Am I prepared to step up and have those difficult conversations when I need to? You have to know how to stay on point, address the facts with an appropriate degree of empathy and emotion, and be prepared for people to respond in any number of ways. -Lori Sawaya, Color Complete

24. How much money am I willing to sink into a business that is not reaching its goals? It’s important to set realistic goals and to have an exit strategy. Even the best ideas are sometimes not successful and at some point, you have to know when to call it a loss and move on to something else. -Brina Bujkovsky, The Younique Boutique

25. What is my exit strategy? Where will the business be 3-5 years out? Start with the end in mind and it will be easier to understand who to begin. -Denise Beeson, DeniseBeeson.com

The moral of the story is… you can’t be afraid to ask yourself the tough questions. The truth may hurt a bit, and expose a few areas for you to work on, but that is all part of your business’ growth process. It’s important to know where your small business stands, so you can map out a plan to reach your goals.

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