Hard Questions

Erin Boeger
5 min readSep 11, 2021
Photo by Jesse Bowser on Unsplash

I had the pleasure (and pain) of owning several restaurants. I launched new restaurants, bought franchises, and even designed a few restaurants literally from the ground up. Now I serve the tech industry and see many of the same problems here. For example, where and how the business starts.

If you were to open a restaurant what are the first things that should focus on?

  • Figure out the menu
  • Develop recipes
  • Develop procedures for making the food
  • Decide on portion control of ingredients
  • Design the store room of the ingredients
  • Find a food vendor
  • Research the best cooking ware
  • Research the best kitchen refrigerator
  • Research the best kitchen stove
  • Design the seating arrangement
  • Hire a professional chef
  • Hire waitstaff
  • Understand the market
  • Find an appropriate location
  • Hundreds more…

New company todo lists, like this, are full of easy questions, hard questions, and get so long it feels daunting. You need to get started but where should you put your energy and focus? Easy questions and tasks or hard questions and tasks?

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Easy questions are questions that can be accomplished by an informed decision, which unfortunately is often just web searches. The hard questions however are, just that, hard. They cannot be easily answered with web searches and require time, effort, and often trials and failures.

Starting a restaurant is the perfect analogy for starting a tech company. Failure rates and reasons are uncannily similar. Instead of chefs and cooks, tech companies have CTO’s and software developers. Both restaurant entrepreneurs and tech entrepreneurs generally start with easy questions and it is understandable why.

Easy questions give us a sense of progress, confidence, and satisfaction. There is a long list of things to do and Googling for answers that can return results to help you feel comfortable about launching a business are hard to resist. Quick answers to easy questions can also feed into our passions.

In the case of a restaurant you may have a huge passion for Thai food and want to share that with the world. Just like a founder of a tech startup may have a passion for solving a problem or disrupting a market and getting into the details of the tech can further fuel a founder’s passion. Passion and energy are great! But that energy can be spent better elsewhere.

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If you were to open an amazing steak house in a predominantly vegetarian community will it matter what kitchen equipment you bought? Will your recipes and processes for delivering awesome steak to waiting tables be of any real value? Highly doubtful.

If you were to open a restaurant in a neighborhood populated predominantly by families with children and both parents working, how would that knowledge affect your menu? Your hours of operation? Would you offer delivery or take out services? Would this information better serve you before you make certain low level decisions? Highly likely.

All those conditions will have a knock on effect all the way down to how you prepare your food, how you serve your food, what food you buy, how you store that food, take out containers, and the list of effects continues on. Yet most still choose the easy questions first. Perhaps because finding answers to easy questions upfront can feel like the right thing to do despite leading to real problems later on.

All that initial momentum and work put you into chasing easy answers may have put you on a path that will lead you down the wrong roads. It generally gets worse, as time goes on, many entrepreneurs fall victim to the fallacy of sunk costs and try to bend but not change. This only prolongs the pain.

How much more successful would a similar restaurant entrepreneur be if they would initially focus on the hard questions like: Who are my customers? What do they want to eat? Where is the best location to reach them? How should we market to them? What is the competition like? Is there even an opportunity in that market? Can I find a profitable niche?

These same rules apply to technology startups. Sometimes deciding the tech stack and tools too far ahead puts an organization down the wrong tech path and even the wrong product path. After a few months, or years, you may find your business is stuck and unable to maneuver into the markets or products you need to be competitive.

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Ask the hard questions first, then let the rest fall into place. Most successful businesses know it is not your products that will make you successful, but how well you know your customers and how to reach them. With all the progress technology has made, and the cornucopia of tools available, it is quite rare that a project will fail because the technology could not be built.

A well designed business concept in the hands of an experienced software professional will be worked out. Just like a restaurant in the right location and in the hands of a professional Chef will stand the higher chance of success. The key is to stay out of their kitchen and let the chef do what they do best.

Take a few minutes to do the research on why tech startups fail. I did, none of the reasons on any of the search results were because the technology could not be worked out. All the top reasons returned, and from my personal experience, were the business team not answering the hard questions and focusing too much on the easy questions (i.e. the technology).

The bottom line is: Answer the hard questions first, focus on your business concept, target audience, and find a software professional to help put your idea into reality. A technology professional you can trust and allow you to continue focusing on the hard questions, because the answers to hard questions will determine your business success the most.

Photo by Clark Tibbs on Unsplash

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