Questions to Ask Before You Quit Your Job

My theory is that the reason head hunters thrive is that candidates are often more comfortable taking insincere flattery from a stranger on LinkedIn than they are having a hard honest conversation with their boss to explore and resolve conflict.

Candidates are often more likely to run from conflict by changing roles prematurely than embracing the conflict with a hard conversation. In reality, it’s much easier to have difficult conversations about what’s on your mind with your employer than having that difficult conversation to give your notice.

If you may be in this position, we’ve developed a framework to help you evaluate your decision and we’ve outlined some questions that you should ask yourself (and in some cases your boss) before you quit your job for another opportunity.

The Decision-Making Framework

Before you decide to leave, it’s essential to work through a series of questions that clarify your situation. Here’s a framework to guide you:

Clarify Your Motivation

Ask yourself: Why are you leaving?

There is usually an emotion behind the desire for change, such as feeling unmotivated or overwhelmed. Dig deeper by repeatedly asking “why?” until you reach the root cause. In short, know whether you’re leaving because of a temporary issue or something that genuinely needs a resolution.

Assess What You’re Running From

Many candidates find it easier to accept insincere flattery from a LinkedIn stranger rather than have a tough, honest conversation with their boss. Ask yourself:

“What are you running from?”

Is it poor decision making, bad luck, or a bruised ego?

Understanding whether you’re escaping conflict or seeking a better opportunity helps you address the real issue at hand.

Validate Your Perspective and Consider the Hidden Costs

It’s important to check if your view is factual or if it might be perceived. Talk to your direct report and colleagues to ensure you have a balanced perspective. Also, consider what you might lose by leaving—not just the salary, but valuable benefits such as flexible schedules or accumulated overtime.

Let’s dig into the framework more deeply:

What’s Your Why?

Before making any decisions, ask yourself: Why are you leaving? There is usually an emotion behind the desire for change. This feeling may signal that you’ve lost motivation. Dig deeper by asking “why?” repeatedly until you reach the root cause. Sometimes, a simple need for change drives you. If you feel restless or unmotivated, identify what is truly missing to decide if you need a change or if it’s something that can be resolved.

Ultimately, we think it’s very worthwhile considering whether something is pushing you out the door or if you’re truly being pulled somewhere else. “What are you running from?” is a loaded question that I regularly ask candidates who work with us.

If you’re uncertain, it can be useful to consider if this is your first career choice blip. Do you have multiple short tenures in your career? If so, why are you jumping around? While it may seem like the norm and you may end up with a higher salary, that comes at a cost of continuity, skills advancement, and can impact your reputation.

It’s really important to dig into this question because if you’re running from something, it’s possible (or even likely) that your next role will have the same result. At this point, I’ve learned that if unless you can properly validate a candidate’s reason for wanting the leave, any further discussion around their career is moot.

Common Reasons Candidates Consider Leaving

While your reason for considering leaving your current position is unique to you, there are some key themes we see in candidates who are looking for a new role:

Bad Manager

A common reason for leaving is inheriting a new manager who drastically changes things. Before you run away, consider whether you can work through these changes. Giving it some time and attempting to adapt might reveal a path forward. If you do identify that you’re just concerned, uneasy, or frustrated about some changes or new challenges, a conversation with your manager should be your first step.

Overlooked for Promotion

Did you ask why? Was your manager able to justify the decision? You may feel disappointed but perhaps you weren’t quite at the level required for promotion this time around and can set yourself up to be next in line, or maybe your manager wasn’t aware of your desire to step up. An open discussion can unveil insights for both you and your employer.

Under-Utilized

We see this one often. Feeling bored or stuck with repetitive work can be frustrating. It’s often a temporary state though that some extra communication with your boss can resolve this feeling and restore your engagement with your work.

Increase in Salary

A headhunter might tempt you with a promise of higher pay, but ask if salary is your only motivator. Consider whether your current firm offers regular performance reviews or salary adjustments and what other money-related motivators you’re feeling. Is salary your primary motivator or are other things important to you? Are you willing to give up everything you have built in your current role to spin the wheel for a higher salary. Try to think about the “why” around salary, is it a nice to have, or critical to your livelihood?

Understanding the “why” behind your salary concerns may open up new opportunities for growth in your current role.

Company Performance

Just like momentum can attract people to an employer, poor performance can push people away. Evaluate the magnitude of any issues and how they impact your role. Determine whether the problem is short term or likely to affect you in the long run.

Unfulfilled Promises

You’ve taken initiative and had the difficult discussion with your manager and shared were things aren’t working and how you feel things could be better. If your company agrees with you and to making changes, have you allowed the enough time for them to start making these changes? Are you being reasonable and planning to follow up several times, maybe after 2 weeks, 1 month, 2 months etc. In any case, if nothing seems to be happening and its more of an empty promise, you will feel better that you gave the benefit of doubt. Giving your employer a chance in most cases can solve many problems and helps an employer see from your perspective. Worst case, if you do ultimately leave, you can refer to this conversation and how much you tried to make it work.

Validating Your Perspective

Is Your Framing Accurate?

Speak with your direct report and others to ensure your view is factual, not just emotional. Ego and anxiety can cloud judgment, so clarifying the facts is essential before you make your next move.

Considering the Hidden Costs of Leaving

What Internal Equity Will You Lose?

Many employees focus solely on salary and overlook other valuable benefits. Think about the perks you take for granted, like flexible schedules or accumulated overtime for extra days off. Losing these can have a big impact on your overall job satisfaction.

The Impact on Your Career

Ask yourself if leaving your role right now might hurt your career development. Staying in a role for at least three years usually allows you to settle in and perform at your best. Constantly switching jobs might suggest that you haven’t given yourself enough time to truly grow in a position.

Weighing Your Options

Before making a final decision, ensure that a new position truly offers a better situation. Consider the following steps:

• Research New Opportunities: Talk to current employees on LinkedIn to get a sense of the day-to-day culture and morale at a potential new job before taking it up.
• Consider Taking a Break: If you’re feeling overworked or depleted, taking a vacation may offer the rest you need, allowing you to reassess your situation with fresh eyes.
• Explore Internal Solutions: Ask if there is a way to improve your situation without switching jobs—sometimes the issues you’re experiencing can be resolved with a well-timed conversation or a new project assignment.

Conclusion

If all else fails, contact Outpost Recruitment and we’ll help you with your next move. Just be sure that you are switching for the right reasons. Taking the time to reflect on these questions can help you make a well-informed decision about your career.