How Dropbox is Democratizing and Scaling Coaching

by Marko Gargenta
Read Time 4 minutes

TechKnowCon believes in the power of continuous learning, knowledge sharing, and peer learning. Leaders and Champions in the technical training space join us and share their stories. This is one of their stories.


During our April 2020 TechKnowCon Roundtable, Dropbox was one of the two companies that presented. Here is what Justin McSharry, Dropbox’s Global Head of Leadership Development, had to say about democratizing and scaling coaching.

About Justin

Justin joined Dropbox in March 2019. Throughout his career, he has always wanted a more people-focused role. After spending a few years in engineering, and twelve years in technical sales in Silicon Valley, Justin sought coaching before becoming a coach himself through a program called Integral Coaching Canada.

The past five years were his career in L&D, first joining Quantcast as the Head of Sales Enablement before moving onto become the Head of L&D. Out of this work, he discovered the connecting theme of coaching, and the power of coaching as the ability to provide systematic, long-term, sustained behavior change.

Coaching results in stronger emotional intelligence, empathy, results, better engagement, and much more within organizations.

Vision at Dropbox

Dropbox’s vision is to be known as a company where leaders learn how to be great leaders, and to be recognized as an industry leader in leadership development. As Justin’s team designs learning experiences and coaching programs, they also want to share what they learn with the community.

On the right side are Core Leadership Programs, which are tracks and programming for different leadership transitions: Aspiring Leads, New Leads, Experienced Leads, and the Executive Coaching Program.

On the left are Accelerator Programs (also known as High Potential Programs – HIPO) at both the senior manager level and the director level. These programs retain and prepare nominated cohorts for future leadership roles.

Executive Coaching Journey at Dropbox





Key Changes to Coaching at Dropbox

Democratizing Coaching

1. Build internal coaching capability

2. Pilot Coaches Corner for ICs and Managers

Piloting a six-month coaching program for select leaders

3. Pilot Team Coaching

4. Leverage technology to support scaling


The hunger and thirst for these programs are clear. People like getting access to coaching and have been providing great feedback. Democratizing coaching is a no-brainer. The goal now is to scale these programs thoughtfully and maintain standards.

Decentralized L&D

Although the 70/20/10 model for learning & development is archaic, there is something to be said about the key argument: a significant portion of what a leader or employee learns is on the job.

The goal of coaching is to occupy that 70%—weave learning experiences into the flow of work, on top of the traditional L&D programs, classrooms, and workshops.

Creating a Deliberately Developmental Organization

This idea comes from the book An Everyone Culture: Becoming a Deliberately Developmental Organization by Robert Kegan and Lisa Laskow Lahey. The goal is to create a coaching culture at Dropbox, where development is woven into the fabric of the company. Here are some steps for creating a DDO:

1. Running internal coaching practice groups for managers

2. Providing training & toolkits on the GROW coaching model

3. Working with C-suite and People team to institute systemic drivers (performance reviews, tie coaching to compensation)



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