Title card with Naomi Hattaway on Leaving Well and title of the episode.

Quitting with Grace: The Art of Leaving a Job Well – BtR 417

Have you ever felt that nagging feeling that it might be time to move on from your job, but weren’t quite sure?

Naomi Hattaway is an expert in helping people navigate those tricky workplace transitions. She shares her framework for leaving well, which covers everything from recognizing the signs that it’s time to go, to ensuring a smooth knowledge transfer, and communicating your decision effectively. Whether you’re an individual contemplating a change or an organization looking to improve your offboarding process, this episode is packed with valuable insights. So stick around!

Should You Stay or Should You Go Now?

Naomi explores a decision-making process of whether to stay or leave a job. It emphasizes the importance of self-reflection, considering factors like values alignment, impact, and long-term goals. 

Key factors to consider when deciding whether to stay or leave a job include:

  • Values alignment: Is there a misalignment between your values and the organization’s values or the way work is done?
  • Impact: Are you still making a meaningful impact in your current role? Is there potential for greater impact elsewhere?
  • Long-term goals: Does your current job align with your long-term career aspirations and personal goals?
  • Work-life balance: Is your current job allowing you to maintain a healthy work-life balance?
  • Growth opportunities: Are there opportunities for growth and development in your current role? Are you able to apply your skills and learn new ones?
  • External factors: Are there external factors like family needs, relocation, or a partner’s job that necessitate a change?
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Strategies on Leaving Well

While we may be leaving a role because of the old-adage that “people don’t quit their jobs they quit their leaders,” keeping an open door for a return may be worth considering.

In my own experience, I have left a few roles where I knew I would not be able to continue working with a specific person, however loved everything about the organization’s mission, vision, and legacy. There is an art to separating from a toxic leader, while keeping bridges intact with the organization overall.

Here are some strategies for ensuring a smooth knowledge transfer when leaving a job:

  • Document processes: Create clear documentation of your key responsibilities and how you accomplish them. This could include step-by-step guides, templates, or checklists.
  • Share important information:  Share relevant files, contact information for key stakeholders, and any insights or tips that would be helpful for your replacement or colleagues taking over your duties.
  • Introduce replacements to key contacts: If possible, personally introduce your replacement or colleagues taking over your work to important clients, partners, or internal team members.
  • Be available for questions: Offer to be available for questions even after you’ve left the company, to ensure a smooth handover.
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Common Mistakes When Leaving a Job

The conversation with Naomi Hattaway covered several mistakes people and organizations make when transitioning out of a job, which can be inferred as common mistakes. Here’s a summarized list:

For Individuals:

  • Not planning for knowledge transfer: Failing to document processes or share crucial information with colleagues or replacements.
  • Burning bridges: Leaving on bad terms or neglecting to maintain positive relationships with former colleagues and the organization.
  • Neglecting self-reflection: Not taking the time to consider their values, impact, and long-term goals before deciding to leave.

For Organizations:

  • Poor communication: Not communicating the departure effectively to the remaining team members, leading to uncertainty and speculation.
  • Ignoring the offboarding process: Failing to treat offboarding with as much care as onboarding, neglecting the impact on the remaining employees and the organization’s culture.
  • Lack of stay interviews: Not conducting stay interviews to understand employee needs and proactively address concerns that might lead to turnover.
  • Not operationalizing values: Failing to clearly define and communicate the organization’s values, leading to misalignment and dissatisfaction among employees.

Naomi Hattaway

Naomi is passionate about accountability and leadership effectiveness. After living across the US, her family moved overseas for four years in both India and Singapore, and after returning, have traipsed their way through Florida, Virginia, Ohio, and Nebraska, and now back in Florida. Her love language? Accountability, tattoos & really good playlists. Naomi consults individuals and organizations on the concept and framework of leaving well, a practice for navigating workplace transitions.

Photo of Naomi Hattaway, expert on employee transitions and leaving well. How can you create a workplace culture where organizational knowledge is retained, dignity of others is preserved, and the door is left open for good performers to return?


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Naomi Hattaway is also the host of the podcast titled Leaving Well with Naomi Hattaway, A Navigation Guide for Workplace Transitions. In this podcast, you can expect to find conversations with experts on topics such as grief, leadership, confidence, career development, and more. We’ll talk with those who have experienced the necessary endings that come with jobs, projects, and roles. And we’ll come together to normalize the experience of change and our impact and legacy in the workplace.

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You can listen to Naomi’s interview of me on the topic of Stake Your Leadership T.E.N.T., servant leadership in the workplace, here on Apple Podcasts or Spotify.

Guest Episodes

Other episodes and articles you’ll enjoy:

3 Crucial Must Haves Before Leaving a Job and Living in Asia – Jimbo Clark BtR 187

JERRY’S SHORT: Before You Quit Your Job Look for These Opportunities First – JS018

How Ken Carfagno Left His Dream Job to Start a Cleaning Business – BtR 299

Connect with me:

Leave a voicemail at (469) 608-0355.

Send an email to [email protected].

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Hosted and Edited by Jerry Dugan


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