Ernest Hemingway was wrong!

5 Questions Leaders Need To Ask Themselves Before Making Decisions

Ernest Hemingway Was Wrong.

I am actually a big fan, but I think he was mistaken with his view of our being clueless at the crossroads in our lives.

“We have to get used to the idea that at the most important crossroads in our life, there are no signs." – Ernest Hemingway

In my job as an executive coach, I believe there are signs, but we may need help in reading them to make an informed decision, to choose the right path. This is where I can help.

As a leader, you are often faced with tough decisions and sometimes under tremendous pressure. Your confidence in your own decision-making skills will be tested again and again. What I provide is a proven method for overcoming uncertainty and fear, for making the right choices for yourself and your company.

In today’s world, there are sometimes too many signs, too much conflicting information, and too many interests to satisfy. And then there are your own inclinations – to keep it simple, play it safe, or be bold and take risks, or try to find some middle ground. One thing is certain, you need to do your homework, consider all your options and explore the impact of each possible choice. I believe my decision-making framework will work for you, will guide you to make the right choice.

The higher you are in an organization, the more impactful your decisions will be on the company, employees, customers and stockholders. Even in your personal decisions, it is important to give yourself time to pause and reflect on the ramifications of your decisions on your career and your family.

As you pause on the brink of a critical decision, here are five questions to ask yourself in your evaluation process:

1. Who Is Impacted and How?

Seeing beyond your decision to its implementation is a must. Unintended consequences can be detrimental to all your plans and weaken your reputation for making sound decisions.

Exercise: Across the top of your chart, add as many columns as you have options. Add a list of all the stakeholders and delineate rows to chart the negative or positive impact each option will have on these stakeholders, including yourself. Be thorough. After you finish with each stakeholder, ask, “What Else?” These two words will slow you down and deepen your inquiry, usually revealing critical information you might otherwise have missed.

Next, rank the stakeholders in order of importance and observe how the scales tip. Use colored highlighters to identify the positive and negative impacts, if that’s visually helpful. Once this is done, put this chart aside as you continue through the questions.

2. How Does Each Decision Map to Your One- Year Plan?

Personally and professionally, a minimum of a one-year plan is essential. Create your plan first and go from there. Stephen Covey famously said, “Begin with the end in mind.” Decide where you want your company to be or what you want to accomplish professionally and then map out how to get there.

Exercise: If you don’t have a strategy yet, it’s time to put it in words, to define the terms that will

guide your company. If the strategy is for your company, get everyone in a room and identify the long-term vision for your business and define the path to get there. Gather ideas and buy-in from all. When evaluating crossroad decisions, determine which ones will keep you on your path. If more than one choice has the potential to keep you on track, choose the one that will get you there faster while keeping you aligned with your values. Make sure everyone in your company has a copy of your mission and the underlying strategy to fulfill this mission. And remember, this is a work in progress to be adjusted as your business and personal goals evolve and as the world around you changes.

3. What Do You Want Your Legacy To Be?

Your legacy is not defined at the end of the road, but rather by the decisions you make, the actions you take and even your mistakes throughout the many phases of your career. Don’t wait until retirement to start thinking about your legacy. Rather, start thinking about it years before you retire, so you can integrate your approach into how you engage on a daily basis.

How do you want to be remembered? Do you want to be the person who transformed the company? Do you want to be the person who held the ship steady? Do you want to be known as a leader who took calculated risks to move the company forward? Do you want to be well-liked? What lasting impact do you want to create at your company?

Exercise: Write down the top 10 things for which you want to be remembered. Once you are clear on your legacy, consider this: How does each option in your decision-making process support

this legacy? If all the possible choices support your legacy, consider yourself fortunate. More than likely, some options will not and need another look.

4. How Does Each Decision Align with Corporate and Personal Values?

Life is about embodying your values. When you live in alignment with your values, life works. When you don’t, life is challenging. It really is that simple. Understanding your company’s values, as well as your personal values, is critical in successfully navigating decisions. At different times in your life and in your company’s evolution, your values may have different weights and priorities, and you may also discover new values. But your core, deeply held values typically remain constant throughout your life.

Before making a decision, make sure you clearly understand your personal values, as well as those of your company. Review each decision to determine whether it is in alignment with your values. It is especially important to identify whether a given decision is diametrically opposed to any of your values. As you did in the impact exercise, writing down and assigning weight to both your personal values and the company’s values will give more diagnostic information to include in the decision-making process.

Exercise: A powerful exercise when examining seemingly opposing values is to imagine the word “and” instead of the word “or.” What would it look like if I could be known for ethical dealings and be

Putting It All Together

the most profitable? How about a strategy that is aggressive and safe? Consider what’s possible and make it happen.

5. What Is Your Intuition Telling You?

Don’t underestimate the power of intuition and visualization. Intuition is the ability to understand something immediately, without the need for conscious reasoning. Intuition allows you to visualize what you feel is going to happen.

Research shows that using intuition helps us make better decisions and gives us more confidence in our decisions. Intuition is not just for the spiritually inclined; it is a scientifically backed skill. Learning to trust your gut can give you a competitive advantage, both in business and in life. Intuition is not only helpful in steering you away from unlit streets and dodgy characters; it can also be a powerful business tool.

Exercise: Visualize each decision as a pathway. Close your eyes and see yourself walking down each road. Pay attention to your body. What images appear before you? Does one direction seem brighter or hold more joy for you? Does one avenue fill you with more angst and tension? Do you feel lighter or feel like you are walking faster down another path?

By integrating intuition and visualization with the critical analysis you did in questions 1-4, the answer should be coming into focus.

Yogi Berra was much more aggressive than Hemingway in his crossroads approach when he famously said, “When you come to a fork in the road, take it.” Funny but not particularly helpful.

Major decisions should not be made lightly. Study the impact, have a plan to make the decision real, consider how each decision fits into your legacy and use your intuition to visualize the final outcome. These are steps in the decision-making process that you can use over and over.

Working with an executive coach like me will help you build this foundational framework and can serve as your base as you move upward to new levels of confidence and success.

As Hemingway said, “There is nothing noble in being superior to your fellow man. True nobility lies in being superior to your former self.” By asking yourself these five questions and taking the time to arrive at the best answer, you will certainly improve your decision-making self. 

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Alison Arnoff is an executive coach and strategy consultant, specializing in challenging and championing successful Entrepreneurs and Tech Leaders to reach new levels of clarity, communication and decision-making confidence and prowess. Alison has more than 25 years’ experience in management, marketing, sales and engineering, having worked for industry leaders like Intel, EMC, and BMC and seven startups resulting in five acquisitions and two IPOs and twice even sold the company to her customers. Alison has a Master’s in Electrical Engineering and was trained by the Coaches Training Institute. She was a nationally ranked and Division 1 swimmer, as well as an amateur triathlete. These days, on most weekends, you will find her on her paddleboard looking for dolphins and whales off the South Bay coast.