Tackle Tough Decisions With These 4 Questions


decision making process
Decision Making Process

My first tough decision came when I decided to join the Navy. After all, this wasn’t a decision that could be reversed the next day if I changed my mind. This was a four year decision that I had to be QUITE certain about before taking the leap into the “unknown” world of the military.

You know, the world where bullets hit everything they’re supposed to…

Where helicopters are called “’choppers” because it sounds cool…

Where everything is “rank and file,” rigid and void of creativity?

Not quite.

At least, that’s how Hollywood portrays the military, but my experience was anything but.

Of course, I didn’t spend my time in the conventional ranks, either. The 13 years I spent as a Navy SEAL taught me many things—far too much to cover here—but one of the most significant, most impactful lessons gleaned from navigating chaos was the need to make tough decisions—decisions that impacted not only myself but those around me and the mission.

Complex situations can leave you wavering somewhere between certainty and uncertainty, which is really another way of saying “I have no idea.” After all, either you know something (whatever that “something” is) or you don’t. And if you don’t, then that’s ok.

Go with it.

Make it happen.

One thing’s for sure: the only certainty that exists alongside indecision is a lack of results if you never try.

You don’t get better doing nothing. Yes, a decision not to act or “not” to make a decision, is still a decision. But if it’s results you want, then task avoidance isn’t the way to go.

Am I stating the obvious here?

Good. Now that you’re aware that indecision and task avoidance run parallel, consider this:

What are you avoiding by NOT making a decision?

Challenges to Decision Making

Note that these are challenges, not impediments to making decisions.

One of my major pet peeves—aside from close talkers, tailgaters and people who don’t listen but instead wait to speak, among many other pet peeves—is the excuse to “wait” for more information.

The problem with waiting for all the “moons to align,” for the “right” information to arrive is this: it never does.

Why doesn’t it? Because perfect doesn’t exist.

The 100% solution, doesn’t exist. And to chase it is an exercise in futility. Actually, it begs the question, “What are you really avoiding by not making said decision?”

How To Navigate Tough Decisions

There are ALL KINDS of decision making frameworks out there, such as the Cynefin framework, the Vroom-Yetton decision tree, or the good old fashioned, “Hold my beer, watch this!”

However you arrive at decisions, know this: a solid process will beat a rigorous analysis any day of the week.

Meaning, that no matter how hard you analyze details, no matter how much focus and effort you put into connecting the dots, your analysis will still fall short to that of a process. Here’s why.

A study by McKinsey & Company revealed that “good analysis in the hands of managers who have good judgment won’t naturally yield good decisions.” In fact, a decision making process, they learned, actually outperformed rigorous analysis by a factor of six! 

mckinsey decision making
mckinsey decision making
If a decision is worth making, it’s worth maximizing. Click To Tweet


A Process Isn’t Everything (But It’s Significant)

Now, this isn’t to say that having a decision making process is the end-all, be-all. For every advantage there’s a disadvantage, and a decision making process is no different.

Here are a few advantages and disadvantages of a decision making process:decision process advantages

A decision making process is important because a strong process will ferret out faulty logic whereas a rigorous analysis may or may not.

However, having a process isn’t a one-stop-shop either.

Sometimes, all you really need to do is ask yourself (or whomever) the right questions.

The keyword here is right because you’re not going to arrive at an accurate conclusion asking shitty questions.

Just think if your sales folks asked terrible questions. How would they qualify customers? The sales cycle would be painstakingly

L-O-N-G-E-R if the rep doesn’t know—or is unwilling—to ask the right questions.

A solid question is a powerful weapon. It can shift your perspective simply by reframing the same problem in a different light. Hell, the entire coaching industry is based on the art of asking questions.

Of course, there different types of questions.

Question Types

There are open-ended questions which require further elaboration (as opposed to a yes/no response).

  • Pros: builds rapport, reveals thinking process of respondent
  • Cons: can take time (especially if the person is a TALKER)

Closed-ended questions are just the opposite: they warrant a yes/no response. They’re typically used to mine for facts, collect data, or send convey message that you’re not interested in having a conversation (one word answers are great for this). The pros and cons of closed-ended questions are:

  • Pros: Quick, may be used to guide a discussion to a predetermined expectation
  • Cons: Don’t inform; surface level only

Diagnostic questions are designed to discover the root of a problem. Think of journalists. When a story breaks, the first thing they must do is diagnose what the problem is and why it’s important so they can assess its value to readers and viewers. Only after they assess its potential impact to the public does it become newsworthy (or not).

Examples of diagnostic questions include:

  • “What’s wrong?”
  • “What’s missing?”
  • “What do we not know?”
  • “How do we know this is true/false?”

Other types of questions include:

Rapport questions to build a bridge between you and somebody who doesn’t want anything to do with you.

  • Example: “Is this how you see yourself?”


Confirmation questions may be used to hold others accountable.

  • Example: “What was unclear about…?”


Clarifying questions are posed to do just that—clarify understanding of what the other person/party said.

  • Example: “Just so I’m clear, do you mind if I summarize what you just said to ensure we’re both on the same page?”


Use These Questions To Navigate Competing Priorities

Yes, “the day” creeps up on us.

It happens.

It creeps up in the sense that what you initially set out to do…sometimes gets accomplished, and sometimes not.

The question is, what changed? Why did you choose distraction B when you were focused on achieving A?

The reason I say choose is because focus is a choice. You choose what you focus on, you choose what you don’t. You also choose your distractions.

What helps me navigate these competing priorities of the day are the following questions:

1.Will this help move my business forward?

Being an entrepreneur, it’s easy—REALLY easy—to go down the a rabbit hole of internet searches; to chase yet another bright shiny ball of information (“Look! A butterfly!”) and be busy, but not productive.

It takes self-awareness to know you’re diverting from the work you need to get done and, more so, a keen understanding of why you want to pursue the alternative.

In other words, if you set out to finish project A but “get” distracted with project B, C, D, and E, then the real question is, what are you avoiding by choosing the latter and ignoring the former?

Smart questions make smarter people, and smarter people make smart decisions.

Smart questions make smarter people, and smarter people make smart decisions. Click To Tweet

2. Is [this] REALLY important right now?

This circles back to question #1 above. Again, what are you avoiding?

3. What’s the RIGHT way to do this?

This can be a difficult question because the natural tendency is to wait for the perfect solution, but we already established that perfect doesn’t exist.

The point in this question is to distinguish between two ways to get things done: A) The right way or B) again. That’s it. Whatever’s worth your time is worth doing right. Time is a precious commodity. It’s something everybody has yet there’s never enough of it.

Manage your choices, not your time.

Manage your choices, not your time. Click To Tweet


4. Do I want this memory?

Not gonna lie, this is a powerful question and it’s one that can bring immediate clarity to your next important decision or action.

Every choice, every decision you make brings with it a consequence. Sometimes that consequence is good, sometimes it’s bad.

Decisions made consecutively over time eventually turn into a memory chain, where thinking of one particular situation may stir up thoughts, emotions and images of another—again, sometimes positive, sometimes not.

The question is, are those memories worth keeping?

If you were to reflect on the past week, month or even year, what memories stand out? What would’ve made them better? Chances are, the most resounding memories are experiences:

  • Time you spend with friends and family.
  • Time you spend interacting with others, learning and doing new things.
  • Time you take to choose to spend time with your kids—intentionally—rather than choose to be focused on something else.

The question here is, what memories do you want to, not only create, but…not regret that you never tried?

The next time you face a complex decision, there are a number of strategies you can employ:

1) Intuition (i.e. no process)

2) Process

3) Questions

Try them all. Test them out. See what works best for you and under what circumstances. The trick is knowing when to weaponize the right strategy for the right decision–and learning from it.

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