Top Questions To Ask An Entrepreneur

Top Questions To Ask An Entrepreneur

Top Questions To Ask An Entrepreneur

Entrepreneurs are notoriously a chatty group.  Being an entrepreneur in many cases requires the ability to communicate complex ideas to both customers, investors, and team members alike.  For this reason, more often than not, entrepreneurs love to talk to would-be and fellow entrepreneurs whenever they get the chance.

There are few things as important as having a mentor when it comes to developing a business or becoming an entrepreneur. Experience triumphs theory and more advanced entrepreneurs are a reservoir of info that you are unlikely to find anywhere else.  Even those that aren’t in your particular field or industry can offer perspective on some of the universal challenges that business owners deal with every day and mistakes to avoid.

Pop into a bar or networking event in any major city, and you’re bound to run into at least one that will answer your questions.  Using these conversations is but one way you can get crucial information about your pursuits. In this brief guide, we are going to go over a few of the most important questions you can ask an entrepreneur.

The main list of things that cover all the essential bases are:

  1. What was your background before starting a business?
  2. How did you decide on what business to start?
  3. What made you want to be an entrepreneur?
  4. What resources did you start with?
  5. What was your first “I can do this moment.”
  6. What was your worst moment?
  7. What were four things you wished someone had told you about being an entrepreneur?
  8. How do you deal with problems and plateaus?

As a disclaimer, some of these questions will land and other times whoever you are talking to may just not answer due to lack of interest, comfort, or for no reason. Don’t get discouraged. The challenge lies in being able to read who you are talking to and knowing which ones apply/would get the best answer.

What was your background before starting a business?

The reason why this is an important question should be apparent. Knowing what an entrepreneur did before they ran a business can give insight into what skills/working history they had that led to their business’s creation.  In some cases, anecdotes, or how they met a key person can give insight into how you can utilize people in your network to move things forward.

Background also can act as a rapport building tool. Finding any similarities or connections you have can help build a bridge between your two paths that can one day lead to a partnership or positive relationship.  Networking is fundamental to being an entrepreneur, and it can be surprising how random conversations can lead to opportunities.

How did you decide on what business to start?

The decision to start a business is a complex one, and there are a few kinds of people who decide to start one:

  1. People that decided to do it out of necessity/opportunity.
  2. People that did it as an extension of a previous hobby.
  3. People that took their skillsets from a job/trade and repurposed it.
  4. It was a sporadic decision.

Each has a unique take on how a business should be run or started. Finding out which you are is important.  Seeing the wide variety of ways that businesses can be created and function can be eye-opening.

What made you want to be an entrepreneur?

Everyone has a story about their breaking point. For one digital nomad, it was a matter of working too many serving shifts (over 60 hours) and needing a change. For others, it was a matter of finding the motivation to go beyond their pay limitations.

Finding out others motivations can give you an idea of what your priorities are and whether they have changed over time.  Every entrepreneur will tell you that what they thought it would be like and what it was like were two different realities.

Top Questions To Ask An Entrepreneur

What resources did you start with?

No two entrepreneurs except partners start off with the same resources, and even in that case, they each have different skill sets (or should).  This is usually one of the easiest questions to ask, as everyone loves to describe how they rose above where they were at before and the journey itself.

On the one hand, these can be thoroughly motivational, much more than the previous question. There will be stories of people who started with $100 and built an empire, and others that started with a lot more but no skills and carved out their little piece of heaven.

Another benefit is that more often than not, for those with limited resources, there will be a tie-in story to how they managed to make the most out of their situation and overcome.  It can get your mind in the right state to figure out any problems/roadblocks that kept you stuck.

What was your first “I can do this moment”?

There is a moment that every entrepreneur experiences when things are so bad it’s hard to take a step forward. Every doubt, every comment from a non-believer, every dark cloud that ever took a moment of your time comes rushing in, and just before everything falls completely apart, there is a glimmer of hope.

This can be in the form of a surprise order, a random last minute opportunity, or some other kind of business breakthrough.  The biggest thing you can ask an entrepreneur is what gave them the faith to keep going and how did it play out.

What were your worst moments?

For perspective, also ask them what their harshest moment was.  Sometimes everything does go wrong, sometimes it all does break down, but that rarely spells the end for those that are willing to persevere.  

Most will tell you that each day where you are responsible for your limitations, work schedule, and as a byproduct, your quality of life is a test.  Its one that will break you and rebuild you day in and day out, and while it can get more comfortable with time, more money usually means more problems.  

Top Questions To Ask An Entrepreneur

What were X things you wished someone had told you about being an entrepreneur?

Depending on how interested the entrepreneur you’re talking to is about sharing, there are usually a few massive moments that stand out as important pivotal points. One of these important pivotal points is screen sharing which you can do by getting on your computer desktop and sharing what is on your screen to a meeting you are having.

There are a few key tips that most entrepreneurs will have on hand (many reflect on wins and losses ALL of the time). Keep track and find a way to implement them into your process.

How do you deal with problems and plateaus?

Putting out fires is a massive part of running a business. No amount of planning, guesswork or experience can prepare you for the realities that come when running a business. Everything from sheisty clients to order mistakes can make your day a living hell, and all business owners know this.

Top Questions To Ask An Entrepreneur

Beyond that, more significant problems that can arise can come from bottlenecks in your business model, sickness, unplanned costs, or some other type of organization problem.  Many business owners are willing to share some of their mistakes or their solution to dealing with problems.

  • This can mean how they negotiated partnerships to offset difficulties with staffing for projects or order deliveries.  
  • It can be about increasing profit when time dedicated via a service is tied into earnings.

A crucial point to take in is how they expanded/scaled their business. Scaling and maintaining quality is the biggest test of a business owner’s ability to systemize their process and make it adaptive.  If you can master this key task while keeping it lean and profitable, you’ll go far.


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