3 Brutal Tools That Expose Hidden Flaws in Every Strategy
I Spent 10 Years Learning to Ask Questions That Actually Uncover Problems
Imagine this. You enter the meeting room and quickly look at your calendar to figure out what this session is all about. You just finished a 1:1 with your tech lead where you had to let them know that they are not going to get the promo they're after this cycle. Before that you had a sync-up with the leads of a cross-org initiative that you're part of. And before that was a postmortem review for that incident from last week.
And you didn't even drink your morning coffee yet.
Now all eyes are on you. The agenda for this meeting is to make some decision. The team came up with several options and it's up to you to make a call. Emotions are high. A wrong decision could lead to throwing away months of work or damaging user trust.
If you've been a manager for a while, this probably sounds like a typical Tuesday.
Your job isn't to make a decision. Your job is to make the best decision with the information that the team has. It's to leverage your experience to help this group of humans uncover the landmines below the surface. The secret is to ask the right questions. Questions that go deep and cause everyone to think harder.
Managers are professional question askers. By the end of this post you'll be able to ask high-signal questions quickly. You'll learn The Hat Analogy, the Mental Walkthrough, and the Question Vault, all powerful tools to add to your leadership toolbox.
So put on your Sherlock Holmes hat, and let's get started.
The Hat Analogy
One of my proudest creations as a tech lead is the Hat Analogy for code reviews. After years of writing and reviewing code, I developed a process that helped me consistently catch bugs in critical code. As I grew in my leadership role, I started teaching this process to others.
The main concept is simple. When you review code, review it in several focused passes. In each pass you look at the code and try to answer a single question. Once you're done with the pass, go back and review the code again, this time trying to answer a different question. These questions are:
Does the code do what it says it does?
Is this code easy to maintain?
How can I break this code?
Over the years, I slowly added questions to this list. For example, I broke down that last question to focus on Usability, Security, and Privacy. The foundation never changed: a targeted multi-pass review of the code led to higher quality software.
I called this process the Hat Analogy.
You start reviewing code wearing the "white hat" and finish it with the "black hat." From an optimistic view of the world to a cynical and pessimistic view. What happens at the edges of the inputs? What unexpected input behaviors can I engineer that will cause the code to break?
This same analogy served me well as a manager too. Instead of looking at lines of code, I used it to review product trade-offs, software architectural decisions, and even organizational design dilemmas. Whenever the team came up with several proposals, I methodically took out hats from my mental box and wore them one at a time.
The Black Hat of the insidious user is always useful. This is a common blind spot of most engineers. Most builders are optimistic by nature, that's the only way to invent a future that doesn't yet exist. The real world is not as forgiving. Yes, even organizational politics in your perfect company.
This hat analogy ended up pairing well with another tool that I learned from a very senior leader early in my leadership career.
The Mental Walkthrough
Do you have a morning routine? Maybe you wake up at 5:00 am and start your day with a cold plunge. If so, great for you. If you're like me, it likely involves more grogginess, prepping food for the kids, and pushing everything forward. And coffee.
We are creatures of habit.
These habits make our lives easier. They also, slowly, blind us. To the wonder of existence and everyday life. Also to user journeys, the struggles of new grads, and the challenges of people who are not native speakers.
When we're in a meeting with a group of humans who worked hard to come up with several potential paths forward we can't be blind. Our habits, at work and in our personal lives, can prevent us from finding the best outcome. The people in the room likely have somewhat similar lived experiences and therefore similar blind spots. Our job is to push through all of this conformity.
The Hat Analogy helps you be conscious in bringing in diverse user personas to these discussions.
The Mental Walkthrough lets you become these user personas. It's a simple thought experiment. Imagine yourself as this persona in a situation that's relevant to the discussion at hand. Then mentally go through the step-by-step actions that this user needs to take. As you're going through this story in your mind, try and find the challenging situations.
For example, if you're debating how to restructure the org to adapt to the latest leadership directive, wear the hat of a specific individual contributor (IC) in your team. Picture yourself as this IC when you hear about the reorg announcement. What are they in the middle of? What are their current personal goals? What will they be afraid of?
Now, start the clock and move forward in time. How will the reorg play out for this specific person? How fast will it be, and what will change about their daily work? When they get back to the office the next day, will they need to change desks?
This thought experiment doesn't take a long time to go through. It can help you identify critical blind spots. Maybe you didn't consider that in Option A of the new org structure three-quarters of the people working towards a promotion will now report to a new manager? Should that be a consideration in how you plan out the reorg?
The Hats Analogy brings structure in how you apply diverse viewpoints to problems. The Mental Walkthrough is an empathy supercharger that lets you dive deeper with each hat. As you employ these two tools you'll be able to ask more powerful questions that lead to higher quality decision-making. And over time, you'll slowly find yourself repeating some of these questions. That's where the third tool comes in.
The Question Vault
Half of leadership is asking the right questions at the right time. Great leaders treat questions seriously. They are question connoisseurs.
Start collecting questions.
I keep a bank of what I call "Power Questions." These are questions that are great at piercing through the noise in a broad range of situations. Questions like: "What problem are you trying to solve?"
Say you're in a heated debate on how to fund a new request from product. When you ask this question, "what problem are we trying to solve?" you enable everyone to take a step back. Why are we even trying to build this new feature? Why does it even matter? In what way? Maybe we can achieve a similar outcome with a quick test to validate the value first?
Or maybe you ask: "How would we accomplish this in one-tenth the time, if we absolutely had to?" The answer may be a hacky cron job that would work most of the time. Throw in some alerting, and this solution may do the job for a few months.
Power questions tend to make everyone reconsider their assumptions and find more creative solutions. As a leader, you have to keep your eyes open and look for power questions. Collect them like my son collects Pokémon cards. Cherish each and every one of them. Put them in your binder and review them, reverently, every once in a while.
Start building your Question Vault.
Summary
The Hat Analogy, the Mental Walkthrough, and the Question Vault are excellent tools to cut through the noise. They will help you adapt quickly to whatever meeting you stumbled into.
Even if you haven't had your morning coffee yet.