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Box of Crayons

Box of Crayons is a learning and development company that designs and delivers learning experiences to help organizations unleash the power of curiosity to create more innovative and engaged company cultures.

Tell us about yourself?

My career began in academia, a pursuit driven by my desire to be a part of conversations I think are important. In 2016, while still writing my dissertation, I embarked on a new path, starting a career in corporate learning and development.

When I joined the company in 2016 – assuring myself this was just a side gig to help make the mortgage – it was specifically to help our Founder, Michael Bungay Stanier, with the publicity of his 2016 book, The Coaching Habit.

This book went on to sell over a million copies, and it soon meant that organizations all over the world started calling Box of Crayons, wanting to know how to launch enterprise solutions to enact his concept around being more “coach-like”. So the company began to change, and FAST.

I quickly found myself on all these calls with senior business and learning executives who were deeply committed to shifting their culture and building leadership capabilities to transform their organizations. They were on the lookout for those collective behaviours that could help deliver better business outcomes.

And me, over here, I was brand new to Learning & Development and “high potentials” and “competency maps” – I mean, I hadn’t even worked in a big organization for any period of time. My “corporate” experience was limited to being an adjunct faculty member and a stint at a tiny literary publishing house that put out pretty obscure stuff.

But in the end, I realized that my proficiency as a “seller” – and to my surprise, I did become pretty proficient – had nothing to do with my deep knowledge of our clients’ business realities and my ability to quickly diagnose their challenges. Because I didn’t have any deep knowledge of what their challenges were. I was too new.

Rather, my success connecting with our clients had to do with my ability to ask the right questions that created the space in which they could articulate their challenges themselves. This willingness to dig a bit deeper despite being out of my depth came from both my training in reading for themes and making connections and through practicing what Box of Crayons teaches… which is how to stay curious longer.

The company grew quickly in those few years. Pretty soon, we needed to hire more people, and I found myself not just selling but leading a newly formed sales division and integrating with other new functions and processes we suddenly needed. By 2019, our Founder had stepped away to start a new adventure, and I was leading the whole company. I bring to the role more than a decade of experience in education and in practising incisive investigation – something that I heartily encourage among the team.

The work with Box of Crayons has brought me to realize that curiosity can be more than just a desire to know something. There is a form of curiosity that is a powerful practice capable of creating connections between people.

It seems natural that I should gravitate toward this framing of curiosity as a practice of creating connection through conversation since this is what literature does, too: it creates a space in which we are given imaginative access to other “selves” and invited to wonder about and identify with points of view that are very different from our own.

When we engage with great stories, we find ourselves simultaneously reflecting on our own experiences while being open to the motivations of – and maybe even rooting for – characters whose actions we find questionable, whose beliefs we don’t hold, and whose ideas we maybe even loathe. In a way, the first “curious” conversation is the one we have with ourselves: it is in this solitude and in curiosity about our own contradictions that we learn to develop a stable sense of self. And this acknowledgement of our own messiness makes it easier for us to accept the complexity of others.

I completed my Ph.D. in English in 2019, and while reading and thinking about literary theory still persists as one of my favourite hobbies, I’m delighted to have found a new set of professional interlocutors.

If you could go back in time a year or two, what piece of advice would you give yourself?

Be more patient, kind, and curious with yourself. Pace yourself; approach the work like your contribution is something that takes shape and has an impact over months and even years.

What problem does your business solve?

Our business helps organizations operationalize curiosity-led behaviours at enterprise scale – behaviours that drive faster problem-solving, stronger accountability, and better clarity, all while strengthening relationships and engagement.

What is the inspiration behind your business?

Box of Crayons was founded by Michael Bungay Stanier in July 2002, inspired by the desire to “unweird coaching” and help busy managers find ways to drive performance while creating the capacity and conditions for themselves to connect to their own great work. Box of Crayons’ offerings still helps that busy manager – along with every other employee profile in an organization.

What is your magic sauce?

Our primary design principle is this: What is the least amount of information that is most useful? Because we start from that principle:

  • Our programs disrupt everyday expectations of corporate training
  • Experience is an equal part of the process
  • Content is practical and easy to apply
  • Complex material delivered simply and accessibly
  • We drive change in a way that serves different kinds of culture
    change initiatives.
  • Learning is authenticated by experience and practice, not
    theoretical constructs

What is the plan for the next 5 years? What do you want to achieve?

We want to continue to grow and scale our offerings, revising our product suite to better suit enterprise organizations and the various learning needs and constraints within them.

What is the biggest challenge you’ve faced so far?

The transition from Founder to CEO was smooth – much smoother than the COVID-19 pandemic that arrived that same year. We managed to pivot our offerings from live to virtual and have since also developed digital and blended learning experiences. This industry is changing rapidly, and so it is a challenge every day to keep focused on our very best clients’ needs so that we can anticipate and shape the needs they’ll have tomorrow.

How can people get involved?

If you’re interested in learning more about our learning experiences for your organization, please be in touch through our website at, or email us at