Get Better Answers By Asking Better Questions.

Hi there, I’m Spencer. In this edition I show you how to invite smart ideas and insights for your career change by asking better questions.

The Problem

You feel stuck making a career change and when you ask for help, you are not getting what you need.

Let’s start by looking at three question types that trip you up.


1. Question is not specific.

These questions are often “open to anything.”

Q: “I’m looking for a marketing role, do you know of anything?”

Me : “Marketing happens at all companies. Give me more to work with.”

Q: “Well, I want to keep my options open. I’m flexible.”

Keeping your options open keeps you from being specific. You are only asking a question, not making commitments.

A better question provides specific details to tell me how to best help you.


2. Question tries to solve for everything at once.

This kind of question packs the entire career change into one big move. This often involves meeting a lot of career criteria for a perfectly imagined future.

It’s simply overwhelming.

A better question makes change manageable and invites serendipity.


3. Question is too focused on getting a job.

In most cases, getting a job is getting ahead of yourself. You likely first need direction. And maybe new skills. And then finding companies that excite you. And then making the case for why to hire you.

A better question aligns with where you are in your career change.

The Solution

Use the How Might I format (HMI)

  • The ‘might’ suggests there are many possible answers, not right answers

  • HMI helps you avoid solving for everything at once

  • HMI helps you be specific to invite helpful insights and ideas

HMI looks like these examples from real career changers.

🤔 How might I discover companies talking poverty through micro-lending and financial education?

🎯 How might I connect with companies addressing mental health issues for Asian American students?

🧠 How might I create my own learning pathway to build the skills needed for data science roles in eSports?

Common Objections

“But I don’t know what I want to do.”

You are not expected to know exactly what you want. It’s ok if you don’t have a strong passion. Shift to a discovery mindset to explore new possibilities for what you might want to do.

“But I don’t want to limit my options.”

Yes you do. This may sound counter-intuitive, but keeping your options open is what is preventing you from making moves that invite delightfully unexpected opportunities. Additionally, Too many options leads to decision paralysis.

Ready to craft better questions?

We made you a step-by-step worksheet. Totes free and ready to download and print.

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