How does your Enneagram, Human Design, and Strengths Top 5 help you with Leaving Well?
By Naomi Hattaway, President and Lead Advisor, 8th & Home
The Leaving Well Translation Guide for nonprofit departures and transitions: CliftonStrengths, Enneagram, and Human Design
Picture this: It's your last board meeting as Executive Director. You've led this organization through a capital campaign, an executive transition before yours, a pandemic, and more than a few impossible budget cycles. You know your StrengthsFinder results by heart. Maybe you've done the Enneagram work. Maybe you've gone deep on Human Design. And still — when someone asks how you're doing with the transition — you don't quite have the words.
I’m here to let you know that this isn’t a failure of self-knowledge, but it IS a gap in your toolkit. The assessments most of us have taken were designed to describe how we show up: our strengths, our coping patterns, our energy type. They are genuinely valuable and useful, so I’m not about to critique them because I love a good personality test and assessment. What I do believe is that none of these were built to help you understand how you leave.
This matters because how we leave is shaped by every departure that came before it—the goodbyes we didn't get to say, the thoughtful transitions that were co-opted, the roles we outgrew but couldn't let go of, the exits we made too fast and the ones we delayed too long.
This article is a translation guide, applying our Leaving Well lens to the tools you may already trust, so you can get more out of what you already know about yourself, and find the language for the part that’s been missing.
CliftonStrengths: You Know What You Do Best, But How Does That Show Up When You Leave?
WHAT IT MEASURES
CliftonStrengths identifies your top natural talent themes across 34 categories, organized into four domains: Executing, Influencing, Relationship Building, and Strategic Thinking. It tells you what energizes you, how you contribute, and where you're likely to thrive. It's a tool built for forward momentum — for understanding how to succeed in what's ahead.
PUTTING A LEAVING WELL LENS ON THIS
What CliftonStrengths doesn't ask is: what happens to those same themes when you're winding down, handing off, or stepping back? Our strengths don't disappear during transitions, I believe they intensify (which isn't always a gift or a blessing!). Here's what that looks like through my own top 5:
Individualization: The leader who sees every person as distinct — who knows exactly how each team member is wired and what they need — may find departure particularly heavy. You've invested in people at a level most leaders don't. Leaving means releasing those relationships without being able to see how the story ends for each of them.
The Leaving Well invitation for Individualization: trust that what you built in people doesn't leave when you do.
Futuristic: Leaders with Futuristic in their top themes can already see the org three years from now, often more clearly than they can see the present transition. The temptation to overshape what comes next — to keep casting vision long past the point when it's yours to cast — is a real risk.
The Leaving Well invitation for Futuristic: the clearest gift you can give your successor is space to find their own vision, not a detailed map of yours.
Input: Input-led leaders collect — information, resources, context, history. In a transition, this becomes both an asset and a trap. The institutional knowledge you carry is genuinely valuable, and it can also become a reason to stay tethered.
The Leaving Well invitation for Input: document what you know, then let go of being the only one who holds it.
Arranger: Arrangers are masterful at orchestrating complexity — moving pieces, optimizing systems, making things work. A transition is, among other things, a massive logistical puzzle, and Arrangers will be tempted to keep solving it past their departure date.
The Leaving Well invitation for Arranger: your successor needs to learn how to arrange things their own way. Handing off the pieces is the job. Staying to rearrange them is not.
Connectedness: The leader who sees how everything is linked — who finds meaning in the larger pattern of things — often experiences departure as part of something bigger than a job change. That can be a genuine source of peace, and it can also become a way of spiritualizing an exit that still needs practical, human attention.
The Leaving Well invitation for Connectedness: the meaning is real. So is the goodbye. Make room for both.
The question CliftonStrengths doesn't ask: Who were you before this role, and who do you become after it? That's where Leaving Well begins.
Enneagram: You Know Your Core Motivation, Now Look at What Drives Your Exit.
WHAT IT MEASURES
The Enneagram identifies nine distinct worldviews — each with a core motivation, a fear, and a pattern of behavior under stress. It's one of the most psychologically rich tools available for understanding why you do what you do, especially when things get hard.
PUTTING A LEAVING WELL LENS ON THIS
The Enneagram is particularly useful in transitions because transitions are stress events. The version of yourself that shows up at departure is often a more compressed, less resourced version of your type. Here's what that can look like in nonprofit leadership.
Type 1 — The Reformer - Ones leave with a list. They want the transition done correctly, thoroughly, and in the right order. The shadow side: perfectionism can delay the actual departure, or create handoff documentation so exhaustive that it overwhelms the successor rather than empowers them.
The Leaving Well question for a One: Can good enough be enough here?
Type 2 — The Helper - Helpers have often shaped an organization around their ability to meet needs — and in leaving, may struggle with who they are when they're no longer needed in that way. Twos can hover, stay too involved, or make themselves indispensable right up until the last day.
The Leaving Well question for a Two: What is this organization's job, versus yours?
Type 3 — The Achiever - Threes are often the most visible leaders in the room — and departure can feel like an identity crisis when the role has been the primary source of worth and recognition. The transition out can trigger overworking, overstating accomplishments, or skipping the grief entirely in favor of the next thing.
The Leaving Well question for a Three: What does success look like if no one is watching?
Type 4 — The Individualist: Fours experience departure as deeply personal — and it often is. The risk is that the transition becomes more about the narrative of their leaving than about the health of the organization moving forward. They may grieve loudly, or withdraw entirely, depending on whether they feel seen in the exit.
The Leaving Well question for a Four: Can this goodbye be meaningful without being about you?
Type 5 — The Investigator: Fives will research the transition, analyze it, and prepare extensively — and then emotionally detach when it's time to actually leave. The exit may look clean from the outside while significant internal processing is still happening in private.
The Leaving Well question for a Five: What would it look like to let people in during this transition, not just after it?
Type 6 — The Loyalist: Sixes are deeply committed to the people and systems they've helped build — which makes departure feel like potential abandonment, both of the organization and by it. They may catastrophize what happens after they leave, or stay hypervigilant about risks right up until the final day.
The Leaving Well question for a Six: What would it take to trust that the organization will be okay without you managing the what-ifs?
Type 7 — The Enthusiast: Sevens are already thinking about what's next before the current chapter has closed. The transition may get reframed as an exciting new beginning so quickly that the ending never really gets honored. The people left behind may feel the departure as abrupt, even when the Seven has been "processing" it for months.
The Leaving Well question for a Seven: What gets lost when you skip straight to the next adventure?
Type 8 — The Challenger - Eights don't leave quietly, and they rarely leave without an opinion about what's going to happen next. The instinct to protect the organization — or the people in it — can make full release genuinely difficult.
The Leaving Well question for an Eight: What does it look like to hand over control and trust someone else with what you built?
Type 9 — The Peacemaker - Nines often avoid the discomfort of the transition by simply... not fully departing. They stay involved at the edges, keep the door open, remain available in ways that make it harder for their successor to fully step in. Their departure may look clean on paper and feel murky in practice.
The Leaving Well question for a Nine: What would it mean to take up space in this exit — and let it matter?
Every Enneagram type carries a story about what departure means. The Enneagram gets you close to that story, and Leaving Well asks you to share it (or “read it”) out loud.
Human Design: You Know Your Energy Type, Now Apply It to How You End Things.
WHAT IT MEASURES
Human Design is less a personality framework and more an operating system — it maps how your energy works, how you're designed to make decisions, and how your aura interacts with the world. It's built on birth data rather than self-report, which means it's less about how you see yourself and more about how you're actually wired.
PUTTING A LEAVING WELL LENS ON THIS
Energy type matters enormously in transitions. Departures are energetically demanding, and each type has a different relationship with initiation, release, and what happens in the space between roles.
Manifestor (9% of the population) - Manifestors are here to initiate — and transitions can feel like being asked to stop mid-sentence. The strategy for Manifestors is to inform, not to ask permission. In a departure, this means proactively communicating the transition rather than resisting the questions. As a Manifestor myself, I've learned that the impulse to simply move when I'm ready — without explaining the why to those around me — creates more resistance than the departure itself.
Invitation for Manifestors: Informing doesn’t mean your shrinking or lessening your power, it’s simply about clearing the path.
Generator (37% of the population) - Generators have sustainable life-force energy — and they are designed to respond rather than initiate. In a departure, this means a Generator leaving before something has truly run its course may feel the friction of that misalignment in their body.
Invitation for Generators: Notice what you're responding to versus what you're forcing. A departure that's right will have a gut-level 'yes' underneath it.
Manifesting Generator (33% of the population) - MGs are fast-moving, multi-passionate, and often out the door before others have registered they were leaving. The risk in transition: they skip steps, delegate before things are fully closed, and underestimate how much their speed can destabilize a team.
Invitation for MGs: Slow down enough to complete the energetic handoff, not just the logistical one.
Projector (20% of the population) - Projectors are the guides — they see systems and people clearly, and they are designed to be recognized and invited rather than to push their way forward. In a departure, Projectors who haven't been seen or honored in their role may carry bitterness into the exit.
Invitation for Projectors: Name what you needed that you didn't receive, not as a grievance but as data for what comes next.
Reflector (1% of the population) - Reflectors absorb and mirror the environment around them, which means they need more time than any other type to process a major transition. The lunar cycle is their decision-making framework for a reason. Asking a Reflector to leave quickly, or to have clear answers about what's next on anyone else's timeline, is asking them to override their design.
Invitation for Reflectors: Protect the time you need, and find the trusted few who can hold that space with you.
Human Design doesn't tell you when to leave or how. But it can tell you something about the energetic conditions under which you're most likely to depart with integrity.
The Gap All Three Share, And the Tool Built for It
Here's what CliftonStrengths, the Enneagram, and Human Design have in common: they all describe who you are, yet none of them ask about your history with leaving.
That history is doing a lot of work whether you examine it or not. The leader who watched a parent leave abruptly—with no goodbye—may replicate that pattern without knowing it. The leader whose first major departure was a firing has a different relationship with exits than the leader whose transitions have always been celebrated. The board member who has never seen a healthy succession modeled up close doesn't know what one looks like.
This is the ground that the Workplace Transitions Archetype was built on.
The Workplace Transitions Archetype assessment, developed by our team at 8th & Home, identifies your personal archetype for how you experience and navigate organizational transitions. It surfaces the patterns—the tendencies that show up at departure, the ways you were shaped by the exits that came before yours, and the default behaviors that can either support or undermine a clean close.
There are four archetypes in the Workplace Transitions framework, modeled on the DiSC profile. Each one names something real about how people leave, and each one offers a pathway toward leaving more intentionally.
Where this becomes most powerful is at the team level. When a departing leader knows their archetype (and when the board, the incoming leader, and the senior team know theirs) you can actually plan a transition together. You can see in advance where the friction is likely to emerge, who needs more runway, who will rush to fill the vacuum, and who is quietly absorbing everyone else's anxiety. That's not just useful. That's the difference between a transition that holds the organization together and one that quietly unravels it.
Take the free Workplace Transitions Archetype assessment at naomihattaway.com/quiz. It takes about five minutes, and it will give you language for what has probably been confusing you for years.
The Language You've Been Missing
Those assessments you've taken may be seen as woo by some, but I believe they offer something real: language for your strengths, your patterns, and your wiring. This matters, and you should use that language. But, you are not just a collection of traits that exist in forward motion. You are also a person with a history of endings: departures that shaped you, transitions that cost you something, goodbyes that didn't land the way you needed them to.
Leaving Well isn't a framework that replaces what you already know about yourself. It's the layer underneath—the one that asks not just who you are, but how you got here, what you're carrying from every role you've ever left, and what it would mean to close this one with intention.
You've been assessed! How will you prepare yourself for what’s next?
For more information about these assessment types, some of my favorite folks to learn from are:
Human Design
Clifton StrengthsFinders
Christine Bizzell, Canon Collaborative
Enneagram
Listen to my podcast episode with Steph here: https://www.ninetypes.co/blog/enneagram-irl-podcast-naomi-hattaway
About the Author
Naomi Hattaway is the President and Lead Advisor of 8th & Home, a Georgia-based consulting firm operating under the brand Leaving Well™. Her work centers on succession planning, interim executive leadership, and organizational transition consulting for nonprofits and the foundations that support them. Learn more at naomihattaway.com.