Yesterday in between meetings I had a little extra time, so I visited a holiday market in NYC to poke around the vendor stalls a bit.

It was mid-morning, so not a ton of crowds and I was often the only person at each of the booths as I was visiting. I stumbled upon a booth selling homemade candles of over a dozen flavors. In the booth, they were organized among different flavor profiles–the musky flavors to the right, the florals to the left, and the best-sellers (as they should be) right up front.

I asked to smell one particular candle whose name called out to me but lacked a description card that detailed the flavor profile. She offered it to me and confessed that it had just been added the day before, so they didn't have a listing card yet. I thought it'd be fun to guess the flavor profile of that flavor and started to offer up some descriptors that came to mind when I smelled it.

Clean laundry.

Fresh.

Cotton.

After the first candle, she offered me a second to try, then a third, and a fourth. For each one, I treated it as a little "taste test challenge of the nose" and first volunteered my ideas before having her reveal the answer as to what was the correct list of ingredients. It felt a little bit like a private wine tasting of a candle shop. We ended up sampling together nearly all of the candles in the store.

Throughout the exchange, I peppered her with questions about her business. Things like:

• How long have they been making candles?

• Are they all handmade?

• Do they sell online too?

• What's her favorite flavor?

• What's the crowd pick favorite?

When I confessed that the floral flavor profiles were my favorite, I found out that it's their specialty area too because they are all florists and sell primarily out of a flower shop cafe in Queens. As these are my all-time favorite kinds of coffee shops to visit, I was delighted to learn this piece of news and she handed me their business card to encourage me to come by their brick-and-mortar shop sometime.

In the end, I bought two candles. As we were checking out, she thanked me for my curiosity and time.

Then she offered me a job to sell candles for them in the booth during the next holiday season.

How to Get Hired by Getting Curious

Too often people assume that you must know the thing you want to pursue before you get a job doing that thing. But as I've spent all of my career learning that moving from one thing to the next is not about having done it before, it's about the express intent to get curious about it.

This has always been LinkedIn's biggest Achilles Heel; despite quite literally having the entire world's careers in the palm of their hands, they still can't seem to accurately predict the chaos and calamity of a modern-day career path. To a large extent, the entirety of their recommendation engine is based solely on jobs you have already done before; not ones that you might get curious about next.

Which is why, when I view my "jobs recommended for you" page on the LinkedIn algorithm, they show me jobs with "General Manager" titles, ones to match a few former roles I've had. The range of organizations that hires general managers ranges from modern corporations to local branches of McDonald's.

You can't keyword match your way into a job.

Now, to be clear, I am not about to drop it all and become a candle seller at the Union Square holiday market. (At least I don't think so. But check in again with me next week...)

But I did want to point out two important things in this exchange:

1. I have zero experience selling candles or homemade goods of any kind from a holiday market, online shop, or storefront operation in NYC.

2. I shared absolutely nothing about myself, my resume, or my career with this individual in the process of our entire exchange.

In other words, she didn't know that I've spent the better part of my adult life curious about the entrepreneurial experience, or that founders are some of my favorite people to spend time with. She didn't know that I've coached early stage business leaders, led workshops on business-building best practices, or even that I'm currently learning a lot on the side about what it takes to start and run and online business as an artist.

All she saw from me was two things:

1. Curiosity

2. Asking good questions

The curiosity comes by tapping into your internal geek, and not being afraid by where it takes you next. The asking good questions comes with the lived experience of many years of paying attention to what that curiosity taught you.

How to Ask Better Questions

Asking questions is quite possibly the single-greatest "work hack" of a career.

A good question can impress your audience and get attention. A great question can cut through the bullshit and demonstrate intelligence—even more effectively than a polished resume or flashy credentials. (Sometimes, it can even get you job offers.)

To sharpen this skill, you might ask yourself first, "What am I trying to learn or understand?" and then, "What's the best question to help me learn that thing?" As you improve, you’ll naturally develop a mental “decision tree” to map out multiple pathways, helping you anticipate and frame the next question in the sequence. This skill allows you to pivot quickly and stay focused on uncovering the insights you need.

These short, focused "question series"—starting with a broad question and narrowing down with precise, targeted follow-ups—will enhance your ability to ask smarter, more effective questions over time.

This skill becomes more important the more you ascend into senior leadership roles, ones that require not just a macro-level view on a problem set, but a keen understanding of how to interpret the guts of the work, or to help you inform a new strategic focus. In these cases, i's not about asking more questions but about asking the right ones with precision and purpose. And as I wrote in my post on Frames of Reference, this often means learning to connect someone else’s perspective to your own.

The good news is that asking questions is a learned skill that you can practice, literally anywhere. So today, why not start by getting curious and asking one more question than you did before?