I Thought More Experience Would Give Me Better Answers. It Gave Me Better Questions Instead

For a long time, I (naively) assumed that becoming a better pilot worked something like this:

🔸 Learn from my mistakes
🔸 Absorb the wisdom from experienced pilots
🔸 Make decisions, log the hours, do it for years

➡️ And then eventually, I’ll have more and better answers to things!

Right?

Well yea, to some extent. But… not in the way I expected.

We don’t publish all our Notes from the Cockpit (like this one) publicly, some are shared only by email. Get the next one sent straight to your inbox ⤵️

Answers used to feel like the goal:

If I didn’t know something, I asked 💬
If I was still unsure, I started digging 🪏

Having an answer to something can feel like competence (even when it isn’t), while not having one can feel like a problem you need to fix.

That mindset makes sense when you’re learning the basics. You need structure. You need certainty. You need some clear “do this, not that” guidance, and a foundation to build on.

But eventually, situations stop fitting neatly into the answers you’ve “collected” over time.

➡️ You start encountering scenarios that look familiar, but aren’t quite the same.

➡️ Conditions that technically fit the book, but feel different.

➡️ Decisions where the “correct” answer depends heavily on assumptions and interpretations that you’re not even fully aware you’re making.

I remember 1 specific start of a HEMS mission where we had to deal with:

🔸 Marginal weather, but in limits
🔸 2 MEL items, but technically no show-stopper
🔸 End of a duty period, but “just about” enough time
🔸 An aircraft that showed signs of an impending avionics issue
🔸 A code red patient that needed to go to a specific hospital surrounded by elevated terrain
🔸 End of daylight approaching

Poor question: Is anything stopping us from going?
Poor answer: technically no, let’s go!

Better question: what is sensible here, what are the assumptions we’re making?
Better answer: while technically we can go, we’re stacking marginal factors in a way that requires nothing else to degrade any further. There’s no margin anywhere, we should decline this mission.

Lesson ➡️ If you ask a narrow question, you arrive at a narrow answer.

So here’s what I learnt the hard way:

The kind of questions you ask before committing to something can matter more than the answers you arrive at.

Some questions smuggle assumptions into your way of thinking, others actively challenge them, like:

🔸 What trade-offs are baked into this procedure?
🔸 How is this different than last time we did this?
🔸 What breaks first if something changes?

In a way, this is part of Threat & Error Management, which we covered here:

Keeping it Simple: Threat and Error Management as a Pilot

Earlier in my flying, I didn’t always have the judgment to ask the right question in the right situation, and even when I did, I didn’t always know what to do with the answers.

But experience slowly built that context.

I started noticing that a technically correct answer isn’t always the safest one, especially if it only works as long as a whole chain of assumptions behaves itself.

My dad used to say this repeatedly:

“You can fly into a mountain while following the book to the letter.”

Just because you have the answer to something doesn’t mean it’s the right thing to do at all times.

I used to look at that with a bit naivety: “that must mean the book’s not right!”

But now, that one is always in the back of my mind 💭

None of this is an argument against having the answers of course. Aviation absolutely depends on them. You can’t question everything all the time, it’d be exhausting for everyone involved.
⠀
But I’ve found it useful to treat answers as starting points, not endpoints.

Looking back (and forward), I don’t think real growth as a pilot is about endlessly acquiring certainty and knowledge like some sort of collection.

If anything, the more experience I’ve gained, the less I’ve felt the need to be confident for confidence’s sake.

Instead, I’ve become more comfortable asking questions earlier, asking them out loud, and testing whether it’s even the right question in the first place.

Competence as a pilot often depends less on the answers you already have, and more on the quality of the questions you’re willing to ask.

Why?

Because experience has a funny way of exposing how conditional most answers really are.

🔸 Weather can be legal but still uncomfortable.
🔸 An aircraft can be serviceable but not quite right.
🔸 A plan can be technically sound but operationally risky.

And suddenly the question changes from:

“What’s the answer to X?”

To:

“What’s different here, and what silly assumptions am I making?”

That’s what a bit more experience gave me (so far): Not better answers, but better questions.

What about you – How have you changed along the way as a pilot? We’d love to hear it!

We don’t publish all our Notes from the Cockpit (like this one) publicly, some are shared only by email. Get the next one sent straight to your inbox ⤵️