Wayfinder

Strategic Planning Services

You know what you want to do.
But how do you get there?

You’ve got 18 priorities—which means you have none.

You have clear goals with measurable outcomes, but no clear path to get there.

You’re working hard, but you need to work smarter.

The daily grind is consuming your focus, making it nearly impossible to think beyond next week, let alone the next five years.

but the real work?

It’s about charting your course for the long haul and tracking the markers along the way.

Wayfinder helps you navigate.

Assess the headwinds before you set sail—not when you’re already in the storm.

Find the tailwinds that will propel you forward. Learn to navigate on cloudy nights with no stars, steer through brewing storms, and most importantly, learn from the ones that already tested you.

Before you can set your course, you need to know where you are.

What’s the root cause of the challenges you face?

…That one recurring obstacle—the one that always seems to stand in the way… it isn’t a distraction.

It is the work.

The path forward is through it.

Find your Way.

How to chart your course…

Wayfinder Strategic Planning Services helps you chart a five-year plan that engages stakeholders with you, not just for them. Drawing from deep expertise in Liberatory Design and Improvement Science, and experience leading one of 3 strategic plan goals at a national non-profit, and consulting for top schools like Polaris Charter Academy and major districts like San Francisco Unified, we are there to guide you and help you learn to chart your own course.

  • Identify the real problems that need solving.

  • Gather and incorporate stakeholder perspectives.

  • Design a strategic plan that is co-created with your community.

  • Build sustainable systems that keep you on course.

You don’t have to get stuck.

Great strategic leadership goes from 30,000ft to 5ft.



Climb the crow’s nest to scan the horizon.
And get down on the deck and listen to your crew.

Strategic planning can be overwhelming, and the day-to-day can swallow it whole. But with the right guidance and loving accountability, you can find your way.

Let’s chart your course together.

Strategic Planning Processes:

  • Can you see it? Can your team? That dream you have, everyone can have.

  • Without goals and a strategy, you just have motion — but not momentum. Which mountain are we to climb?Getting to the mountain top starts with pointing to it.

  • If you chance two rabbits, both will escape.

    Get clear on your focus and your strategy before time, people and impact slip away.

  • Got a plan? Does it have clarity on who is doing what? By when?

    Did you plan for when the train is coming into the station to bring supplies needed to fix the trucks needed to bring the food to the people?

    Goals and vision are lovely, but the people will starve without a strong plan — and execution is where we so often fall down.

  • Are you on track?

    Are you sure?

    How do you know?

    Let’s set those markers up and figure out how to get elegantly simple in how we monitor progress.

    Because what gets measured gets done.

  • Without data, evidence and analysis, you don’t know if you are on course or 5º off. And 5º off means you end up lost at sea. Get your bearings — from truth-telling of your your compass and the wisdom of your people.

  • None of this matters if it is just you pulling. You cannot do it alone — and you shouldn’t try. Make your stakeholders folks you can’t wait to engage in your problems so they can pull with you — not people you are afraid to tell the truth. People want to help — they just need to know you need them and how.

Compelling Vision.
Exceptional Strategy.
Impactful Execution.
They are not easy, but they are not as complex as you think.

Why work with Ryan for your Strategic Planning?

Ryan was an integral part of our strategic planning in shifting the literacy practices in our Middle School English Language Arts Classrooms in San Francisco Unified School District. Ryan facilitated impactful meetings with district and site based leaders that led to a redesign of our district wide and site based structures. He brings an equity mindset to the work and balances high expectations as a change agent while understanding the complexities of a large urban school district. We could not have made the progress we have without Ryan’s leadership and collaboration.  

Lisa Levin, Supervisor of K-12 English Language Arts
San Francisco Unified School District