How Dropbox is democratizing and scaling coaching

Estimated reading time: 5 minutes


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


      • Pilot Foundational Programs

      • Built the Leadership Development Team

      • Stephanie Redding runs the core programs

      • Reese Haydon runs the executive coaching and accelerator programs


        • Enhance external coaching program

        • Pilot mid-tier coaching vendors

        • Emerging lower cost but high-quality external coaching vendors that can support mid-tier and senior manager levels

        • Train internal coaches

        • Establish a training curriculum and coaching standards

        • Pilot Coaches Corner, internal exec coaching and team coaching

        • 30/60 minute spot coaching

        • A six-month internal executive coaching


          • Expand internal coach pool and launch Coaches Corner and exec coaching broadly

          • Establish the right amount of trained coaches at the right level of standards to apply this across the organization—2,800 employees

          • Pilot internal leader practice groups

          • Establish Coaching Center of Excellence


            • Serve as consultants to the business

            • Establish multi-year learning journeys for executives

            • Drive DDO (deliberately developmental organization)

          Key changes to coaching at Dropbox

              • Renegotiated rates aligned with industry and peer group

              • Stronger, more diverse, global coach network

              • Increased protection with Coaching @ Dropbox policies

              • Strategically aligned Quarterly Coach Forum

              • Standardized intake, matching, and engagement process

              • Coaches Corner pilot running for ICs and Managers

            Democratizing coaching

            1. Build internal coaching capability

                • L&D team, People team, broader Dropbox (ICF certified coaches)

                • Coach training (14-17hrs of training and observation)

              2. Pilot Coaches Corner for ICs and managers

                  • Every Individual Contributor will get a 30-minute session with a coach to gain clarity on a goal, get unstuck on a situation, and move forward

                  • Managers will have access to 60-minute sessions

                Piloting a six-month coaching program for select leaders

                3. Pilot team coaching

                    • With different formats, this allows more people to get access to coaching

                    • HIPO cohorts break up into small groups to coach each other around a project

                  4. Leverage technology to support scaling

                      • Calendar tools and other technology to help scale these programs


                    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:

                    • Running internal coaching practice groups for managers
                        • They are not only getting coached, but they are coaching each other, learning models and practicing them deliberately
                      • Providing training & toolkits on the GROW coaching model
                      • Working with C-suite and People team to institute systemic drivers (performance reviews, tie coaching to compensation)

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