The best kind of CEO shadow

This program for top performers is a true win-win

Photo by Daniel Polo on Unsplash

The shift towards distributed/remote is causing many companies to revisit their core HR programs with the realization that simply “doing what we did before, but virtually” is not a long-term solution. In particular, engaging, developing and retaining top talent has been top of mind for many leaders since this shift unlocks new opportunities for these individuals, creating a critical “shields down” moment. 

 Luckily, this is another area where many companies can (should?) take a page out of GitLab’s handbook (pun intended) and consider implementing a CEO shadow program for their top talent: 

GitLab’s CEO Shadow Program 

In typical GitLab fashion, the link above describes their CEO Shadow Program in full transparency and almost-excruciating level of detail, resulting in an 8,5000-word document. Below I’m hoping to do my best in highlighting the key design elements that are worth considering when implementing a similar program elsewhere, using 95% fewer words. 

Goal 

The goal of the program is to help participants globally optimize their work by gaining a deeper understanding of how GitLab works, and what it aims to accomplish, as well as building cross-functional relationships with other members of the program’s cohort. For the CEO, it’s an opportunity to build a personal relationship with team members across the company and learn about challenges and opportunities through their unique perspective. 

Eligibility & Application

In addition baseline tenure (at least 1 month, preferably 3) the eligibility criteria aim the program at employees on the managerial track with large spans of control, senior individual contributors, cultural leaders and under-represented groups (both minorities and geographies). The application process is driven by the employee, requesting a particular slot on the schedule, highlighting how they meet their eligibility criteria and providing confirmation from their manager that they meet the criteria.  

Rhythm 

The program runs on an on-going basis with a few rare exceptions (CEO PTO, etc.). Participants shadow the CEO for two weeks with one week overlap, so during the first week a participant is trained by the outgoing person and during the second week, they train the incoming person. This is a good place to highlight the extra consideration that GitLab made for parents — highlighting specific “parent-friendly” slots in which full week participation is not required or the weeks are inconsecutive, and paying for childcare while parents participate in the program. 

Prep-work

Participants are expected to prepare for their time in the shadow program by connecting with co-shadows and program alumni, preparing a formal onboarding program (off a template), and getting up to speed on the work currently in-flight (projects and calendar) and the CEO himself. 

Format

The format is pretty straight forward. Participants are expected to perform a set of small administrative/operational/documentation tasks that can be completed during their time in the program and be part of almost any conversation that the CEO is having with a very small subset of explicit exceptions. Detailed guidance is available on everything from what to wear, through how to present yourself and act during meetings, to how to navigate the CEO’s home office (aka “Mission Control”). Of note is the awesome expectations to “speak up when the CEO displays flawed behavior” which probably merits a post of its own. The specificity in both describing them and validating/inviting the way you can respond to them is truly inspiring. 

In Sum

A CEO shadow program can be a phenomenal opportunity to help retain top talent. If you’re considering starting such a program in your own organization, the GitLab handbook page is a comprehensive jumping-off point that can help ensure that you got all your bases covered. You can refine, modify and iterate from there.

The best kind of CEO shadow

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