Ok, so… I don't wanna toot my own horn or anything, but at school, I was a pretty good student.
Most exams weren't hard for me. Not because I was smart, but because they were just memorization. Learn the steps from past problems, then regurgitate them on the final exam.
I got away with the same approach in university. Well, apart from one class: Dr. Roberts' class.
For his problem sets, he didn't just use previous problems and change the numbers. Instead, he'd create new problems with unusual twists that we actually had to think about. Rote memorization was useless. We had to figure things out.
It was the most annoying, frustrating, but valuable class I ever took. (I never did well in it either.)
But here's the bigger lesson: most of your career won't come with step-by-step instructions. You'll face situations where there's no obvious playbook, no clear right answer, and no YouTube tutorial to follow.
And your ability to figure things out anyway…
That's what separates people who get promoted from those who stay stuck.
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.
🧩 Define the work
Here's the core skill: taking a vague, open-ended problem and breaking it down into specific, actionable tasks.
This is what I mean by "define the work."
Take something like "how do we sell this new tech in Europe?" That's huge and overwhelming. But you can break it down:
First, which countries need our tech most?
That leads to specific tasks: call European contacts, research market data, hire experts for local insights, contact regulatory bodies, book meetings with distributors.
Suddenly you've turned one impossible question into a list of concrete things you can actually do.
As you move up in your career, more of your job becomes defining work rather than just executing it.
A junior employee gets clear tasks. A senior employee figures out what the tasks should be in the first place (and what tasks others should do).
👏 Think (potential) solutions, not problems
Low-level employees bring problems to their boss. Stronger employees bring problems with potential solutions.
When you hit a roadblock, don't immediately run to your manager saying "I don't know what to do" Spend some brain calories first. Come up with at least one possible approach, and then take it to your senior.
- ❌ 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?"
This shift in how you approach problems changes how people see you. You become someone who solves things rather than someone who needs things solved for them.
🎱 Use AI to improve your problem-solving
With ChatGPT and AI tools everywhere, you might think independent thinking matters less. Actually, it matters more.
AI is incredible, but it can only work with what you give it. You can't just say "ChatGPT, solve my business problem." You need to know what questions to ask first, and often direct it in the right way.
The better you get at breaking down problems and thinking through solutions, the better you'll be at using AI to help you. Try this: next time you're stuck on something, work through your own approach first, then use AI to refine or challenge your thinking.
Something like: "Here's the problem I'm facing: [problem]. My initial approach would be: [your solution]. What am I missing? What would you do differently?"
Your AI becomes a thinking partner, not a replacement for thinking.
🌐 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 some of my underlying assumptions were wrong. And I've gotten better at asking the right questions when facing uncertainty.
This isn't about being right — it's about training your brain to work with incomplete information and make reasonable guesses. Don't be too lazy to think.
📊 Plan for a range of outcomes
Since you're dealing with unclear situations, the outcomes will be unclear too. Think through what might happen and prepare for different possibilities.
This doesn't mean creating elaborate contingency plans for everything. Just ask yourself: "What if this goes really well? What if it goes poorly? What if something completely unexpected happens?"
Having thought through different scenarios means you won't be paralyzed when things don't go exactly as planned.
The bottom line: figuring things out independently is the skill that moves careers forward. It's what transforms you from someone who executes instructions into someone who creates the instructions for others to follow.
And in a world where AI can handle more routine tasks, the ability to think through complex, unclear situations becomes even more valuable. That's something no algorithm can do for you.
🔍 Go to the source for data
One of the best ways to figure things out is to get information directly rather than relying on assumptions or secondhand reports.
I get career questions all the time like "Should I switch to X industry?" My answer is always: talk to people actually doing that work. Find out what it's really like day-to-day.
Make this a habit at work too. If you're wondering whether users like a new feature, don't just look at summary reports. Dig into the actual user feedback and survey data yourself.
🧪 Run small tests
Sometimes you can't eliminate all the uncertainty. That's fine. Start small and adjust as you learn.
Say you're tasked with increasing brand awareness but aren't sure which marketing channels will work best. Don't bet everything on one strategy. Test a few approaches with small budgets, then double down on what shows promise.
Or if you're considering a career change but aren't sure it's right for you, start with volunteer work or a side project in that field. Test drive it before making the full commitment.
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.
