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Think Better: 3 Reasons to Ask the Hard Questions

I’m sure we have all experienced this at some point in our lives: that crushing feeling of helplessness and frustration in the face of a challenging situation.

I felt this way often in my past hedge fund life. Now that I’m trying to bring a product to launch, I feel this way all. the. damn. time.

In the corporate landscape, particularly in the hedge fund world, the issues are complex and things move quickly. Extremely quickly.

I remember the not-so-fond feeling of panic that would swell up in my chest, as I frantically sifted through portfolio data troubleshooting the root cause of an incorrect trade. If you think Eminem’s palms were sweaty, try having a portfolio manager breathing impatiently into your headset waiting for you to explain why it looks like his fund suddenly lost millions of dollars.

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With the time pressure to perform, I remember I would often think: “I wish I were smarter. I wish I were better.

While invisible on the outside, this emotional suffering is acute — like a knife stab to the chest.

Heart wrenching.

Please and thank you. No drama or anything.

I continue to work on managing this feeling to this day. These days, in moments when I feel this, it’s often helpful to remind myself that the solution I’m really looking for is how to problem-solve better.

When facing challenges or roadblocks to my productivity, I’ve found studying methods of critical thinking and problem solving as one of the most effective ways to manage negative emotions of frustration or overwhelm.

This can often be boiled down into a key skill: asking better questions.

Below are reasons why it’s more important to invest time in questions, rather than answers.

1. Accelerate Learning

“Although providing employees with answers to their problems often may be the most efficient way to get things done, the short-term gain is overshadowed by long-term costs. By taking the expedient route, you impede direct reports’ development, cheat yourself of access to some potentially fresh and powerful ideas, and place an undue burden on your own shoulders.”

Source: How to Ask Better Questions, Harvard Business Review

While it may be far easier to Google the solution or ask for help, the benefit of asking questions to identify solutions on our own compounds in value over time by allowing us to think more creatively. This gives us the ability to make new connections and better forms of pattern identification.

As we learn to ask ourselves questions, this allows us to grow as independent thinkers and boost our productivity in the long term as we improve our problem solving skills.

2. Understand the Problem

“Often, a key reason people are stuck, unable to solve the problem, is that they are not applying all of the relevant information stashed away in the unlit corners of their minds. Over and over, as I ask questions to try to understand a problem a client is trying to solve, the client will have a sudden AHA! and solve the problem right in front of me. Of course, this doesn’t happen every time, but the process of asking and answering great questions always shifts our thinking in useful ways.“

Source: Questions to Explore Problems, Dale Emery

Intentional questions provide a clear landscape of the problem at hand as well as the clarity to test precise solutions down the line. To solve a problem well first takes understanding the problem well enough to realize it is actually not a problem, just a solution that has not been executed yet.

Asking questions to first describe the question before diving into ‘why’ it is happening objectively assesses the factual data to piece together the complexities of the scenario. By asking better questions, this leads to better problem solvings because they deliver you to a fundamentally more robust answer.

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3. Build Self-Awareness.

“When you don’t take the time to understand yourself and who you are, your sense of individuality weakens. You become easily influenced and pushed into a lifestyle that doesn’t represent who you are. The good news is you can gradually transition into the life you want by periodically “checking in” with yourself – the better you understand yourself, the easier it will be to steer your life in the right direction.”

Source: 25 Questions That Help You Understand Yourself and Your True Potential, Lifehack

Humans are one of the few creatures on this planet that have the ability to reflect on our own selves through our thoughts, feelings, behaviors, over time. Asking yourself questions can be a fast way of checking in with yourself and is an active form of self-reflection.

By taking the time to ask yourself questions and actively think about earlier experiences, you can better understand yourself and how you relate to your environment. These questions help you understand the patterns of what you did well and what you could do better in future instances that are similar.

In summary,

Before looking for solutions to any scenarios, the majority of effort should be in asking questions. By asking the right questions, you unlock the ability to enhance learning, problem solve better, and build self-awareness.


Use questions to:

  • Accelerate learning
  • Understand the problem
  • Build self-awareness

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