You Really Should Question Everything…

The Case for Why You Should Question Everything (to a Point)

What comes to mind when I say something like: ‘Question Everything’? A few different images could have popped into your head. Maybe you saw an inquisitive 6-year-old; the kind who relentlessly asks ‘why?’ after every answer and is never satisfied. Or perhaps you saw some angst-filled person obsessed with finding deep, cosmic understanding; the ‘how do I know I’m even really me?’ type who wrestles with unanswerable questions. I’m going to shoot for something in between those two extremes. I want to lay out the case for why you should ask a lot of questions and I plan to do it against the backdrop of the universally applicable (yet eminently hair-raising) problem: ‘What’s for dinner?’

Before we jump into that minefield, it’s worth clarifying a few points:

  • When I say: ‘ask a lot of questions’, I don’t mean endlessly asking ‘why?’ to everything. That is unhelpful (and could result in bodily injury if you’re annoying enough). I mean asking the right kind of questions, based on your current point in the process and the task(s) in front of you. This will hopefully become clear as we walk through our example. Just remember – the questions you ask must be targeted!

  • The goal of asking questions the way I’m talking about here is NOT to have all the answers before making a decision or taking an action. It’s not driven by self-doubt or paranoia that you’ve missed something. The goal here is to double-check that the plan is as correct as it can be based on the available information at the time. It’s about ensuring you’ve taken the time to consider possible results of whatever action you’re about to take, not that you have endless contingency plans in place. This is another point that will hopefully be made clear through our example. Keep in mind – the questions you ask must have an answer and a scope!

So, What’s for Dinner?

Let’s say that you are hanging out with your favorite group of people. At some point, the dreaded question comes up: ‘What’s for dinner?’ After your internal panic dies down, think about what you normally do in that situation. To make it a little easier, we’ll assume that everyone has agreed to order take-out. So, what happens next? For most of us, some version of the following occurs:

  • Information gathering happens - Phones come out and people look for what options are close by. They’ve already started asking targeted questions, like: ‘what restaurants are near us?’ and ‘which ones offer take-out?’

  • Down-selection happens – Conversations pop up and people start narrowing down the list of potential food choices. They’ve asked even more targeted questions, such as: ‘what does everyone feel like having?’

  • Decisions are made – Once all the targeted questions of where to order are answered, then each person must decide what to eat. They start asking more targeted questions, but with a different focus: ‘what do I want to eat from Kung Pao Palace*?”

*Author’s Note: I made up a plausible sounding restaurant for the purposes of this example. I have no idea if Kung Pao Palace is a real place and therefore cannot endorse or promote such a restaurant if it does exist.

To make it easier to see what we’re talking about, let’s break down what’s happening using a tiered approach. The highest tier will have the broadest focus, while the lowest tier will have the narrowest focus. Right now, we’re talking about the perspective of the group as a whole and we can say:

  1. The team identified a problem - they’re hungry.

  2. They came together to reach a solution - they need to get food in order to not be hungry.

  3. Each team member identified their piece that needed to be incorporated into that overall solution - their part of the order. 

  4. The solution was implemented - someone called the order into the Kung Pao Palace.

The team was focused on a strategic problem and asked questions targeted to a decision at the that level. In our personal lives, we do things like this all the time without even thinking about it consciously. In a work setting, people sometimes struggle with reaching a workable solution. We’ll get into reasons why that happens after we’ve finished our example, but first let’s keep it moving! Everyone is hungry!

The order is in. The make-believe staff of the Kung Pao Palace is diligently preparing the team’s order and you’re tasked with retrieving it. What happens now? The next level of our tier approach will look at the collection of tasks each individual needs to accomplish to deliver (pun intended) their piece of the solution. To keep things simple, we’ll assume the other members of the group are doing their own thing and just focus on things assigned to you.

In general, it goes something like this:

  • Information gathering happens – Your phone comes out again and you pull up your favorite direction-providing app. Even if you know how to get to the restaurant, you may still use the app to let you know if traffic is bad or which route is faster. You’ve already asked targeted questions, like: ‘how’s traffic right now?’ or ‘which way should I go?’

  • Down-selection happens – The super-smart app developer folks have used their big brains to crunch all the numbers and provide you with several options of route based on their list of targeted questions. You simply need to tap the route you want and ‘Presto!’ 

  • Decisions are made – You tap on the ‘Go’ button and begin your journey to the land of promise and delicious dumplings: Kung Pao Palace.

We went from looking at what the entire team was doing to looking at what a specific member is working on. The list of things that need to get done has become more focused, because you have a specific part of the overall solution to consider. We are closer to the actual action being implemented, but not quite there yet: 

  1. The team member was assigned a task – you must get the team’s food and make it snappy! (People are getting a little hangry).

  2. The team member figured out how they wanted to do the task - you decided to focus on driving and let the app do the navigation.

  3. The team member stared executing the task - you started driving.

The team member was focused on figuring out how to complete their specific pieces and again used questions targeted at the appropriate level to reach a decision. We’re two-for-two on things we do all the time. We naturally get to an answer without needing a lot of extra input or required thinking. It’s almost like we’ve practiced it or something, but we’ll go into more details about that later. You need to get moving! 

You dutifully set out to retrieve the take-out order from Kung Pao Palace. For this part, we’ll assume that you’re a good driver. Being a good driver, you follow all the required laws and regulations. You never speed, always signal your intentions for the other drivers, and would definitely not read an article about questioning everything while driving at any point. (Speaking of which, you should probably focus on the road. You are driving right now…) So, let’s look at what’s involved:

  • Information gathering happens – You are watching your surroundings and taking input from your trusty direction-providing app. During the trip, you constantly ask yourself targeted questions, like: ‘is there enough space between me and others?’ or ‘when do I need to move over for my next turn?’

  • Down-selection happens – When the time comes for you to move over, you signal your intentions, check that the area is clear, and look over your shoulder (because we said you’re a good driver, remember?). You ask yourself ‘is it safe to move over?’ and then double-check to make sure you have all the information you need to confirm. 

  • Decisions are made – You move over and make the turn into the parking lot of the Kung Pao Palace!

We said the lowest tier of our approach has the narrowest focus, on the exact activity being worked/as it’s being worked. That sounds like driving. Which means our final breakdown looks something like this:

  1. While executing the task according to plan, the team member was constantly asking themselves targeted questions that were directly focused on the work that needed to be done – you were driving safely and wanted to continue driving safely.

  2. The team member verified that expectations matched reality (to the best of their ability) - They asked questions to ensure they were doing the right thing and double-checked the best they could - you didn’t blindly follow instructions from the app which would not have been driving safely. You merged that info with the things you do as a safe driver: signaling properly, checking your blind spots before moving over, etc.

  3. The team member successfully executed the task - you made it to the Kung Pao Palace safely.

In this case, you used targeted questions while doing the work to help you get the job done. That’s three-for-three on things we do all the time. Since you did such as great job, we’ll finish up our example by saying you made it all the way back to the group with piping hot take-out! You are celebrated as the hero of the day and get the extra dumpling as a reward.

How to Question Everything in Four Easy Steps

You enjoy the imaginary spoils of your imaginary hard work. I’ll wrap up by explaining why you should even care about the topic of questioning things. A lot of times, people get the entire concept really wrong. They convince themselves that in some situations making decisions/taking actions is somehow different (or more difficult) than it is ordinarily. I would humbly say it’s not. There is absolutely no difference, and I can prove it.

You make consequential decisions all the time. Take driving for example. If you decide not to stop at that red light, there are some dire consequences. As a driver, you ask yourself (at some level) what the wise thing to do would be. Changing lanes without looking? Same situation, same stakes, same questions. We do it thousands of times in our daily lives and it barely even registers. 

What is the main difference between driving and some other risky scenario? I would say: practice! We do it so much, we don’t think about driving for the most part. From the perspective of an outsider, driving involves making important decisions on a timetable, with potentially life-changing consequences, and constantly changing circumstances. All while hurling ourselves along inside tons of metal at breakneck speed. From the perspective of an insider, we’re listening to an app tell us where to turn and daydreaming about dumplings. We manage to do that because we’ve practiced the task. A lot!

But what happens when we come across something new? It’s unfamiliar. We get nervous because we aren’t so sure of what to do anymore. We start feeling pressure. We haven’t practiced enough to know how to instinctively handle the situation. It happens all the time. Especially in the workplace. Management can’t decide which new course of action to take. Coworkers who can’t seem to figure out exactly how to do their portion of the new product. Sometimes we can’t make a tough decision for ourselves because we’re too close to the problem and don’t have proper perspective. We’ve already touched on a couple of examples of why it happens. Anyone can fall prey to things like:

  • Trying to have all the answers before making a decision or taking an action.

  • Having too much information and not being able to decide on how to use it.

  • Self-doubt or paranoia that something has been missed.

Questioning Everything Effectively

So how can we avoid those traps? How can we be sure we’re on the right track and avoid trouble in the first place? How do we get in the driver’s seat, so to speak? By getting yourself into the practice of questioning everything in an effective way! Here are my recommendations on how to start:

1. Make it a habit to ask yourself questions like:

  •  Is this the best way to do things?

  •  How do I know?

  •  What am I missing?

  •  Am I looking at this the right way?

  •  Who else can I ask for input?

  •  Does their input change anything?

2. Understand the goal when you ask questions. This isn’t about self-doubt or covering every base. It’s about making sure you have what you need to make a decision about the task at hand. It’s the same as checking your blind spots while driving. You check them, incorporate that information, and adjust your plan accordingly. You don’t veer to the shoulder, screech to a halt, and wait for every other driver to move off the road.

3. Target the questions for what you’re trying to do. Knowing the number of pages in War and Peace will not help the group answer the question of ‘what’s for dinner?’ Asking people their likes/dislikes/allergies would be very helpful. Knowing the correct internal temperature to heat a dumpling to is useful if you’re cooking dumplings, but not so much if you’re just eating them. Figure out what level you’re at and scope your questions appropriately. 

4. If you’re still having trouble getting to a solution, you might be asking the wrong people. Maybe it’s time to find new people and new ideas!

Now go practice! Good Luck!

Thanks for reading! Please let me know what you think. I respond to all comments personally.

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