The One Question That Can Transform Your Business

Jayson DeMers
4 min readOct 6, 2020

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Photo by Brooke Lark on Unsplash

Entrepreneurship is all about finding answers. Your entire business is an answer to a common consumer problem, or need. Your business plan is a general answer to the most common questions that investors and lenders ask regarding your viability and potential for growth. When you look for new clients, you’ll be answering a barrage of questions about what your business can do for them.

But if you want to grow your business to anything beyond a simple startup, you need to ask critical, hard questions. You need to force yourself to evaluate your operations objectively, thoroughly, and maybe even harshly to find new answers that help you drive the business forward.

I’m sure you can think of hundreds of little questions to ask, like “how can I become more profitable?” or “what can I offer that my competitors can’t,” which are certainly important. But there’s one big question that surpasses all of them in importance, and it can completely transform your business: what if?

If you think this is a cop-out, bear with me. I understand that this is a vague question, and one that in actual use, will transform into lots of different questions, but there are a few key qualities about its open-ended, prodding nature that make it essential for transforming a business.

Forced Imagination

Closed questions like “how can this be better” tend to force your mind down a specific path. You list a handful of potential options, and maybe consider a few extra factors like the degree of effort it would take to implement an option or whether one option will offer a greater improvement than another. Open questions like “what if” force you to imagine the effects of any option you’re considering.

Let’s say you ask “How can this be better?” in regard to your content marketing strategy. You might list including more interviews, or doubling your post frequency, or engaging with more influencers on social media. That “what if” application takes this to the next level — what if you do include more interviews in your content strategy? How much effort will it take? How will your users respond? What tangible benefits do you hope to see? Who would you start with?

As you can see, what masquerades as one question is actually an exercise in exploring dozens (or hundreds) of smaller component questions. This branching, explorative system forces you to consider more qualities and effects of each possible decision, and gives you a more thorough, high-level view of the possibilities.

Openness to Research

The individual branches that stem from your original what-if exploration often demand additional research to fully understand the ramifications or benefits of the new option. Take my example above, with “what if I include more interviews in my content strategy?” One of the stemming questions from this initial probe is “How much effort will it take?” You can speculate openly about this, but it’s better if you talk to other people in your industry and see how much time they spend on interviews to get a more objective picture. The same can be said of “How will your users respond?” and almost any other stemming question you can think of.

The more research you do to satisfy these branching questions, the more logical a conclusion you’ll be able to find.

Infinite Applicability

“What if” is a question that can be applied to literally any situation or circumstance. Making it a common fixture in your evaluative process will force you to undergo this system of exploration, branching questions, imagination, and research. Though the human mind automatically undergoes a “what if” scenario process for almost every idea that crosses it, formalizing the process using notes, a whiteboard, or even a brainstorming session with the team can open you to areas you might not have otherwise considered.

In Practical Use

Ultimately, the question “what if?” is more of a thought experiment than a traditional question. But like with most things in life, you’re going to get out of it what you put into it. If you ask the question and think up a handful of vague, simple responses, you aren’t going to walk away with much more information or awareness than you started with. If you instead take a few hours to sit down and map out the possibilities ahead of you, you’ll walk away with far greater benefits. Similarly, the more scenarios and options you apply this “what if” thinking to, the more you’ll grow to understand your business’s position.

What I’m driving at here is a forced evaluative process that leads you to brainstorm, research, imagine, and speculate all at the same time. Lending yourself to this process enables you to see your business from a higher perspective and think more critically about the issues you encounter.

For more content like this, be sure to check out my podcast, The Entrepreneur Cast!

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Jayson DeMers
Jayson DeMers

Written by Jayson DeMers

CEO of EmailAnalytics (emailanalytics.com), a productivity tool that visualizes team email activity, and measures email response time. Check out the free trial!

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