The questions you need to ask before quitting your job

Estimated reading time: 7 minutes

Making the decision to leave your job can be daunting, even if you know you’re ready for something new and are confident you’ve outgrown your current role. 

Beyond being secure in the decision, the path afterwards is filled with uncertainty. How do you decide whether you want to move on to a new company or if your best outcome is to find a new internal opportunity? 

Take a step back and tease apart your current feelings. What are your likes and dislikes in this role? You know you want something new, but how new? What amount of change is going to feel like a reset? Even if you make a change, are your dislikes going to follow you?

What do you like?

Before you start considering your future options, it’s good to reflect on what has led you to this point. There’ll undoubtedly be things you know you dislike, but your first step is to actually understand what you like about your current job.

The reason to start here is that, when you’re ready to move on, finding the positives is often the hardest thing to do. It’s easier to lean into the negatives. But the reality is that there are likely aspects of this job that work with your career goals, the needs of your non-work life, and your day-to-day happiness. Reflecting on these likes will help you make a list of things you want your next role to have as well, to make sure you don’t take them for granted.

To help you narrow down what these things are, ask yourself:

• Do you have an attachment to your current domain?
  • If you find your current domain interesting and you have developed strong knowledge in the space, in addition to your technical skillset, then looking for a job where that domain knowledge is transferable will likely give you a leg up and may position you for a title change
• Are you committed to working with this specific tech stack?
  • Every job change is a fresh chance to revisit whether you want to be a specialist or a generalist in your career. If you find yourself feeling like you’re bored by the repetitive nature of your work, you may consider whether a new challenge or learning opportunity would be right for you. 
• Do you prefer a particular company or team size?
  • If you’re working on a smaller team and have found the many hats you have to wear a burden, then it might be time to look into roles on larger orgs with more specific boundaries of responsibility
• Do you want to serve the same user type or persona?
  • If you find support questions and feedback from the population at larger frustrating, perhaps developing for a more internal facing set of users will be a better fit.
• What aspects of the company culture do you value?
  • If you’re used to a flat organization where hierarchy has little impact on who makes decisions and how work gets done, then moving to a larger fortune 500 organization with 10 layers of leadership may not be a good fit.
• Are certain tools key to your productivity?
  • If using Slack is muscle memory and Teams will have a non-trivial impact on your efficiency and communication then maybe you want to stay away from an organization that operates exclusively with Teams.

Some things will be nice-to-haves, others will be deal-breakers. But making this list before considering other opportunities ensures you’re making a more objective decision about what’s important to you.

What organizational aspects don’t you like?

Often, it’ll be the things you don’t like about a team/company/product that spur you on to resign. As with all jobs, some things are too specific to matter, like individuals, but other things may be patterns or trends you’re looking to avoid. 

Here are some reasons you may be unhappy in your current position that you want to poke at when exploring prospective roles. There are ways to ask about these potential red flags in a more subtle and illustrative way, ensuring you avoid canned answers.

• Instability and turnover
  • What is the re-org frequency in this space? How many managers have you had in the last three years?
• Top-down prioritization
  • How does planning work? Who decides what the most impactful work is and its timeline for completion?
• Limited opportunities for growth
  • What has your evolution looked like in your time at the company? Where are you looking to grow? What do you see as opportunities for increased impact in the position I’m interviewing for?
• Overly political environment
  • How open are your peers, leaders and executives to feedback? How does misalignment get addressed?
• Stale technology, want to be bleeding edge
  • What is the current tech stack and how do you assess adding new tools and technologies? What kind of vetting process is necessary for bringing in a new dependency?

The list could go on and on. But understanding what you don’t want helps to ensure you don’t step into a new role with all the same pitfalls as the last. New things are shiny at first – don’t let that distract you from your goals.

Values matter

Beyond your likes and organizational dislikes, you’re also a person. Make sure you understand what matters most to you as an individual. Sometimes during job searches, we lose sight of our personal lives and start considering concessions because we can’t accurately conceptualize the impact. What are your deal breakers? What is most aligned with the work-life balance you seek at this moment in time?

• Is on-site a deal breaker?
• What kind of on-call schedule works for you?
• If the team works PST hours, and you’re EST, does that work for your family?
• What does PTO look like and how flexible is it?
• Do you feel good about working for a company that contributes this product to the world?
• What title are you seeking? How much does it actually matter to you, or is it a proxy for compensation and perception of value? If you were at a more established company, would it matter more or less? Start up? Ideally you’ve looked yourself in the mirror on this one before someone offers you a flashy title that speaks to your ego but offers little else.

These things are often a combination of work schedules, benefits, and the company itself. When interviewing, you can sometimes get caught up in how much you enjoy the folks you’re talking to. They seem great, collaborative, and happy at the organization! This might distract you from digging into these areas, if they’re happy surely you will be too. 

Be sure not to miss out on asking these questions. Whether it’s keeping a list of them or including them in a follow up email when you run out of time, you’ll want to have these answers when considering next steps. 

Into the unknown

After evaluating all your options, you might come to the decision that an internal transition is more attractive than an external one. This could be for the simple reason that you like the perks at the company, or you enjoy the culture, but internal transfers should have the same level of scrutiny as external offers. 

When it comes time, be scrupulous with interviewing the team and leaders. And be sure you understand what your day-to-day would look like as well as your career growth.

The benefit of internal transfers is that you can know so much more about the company culture, the benefits and compensation, their code, their docs, and the people you’ve worked with. So use that to your advantage when evaluating them. 

The reality of internal vs external jobs is that they come down to how happy you are with what you know. And how much risk you want to take with something you don’t. 

No wrong choices

This is a tough job market, so I won’t assume you’re weighing multiple offers. And even if you are, sometimes the pros/cons are so cut and dry that there isn’t much of a decision to make at all. 

But, if you find yourself with the luxury of deciding between multiple options, and there isn’t a clear-cut choice, try not to panic. Like any other transition, choosing a new job can be anxiety-inducing because you understand there to be a right choice and a wrong choice. The right choice ensures your career ends up in a better place, and the wrong one means you can never be as happy as you would have if you made the “right” choice. But that’s a false dichotomy. Choosing a new job is selecting the next step in your career journey, not your ultimate destination.

Make the choice that feels right to you, at this moment, with the information you have. Then there can’t be any regrets. You don’t know what you don’t know.

Deadline: January 4, 2026

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Final thoughts

No one’s decision-making matrix in a job search will look the same. We all have our own preferences, risk assessments, and experiences. In order to determine what matters the most to you, use the prompts and questions above. Once you have the answers to those questions, it’s easier to navigate job postings, initial interviews, and offer letters.