100 Critical Questions Every Entrepreneur & CEO Need To Ask Themselves For Their Business Success

100 right questions to ask for business success


  1. Do you take a step back from the daily details to assess the performance/productivity of your business on a regular basis, at least monthly? When was the last time you revisited it? Proper and frequent evaluation of the big picture allows you to see crucial trends in time.
  2. With the knowledge you have acquired, if you could start over, how would you re-enter your business? Can you implement now whatever you would do differently?
  3. Are you ruthlessly ensuring there is absolutely no waste and only proper use of all resources?
  4. Do you have key metrics that you are using to measure performance of your organization? For example: Accounts receivable aging, Year-Over-Year Revenue Growth Rate, Inventory Turnover Ratio, Cash Conversion Cycle. If not yet, define those that can offer you the most critical information which can help you to make impactful changes, and start tracking it now.
  5. Do you have under-utilized assets? What assets does the business have at its disposal that are not being used?  Auction off or lease such assets and return the proceeds to the business.
  6. How often does your company review each key team or department to optimize your processes? For example, who updates your knowledge base and web FAQ page based on customer feedback? Important activities demand frequent appraisal, monitoring and organization-wide awareness.
  7. Do your current staff, consultants and contractors have the right skills and expertise matched to the market demand? Or, would you be better off outsourcing the activity?
  8. How do you ensure that your current staff members, consultants and contractors are highly motivated? Creating an environment that is inspiring and supportive is vital. Do you offer transparency and an opportunity to be involved in important decisions? Do you offer training and other professional advancement opportunities? Do you offer work/life balance and performance based rewards?
  9. Do you take time to revisit the core reasons you got into business? This way, you will maintain your focus, motivation and clarity which will lead to better business decisions.
  10. Is the relationship between employees, consultants and management on all levels honest, transparent, in the best interest of the business? The quality of your decisions and public perception will be influenced by the relationships that prevail in your organization.
  11. Am I using the most effective technology? Today technology is vital to creating cost effectiveness.
  12. Do you think your stronger employees and contractors see themselves still part of your organization in two years? If your stronger employees do not see themselves in your firm in the foreseeable future then there is the risk of losing your experienced team members.
  13. When facing challenges do you ask yourself what your role model entrepreneur or CEO would do if they were in charge? Research what others did when faced with the same challenge. Ask for advice from your managers.
  14. Have you considered bringing in a new CEO to your business to take it to the next level? You could remain an owner and a visionary, but leave operations to someone with skills that you might be missing?
  15. Have you asked yourself recently “What is it like to work for me”? Do your employees relate to you as a person and a leader? Is your management style consciously chosen to produce positive transformation in your business and the lives of your employees?
  16. Is the product or service you are providing still relevant today and into the future? Are you constantly testing how well you are meeting your customers’ expectations?
  17. How are you planning to remain relevant 5 years from now?
  18. Do you take time to imagine how someone could we put you out of business? Become your own fierce competitor and start imagining what you might try to put “us” out of business. It will help you spot your weaknesses and keep your competitive edge.
  19. Are you employees understating the assignments and looking into them as seriously as you want them to? Does individual in your organization believe that together you can change the world?
  20. How are you using your time? Look at your calendar for the next few weeks, and assess how wisely you are using your time. You need to be using most of your time taking care of mid to long-term priorities that will ensure health for your business – yourself – your family – your community and industry. You need to seth aside enough time to handle everything that shows up as urgent or critical.
  21. I am I getting timely information about the market? Information is key for entrepreneurs and management to run business successfully. Being the first to access and assess information, makes adjustments, introduces something new is a crucial advantage.
  22. Have you managed to cross the cultural gaps from human resource, marketing and customer service stand point? … In your communication materials? Each cultural and lifestyle segment of your audience might not only communicate differently but also live and make buying decisions based on very different values? Do your employees understand this and other diversity issues and are they handling them effectively?
  23. Do the vision and company direction “stick” even when management isn’t around? Management needs to create a culture of shared values, live the example and make hiring, promotion and other decisions that clearly reflect those values.
  24. Have you clearly identified the unique production and operational resources in your business (know how, unique skills of your staff, unique processes, innovative products)? Do you manage to balance between seeking for new innovative solutions and leveraging proven existing ones?
  25. It’s a given that the future is uncertain, but do you have processes in place to help see new market trends coming and to put measures in place now to protect you from such shocks?
  26. Have you considered hiring offshore employees if you are understaffed and short on budget, or if your vacancies have been open for too long due to high market demand for certain skills? Hiring offshore teams can be very cost effective but require streamlined training and highly optimized quality control processes.
  27. Are your employees self-motivated and able to work remotely? You should come up with ways to support their desire for convenience and independence, and provide them with sufficient tools, training and performance assessment models that can support lifestyle for your teams and effective productivity.
  28. How clear is communication in your organization? How often does work need to be redone due to miscommunication? How often do conflicts within the team and with clients arise? An effective communication system and systems to mitigate misperceived meanings are vital for any business to survive, especially those with a significant virtual operation.
  29. Are you good at building and maintaining relationships? What is your client retention ratio?  Do you have strategies to create loyalty in your employees? What role do you and your management play in limiting employee turn over and building customer loyalty? Do you provide quality service not only to customers but also to your team members?


  1. Is your business conducting its activities according to its mission statement, values and your sense of purpose as an entrepreneur?
  2. Are your goals realistic? If yes, maybe they are too realistic and not challenging enough? If they are absolutely unrealistic and your business objectives are not attainable, do they demotivate you and your staff? Ensure the balance – be realistic while still shooting for the stars.
  3. Do you have well-documented strategic and tactical plans your whole business has bought into? How often do you revise them? When was the last time you made an adjustment considering latest economic shifts, competitive environment, your own inner growth and evolution of the vision for your life?
  4. Are you giving the business enough of your personal attention and energy and modeling behaviors you want for your business?
  5. Do you have enough resources to implement your long term vision? If the resources to realize the activities in the business are not sufficient or efficient, what are you planning to do about it? Are you planning to grow organically at a slower pace? Or will you seek additional resources to scale faster? Are you willing to sacrifice the convenience of a self-funded business and let go of some control?
  6. Is your business growing or experiencing stagnation? Do your strategies need to be revision or better execution? Has your business strayed from its key values? What has changed in top management? Do you need a turnaround?
  7. Has the business achieved a majority of its milestones recently? Have you enthusiastically acknowledged and appropriately rewarded all those responsible?
  8. What about the challenges and patterns recurring in your business can inspire you as an entrepreneur to do focused inner work and engage mentors and coaches who can help you see your blind spots?
  9. Have all the challenges recognized in the past been completely addressed? Or has your team become distracted and failed to finish the job? What is your role in it? What could you do differently? What commitments can you make today based on lessons you have learned?
  10. Do you rely only on yourself or do you once in a while give up the “knower” role and seek the professional opinion of a third party on how to implement your business strategies? This is vital and necessary – we can never know everything, especially because we are too close to our business affairs. The more frequently a business gets expert advice the more productive it gets, and the easier your life as an entrepreneur becomes.
  11. Have you been effectively enrolled all your team members in overseeing the implementation of your business plan? Do your guidelines balance strict and vigilant supervision of management with as much as possible built “from the bottom”, using the enthusiasm of your team and self-regulation?
  12. If you leave the business, will the engine still run or will the business collapse? Have you trained your team to take ownership of the day to day activities.
  13. Is the business operating in the product/line of service for which it was designed? Or you have you strayed or pivoted into new area and need new guidelines/strategic plans.


  1. Is there some way you are saying “no” to customers for no reason? You may have created your customer policies at a time when you lacked resources, technology had yet to be created, or low service levels were the industry norm. Have those circumstances changed?
  2. Do you aggressively solicit customer feedback to improve product, service and your brand? Do you send surveys, do you have dedicated account mangers that interview customers, or have you implemented means for getting direct and detailed customer feedback?
  3. Is your product or service a quantum leap from what’s out there and are you leading a “revolution”, creating a movement? If you are, how are you letting the market know about it?
  4. Do you have something that makes you or your business controversial?  Controversy creates publicity. ☺ Do you publish controversial articles and papers? Do you as a leader give controversial public speeches and media appearances? How does your ecosystem reflect the fact that you are a revolution incarnate?  :-)
  5. Have you arranged your customer priorities? Who are your, let’s say, top 50 customers? It is important to prioritize your most profitable customers and your most active brand advocates.
  6. Do you have a call for action in all your communication materials that promotes a sense of urgency? What will make your customers act now? Have you considered time-bound incentives to stimulate customers to come to you now rather than later?
  7. Do you use complimentary tactics that you can use simultaneously to attract customers? In this case too many cooks might improve the broth.
  8. Do you really know your customers? Do you know their psychographic details, lifestyle, habits, challenges they are looking to solve? Do you know what makes them tick, what is their lingo in relation to your industry? Such detailed information allows the company to interact with targets in new ways and to assess current product development and marketing roadmaps.
  9. What specific unconscious barriers might have you created to getting the market share you desire?
  10. Do you create barriers to entry for your customers? Are there customers who can’t access your offer because they lack skills or find it inconvenient to access your solutions?
  11. Do you have customers in your current client base pushing you to the limit day in and day out? Getting one reliable customer may be better than many “difficult” customers. Aim to get a customer who will push you to deliver and this customer will act as a good reference. But, firing difficult customers who drain life out of your team can also be a good idea.
  12. Do you have strategies to turn your customers into raving fans, not just buyers? Are you making sure that your current customers are excited and anticipating new offers, that they love your products and what the company stands for, and want more of you?
  13. Do you get a high volume of return customers? If not, this might mean that that there is something wrong with the quality or relevancy of your currently offerings. Always ask for reviews, case studies and testimonials from customers where possible. Honest customer feedback can suggest vital product modifications. If your business model doesn’t currently provide an opportunity for repeat business, you might consider a revision of your business model, so you venture into some recurring business and options to up-sell.
  14. Are your promotions reaching your target markets? If the promotions are not reaching the target market then it is worth putting effort into optimizing your campaigns, and if they still underperform, testing alternative promotion methods.
  15. Are all of your marketing tools adding to your strategic cohesion and are all your messages in alignment? If not, which are out of alignment and how can you fix it ASAP? Lack of clarity in your message will have significant negative impacts on the performance of your marketing strategy.
  16. Is company collateral including your website really as catchy and highly converting as it should be? Is the web site updated and optimized for conversion? Is it designed in such manner that the target market knows it is for them and can interact with it on all devices and in all browsers your customers are using?
  17. Do you learn from your competitors? Do you understand their journey, do you research press to get an understanding of their vision and strategies? Can you predict where they will be in relation to your company next year?
  18. If a new competing product is a threat to the survival of your business have you considered factoring it into your product line, producing a superior analog and/or offering a superior customer service to keep your competitive edge?
  19. Is it time for you to consider expansion? Will it increase or decrease your profit margins?Gain market share?
  20. Have you considered business expansion through franchising?
  21. Are you customer acquisition costs reasonable? Sit down with your team and get creative about the challenges and seek alternatives. Where/how can your target market be reached with better ROI?
  22. Do you have a clear map of your customer’s journey? It is important that when they finally come to you they are provided with an easy path to purchasing from you.
  23. Have you recently taken time to optimize your lead nurturing and customer engagement campaigns? Do you keep up to date records on your prospects and customers? It’s your job to keep following up, and testing various methods to implement communication tactics that convert into sales.
  24. Do you know how much price is a deciding factor for your potential customers? You need to know the elasticity of the demand. How easily would your customers change suppliers if you changed the price? If they are inelastic, you may increase the prices without worrying about them shifting to other suppliers, otherwise you might want to consider running some specials to satisfy their hunger for the best deal.
  25. Do you reward your customers for referrals? Do all of your customers know about your reward programs? You may offer discounts, gifts or other incentives to customers who refer new business to you, but you also need to make sure that your referral program is regularly communicated to your customers.
  26. Do you have an offer that is irresistible? You should take time to find a niche and create an irresistible offer that is specific to your company. It’s not only about competitive advantage, but also about virality of your offer and an opportunity for up-sell with your other products and programs.
  27. Is a high enough percentage of your target market aware of, and more importantly care about you? If your target market does not know or care about your existence then it is important to review your marketing strategies – engagement tactics, educational campaigns and public relations.
  28. Do you have any celebrities or influencers in your network? Having a celebrity relate to a business can be an effective way to get your business known.
  29. Do you know where is your market underserved? This will lead to more precise product promotions, targeted to a specific market, or to creating new offerings, and maybe extension of your product line.
  30. Do you have valid and reasonable ways to handle a client who has very high expectations that are unachievable by you? You want to satisfy your customer but you do not have the ability to do it, what can you do?
  31. Are you trying to penetrate an impossible market? There are markets that may be hard to penetrate due to tastes and preferences or the presence of a large competitor.
  32. Are you satisfied with ROI from your digital marketing? What would it take to increase it? Do you need to scale your digital operation? Do you need to hire [more] skillful team members or consultants?
  33. Are you satisfied with your web traffic conversion ratio? Does your marketing team constantly innovate on designing, testing and optimizing new sales funnels?
  34. Are you as good thought leader as you can be? Do you train your executive team members to become batter brand advocates? Do you encourage your team members to actively seek opportunities to speak on behalf of the company (under the supervision of your PR/communications professional)?
  35. Do you constantly produce high quality content to promote your thought leadership position in press and through social media? Is every piece of your content worthy of your audience’s  time? Is it simply written for search engine optimization or just because your blog needs more articles? How many people shared your content last month? If not enough, maybe it is time to change your content strategy and/or hire better writers who understand your market needs and are skilled in copywriting for the web?
  36. Do you understand your social media footprint? Do you constantly optimize your social audience engagement tactics? Are you doing what you can every day to increase your social reach?
  37. Are you constantly monitoring your sales lead conversion ratio? What are your results from each lead source, for each campaign, for each media or marketing channel? You might be losing money pursuing low ROI opportunities and leaving money on the table by not scaling your best programs.
  38. Is the image/personality of your company is still relevant? You might have hired a branding expert many years ago, but is the message still relevant? What does the market see when they look at your business? is it modern enough or outdated? A business identity should attract a certain market and be able to evolve with the market.
  39. Do you utilize performance marketing models? Do you empower your marketing partners to share your risks at least partially? Do you keep them accountable for deliverables?
  40. Do you allow your Ego drive your marketing decisions? Do you pay for unnecessary vanity items despite budgetary restrictions (press appearances that don’t convert into sales, VIP memberships, etc…)
  41. Do you personally represent your brand in the best possible manner? Does your behavior in public, the way you speak, dress and act corresponds with the language of your brand?


  1. Do your partnerships return enough ROI for your time and other resources?
  2. Do you help your suppliers to deliver on time, by optimizing your procurement processes? Do you provide your resellers with the best training and marketing collateral you can afford? Do you optimize your marketing programs to help them sell your offers?
  3. Are your brand and profit margins safe with middlemen? Resellers care more about their profits than the profits of your company which might lead to and customer dissatisfaction and negative reputation.
  4. Are you better off with your current partnerships than you were before the partnership in terms of debt to equity ratio or other critical parameters? Does this partnership add enough value to the business? Is it a keeper or is it time to part with a particular partner?
  5. If you have partners, are they self-motivated about being in collaboration with you? Do you have plans in place to motivate them on a regular basis and have automated programs in place to streamline that process? Setting achievable targets and clear processes to actually achieve them is a big motivational measure for your partners and investors.
  6. Are you getting the best services from your suppliers? Are your supplier providing the highest quality? Can you get higher discounts or lower prices for the same quality?


  1. How long do you take to pay your suppliers? Paying them late might lead to penalties or higher prices being charged for services in the future and paying them too early may lead to short-term cash flow problems. Plan for the best time to pay your suppliers, keep relationships in integrity and make it a win-win.
  2. Do you have money ready for speculative and precautionary reasons? You need money available to fund critical activities.
  3. Where is your organization losing money and what are the reasons? Have you made a conscious choice or just procrastinating? Let’s say a product or department is losing money, are there justified reasons why you keep them?
  4. Have you arranged your expenses according to your priorities? If at any time you are short of funds can you easily identify the expenses that should be paid first?
  5. Are your products priced according to the market demand? Have you established a way to monitor the prices of your products or services in relation to competition and market trends?
  6. Are you reinvesting your profits wisely? What factors affect your decisions about using profits?
  7. Are you constantly looking for ways to minimize business costs without compromising quality?
  8. How much have you invested in the business so far? Would your money yield more return if invested elsewhere?
  9. Is the profit you are making worth the hard work you are putting in? Does your lifestyle reflect the efforts you are putting into your business? Maybe it’s time to change the nature of your business entirely?
  10. Have you built necessary relationships and have a source where you can get contingency funds in case of cash flow emergency? Do you allocate time to create long term relationships with potential lenders and investors now, before you need funds.
  11. Do you have necessary insurance and other security to prevent theft, embezzlement and sudden loss?

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