Ok, so… I don’t wanna toot my own horn or anything, but at school, I was a pretty good student.
Most exams, for me, weren’t hard.
Not because I was smart, but because exams mostly were just a case of memorizing my notes/text book, finding out the exact steps used to solve past exam problems, then regurgitating for the final exam.
And in university, I got away with doing the same thing. Well, apart from one class:
Dr. Roberts’ class.
You see, for Dr Roberts’ problem sets, he didn’t just use previous problems and change the numbers. No. In fact, for his assignments, he wouldn’t even give us problems similar to the ones we’d solved in class.
Instead, he’d create new problems with unusual twists. That we actually had to THINK about.
In other words.. rote-memorization was useless…
And we had to use brain calories instead.
It was perhaps the most annoying, frustrating, but most valuable and stimulating class I ever took at university. (I never did well in it either)
And not because of what I learned in it, necessarily.
But for the bigger lesson.
That sometimes…
You’re gonna have to deal with problems that don’t come gift-wrapped with an instruction manual, or can be solved by a “how-to” video on Youtube.
And it’s the ability to grapple with these problems - i.e with ambiguity - that separates the leaders in their field from the followers.
And what, with rapid tech change opening up new frontiers at a crazy rate, I thought I’d devote this edition of Coached to help you cultivate this skill.
Let’s go.
🤔 Wait, what actually IS ambiguity?
Ambiguity = the unknown.
In your career, it usually means open-ended problems with no clear right or wrong answer.
It’s the difference between “how many orders do we have to fill this week,” versus “how do we sell this new tech in Europe?”
🧩 Define the work
Here’s a handy rule of thumb:
Your ability to deal with ambiguity = your ability to break down an open-ended problem with no clear answer into clearly-defined tasks.
This is what I mean by “define the work”.
Take “how do we sell this tech in Europe?”, for example. That’s a huge question that’d need to be broken down question-by-question into a series of steps.
You might start by asking, “ which countries need (and want) our tech the most?
And from there, you can define the work:
=> Get on the phone to European contacts, spend some time on the ground, hire an expert network to give you an overview of the market there, contact regulatory bodies, book meetings with distributors etc etc.
N.B:
As you increase in pay grade, the more work (particularly other people’s work) you’ll have to define.
(A janitor defines only his own work, but a CEO defines the whole company’s work.)
=> The takeaway: Get better at defining and scoping out work.
👏 Think (potential) solutions, not problems
Piggy-backing off that last point:
Low-ranking employees pass ambiguity up to seniors. Seniors turn ambiguous problems into work for juniors.
=> If you want to rise the ranks, don’t just take problems to your seniors. Invest some brain calories, and come up with a possible solution yourself, and then take it to your senior.
Specifically, when approaching people or seniors to get guidance:
- ❌ Bad: Don't just say, "How do I do this?"
- ✅ Good: Instead, try: "I ran into X issue. My plan would be to do Y to solve it. Am I thinking about this the right way?"
🌐 No Google allowed
A habit I find useful:
Whenever I want to know the answer to something, I’ll try to work it out myself first.
For example, "How long is the flight from New York City to Tokyo?"
I've never flown that route, but I know flying from NYC to London takes around 7 hours, and London is about halfway between NYC and Tokyo. So doubling that time, I'd estimate the flight to Tokyo to be around 14 hours.
checks Google
11 hours?! Wow, my reasoning sucks!
But that's useful. Now I know that some of my underlying assumptions must be wrong. And we've gotten better at asking the right questions when ambiguous.
Don't be too lazy to think.
📊 Plan for a range of outcomes
I learned this one playing hours of poker when I was in college (more on this in a future email!):
Since you never know your opponent’s cards, you have to constantly analyze best and worst case scenarios and plan for different outcomes.
Remember:
Ambiguities in the inputs = ambiguities in the outputs.
🔍 Go to the source for data
(aka: reducing the ambiguity!)
One of the most common career questions I get: “Should I switch careers to X?”
My answer is always: get more information from the source. Speak to people in X industry, find out if it’s the kind of work you’ll enjoy and if it’s worth pursuing.
This is something you should make a habit of doing at work too. Let's say you're a product manager wondering if users like a new feature you've released. Don't just rely on second-hand reports or assumptions. Dive into the granular survey data and user feedback directly.
🧪 Conduct mini-experiments
In many cases, you won’t be able to eliminate all the ambiguity. There’s always going to be some “fog of war”.
So the best thing to do is make a mini-experiment, and then adjust as you go.
Example 1:
Let's say you're a marketing manager tasked with increasing brand awareness. There's ambiguity around which channels will be most effective. Instead of going all-in on one strategy, run small tests. Put a small budget behind one, then double down on what works.
Example 2:
You’re unsure if a career change is right for you. So, volunteer or work part-time in evenings and weekends at the job you want, then back off or dive in based on whether you like it.
