Personal questions to ask yourself at the beginning of every new startup idea

Along the years, I’ve been involved in 6 startups from the beginning, meaning idea level and team forming. While being quite enthusiastic about various ideas, it was easy to jump towards implementation. 

We were focusing on the idea validation, business cases, revenue model but often we forgot to ask ourselves more important questions.

As an entrepreneur, there are many specific questions that you should ask yourself in order to grow not only oneself, but also your business idea. Sometimes, you are one question away from changing your life, you just need to find the right one to address it to yourself. 

Francis Bacon, an English philosopher, once said “A prudent question is one-half of wisdom.” Meaning, that the right question asked even without the answer is already half the insight. Moreover, from Napoleon’s point of view, the words HOW and WHY cannot be used too often, because knowledge comes from inquisitiveness.

Below you can see some personal questions that I'd have very much appreciated to be asked during those moments as these would have probably saved time and energy for me and the team and might have guided us to even drop some ideas aside. 

At first we will focus on your relationship with this new startup and the why and then we’ll move on to various aspects regarding your potential role in it.

1. What is your vision on the project? 

In order to clarify and understand what your plan is, you need to have a clear vision. You should develop and write down your personal and professional desires with medium term and long term goals. You don’t need to build this as a plan, because in time it will change as your personal and professional circumstances change. The purpose of this is to have an understanding of what you want to accomplish and how you will achieve it. 

This vision needs to inspire you, it’s not just about the business opportunity but it’s also about the impact you will have in the world. If you cannot find one, sooner or later in the startup life, when the challenges will be quite big you will probably give up on the project/startup. The vision is the one that guides in the darkest times. 

As soon as you know your vision, people around you will start noticing you’re doing things differently. It also means that you kind of know the level of sacrifice, the level of detail, the kind of team mates you need, all of these things have to be tight to the vision that you have.  

2. What is your motivation for doing this particular project/startup?

Being an entrepreneur and not an employee is a lot more harder and challenging than you would think. This is why, when starting a new project/business and along the way you are in need of a great amount of motivation, which will help you go through every obstacle that will come your way in time. Also, you have to find a way to self-motivate yourself, in order for you to remain inspired, disciplined and organized.

It’s also important to reflect on how much is the ego driving your actions towards this startup. Ego is not necessarily a bad thing, but it can be used to push the startup forward. The better you understand your motivation and motives, the better your performance can become.

3. How much do you want to scale your business?

A lot of people say: “I don't know. I guess I will find out when I go through it. We will see.” But you should be more clear about your ambition. In business you should know how big you want to build your company. You want to be a local impactful startup in a city where everybody knows you or you want your startup to be a big player in a region or globally. You don’t need to follow the dogma of going global, but to understand your own ambition for scaling.

4. What values do you look to have in the startup team? How do you want to have the team culture?

“Culture eats strategy for breakfast” is a famous quote from legendary management consultant and writer Peter Drucker.

Beyond how the startup will evolve in connection with customers and the outside world, the team will be the engine for all these and the startup will be an image of the values and culture you instill in the team. So, make a list of values that you want to have them integrated in your culture; make conscious choices about them and see if they are reflected in the work you do and ask yourself if you are walking that path desired.

5. What are your weaknesses?

You may be great in operational, coding, design, sales, but for sure you have a lot of areas where you are not good. The reason why you should know as soon as possible what your weak areas, is to hire people who are strong in those areas. This way, your weakness will no longer be highlighted, because you hired the right people who were better than you in those areas.

6. Where is my time being wasted?

An important question to ask yourself and reflect on it as you should put your time in areas with the biggest return, not areas which aren’t worth it, although you like them. The point is to prioritize based on what you can do and what you know; to find out the areas in which you are most effective and gather other people around to complement.

7. What usually blocks you from starting or doing things?

We all procrastinate various things, consciously sometimes, subconsciously most of the time. Usually the blockages come from a psychological trauma or negative association about that particular situation. Our patterns kick in and we easily can slide into not acting in the right way. 

The entrepreneurial journey is quite often an inwards journey of self-understanding and growing awareness of oneself. If you’re being honest with yourself, you’ll see that root cause in any failure is something that is traced back to one of your patterns and behaviours as founder. This doesn’t mean you should be harsh with yourself, but to understand what happens, deconstruct the pattern of acting and to change it.


By asking yourself these questions and practicing an ongoing reflection, you can remain focused on your goals and long term vision. Whenever you want to step back to get an overall view on your progress, take a few minutes to run through the aforementioned questions. Doing so will reconfirm your motivation and will give you new ways to implement in the future. 

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