Ok, friends, I'm back with another edition of Coached — your personal mentorship email that takes a few minutes to read, but speeds up your career by years. |
Today's Mentor's Corner is about a skill that's never taught. But it's what I think separates those who do well in senior roles from those who struggle: the ability to deal with ambiguity and unknowns. |
It's something I've had to get a lot better at while starting/growing Resume Worded, so I'll take you through what's helped me. Later in the email, I've also included some tips if you're on a job search. |
Finally, thank you to those who've been sharing my emails with their colleagues, clients and peers. It's fulfilling to see them reach more people! If you enjoy my emails and think they could help others too, please share them. |
Estimated read time: 5 minutes 55 seconds |
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🌐 A post I thought you'd enjoy |
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Before we get into it, here's a snippet of a post I made on LinkedIn this week — it's on a few mistakes I made as a first-time manager: |
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If you're not following me on LinkedIn yet, I share bite-sized, candid career advice like this on there pretty regularly. People tell me it gives them an easy way to stay motivated and learn how to navigate their careers. |
Follow me there so you don't miss a key insight. |
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📈 Mentor's Corner Insights put together by me. One practical lesson a week that will make a measurable impact on your career, delivered right to you — for $0. |
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The skill you need to learn: dealing with ambiguity |
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. |
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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?" |
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| | | | …by the way, if you use LinkedIn, go to my profile and hit the 'Follow' button. I share a mix of practical career strategy and mid-week motivation — stuff that makes it easy to keep your career on track. | Topics coming up this week: negotiation hacks, how to build instant rapport with anyone + more. See you there. | alright, let's get back to my essay… |
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🧩 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. |
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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. |
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👏 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?"
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🌐 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. |
 | source: Elio Scordio |
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📊 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. |
 | (lol) |
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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. |
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Before I wrap up, I need something from you. |
These emails take me freakin' forever to write up. And cost a lot in email sending costs. But yet I don't litter them with ads nor paywall the best parts. |
That said, there is a (non-monetary) fee for them: |
If an email changes the way you think, opens your mind to a new perspective, or gives you an insight you get value from, please do one of these things: |
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Stuff like this helps and makes all the efforts feel worth it — thank you. |
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Use code COACHEDREADER to get a quarter off your rewrite. Order a resume rewrite |  |
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 | especially appreciating my coffee today |
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🔎 Speed Up Your Job Search One actionable piece of advice to help you hack your job search. |
Why and how you should quantify your resume |
Read the full article here. |
When friends come to me for help on their resumes, the most impactful change I tell them to make is to use specific hard numbers when talking about their accomplishments. |
I'll use an example to explain... |
Here's a bad line I might see on a resume: |
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This is a pretty biased statement. Just because you say you have excellent design skills doesn't mean a hiring manager is going to believe you. |
Let's transform this by using hard numbers and being more specific: |
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Note how we use a hard number, specifically the time you saved, to show hiring managers how our work made an impact on our employer. |
This is called 'quantifying' your bullet points. Hard numbers support your narrative and, on your resume, make your skills undebatable. |
🎯 You should use a tool like Score My Resume to find out if your resume is effective enough. It'll analyze each line on your resume, plus the Magic Write feature will give you ideas on how to quantify your bullet points, even if you haven't worked in a sales role or don't have access to numbers. |
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What'd you think of today's edition? |
👍 I loved it. |
🤔 Pretty average, step it up. |
🤢 You didn't bring enough value. |
Here are some reviews of last week's email. Leave one here. |
 | appreciate the thoughtful review, Rob! more dry humor coming :) |
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 | welcome aboard, Tiffane! I hope to see you around |
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If you're new here, hi! |
Hey, I'm Rohan. Some people are into yoga, others are into fishing - me, I'm all about self-improvement. Years ago, I got fed up with the fluff that passes for career advice out there. So, I started Resume Worded and this email series, Coached, to share the industry insider info I was learning. |
Think of this email as your weekly dose of career coaching you didn't know you needed. No fluff, no platitudes, no-BS — just real stuff that you need to hear to shape your career into what you want it to be. |
Until next time, |
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Rohan
Founder at Coached & Resume Worded |
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P. S. To make sure your career never goes off the rails, don't miss my future emails. A simple way to make sure you get each email is: |
If you're using Gmail, hit the 3 dots at the top-right corner, and choose Move to -> Primary. Or drag this email to Primary if you're on your computer. If you're using Apple Mail, tap on our email address at the top of this email (next to "From:" on mobile) and click "Add to VIPs.".
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