A Great Leader's Guide to Making Impossible Decisions

Have you ever been presented with a set of seemingly impossible choices? Being at a crossroads is never easy. In a position of leadership, it can be even more challenging, knowing that every eye is on you—some waiting for guidance and reassurance, and some, maybe, waiting for you to fail.

When faced with a big decision and a paralyzing choice, making the call can be daunting beyond belief. So how do you decide, either when the path isn't clear or the consequences of the outcome feel too big to bear?

Here are my top tips on how to make life's biggest decisions when you're in a position of leadership.


How to Make Tough Decisions as a Great Leader

1) Consult only a few trusted advisers.

When faced with daunting decisions, the temptation is to gather as many opinions and perspectives as possible in the search for true objectivity. However, if you try to get information and opinions from as many people as you are able to in the search for insights, you may find yourself further overloaded and overwhelmed.

Instead, limit the advice that you take to just a handful of people you truly trust and respect. That way, you don't take advice from people who aren't versed in the situation at hand or people whose opinion you don't think all that highly of. Allow people to weigh in only when you request their advice and keep it as limited as possible.

2) Be aware of what really matters.

When faced with difficult decisions, discerning the differences and minutiae between the options at hand is often challenging. Your choices can seem similar on the surface level, or details that stand out as different might not be of real consequence.

A valuable exercise is to sit down and develop a list of real, impactful differences and outcomes based on your choices, as well as their similarities. Put some real effort into weighing and analyzing your options in a formalized setting versus talking it out or ruminating. Writing things down will help you sort through the information. Sometimes seeing it in front of you can make all the difference in the world.

3) Kick emotions to the curb.

Emotions are messy. One of the things I talk about in the context of real estate investment is the danger of getting emotionally attached to properties. When important decisions are made based on emotions—be it fear, excitement, or love—it clouds your judgment. For you to make a sound decision as a leader, you must put your emotions to the side.

This begins by recognizing how you feel about the decision at hand, the options on the table, and the prospects for the future. Recognize rational and irrational emotions alike, and then set them aside in favor of the objective truths you've discovered through counsel and analysis.

4) Ignore the temptation to compare.

While we can learn a great deal from the successes of others, using another person's experiences as a template to deal with your own dilemma is usually a recipe for disaster. While we can often apply the principles learned from the lives of the successful among us in our field and from many a great leader, we can't make the mistake of comparing and trying to replicate their decisionmaking in our unique circumstances.

They sold, so we should sell. They took this action, so we should also take this action. What matters more is the motivation and the principle behind the action. If you want to look to others to model leadership and decision making, by all means.

However, don't make the mistake of believing that you can replicate their success by making the same decisions. Own your own choices for where you are right now. Your circumstances are not their circumstances.

5) Don't fixate on regrets and “what if’s”

Lastly, don't fixate on regrets. Big decisions create big anxieties. We all can fear what can happen if we make the wrong decision. But I can tell you what will happen: the world will keep turning. You can bounce back from just about anything. Whatever the decision is, put it in perspective. Evaluate your risk well before you take the plunge, but don't fixate on regret, especially before you jump in with both feet.

There's no sense in kicking yourself and thinking “if only.” You are where you are, and you can only move forward. There is no going back.

What big decision last left you feeling stumped? Let me know how you made it through in the comments.