Coaching, Training, &
Guidance through Complexity

sustain what works
nurture good patterns
stimulate growth
intervene with integrity


Cultivate Strategy is a facilitation, process consulting, and complexity coaching firm that helps nonprofit and local government clients adapt to face complex, unpredictable circumstances. We specialize in human-centered, incremental, and collaborative approaches to organizational challenges.

Gauge how inclusive your organizational culture really is. We offer the Diamond Inclusiveness Assessment™ process in partnership with BIPOC colleagues, as well as trainings on gender, neurodiversity, and "Minnesota Nice." 

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Cultivate inspiration and energy with dynamic training and leadership coaching. We offer courses in facilitation, conflict-engagement, and emotional intelligence—with 1-on-1 support for perceptive leaders who yearn for new leadership models in an uncertain world.

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Move in the right direction without leaving anyone out. We specialize in narrative and network assessments that prepare clients for apt decision-making in strategic and experimental planning processes.

Harness the power of your networks and the stories that shape them. We provide inclusive community and organizational development services tailored to your context—from effective process design, to creative event hosting, to meaningful communications that acknowledge power dynamics.

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Create online gatherings that bridge the distance. We model ways to create healthy, meaningful connection and generate action that matters. Ditch the tech management and experience how productive online meetings can be.

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What Clients Say


The Learning Collaborative meeting you led was incredibly helpful. It has helped us to reinforce the technical assistance we provide by reminding the group that our support is geared toward the directions [project sites] set themselves.

Sarah Salomon

Project Lead,
Foundation for Healthy


This was our moment of clarity. ...It will help our organization move past the unspoken obstacles that have hindered our progress.

We came into the meeting with heavy tensions and left with clear, executable action steps. Bravo!

Board Development

Organizing for Change


Sherry knows the complexities of my community and the many layers of things I'm navigating. Our work focuses me; it's somehow both streamlining and expansive all at the same time.


And the journals are such a helpful supplement between our coaching calls …clearly adapted for my context.

Sarah Casey

Tibbets UMC



Cultivate Strategy went well beyond the numbers, the metrics... They told a number of stories.


It just gave me such pride and confidence in the people we have working for us.


I think we got some great feedback on how to engage our staff in terms of what their needs are.

Jane Prince

Council Member,
City of Saint Paul


The theme of “belonging” was discussed in many different ways, and the carefully designed workshop format provided opportunities for all who were present to engage in serious reflection and sharing of opinions about that theme.

Tim Callahan

Bastyr University


“How do we cultivate the muscle of radical imagination needed to dream together beyond fear?”

- adrienne maree brown