Welcome to The Breakroom

At one point in my career, I was in a role that asked one person to carry more functions, responsibilities, and organizational needs than the position could reasonably hold. I did what a lot of capable people do when the work doesn't quite fit the role: I worked harder. I learned more, built systems, figured things out, carried what was unclear, and tried to make the job work because I cared about the work and assumed that was part of being good at it.

It took me some time to understand that working harder was never going to solve it. What felt like an individual capacity problem was structural. The role had become one of the places where organizational needs accumulated, without anyone stepping back to ask whether they still belonged together.

And honestly, it felt familiar. For years, the message had been that being a good team member meant stepping in, helping where you could, and doing what needed to be done. In education and nonprofit work alike, that's just what we did. The line between being committed to the work and compensating for the way the work was structured wasn't always easy to see.

As I gained exposure to different kinds of organizations, I began to understand that it didn't have to operate that way. What I'd accepted as part of doing meaningful work wasn't inevitable. Organizations could make different choices about roles, capacity, decision-making, and how work was distributed. Once I had language for it, I started recognizing versions of the same pattern everywhere.

Sometimes Nobody Designed the Dysfunction

Organizations rarely wake up one morning and intentionally create an impossible job, an unclear reporting structure, or a process that requires six people to approve a $200 decision.

More often, things accumulate. Programs get added. Staff leave, and their responsibilities get divided among whoever remains or whoever is most capable. Funding changes. Leaders take on more functions because there's no one else. Temporary workarounds become permanent. New roles get created to absorb the overflow rather than to meet an actual organizational need. Eventually everyone's operating inside a structure that feels permanent even though no one really designed it.

When it stops working, we tend to locate the problem in people. We call it time management, delegation, communication, burnout, or a bad hire. Sometimes those things are true. But often they're symptoms of decisions made in the moment rather than strategically. Over time, the cost shows up in the people, the culture, and the work itself.

That idea sits underneath a lot of what eventually became The Workroom.

How the Work Shaped The Workroom

When I started The Workroom, I knew I wanted to help organizations work better.

Earlier in my career, the workroom was where I'd bind proposal books to go out to clients. It was always a little messy, but what came out at the end was good. That's the same spirit I brought to founding The Workroom two years ago. What became clearer through the actual client work was what "work better" and "good" really meant.

Organizations rarely call because they believe they have an organizational design problem. They call because something isn't working the way it should, or a leader is carrying too much. They may need a process, more capacity, clearer roles, or help getting from where they are to what comes next. Once we get into the work, the presenting problem usually leads somewhere deeper. Who owns this? Who's allowed to decide? Why does this role exist? Are we adding capacity, or moving the same ambiguity to another person?

Those questions have shaped The Workroom as much as any business plan ever could. Different clients bring different challenges, but the underlying patterns show up again and again across organizations, sectors, and stages of growth.

The Workroom didn't pivot away from the work. We became more precise because of the work.

I eventually realized I'd been asking the same question across my whole career, in different forms: how do we know when an organization is ready? Ready to hire. Ready to grow. Ready to take the funding, add the program, absorb the change.

Over time, that question became The Workroom Operational Readiness Framework. It gave language and structure to what I'd already been looking for in the work: understanding what's happening, figuring out what needs to change, and helping organizations carry that change through when implementation is the hard part.

That's the work underneath our promise: we make the organization work so leaders can actually lead.

As that work has evolved, I've also wanted a place to talk about the thinking underneath it, not just the final recommendation or the polished deliverable at the end.

That's Where The Breakroom Comes In

When I worked in schools, some of the best conversations didn't happen in formal meetings. They happened afterward. Someone would stop by another person's room. We'd stand in the hallway for a few minutes, or end up together in the breakroom, and someone would eventually say some version of, "Okay, what do you really think?"

That was usually when the useful conversation started. We'd bounce ideas off each other, compare what we were noticing, test something that wasn't fully formed yet, or ask the question that didn't quite fit into the meeting. It wasn't always about having an answer. A lot of the time, we were trying to make sense of what we were seeing.

That's how I think about The Breakroom.

It's the meeting after the meeting. The place where we can talk a little more plainly about how work really works, why some organizational problems keep resurfacing, and what may be sitting underneath the issue everyone's trying to solve.

Here, we can talk about why "the Executive Director has too much to do" isn't yet a job description. Why "hybrid" isn't a work arrangement until everyone knows what it means. Why a new employee can have the title while someone else still has the work.

Some of these conversations come from patterns I see repeatedly in client work and others are things I'm still thinking through myself.

The Opportunity Board Is Part of This Too

In a small organization, every role carries more weight. One unclear hire can affect a whole team, and one well-designed role can create capacity far beyond the person sitting in it. That makes the decision to add someone one of the clearest places organizational readiness shows up.

That's where the Opportunity Board comes in.

Nonprofits, small businesses, and civic organizations already carry big work across relatively small teams. The idea behind the Opportunity Board is simple: if organizations make more of the hard decisions before they post, employers and candidates both have better information to work with. If an organization has to be more specific about what it needs, what it can offer, and what success should look like before it posts, candidates get better information and employers have to make some of the decisions that are easy to postpone until later.

The Board isn't designed to make posting an opportunity as frictionless as possible. Some friction is useful. If an employer reaches a question about compensation, work arrangement, hiring timeline, or what success should look like and has to stop and think, that isn't a flaw in the process.

That is the process doing some of its most important work.

Candidates shouldn't have to reach the final interview to discover what an organization hasn't decided yet. And organizations deserve better than hiring talented people into roles that were never fully designed, hoping the person will somehow make the ambiguity disappear.

That's why the first collection here in The Breakroom focuses on Opportunity Readiness: the decisions that come before the posting, the interview, the board recruitment process, or the first day.

Come Sit With Us

Organizations are made of people, history, money, power, systems, relationships, and circumstances. The interesting problems are rarely clean. However, I do think we can get better at naming what's happening. We can stop treating every capacity problem as a hiring problem. We can stop asking individual employees to compensate indefinitely for structural ambiguity. We can design roles more intentionally, make clearer decisions about who owns what, and build organizations that are better able to carry the work they say matters.

That's what The Workroom is about.

The Breakroom is where we get to talk about it a little more plainly.

Welcome to The Breakroom.