How asking the right questions led me to the right job

The amount of time you invest and the criteria you use are crucial in a job search.

My “aha” moment wasn’t really an “aha” moment.

It happened gradually, over the summer, and forced me to crystallize exactly what I wanted in this next phase of my career. What I ultimately found was a clearer path to fulfillment.

This journey came with amazing highs and emotionally draining lows. My hope is that my experiences and strategies learned along the way can help others in their job searches.

(Spoiler alert: You’re reading this on Tally’s blog, so you know where I landed.)

Here’s how it all went down...

Two years ago, I left a great job at LinkedIn to attend Harvard Business School. I wanted to reflect, explore and, eventually, hone in on a function and industry for the long term. Time away from the daily grind also helped me realize a few routes (venture capital, sports management) I didn’t want to pursue, at least for now.

I graduated in May knowing that what excites me most is developing relationships and rallying teams around a vision to build tech products that help people at scale. But I was still unsure about how that translated into a career and where.

Don’t get me wrong: I had plenty of ideas. I started by asking mentors, former colleagues and professors for advice and referrals, which helped me land a handful of interviews. But I made several mistakes during those early interviews — I hadn’t interviewed in more than five years and was rusty — and those mistakes led to rejections.

So, I took a few weeks off to work on my weaknesses before starting up again. The next time around, the interviews went well, and I was fortunate to convert conversations into offers.

I should have been elated, but something was still missing. I wasn’t jumping-out-of-bed excited about any of the opportunities. I realized I had taken a data-driven approach to my job search, scouring databases and popular lists from Wealthfront and Y-Combinator, but those lists only scratched the surface of what I was looking for in an employer.

I needed to look inward.

That realization forced me to codify a set of criteria and a series of questions that became the bedrock of my job search. For me, it came down to three things: people, passion, and opportunity.

People

Throughout my career, this has been my No. 1 non-negotiable. Given the amount of time we spend working, the people we work with have an outsized influence on the way we act and think, as well as the work we aspire to do.

The relationships we develop at work can last a lifetime. My former colleagues, managers, mentors, and role models continue to be a huge source of help and I’m forever grateful for that.

Here are a few questions I asked when networking and interviewing:

• What motivates you? Test them for passion and excitement. In the case of early stage companies, assess how hungry the founding team is. Figure out if the founders are committed to the company’s mission or if they’re just in it for the money.

• How do you make decisions? Take it further and ask about a time when they faced an ethical conflict. This question is profoundly helpful to get insight into the values and guiding principles of both the individual and the company. Look for alignment with your individual values. Trust your gut. Do not compromise.

• How did you define the company’s values? This one is for founders or executives. They should be able to say why they chose the values and how they are reinforced.

• What’s a story that uniquely describes the company’s culture? What you’re looking for here is a story you would not hear elsewhere.

• Would I hire this person? This last one is a question for yourself. If you were to start a company tomorrow, would you hire this person? Is this person inspiring and trustworthy?

Once I started asking these questions, I began to get a lot of positive feedback. People could tell I was well-informed and cared about the company. These questions showed that I understood the job and direction the business is headed, which, ultimately, made hiring managers more inclined to take a bet on me.

Passion

This was the toughest to define. I’ve always read about the importance of “finding your true calling” and “following your passion.” But those things weren’t always clear to me until recently.

So, in trying to determine my passion, I asked myself some questions:

• Which problems resonate with me personally? Which topics do I repeatedly think about? What do I enjoy talking about with family and friends?

• What do I read about most on my phone? What kind of apps are on my phone’s home screen?

  One of the best pieces of advice I received from a professor at business school was to

  conduct the Wall Street Journal test: What do you read about when you pick up the newspaper? Whatever it is, that’s a strong passion area. I took this and modified it to the phone test. The stories I read and the apps I use regularly are a great indicator of the things I care about most.

• How can I make the largest impact on the everyday lives of people?

• Am I prepared to dedicate this phase of my career to solving this problem?

• Will I regret not helping to solve this problem?

In my case, the initial answers were fintech, health tech, and productivity/collaboration. But fintech won by a mile for a few reasons:

• As an immigrant, personal finance has been a source of stress and anxiety for the past decade — from opening a bank account and getting my first credit card to paying off student loans and saving for retirement. And with each passing year, my personal finances continue to get more and more complicated.

• Fintech posts contribute the majority of the recommended content on my Google News home screen, and I have more than 20 fintech apps on my phone. I’m always on the hunt for personal finance hacks that can help solve my problems and put me at ease.

• Nearly 80% of Americans today live paycheck to paycheck. The chance to leverage technology to build financial products that tangibly improve people’s lives spoke to me directly and deeply.

For me, these questions tied back to some of the criteria I look for in people. I clearly identified the problems that I was most passionate about solving, and then looked for alignment in companies looking to solve the same problems.

Some wise words from organizational psychologist Adam Grant also helped during my search: “At the heart of meaningful work is the belief that your product makes other people’s lives better. When that belief gets shaken, ask, ‘Who would be worse off if my product didn't exist?"

Opportunity

This was the final piece of the puzzle. Entering the next stage of my career, I was itching to have more 0-to-1 experiences (creating from the ground up) to build a more holistic product management skill set.

To make sure my new role would provide me with the opportunity I was seeking, I asked myself:

• Will this role challenge me on a daily basis?

• Will I be able to accelerate my learning cycles?

• Am I gaining exposure to emerging technologies?

• Is there room to grow?

• What options will this role open up in the future?

• Does it bring me closer to my long-term goals?

When I consider my “role” at a company, I think about the impact I’ll have on a company’s trajectory. What mattered was an opportunity to make an impact and learn.

(Caveat: I asked many more questions about the product, company, financials and whatnot before making my decision. The above questions I shared are simply a roadmap to reach the final stage.)

Decision

Once I established my criteria and was given a chance to ask my questions, my decision became much easier. I won’t run through all the details of how Tally met the above three criteria (there are too many!), but here are a few snippets that got me excited:

• People: Tally co-founders Jason and Jasper repeatedly spoke about their passion for building products that alleviate the stress and anxiety associated with personal finance and their commitment to building an enduring company. I was fascinated by the fact that they had conducted interviews with every employee to codify Tally’s values. Plus, they had previously co-founded another startup and were making a point of learning from past mistakes.

• Passion: Tally has a unique approach to helping Americans with personal finance. There’s a sea of apps for investing, but only a handful address the complex problem of helping people become debt-free. Tally’s mission (

  ) and long-term vision (automating consumers’ whole financial lives) resonate strongly with me. I didn’t want to look back in a few years regretting that I didn’t try to solve a problem that is personally meaningful to me.

• Opportunity: As Tally's first Product hire, I'll be heading up product strategy and execution, building out the product organization, defining processes and shaping the team culture. The role allows me to not only apply past learning to help the team move forward but also pushes me to tackle new challenges, accelerating my learning and growth. All in all, this is just the challenge I was looking for.

Finding the right fit can be a challenging experience. I feel fortunate to have had the opportunity to explore my passions and meet so many fascinating and brilliant people on my road to Tally. And I'm glad I now have the criteria and specific questions needed to guide my career direction and choices. I hope my story and criteria can help others define what matters to them most as they prepare to take that next step.