How to Know When It’s Time to Quit a job (and How to Quit Well)
- Shiv Martin
- 3 days ago
- 6 min read
A Mediator’s Step-by-Step Guide for Employees, Leaders, and HR Practitioners
January often brings a particular kind of clarity. Time away from work creates distance, and distance makes it easier to see what has quietly become unsustainable. Many people search for signs of when to quit a job, but few are supported to do it well.
As a workplace mediator and conflict resolution trainer, I regularly work with people who are in the midst of deciding whether to stay or leave their role. Often, this decision has been forming privately for months before it is ever spoken aloud. People remain professional, continue to perform, and keep showing up, while internally weighing up whether they can keep going in the same way.
I have also been on the other side of that decision myself. Some of the most important career decisions I have made came after stepping away from work long enough to see it clearly.
This guide is designed to support thoughtful, lawful, and respectful decision-making around quitting. It focuses on how to decide whether it is time to leave, and how to do so in a way that preserves dignity, relationships, and future options.
While this article is written primarily for individuals considering resignation, it is also relevant for leaders and HR practitioners navigating performance, fit, or exit conversations.
A note for leaders, managers, and HR Practitioners
Before moving into the step-by-step guide, it is important to acknowledge that many readers approach this topic from the other side of the table.
Leaders and HR practitioners are often supporting employees where a role is no longer the right fit. There is no shame, and nothing inherently wrong, in recognising this. In fact, avoiding these conversations frequently prolongs distress, underperformance, and conflict.
Handled well, conversations about role fit or exit can be respectful, humane, and legally sound. Handled poorly, they can escalate conflict, damage trust, and expose organisations to unnecessary risk.
Encouraging or signalling that someone may need to move on is not a casual conversation. Leaders need to have their ducks in a row first. That includes understanding legal and procedural obligations, being clear on the basis for the discussion, and applying strong negotiation, communication, and emotional regulation skills.
These discussions sit at the intersection of employment law, procedural fairness, and human behaviour. This article focuses on individuals making the decision to quit. If you are a leader or HR practitioner navigating these conversations, I have extensive experience supporting organisations to approach them safely and constructively. You are very welcome to get in touch.
Step 1: Don’t decide in the middle of a conflict
In mediation, timing matters. Decisions made when emotions are running high are rarely the best decisions.
Many people decide to quit immediately after a triggering event. A difficult meeting. A conflict with a manager or colleague. A decision that feels unfair, dismissive, or poorly handled. These moments matter, but they should not be the sole basis for a major career decision.
When emotions are heightened, our thinking narrows. We default to avoidance or escape. That does not mean quitting is wrong. It means the decision deserves space.
Before deciding anything, focus on stabilisation rather than resolution.
Conversation starter:“I don’t need to decide today. I need to understand what just happened and why it affected me so strongly.”
Step 2: Name the real issue, not just the exit
In conflict resolution work, clarity changes everything. Many people say “I need to quit” when what they actually need is change.
Change in workload. Change in boundaries. Change in expectations. Change in leadership support. Change in the type of work they are doing.
Without naming the real issue, quitting can feel like the only option. With clarity, other pathways often emerge.
Break your role down into components: tasks, workload, autonomy, relationships, values alignment, and growth. Identify which elements are not working.
Conversation starter:“If I stayed, what specifically would need to change for this role to be workable?”
Step 3: Burnout, job misfit, and workplace conditions?
From both mediation and HR perspectives, this distinction is critical.
Burnout
Burnout is a recognised response to prolonged, unmanaged workplace stress. It is shaped by workload, lack of control, unclear expectations, insufficient recognition, strained relationships, and value conflict.
Starting a new role while already depleted often makes recovery harder, not easier.
Misfit
Sometimes the issue is not the organisation or the manager, but the nature of the work itself. The tasks, systems, or demands no longer align with how you think, work, or find meaning.
Changing organisations without changing the work often recreates the problem.
Workplace conditions
In some cases, culture, leadership behaviour, or systems are unsafe or immovable. Where psychological safety or procedural fairness is compromised, leaving may be the healthiest option.
Understanding which category you are in informs the right next step.
Conversation starter:“ Am I trying to escape exhaustion, a workplace environment, or work that no longer fits me?”
Step 4: Have one structured conversation before you quit
In mediation, it is common to discover that people resigned without ever articulating what they needed. Not because they lacked insight, but because they assumed the answer would be no, or feared making the situation worse.
If it is safe to do so, consider one intentional, well-prepared conversation. This is not a venting session. It is a focused discussion about sustainability and expectations.
This conversation may confirm that leaving is the right decision. It may also lead to adjustments that make staying possible.
Either outcome is valuable.
Conversation starter:“I want to talk about what I would need for this role to be sustainable. I’m not making a final decision yet, but I need to be honest about where I’m at.”
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Step 5: Decide using three options, not two
In conflict situations, binary thinking increases pressure and reduces choice. Most people frame quitting as stay or leave, when there are usually three options:
Stay and stabilise
Stay and redesign
Leave with intention
Each option involves trade-offs. The aim is not perfection, but alignment with your values, capacity, and longer-term goals.
Conversation starter:“If I wasn’t allowed to quit for six months, what would need to change? If I was definitely leaving, what would I want to preserve?”
Step 6: How to quit a job well is a conflict management skill
Quitting well is a professional and relational skill. It draws on many of the same principles as effective mediation: clarity, timing, respectful communication, and boundary-setting.
Quitting well usually involves:
choosing your timing carefully
having a conversation before sending an email
keeping your explanation clear and proportionate
managing emotions without oversharing
maintaining professional boundaries during notice
You do not owe anyone your full story. You do owe yourself a clean, lawful, and respectful exit.
Conversation starter:“I’ve made a decision to resign. This hasn’t been a quick choice, and I’d like to talk through timing, handover, and communication.”
Step 7: Don’t carry unresolved conflict into the next role
This is the step most often skipped, and the one that matters most for long-term outcomes.
Unresolved conflict has a habit of following people. Without reflection, the same patterns reappear in new environments: blurred boundaries, over-functioning, avoidance of difficult conversations, or tolerating conditions that are not sustainable.
Before starting your next role, reflect on:
the boundaries you didn’t hold
the early warning signs you ignored
how conflict was handled, and how you responded
what you would address earlier next time
This is not about blame. It is about learning.
From a mediation perspective, quitting without reflection often means repeating the same conflict in a different setting.
If possible, build in recovery time between roles. Even a short pause allows your nervous system to settle and your thinking to reset.
Conversation starter:“What do I want to do differently next time, even if things feel good at the start?”
Final reflections
The best quitting decisions are not driven by escape. They are driven by clarity, intention, and a sense of what you are moving towards.
Whether you are deciding to quit, supporting someone else through that decision, or navigating a difficult HR or performance conversation, these moments benefit from structure, procedural fairness, and care.
These are not just employment decisions. They are human conversations.
If you would like support thinking this through, preparing for a conversation, or managing conflict in your workplace, you don’t have to do it alone.
Hi, I’m Shiv Martin. I’m a nationally accredited mediator, lawyer, conciliator, and conflict management specialist with over a decade of experience working across government, business, and community settings. I support teams to navigate complex and emotionally charged situations through mediation and conciliation, conflict skills training, facilitation, and practical advice on policies and processes. My approach is grounded in law, psychology, and real-world dispute resolution, with a strong focus on clarity, fairness, and workable outcomes.
If you’d like to talk about how I can help you or your organisation, you can get in touch here: 👉 www.shivmartin.com/contact
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