About Roberto

I pay attention to the business, the relationships around it, and the patterns a leader cannot easily see from within.

My work draws on strategy, organizational leadership, facilitation, negotiation, and the kind of listening that makes hidden assumptions easier to recognize.

Roberto Chavarria

I tend to see how the pieces of a complicated situation connect: the strategic question, the people carrying it, and the pattern underneath the latest problem.

I also notice when capable people are using the same words to describe different realities. Strategic disagreement often begins there. Helping people understand what is actually being said—and what remains unspoken—can change the possibilities available to the whole business.

I bring perspective and advice when I have something useful to offer. I do not assume that an outside expert should prescribe the answer. The leader remains closest to the company and responsible for the choice. My job is to help them see enough of the situation to use that responsibility well.

The work that shaped me

Most of what I know was learned inside ambitious work.

From the beginning of my career, I have been drawn to the strategic questions inside organizations trying to accomplish something difficult. Strategy became real to me through store layouts, inventory systems, startup launches, investment decisions, operating models, leadership transitions, and the people who had to make each idea work.

My first roles in Costa Rica put me close to operating leaders and immediate business results. At Corporación Musmanni, one of the country's largest bakery and convenience-store chains, I helped rethink how non-franchised stores used their floor space; one redesign increased sales by as much as 80 percent. At Casa Blanca, then one of Costa Rica's largest retailers, I led the design and relocation of a central distribution center intended to resolve persistent inventory problems. I learned to move between the larger strategic picture and the operational detail, and to respect how quickly an elegant idea meets constraints once other people must carry it.

I then co-founded TicoPlan, a bootstrapped dental-tourism startup. It taught me product development and launch from the founder's side, including the uncertainty and the distance between an interesting idea and a business people will actually choose. A potential investor later invited me to join ÍCARO, an angel investment firm, where I developed strategic executive plans and analyzed investments between $200,000 and $1 million in early-stage companies ranging from geolocated advertising to engineered biotechnology. I came to know both sides of the table: the founder asking others to believe in a possibility and the analyst responsible for deciding whether the evidence justified that belief.

At One Earth Future, a foundation that incubated peacebuilding programs, I spent seven years helping the organization develop, test, and improve ambitious approaches to peacebuilding and economic development. I joined its Future Labs team to create a new Program Development Process. The process brought ideas such as stakeholder validation, rigorous problem definition, and proof-of-concept testing into how programs were designed before their scope or scale expanded. It eventually became the strategic framework for the foundation as a whole.

My role kept expanding. I moved from new-program development into the strategy of the incubator itself, helped existing programs sharpen their purpose and value proposition, served as a close strategic partner and de facto chief of staff through a leadership transition, and eventually led Impact, Learning & Accountability. I built frameworks for articulating strategy and measuring success, generated information leaders could use to make decisions, and designed sensemaking and planning sessions that helped teams learn and adjust. The work ranged from foundation-wide systems to workshops with teams pursuing ex-combatant reincorporation and rural economic development in Colombia.

Those years were not clean case studies. I saw thoughtful strategies fail when people carried different pictures of the problem. I saw measurement become reporting theater when it was disconnected from real decisions. I had hard conversations, pushed new approaches through doubt, revised them when the evidence required it, and learned how much organizational change depends on trust, language, and the quality of the relationships carrying it.

I later returned to the operating side as a partner in Everland, an owner-financed rural-land business, before choosing to exit and pursue other ventures. Today I continue to hold responsibility inside organizations with audacious missions. At the Society, I began with a diagnostic of the organization's challenges and opportunities, built a plan for addressing them, and helped carry a broad organizational revamp into practice. As a co-founder and operating leader at the Human Institute, I am helping turn an ambitious vision into a more coherent and durable organization.

I have now sat in many seats: founder, partner, project manager, department leader, investment analyst, facilitator, operator, and advisor to the person ultimately responsible. I know the experience of being the leader receiving advice and of being the advisor whose job is to challenge a leader without taking their authority away. I have made good calls and bad ones, launched things, ended things, watched others make mistakes, and learned from my own. I am still learning. What I bring was earned close to the consequences: an ability to see the whole, ask the question that matters, name what is being avoided, and help an ambitious goal take form in decisions, relationships, and work people can actually carry.

Roberto Chavarria facilitating a leadership workshop
Working with the whole room.  Helping people recognize what is happening and make choices they can carry together.
Why Clearly Audacious

I have a lot of faith in people who are willing to name an audacious vision.

There is something deeply human about seeing a possibility that does not exist yet and taking responsibility for trying to bring it into form.

Starting a company is an extraordinary act. A founder takes an idea the world has not agreed to yet, puts their own time, reputation, money, and relationships behind it, and asks other people to help make it real. I respect the courage it takes to say that something could be better and then accept responsibility for building it.

Companies and organizations give people a way to contribute something together: a valuable product, meaningful employment, a better way of working, or an explicit social mission. The label matters less to me than the seriousness with which a leader holds the opportunity and the responsibility that comes with it.

Ambition can become disconnected from the motivation that gave rise to it. Pressure, conflict, repeated pivots, and the daily demands of running the company can erode clarity and confidence in the goal. I want to help leaders stay connected to what they are trying to make possible while becoming more effective, honest, and courageous in how they pursue it.

This work often appears as strategy, leadership, plans, roles, communication, or execution. Underneath all of it are people. People carry the vision, misunderstand one another, lose confidence, make commitments, recover trust, and move. I want to be a partner to the people who have taken up that challenge.

“Some people see things as they are and say, ‘Why?’I dream of things that never were and say, ‘Why not?’”
George Bernard Shaw
Who I work with

Founders, entrepreneurs, and executives willing to look closely at the business—and at their own part in what happens next.

You bring a real question and are willing to examine your own part in it.

You want an independent partner who can hold complexity, challenge your current reading of the situation, and help turn understanding into decisions and action. The relationship is most useful when you have enough authority to act on what becomes clear.

I am based in Boulder, Colorado, and work with leaders across Boulder, Denver, and beyond.

Start a conversation

If you are building something ambitious and an important issue is limiting progress, tell me what is happening.

We can begin with the goal, decision, relationship, or leadership challenge that brought you here.