An organizational design and leadership development firm



Owl, Fox & Dean is the professional consulting work of Caleb Dean.

He provides strategic capacity to growing and changing companies, creative agencies and teams, and complex multi-stakeholder projects.



Through facilitated dialogue, active inquiry, and deep listening, Caleb’s approach applies curiosity, empathy, and courage to help individuals and teams respond to complex challenges and unique opportunities.

His work allows clients to go deeper and further more quickly, addressing underlying systems and moving toward energetic and durable solutions that align brand strategy, business model, and organizational culture.


He works predominantly with three types of groups:

(1) Growing and Changing Companies

He provides strategic capacity for leadership teams to have critical conversations and design and implement initiatives in order to quickly respond to growth and change opportunities.

(2) Creative Agencies and Teams

He provides strategic insight and direction to multidisciplinary creative teams in order to increase impact and relevance of client work.

(3) Diverse Multi-Stakeholder Groups

He facilitates complex conversations with multi-stakeholder groups in order to clarify vision, increase positive impact, and deepen value for those involved.


What Clients Say


“Instrument engaged with Caleb and his team on an extensive leadership coaching exercise for just about every employee here. We couldn’t be happier with the results and it’s showing across all disciplines and levels. Caleb crafted his plan with a broad strategy, but tailored his approach to the individual, making everyone feel special while still attacking broader goals for the team. Instrument partners worked directly with Caleb to review his findings and results and also integrated his suggestions in our team reviews and individual career development. Honestly, I’ve never been a fan of outside consultants, we’ve always handled our internal development ourselves. But Caleb listened and tuned his program to the evolving needs of our studio to bring about the most effective results. I’m proud to have worked with Caleb and our team members routinely mention their interactions with Caleb and his team among the highlights of their career at Instrument. We look forward to round 2 whenever that may be and expect Caleb to have huge success with any client he partners with. ”

— Vince Lavecchia, Partner & COO at Instrument

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“My team needed a facilitator to help a group of government elites come to consensus on their learnings, the group’s next steps and key deliverables. This was after a productive, but long four days of meetings. Caleb and his team did a fantastic job of guiding the group to uncover what they had learned, what was of value to them, and how they could progress the work they had started in Boston, once they went home. I appreciated Caleb’s thoughtfulness and preparation in understanding the group and their goals, as well as his follow-through after the facilitation. His deep understanding of organizational dynamics, as well as the group’s context drove to a successful result for both the group as well as my team.”

— Cathy Wissink, Senior Director, Technology and Civic Engagement at Microsoft New England


“Caleb is professionally impeccable and I do not say this lightly. After just two months of working together, his notes, words, questions and frameworks have left lasting impressions. Literally daily, I reflect on one or more elements of what he taught me. His superpowers are listening and intuitive translation of the jumble of story that each of us carries around in our head. I heartily recommend him as a coach and am happy to have conversations to that end. Impeccable.”

— Rachel Greenberger - Director, Food Sol at Babson College