6 Ways to Make Hard Decisions Easier as a Leader

Jayson DeMers
4 min readAug 17, 2020
Photo by Markus Spiske on Unsplash

Leadership is mentally and emotionally demanding.

Not only will you need to temper your emotions to keep your team inspired, you’ll also be the point person for almost every hard decision your business makes. You’re the one who has to make the call, and you’re the one who has to deal with the consequences. It’s no wonder why depression affects entrepreneurs more than the average population.

Sooner or later, you’ll be forced to make a tough call; it might mean firing an employee you’re personally close with, making a risky strategic change for the business, or ending a long-term partnership.

Fortunately, there are some strategies you can use to make the decision easier, in terms of both finding a better option and resisting the stress and burdens that come along with it.

Making Hard Decisions Easier

Try using these tactics the next time you’re forced to make a hard decision.

1. Reduce decision fatigue. Decision fatigue is a documented phenomenon that sets in when you make too many successive decisions. Even small decisions, like picking what to wear or ordering a meal, can accumulate the stress of decision making and make bigger decisions more stressful to approach. You can reduce decision fatigue by spending less time on small-scale decisions. Build habits that are repeatable, and let other people (like your assistants or coworkers) decide things that don’t have much impact on you or your business.

2. Take yourself out of the equation. According to the New York Times, one of the best ways to make decisions is to remove yourself from the picture altogether. Imagine that this isn’t your company — instead, it belongs to a friend, and you’re advising them on what to do. Describe the situation, out loud, as if the people and organizations involved were total strangers. If your friend came to you with this story, what would you tell them to do? Oftentimes, it’s easier to see the answer when we’re removed from the situation because the stakes are lower — but the answer is just as good.

3. Create a firm deadline. A big problem many entrepreneurs have with decision making is being decisive in a timely manner; in other words, they procrastinate. It calls to mind Parkinson’s Law; essentially, the amount of time it takes to do a task swells to fill the amount of time allotted for it. If you give yourself a month to make a decision, you’re going to take a month. If you give yourself a day, you’re going to take a day. Obviously, you don’t want to rush decisions with major consequences, but you’ll also want to set a strict timetable so you don’t procrastinate too long, wasting time and mental resources in the process.

4. Limit the factors you use to make your decision. The paradox of choice is a perplexing case of human psychology. The more options you have to consider, the harder it is to make a choice — and the less satisfied you are with that choice once you make it. You can compensate for this by limiting the number of options you have to choose from, and the number of variables you consider when choosing between them. For example, you could narrow your choice down to two vendors, and decide to make your decision based on cost only, or based only on the quality of the working relationship.

5. Quantify your options. As a business owner, quantifiable decisions are easy to make. For example, if your marketing strategy makes more money than it costs, it’s worth keeping. If you want to make your hard decision a little easier, try reducing everything to quantifiable variables. This may take some extra effort upfront, but the best answer will be obvious when you’re done. For example, if you’re stuck between hiring two candidates, start rating them on different factors, like experience, value, and culture fit. Ultimately, the candidate who racks up the most points is your winner.

6. Focus on long-term thinking. It’s tempting to think about the short-term repercussions of your decisions as a worst-case scenario, but try thinking about the long term instead. If this decision is the wrong one, how will this affect your life in three years? What about five years? Most bad decisions can be recovered from in the span of a year or two — even the big ones — so don’t beat yourself up over the worst-case possibilities. This is also a way to distance yourself from the equation.

Procrastinating isn’t a good idea. Delegating is possible in some situations, but generally inadvisable. If you want to be a successful leader, you need to learn how to handle tough decisions rather than avoid them.

It may take some practice, but decisiveness is like any other skill; the more time you invest in it, the better you’ll become.

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

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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!