100 Questions Every Entrepreneur Has To Ask Himself: My Effect On Success Or Failure Of My Venture, Beyond The Feasibility Of A Product & Business Tactics

Effect On Success Or Failure Of My Venture, Beyond The Feasibility Of A Product & Business Tactics

Ask Yourself… How am I in the way, in many different ways?

Let’s look at the effect of your SELF-IDENTITY & EGO:

The Ego identity fears failure, because failure is viewed as a bad reflection on the self. The wise leader needs to create distance from Ego fears and defenses to make sure they don’t get in the way of success.
Ask yourself these questions:

  1. Is there anyone I am trying to impress? Is it preventing me from doing things I want to try? Is it because I want to appear worthy of their attention or respect? Do I want power or social status?
  2. Am I insecure? If so, can I figure out how to overcome these feelings? Failure is not in itself a problem as much as is your perspective on it.
  3. Have I ignored others’ feedback about myself or my business practices because I didn’t want to admit failure? Could I have learned more from the feedback if I took it with a view toward learning, rather than taking it personally?
  4. Do I actually have the skills to complete the task? Are there areas for improvement? Is there anything in the way of me developing emotional intelligence, the latest technical skills, or leadership practices?
  5. Do I go beyond my comfort zone, or do I choose to spend most of my time with those who are like me? Do I take a risk and meet new people in my professional ecosystem, especially those who seem different from me?
  6. Do I hold on to control too tightly? Have I learned that control is an illusion? Can I delegate to others, and trust others to do a job?
  7. Do I micromanage? If so, why? Can I overcome that mistrust and recognize that others can do the job better when taught, encouraged and given space to grow into?
  8. Do I think I know more than others? If so, can I recognize times that has proved to be a liability?
  9. Am I humble, or do I feel a need to boast? Can I see how this might isolate me or make me a less effective leader?
  10. Do I actively seek out those who will tell me the hard truth about myself? Or do I shy away from constructive criticism?
  11. Do I acknowledge others for their success and recognize those who helped me to get where I am today?
  12. Do I listen to my employees and seriously consider their suggestions, either about myself or the business, or do I unconsciously dismiss, argue or disagree with what they are saying?
  13. Do I feel the need to lead every meeting? Why would anyone else bother to or risk talking after the boss has offered his/her opinion?
  14. Do I reflect on my shortcomings and try to figure out ways to overcome them? Do I work to better myself? Do I ask others for ways to improve myself?
  15. Do I ever apologize? If not, why not? Do I see myself as above apologizing? This can lead to unhealthy relationships with others and failure in your business and personal life.
  16. Do I expect others to apologize for minor mistakes? Is it to make myself feel superior? If so, recognize that just because someone apologizes does not mean that they respect you or “see the error of their ways.”
  17. Do I acknowledge others’merits and capabilities, or do I mostly focus on my own? Do I generously share credit with others, or do I prefer to take all the credit for myself?
  18. Am I reluctant to accept responsibility? Is it because I don’t want to be seen in a bad light? Shying away from responsibility can make you look worse than if you owned up to your mistakes. Not taking responsibility means you miss out on great learning opportunities and fail to develop over time.
  19. Do I consider myself to be a confident person? Do I challenge myself to get over my insecurities so they don’t keep me from reaching my goals?
  20. Do I seek out the emotional support of others when I am frustrated or feel the need to vent? Do I recognize that relationships are important to my well-being, and consequently, to the success of my business?
  21. Do I take the time to listen to employee complaints, or have set up a system of anonymous reviews? Do I take these reviews seriously, and work to not take them personally? Reviews are important, and the health of a company rests on the interpersonal relationships of its employees.
  22. Do I refuse to try new things or ways, because I fear the judgements of others?
  23. Do I try to connect ideas and individuals between departments, to create a more collaborative environment in my company? Collaboration is essential for building up a company and making it more effective.

Sounds familiar? Book your introductory coaching session and let’s discuss your needs.

Now… Let’s talk about your BLIND SPOTS:

Blind spots prevent you from seeing things as they actually are. Blind spots also prevent you from seeing yourself clearly, keeping you from understanding how to become a better, more successful leader. Blind spots are by definition impossible for you to see, so they are hard to uncover, and even harder to overcome, but they can be handled by engaging objective, constructive outside perspective.

Ask yourself these questions to identify your blind spots:

  1. Do you believe based on data, or based on something you think or feel is true? Do you choose data that fits in with what you already believe?
  2. Do you question yourself, act as your own devil’s advocate? Keep asking questions to get at the details and what needs to be focused on.
  3. Do you invite your team to question your thoughts, and encourage them to suggest alternatives? Are you really open to suggestion?
  4. Would you rather go do things alone rather than ask for others’input?
  5. Do actively seek to pick up on the feelings and thoughts of those around you? A major blind spot is being unaware of the unintended consequences and effect on others of your behaviors. If you are unaware you might overreact when others act frustrated, hurt, angry, or upset.
  6. Do you bottle things up? Do you avoid difficult conversations?
  7. Can you accurately judge when you are clear, making your point and being understood by others? If not, why not?
  8. Do you get out of your comfort zone and away from routines?
  9. Do you blindly respect hierarchy? Or do you understand superiors can make mistakes and are human?
  10. Can you see things from the customers’perspective?
  11. Do you give up too easily if things don’t go well right away?
  12. Are you consistently proactive and disciplined?
  13. Does fear cause you to“win at all costs”, cheat others, bully employees, never rest?
  14. Do you feel angry or resentful when faced with problems?
  15. Do you ever make assumptions about people, including assuming you know all about them and their abilities? Are you stuck in the past about how you evaluate others and yourself, or do I see people, things and yourself, as dynamic and capable of transformation?
  16. Do you spend time learning how to improve the way we communicate and express ourselves to each other? Being able to communicate effectively and with empathy is the best way to establish and maintain solid relationships.

Understand your COGNITIVE BIASES:

Cognitive biases are patterns of thinking that are shortcuts, or heuristics, that the brain uses. They save time and are efficient, but they can cause issues because they are not rooted in rational problem solving. Cognitive biases are quick and intuitive, but prone to error.

Ask yourself these questions and do these things:

  1. Do I pause to consciously question myself and pick apart my thoughts? Confirmation bias is a human tendency to take the first piece of information we come across and process it in ways that fit our current model of thinking or of knowledge. To solve this bias, become your own devil’s advocate.
  2. Am I really looking at all the information before making a decision, or am I just picking the information and focusing on the things that fit my preconceived notions? This is again confirmation bias at work.
  3. Keep a decisions diary. Write down your thought processes relating to a decision. Then regularly sit down and ask yourself these questions as you go through past entries: Did my thought process make sense? What can I learn from what worked and what didn’t? Is there something that would work better, knowing what I know now?
  4. Am I wanting to be part of the group, or keep the harmony within a group to the point where it’s led to irrational thinking and poor decision-making. Find ways to encourage independent thought, both in others and yourself. Ask yourself: am I inhibiting myself from going along with the crowd, or am I pushing boundaries and asking the hard questions?
  5. Do I agree with what is happening or what is being planned on, or am I just going along because everyone else is. Have I thought for myself or have I simply gone with the flow? Bandwagon effect is the cousin of groupthink. In the bandwagon effect, people adopt a certain belief the more others do. This is why meetings can be so unproductive.
  6. Always ask yourself whether there are ways to improve XYZ, because there surely are. Choice-supportive bias is when you tend to view your choices and decisions as being positive and good, even if there are apparent flaws. If necessary, consult others, including customers, and seriously consider what they say.
  7. Am I judging someone as insensitive, unproductive, indifferent, or any other quality, or have I fully considered their circumstances? Fundamental attribution error is when you attribute someone’s behavior as being an intrinsic quality of their personality rather than attributing their behavior to the situation they are in. Knowing what people are going through will help you to understand them, and help you approach them in more productive ways.
  8. The Galatea effect is where people either perform in direct relation to what they think they can do. This is similar to Ford’s famous quote, “Whether you think you can or cannot, you’re right.”Do you envision yourself succeeding, and instead of focusing on all the ways you could fail, think about performing well and succeeding?
  9. Do I impatiently demand immediate results, or can I wait to get bigger and better results? Hyperbolic discounting is the tendency of people to want a payoff sooner, rather than waiting for a larger payoff later. This is similar to the marshmallow experiment on delayed gratification, where young children were given the opportunity to have either one marshmallow immediately, or wait a few minutes and get two marshmallows. The children who could wait proved more successful in life.
  10. Am I focusing on all the things I have done wrong, or do I take the time to appreciate positive events and successes? Negativity bias is where people place more emphasis on negative things rather than on positive ones.
  11. Outcome bias is the tendency to judge a decision based on the outcome rather than the process of decision-making. Even if you win a lot of money gambling, is gambling really the best way to make money?
  12. Have I truly given myself enough time? Planning fallacy is the tendency to underestimate how much time it will take to complete a task. Make sure you give yourself enough time to complete a given task.
  13. Am I doing something just to prove I am independent of someone with whom I work? Reactance is the desire to do the opposite of what someone else wants you to do to prove your independence from them.
  14. Does new information have more clout than old information, or is the new info lacking something that the old info provided? Recency is the tendency to weigh more recent information more heavily than previous information.
  15. What checks are in place to help you resist temptation? Restraint bias is the tendency to overestimate how much restraint you will have in the face of temptation.
  16. Have I spoken to others about how to manage their perceptions? Selective perception is when you allow your expectations to affect how you perceive the world.
  17. Am I focusing only on what has gone well, rather than taking the time to learn from mistakes? Self-enhancing transmission bias is the tendency to relay your successes more than failures. This leads to false perceptions and can lead to inaccurately assessing a situation.
  18. Am I being fair and open to others, or have I made unconscious judgments about them based on some quality? Stereotyping is a common bias where people expect a certain group to have certain qualities, even though the qualities are not accurate or apparent.
  19. Can I admit I don’t know it all? Shock and awe bias is the tendency to believe that our intelligence is enough to solve a problem or complete a task.
  20. Do I blindly obey those in higher positions, because I am afraid to speak up? Obedience bias consists of following those in authority, because they are viewed as being more competent and powerful.


Ask yourself these questions:

  1. What if I could not fail? What kind of life would I go for?
  2. What if I do fail? What are the consequences? Do I know how to emotionally handle failure?
  3. Do I take failure personally, or have enough perspective to go back with an impartial eye and see if there was something I could have done better? What about what others could have done better?
  4. Am I comfortable giving criticism to others with empathy? Do I shy away from the responsibility, because I am afraid of not being liked? Supportive assessments benefit people and help them improve their functional skills.
  5. Am I comfortable receiving criticism from co-workers and not taking it personally?
  6. Am I afraid to negotiate? Do I shy away from asking for a raise?
  7. Do I value my worth, see myself as an asset to the company? If not, do I try to build up my skills? If I don’t, no one will.
  8. Do I envision myself succeeding? It’s an important aspect of neuroscience: if you see yourself, step by step, succeeding in a plan, you will increase your chances of succeeding. It is important to envision yourself reaching your goals, in order to actually reach them.
  9. What might be holding me back? Is there anything I can do right now to begin moving toward success?
  10. Say you did fail: was there anything that went right in this failure? Make each event a source of knowledge and growth.
  11. Is there anything I can do to make sure I reach my goals? Were there specific obstacles or false beliefs I have that got in the way? Can I change those false beliefs so they don’t continue getting in the way?
  12. Are there any “crazy ideas”I don’t try out because I’m afraid? Is it something I can try out right now?
  13. Was my biggest failure a lack of discipline, not following up with customers or clients, not keeping in touch with contacts, etc.? What can I do to make sure I don’t continue making those errors? What caused the errors in the first place?
  14. Is there anything I can do to make sure I don’t fail? Have I seriously considered hiring or consulting experts? How do I feel about asking for help?
  15. Looking back on the past year, is there anything I would have done differently? Am I doing the same thing this year I did last, or have I improved?
  16. Is there anything in my business that I need to let go of, such as a product that is no longer feasible or viable? Is there a way to replace such a product with a better, more viable one?
  17. If you didn’t have to worry about time or money, what would you do differently? After thinking about those things, now ask yourself, how could I realistically still do those things, factoring in time and money?
  18. If I didn’t have to follow the rules, what would I do differently? Get in the mindset of “Rules be damned”for a moment, and brainstorm. Following the rules can create mental blocks against improvement. Ask yourself if you have been following the rules to the point where you are doing the same things but never improving.
  19. Have I played recently? Have I “let loose”in healthy ways? If not, ask yourself why. Am I afraid? Do I just not think it’s important? Do I think I don’t have time? Play is important to creativity and improvement. Author Roger Von Oech wrote, “Necessity may be the mother of invention, but play is certainly the father.”
  20. Do I only learn things to be a Jack-of-all-trades? Or do I seek to be a master-of-something?
  21. Ask yourself if there are other companies, or even other people doing similar things you are doing. Look at them not only as competitors, but as potential collaborators.
  22. Before I start a project, what’s my planning process? What are all the steps I need to take from start to finish to complete this project? How can I make room for modifications?
  23. Do I have a backup plan? Redundant planning is essential for success.
  24. Do I trust others to complete tasks for me? Do I outsource to save myself stress?
  25. Do I have the knowledge to execute my plans? If not, are there others who can teach me? Can I find courses online? What about using Khan Academy, Coursera, iTunesU, MITWorld Open Courseware, etc. to teach me the things I need to succeed? What about engaging with an Executive Coach?
  26. Do I make good use of conferences in my field, to learn more about new things and to make new connections? It is important to continue learning and developing relationships with those in your field. Asking others for their input can help you.
  27. Do I procrastinate? When you find yourself procrastinating, sit down with a journal or piece of paper, or in front of your computer and ask yourself, is there a reason I don’t want to start? Am I afraid? Bored? Feeling lazy? Disbelieve your thoughts and feelings and discover ways to overcome them. When we procrastinate, there is always a reason, even if it is simply a matter of not being interested in the task.
  28. Do I follow a code of ethics? Ethics is important in a company and keeps relationships productive and healthy.
  29. Do I take breaks from my tasks, especially when I hit mental roadblocks? Do I recognize that taking a step back can bring me more clarity? Breaks are healthy, and are not a sign of laziness. Moving is a simple way to get blood flowing, relax, and interact with other colleagues. Or do I sit at my desk most of the day, hurting my health and reducing my productivity?
  30. Do I take the time to meditate throughout the day, and have tried to make it a daily habit? Meditation can help us focus, stimulate creativity and reduce stress.
  31. Do I use my lunch break effectively to get outside, to walk around, get some exercise, take a refreshing walk in a park, go out with friends, meet a spouse for lunch and/or catch up on the day?

Create the environment of SOCIAL SUPPORT:

Social support is important in the best of times, and in the worst of times. You need a solid group of people to support you in your successes and failures.

Ask yourself these questions:

  1. Do I have friends who are willing to listen to me? Do I feel heard? Do I feel like people care about me? Do I try to make others feel heard and attended to?  Do I value relationships and recognize they’re important for my success? We need healthy relationships to prosper.
  2. Are there mentors in my life? Is there anyone who can guide me objectively? We all need guidance. Having someone who is more experienced to guide us is a great asset in life, a good source of learning and encouragement.
  3. Does my social support criticize? Or do they encourage me when I need them to? Do I take the time to encourage them in their endeavors? We all need to feel encouraged. When we do not feel so, we can become discouraged, and that can lead to procrastination of tasks, or even abandonment. Conversely, we also need to encourage others in their goals, to help them work through harder times.
  4. Does my social support tell me the truth without being harsh? We all need those whom we can trust to tell us the truth without necessarily shielding us from it.
  5. Do I ever express gratitude to my social support? Do I actively tell them I am thankful to have them around me, supporting me? If not, why?
  6. Do I regularly keep in touch with my social support, or do I only go to them when I need something from them? Can this lead to them feeling “used and unappreciated?”
  7. Do I befriend those who seem like they are on the fringes of the social environment? Do I make them feel welcome? Am I warm and engaging?
  8. If I’m the one feeling on the fringes of the social environment, am I making an effort to connect with others or do my actions only serve to keep me on the fringes?
  9. Do I strike up conversations with strangers? Do I learn something from them? Do I try to make a point to learn something new every day from those around me?
  10. Do I only send out emails to coworkers, or do I visit their desks? Do I have “water-cooler conversations?”If the business is virtual, do I schedule meetings on Skype or Facetime? Perhaps in person?
  11. Do I give back anything to my social support, or do I mostly take?

Sounds familiar? Book your introductory coaching session and let’s discuss your needs.

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