Messy problems,
welcome here.

Sideyard Studio partners with organizations, teams, and small businesses on learning design, clear strategy, and facilitation that gets people unstuck — with a civic designer's love for places and the people who live in them.

A studio for learning design, strategy, facilitation, and healthier teams — rooted in Oakland and built for people doing meaningful work in the everyday world.

What I offer

Four ways we can work together

Every engagement starts with your actual situation — not a template. These are the four kinds of help I'm asked for most.

Learning & experience design

Trainings, workshops, curricula, events

  • Build or refresh trainings, workshops, curricula, or events
  • Audit existing experiences and make rapid, practical improvements
  • Design pilot programs or entirely new offerings from scratch

Strategy & structured problem solving

From ambiguity to a plan you can act on

  • Turn big, ambiguous questions into clear strategies, frameworks, or roadmaps
  • Conduct empathy interviews and synthesize insights to guide solutions
  • Translate organizational goals into concrete, sequenced action plans

Facilitating clarity & decisions

Sprints, retreats, and working sessions

  • Lead design sprints or strategy sessions that align teams quickly
  • Turn messy problems into clear plans, prototypes, or decisions
  • Facilitate retreats and cross-functional working sessions

Human-centered people management

Coaching for managers and leaders

  • Coach managers on feedback, supporting staff, and building healthy, inclusive team culture
  • Help leaders read team dynamics, unblock interpersonal challenges, and strengthen communication
  • Support leaders in aligning expectations, setting norms, and improving team workflows

Not sure which of these you need? That's usually a good sign we should just talk. Tell me what's going on and I'll point you in the right direction — even if it's not me.

How I work

From tangled to actionable, in four moves

Listen first

Empathy interviews, stakeholder conversations, and honest questions — so the actual problem shows up before we start solving the guessed one.

Frame it clearly

Big, ambiguous questions get distilled into frameworks, criteria, and a shared picture of what "good" actually looks like.

Build something tangible

A training, a roadmap, a pilot, a prototype — a concrete artifact your team can react to, use, and be proud of.

Align & hand off

Facilitated decisions, clear owners, and sequenced next steps — so momentum survives long after the engagement ends.

Why “Sideyard”?

The overlooked space between the front yard and the back

The backyard is private. The front yard is public-facing. The side yard is the in-between — semi-public, semi-private, easy to overlook. It's where neighbors talk over the fence, where stuff gets built, where bikes get stored, plants grow, and kids cut through. A little improvised, and full of possibility.

That's how I see organizations, teams, and communities, too. The most interesting work usually lives in the in-between spaces: between strategy and execution, between a business and its neighborhood, between what a program is and what it could become. My job is to see the possibility in places and systems other people overlook — then help you make something of it.

Sideyard Studio is rooted in Oakland, California — and open to work anywhere people are building something worth building.

Tess Brustein, founder of Sideyard Studio

About

Hi, I'm Tess.

I'm the whole studio — researcher, designer, facilitator, and thought partner in one. I came up through learning design and education, which means I can't help asking: how does someone experience this, and what do they walk away knowing or being able to do?

Along the way I've been a classroom teacher, a learning designer, and a leader of teams — and I founded and ran an education technology company, so I've sat on every side of the table: building the program, managing the people, and living with the results.

That habit of designing for the learner turns out to work everywhere: training programs, strategy offsites, manager coaching, pilot programs, and neighborhood-scale problem solving.

Organizations and teams bring me in when the stakes are high and the path isn't obvious yet. I bring structure, warmth, and a bias toward decisions over deliberation.

Find me on LinkedIn →

Based inOakland, CA
EngagementsProjects, sprints & retainers
ApproachHands-on, with collaborators as needed

Get in touch

Tell me what you're working on

Whether you have a defined project or just a nagging sense that something isn't working — send a note. I'll reply personally, usually within a couple of days.