

Blog
How Dropbox is democratizing and scaling coaching

Marko Gargenta
Founder & CEO, PlusPlus
Overview
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
2019
Pilot Foundational Programs
Built the Leadership Development Team
Stephanie Redding runs the core programs
Reese Haydon runs the executive coaching and accelerator programs
2020
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
2021
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
2022
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
Demand
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)
Discover PlusPIus
Learn more about how to create blended learning programs with PlusPlus.






