33 Questions to Ask to Help You Decide Whether to Leave a Job

4 min readJun 22, 2021

“If I had an hour to solve a problem I’d spend 55 minutes thinking about the problem and 5 minutes thinking about solutions.” — Albert Einstein

Part of understanding the problem is making sure you’re asking the right questions.

Unfortunately, we’re not taught in school how to ask ourselves better questions. Our natural inclination is to ask “why” questions like “why me” which send us into a downward spiral.

But when we change our questions, we change our lives.

By asking better quality questions, we gain better quality insights that can lead to powerful transformations.

Below are a series of questions I gathered from my coaching courses and friends, I found online, and I created over the past five years to identify my vision for my career and determine if I should stay or leave a job or organization.

Spend time reflecting and journaling on all or some of the questions below.

First, see if it’s the role, company, or you:

When I look at the opportunities ahead of me at my job, how do I feel?
When was the last time I woke up excited or feeling optimistic about the role/company? What happened right after that?
What specifically about my current situation is frustrating me?
What would it take for me to be happy at my current job? What would make me want to stay?
What problems do I expect quitting my job to solve? Will these show up in a different company? How might addressing these now benefit me?
Have I taken every action possible to make my current job workable?
Where am I not being honest with myself?
Am I still excited about my work — or am I holding onto this job because it’s what I’m used to, because it’s what I thought I wanted to do, or because I’m afraid to make a change? Or is it the person I used to be, and now I am growing into something and someone different?
Am I running away from something or toward something?
Where am I being too flexible? Too rigid?
Are there other roles, opportunities, projects, or clients I could work on at my current job that are interesting to me — or not?
Where does my current employer share similar values (e.g., growth, learning, contribution) that are most important to me? Where are our values misaligned?
If my boss fired me right now, what would my reaction be?
What’s making this decision particularly difficult for me right now?

Tap into your heart, values, & dreams a bit:

Am I burnt out and would taking time for self-care, vacation, or getting help with stress solve the issue?
What are my strengths? How am I using them in my current role? How could I increase how much I’m using them?
Do I want to do this (role/company) for the next five years? Thinking this far ahead, what do I notice happens inside my body?
If there were no consequences, what would I do?
What was the original vision when I started my career? How has it changed? What aspects of my current job directly relate to my vision?
What do I want for my job, career, and life? What do I really want?
Where does my work currently align with my greater interests, passions, and goals in life? Where is it not aligned?
What do I want my life to look like in five years? What do I want to be doing in five years? What part of that could I be doing right now? How can I plan and prepare so that I can be in that position in five years?
If I could do what I do best consistently, what might be possible?
If I was more willing to step outside of my comfort zone, what opportunities would arise for me?
What would I pursue if I knew I couldn’t fail?

Tap into your head & reasoning a bit:

Can I defend my choice to leave, even if others disagree with it?
Do I have a thoughtful, realistic plan for attaining my next job?
Am I willing and able to forego benefits like health insurance and retirement contributions until I get my next job?
Do I have the support of my family and friends? Do I need it?

Integrating your learning:

What’s emerging here for me? What new connections am I making?
What’s been my major insight/discovery so far?
If there was one thing that hasn’t been addressed to reach a deeper level of clarity, what would it be?
What are my next steps?

I hope these questions act as a catalyst for you and uncover insights you might not have had previously. If, in the end, you decide it’s time to go, exit with grace and gratitude for this chapter of your life and all of the learnings it provided.

Additional resources

Free Guide: “Stay or Go Guide: Questions to Help You Decide Whether to Leave a Job” This is even more comprehensive than the questions above, so if you’re still feeling stuck, or are on the cusp of a breakthrough, this guide will help.
Course: “Should I stay or leave” by Career Coach Darcy Eikenberg. This course and Darcy’s coaching were instrumental to me when I was first deciding whether to leave a prior organization.
Book: Designing Your Life by Bill Burnett and Dave Evans
Career or life coaching! You can learn more about the power of coaching here.

Special thanks

Big thanks to Robbie Abed, Erin Van Der Meer for some of the questions provided, my friend Stephanie Ciccone-Nascimento for the inspiration to think bigger, and thanks to my personal coach Julia Tolstunova for holding space for me and championing me.

Originally published at https://www.thrivecoaching.io.