Questions to Ask Yourself to Help You Make the Right Business Decision - Rolling Stone
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10 Questions to Ask Yourself to Determine if You’re Making the Right Business Decision

Sometimes just one question can let you know you’re on the right track.

Woman sits at desk thinking.Woman sits at desk thinking.

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Opinions expressed are solely those of the author and do not reflect the views of Rolling Stone editors or publishers.

Business is full of tough decisions. During the course of a day, an entrepreneur could find themselves making anywhere from one to hundreds of tough decisions, big or small. While experience and time help make the decision-making process easier for many business owners, they can still often benefit from asking themselves a few clarifying questions.

Below, a panel of Rolling Stone Culture Council members each share a question an entrepreneur can ask themselves before making a tough decision to ensure they’re on the right track.

Is This Decision Rational or Emotional?

After many years of operating from my ego early in my career, I learned the error of my ways and now do my best to keep my ego out of my decision making. It’s not always perfect, but this question helps me see the forest for the trees and gut-check myself if I’m being irrational or reacting out of a sense of pride or ego. – Harrison Wise, Wise Collective Inc.

Does This Decision Support Our Mission Statement?

When all aspects of a decision have been considered and it is still a difficult choice, I ask myself if it supports our mission statement. Every business should have a mission statement that speaks to the core focus of the business. Decisions made need to further your business on its mission, not pull it in another direction. – Sheila Dedenbach, Heavenly Sweet

Do I Have Buy-In From the Team?

One question I’d ask myself when making a tough decision is, “Is my team behind it?” It’s all well and good making a decision, but unless you have the follow-through from your team, your decision will struggle to make a real impact. – Robbie Murch, BUMP

Who Is This Helping?

When I had my own business, I got occasional advice that directly contradicted what I believed and wanted to do with my own company. Entrepreneurs are idealistic people; we get into our own businesses because we fundamentally want something to change. Letting crucial decisions be guided by those who don’t share your beliefs subverts the whole point, sometimes absurdly. – Cate Rubenstein

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Does This Decision Align With My Business Strategy?

From experience with clients and myself, I have seen that most tough decisions are paired with many possible “solutions” that can take you into tangents not relevant to what you are doing. Your business strategy should guide your decisions if it is done right. Of course, if your business strategy is not working, then fix it first. – Rene Nunez, Sensum

Will I Still Maintain Compliance?

My firm primarily represents cannabis and psychedelic clients for whom the essential underlying question to all decisions is, “Will I still maintain compliance?” Regardless of your industry, identifying possible regulatory risks is fundamental. You soon won’t have any decisions to make at all if your business falls out of compliance. You then risk losing clout and even having licenses revoked. – Evan Nison, NisonCo

How Large Is the Loss?

This question clarifies what’s at stake if this decision was to fail. By asking how large the loss is, you’re also mentally prepared to have all that you’ve listed come to zero. If the loss is not too large, I would say take a risk, and then evaluate in a certain time frame. – Candice Georgiadis, Digital Day

Will This Set Me Up for Long-Term Success?

When making a tough business decision, it’s important to determine which choice will create the most long-term success. Making decisions that focus on setting your company up for scaling will allow you to encounter fewer problems down the road. – King Holder, PROCUSSION

Does This Decision Make the World a Better Place?

Will this make the world a better place? — It’s both as simple and endlessly complex as that. All of my business decisions are made not only in the hope of making a profit, but also in the hope of improving the lives of others as much as possible. No decision is made in a vacuum, so I believe stepping back and talking to the people it will impact most directly is an excellent place to begin assessing such issues. – Jeffrey M. Zucker, Green Lion Partners

What Effect Does This Have on My Team?

I ask myself what positive or negative effect my decision might have on the team. Asking myself questions before tough decisions helps guide me to the best decision I can make with the information I have. – Adam Rumanek, Aux Mode Inc.

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