Taking Care and Leaving Well

It’s time to look ourselves in the mirror and admit we play a powerful role in the system. We can either exist outside of our power, or choose to decide, to shift culture, and to create transformation.
— Naomi Hattaway

The one constant discussion had with folks who work at nonprofit organizations in the human services / community organizing / social justice space is about caretaking and #LeavingWell. However, most people don’t identify the theme as such, or know it yet.

The popular videos of Nicole Olive and Vu Le always feel so incredibly appropriate (as you can see in the comment section of nearly every nonprofit related video they create) because they are bringing to light issues that we all know to be true, and have experienced ourselves. 

I’d like to offer that we have just as much responsibility for the environment and culture in nonprofits as those who we point fingers at, typically the executive directors, board of directors, and funders. This short piece offers the radically candid suggestion that we decide, we shift culture, and we create transformation. While it feels good to complain together about toxicity in our organizations, or we feel seen and acknowledged for what we’ve gone through, when we see a skit or comedy around the topic, it doesn’t support upriver change in the system and world we’ve all pledged to change for the better.


In Radical Candor by Kim Scott, she defines radical candor as caring personally, and challenging directly. 

Caring personally is the antidote to robotic professionalism and managerial arrogance. Caring personally is not about memorizing birthdays and names of family members. It’s about acknowledging we are all people with lives and aspirations that extend beyond those related to our shared work. It’s about finding time for real conversations, learning what’s important to people, about what makes us want to get out of bed in the morning and go to work - and what has the opposite effect. Challenge directly helps build trusting relationships, to enable a reciprocal dynamic.

I will state clearly here that I’ve yet to work in or with a nonprofit space that has had the safety, or organizational norm to hold space for radical candor. At the same time, I will offer that we - one at a time, in each of our organizations - must begin taking the posture of “we decide, we shift culture, we create transformation”. 

Health and wellness must happen in the workforce, first.
— Jaiya John

“We are responsible for each other’s wellness, regardless of position. Staff is not powerless, but powerful in their duty to support and care for themselves and their leadership. Whatever we are practicing and experiencing, we will administer. Service capacity is an outcome of investment in workforce wellness. We can keep looking for a magic potion to change our reality, or we can simply take better care.” -Jaiya John

Written by Jaiya John, the book Your Caring Heart: Renewal for Helping Professionals and Systems is on my highly recommended list for frontline staff, outreach providers, those in human services, or as Jaiya describes:

A helping professional is defined as someone who provides support, directly or indirectly, to others who are in significant need. If what you do affects vulnerable lives, this book is for you. And, if you are an administrator, an executive, then you, my friend, should care about agency, worker, and leader wellness because this absolutely determines the bottom line (fiscal), the top line (political), and the real line (social, generational outcomes).

In Jaiya’s book, he addresses the same concept of caring for each other that Kim did in her book. Taking an in-depth look at the idea of mutual care as necessary for those in helping professionals, the benefits can include (but not be limited to):

  • Staff feel safer and more relaxed

  • Staff operate at a higher level

  • Staff are freed to apply their gifts

  • Less days lost to unwellness

  • Greater efficiency and higher morale

  • More trust, effective communication and understanding

  • Less misunderstanding and conflict

  • Staff and leadership feel more empowered, validated, and supported

  • Stronger teams and teamwork

  • Minimized impact of stress and trauma

  • Less staff and leadership turnover

  • Stronger culture and continuity of values

As you read that list, what else comes to mind for you? What do you think of when considering your current work environment, or those you’ve had in the past?

The most poignant opportunity I see for culture change is in the realm of transition and grief. If more of us - regardless of position or title - took an attitude of caring well and caring personally whenever a transition or leaving happens, I know an incredibly powerful shift would happen.

Systems that don’t hold space and permission for grieving become depressed places of chronic, unreleased grief. Working with others in your cause brings grief. People change their positions, are promoted, leave the job. Formal leaders transition away. Those left behind feel abandoned, even lost. We grieve these various relationships and their influence, which is a good thing. A reflection of the meaning the relationships have to us. A testimony to the bonds and journey. Healthy grieving celebrates the memories, even the challenging ones. It is a storytelling river that goes on for years. Our relationships become legend, and in becoming legend, serve as mortar for the foundation of a relational system. -from Your Caring Heart

Change is inevitable, and so are necessary endings. We naturally fear change because of the unknown and disruption, however transition can be - when acknowledged and support is offered - a healthy and potent opportunity for growth and foundational structure. 

“Service capacity is an outcome of investment in workforce wellness.” -Jaiya John

Think about the last time someone left an organization or project you were working on. Or think collectively about each time it’s happened. Did it go smoothly? Was it challenging, but supportive? Was it transparent and carried out with helpful communication? 

The concept of caring personally aligns with so many tenets of #LeavingWell. Part of the genius of #LeavingWell is that you can put the framework into play long before you plan to transition to the next project, role, or organization. 

If one advances confidently in the direction of his dreams, and endeavors to live the life which he has imagined, he will meet with a success unexpected in common hours. He will put some things behind, will pass an invisible boundary . . . If you have built castles in the air, your work need not be lost; that is where they should be. Now put the foundations under them.” -Thoreau

In putting the foundations under those “castles in the air”, the correlation to the nonprofit world is to intentionally design your legacy, to take care of your imprint, and affect the climate.

“Three points of vulnerability exist in your work life: when you enter, while you exist, and as you leave. As you enter, you bring both beauty and baggage. Your greatest duty at work is not to survive but to affect the climate.” -Jaiya John

So what can you do about radical candor, caring personally, and leaving well? Not caring for each other is a habit, so then, the opposite must be practiced and ritualized so that it can become a habit.

Care Personally:

  • Start a conversation with your direct report, or someone on your board of directors, or a peer / colleague, and ask them to share a bit about their life story.

  • Listen (truly listen) for the connection points of their experience and history to the mission of your work, or the values of your organization. 

  • Verbally acknowledge the correlation you’ve drawn, and name their impact and contribution to the legacy of not only their name and work, but that of the system change you’re working together towards.

Mutual Care:

  • If your organization has recently had a transition, or one is looming, offer to host a casual gathering of your peers. From Jaiya: “craft an agenda of laughter, cleansing tears, remembrance, broadening of perspective, and lightening of heart.”

  • Make a list of the amazing teachings, skills, value, and culture components that you feel that person could “take with them” as they leave (or past tense, if it’s already happened).

  • Where are there gaps, as that person transitions from the project or organization? Where are the opportunities for those who are staying to take up those identified items?

  • Talk candidly about the legacy of those who have left in the past. Examine opportunities in your own work life to proactively design your own legacy, even as you process and grieve the exit of others. 

  • Where are the opportunities for each of you to contribute to the future health of the organization? 

*page 115 of Jaiya’s book has an amazing section on how to advocate for wellness in an unwell system! Page 117 is a beautiful lesson on grief in the workplace!

Over 4000 people have worked on this mission. There’s no one person who can really get their arms around the whole thing and say ‘I understand everything about this vehicle’.”  -Steve Squyres (who led the Mars Exploration Rover Mission)

Just as one person is not wholly responsible for the outcomes and success of projects and organizational impact, one person leaving is not the end of the world or a disaster for your projects or organization. However, ONE person can start the revolution and shift in our systems around caring for one another. I challenge you to find the opportunities to care personally and care well for each other during transition (whether happening currently or in the past), identify the areas where you need to decide, where you need to shift culture, and where you need to act in order to create transformation.

To learn more about #LeavingWell and the benefits it can offer you or your organization, please reach out. I’d love to talk with you about your current situation and be of service through my #LeavingWell consulting practice.

For the other articles on #LeavingWell: Transition Category

🎧 Legacy By Design: #LeavingWell podcast episode with Sundae Bean

Recommended reading:

Radical Candor

Your Caring Heart

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Career B*tches: Leaving Well