Issue 34: Crafting Playbooks as a Chief of Staff
Planning, creating, and updating playbooks will help you scale your efficiency as a Chief of Staff
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This week’s issue is co-written by Fatema Kothari. Fatema Kothari was most recently the Director of Operations and Chief of Staff for Microsoft's Airband Initiative, where she led their efforts to expand internet connectivity and digital solutions to unserved rural communities both in the US and globally. Her previous experience spans working as an operator for both Fortune50 companies as well as startups, and she has a knack for bringing chaos to order in organizations that need it the most. She also currently serves on the Board for the Internet Society - SF Bay Area, avidly advocating an open Internet that is accessible to everyone.
How can Chiefs of Staff Master the Art of Playbooks?
In the fast-paced realm of the technology industry, where change is the only constant, the role of a Chief of Staff is akin to steering a ship through turbulent waters. In this dynamic environment, creating playbooks isn't just a mundane task - it's a strategic move that can make or break the success of an organization.
These playbooks extend detailing tasks and to-dos, allowing for tailored development to address diverse priorities and operational functions. An end-to-end Rhythm of Business (RoB) operations playbook can be a cornerstone in any business and a great centralized hub for the company. Furthermore, specialized playbooks for distinct projects and functions, such as financial operations or administrative tasks, can be autonomously established and seamlessly integrated into this centralized RoB playbook. This strategic approach of documentation ensures a cohesive and effective orchestration of key operational facets, aligning with the nuanced responsibilities of the Chief of Staff.
Now let's unravel the layers of the perfect playbook.
Characteristics of a Successful Playbook
💡 Informative Insights: The foundation of an effective playbook lies in its informativeness. Every piece of knowledge, from the macro-level organizational strategies to micro-level tactical maneuvers, should find a home in these pages. Playbooks should contain repeatable processes. If it’s a one task you’re delegating, it can be between you and that person.
🧭 Easy Navigation: A successful playbook is not just informative but also easily navigable. A Chief of Staff must design playbooks with user-friendly interfaces, enabling team members to access relevant information swiftly, like flipping to the right page in a well-indexed novel. Depending on your team’s tech stack, you might already be using OneNote, Quip, Notion, etc. Many of these tools already come with built in navigation templates that you can repurpose for your team.
💗 Inclusive for all Departments: Tech thrives on diversity, and so should playbooks. An inclusive playbook accommodates the diverse backgrounds, roles, and perspectives within an organization. It's not a one-size-fits-all document but a tailored experience for every team member. Remember that not all sales people speak tech and not all engineers speak sales. Include glossaries of terms and don’t forget to spell out acronyms so that the playbooks are accessible for everyone.
🌱 Adaptive and Ever Changing: In the ever-evolving tech landscape, rigidity is a recipe for obsolescence. Playbooks, therefore, should be living documents—constantly evolving and adapting to new challenges. The playbook is the opposite of a crockpot, absolutely don’t “set it and forget it.” Instead, revisit these playbooks regular, updating them when processes change.
🎨 Creativity Unleashed: Just because a playbook is work related, doesn’t mean it can’t be creative. Creativity is often seen as the antithesis of structure, but in playbooks, they are symbiotic. Visual elements, storytelling, and interactive features can transform a mundane document into an engaging and memorable resource. Inside jokes or memes can infuse your company’s culture into the playbook and make it a more enjoyable read for team members.
(Additional Note from Clara: When I worked at On Deck, we loved nautical puns so we found every opportunity to use them in any written documentation!)
Steps to Creating a Playbook
Ok so now that we know what makes a playbook successful, how do we go about building one?
🔎 Identify a Process Worth Documenting: First start with a process audit within your company to see what processes are worth documenting. Maybe even take a look at your own slate of responsibilities to see if there are repeatable “plays” that you’re replicating time after time.
Some topics that make for great playbooks include:
Knowledge Transfer - are there areas of expertise that you hold that no one else in the company knows about?
Risk Mitigation - are there contingency plans and risk mitigation strategies that can be documented (ie CEO needs to go on an immediate leave of absence)?
Operational Efficiency - are there multiple ways of doing something and the organization would be better served if there was one consistent way?
Decision Making - are there certain ways your company comes to decisions? These can be documented for new hires to learn and for team members to refer to when faced with hard decisions.
🧺 Gather Relevant Documentation: Start with a brain dump of everything that is relevant to this playbook. Don’t worry about formatting here - this is about information retrieval. Drop links, graphics, documents, and anything else that is related to the playbook you’re building. The key here to make sure you’re collecting anything that has been written about this process already so you don’t have to go through the motions of duplicating work.
🎤 Interview Associated Parties: Once you have collected all the documentation that you can, gather the affiliated team members who would use or be a part of this process to chime in. Ask them how they are currently executing this process - look for similarities or disparities. We even suggest using an AI note taking tool like Ambient to record your calls and summarize them so you don’t have to manually take notes while you converse.
This step also ensures that you’re getting the buy in of these team members even before you create the playbook. They should know that this information is going to be used to help standardize procedures and hopefully get everyone on the same page to increase efficiency. When team members see a playbook presented for use, it should not be a surprise to them!
🖼️ Set the Stage: Now you can start writing! We mentioned a few documentation tools above, but a few more of note for playbooks specifically include Trainual and even GitHub. At the top of each playbook, set the stage for your readers. Give them an overview of what to expect in this document and when to use this process. Keep this format consistent with all your playbooks to create a uniform approach across the organization.
In the example below, you can see that there are several categories that should be included in each overview section including: purpose, frequency/cadence, desired output, etc. For more templates and examples, check out Fatema’s collection here!
📝 Write Out the Process: With all the information you’ve gathered, you can now detail the process in your playbook. Don’t feel constrained to only words. Break up the text with Loom videos or screenshots to help team members visualize the process. This is also a great place to insert jokes and memes that are relevant to your company’s culture, infusing humor. If your company is more corporate and stays away from more casual writing, make sure you keep to the tone of what your company dictates as well. As a Chief of Staff, you’re a carrier of culture and that can be highlighted through organizational wide communications like playbooks.
(Additional Note from Clara: Something I liked including in my playbooks was an “Archive” section where I would list and reference all previous documentation and links. That way people could see what I had referenced in writing up this playbook and know that I wasn’t just making things up from scratch.)
☎️ Add in Contact Information: This step is especially important if the processes being documented involve risk mitigation or emergency situations. The contact person for each playbook is the one who is responsible for making sure the playbook stays up to date so don’t surprise them with this responsibility! Sometimes there will be a handoff where the Chief of Staff is the author and key point of contact for a playbook, but as your role changes and evolves, certain processes may be handed off or re-delegated to others. Make sure the playbook transfer is a part of the delegation process so that documentation is continuously updated and the team knows who to turn to when there’s a hiccup in the operation.
(Additional Note from Clara: Ideally the contact person for every process is not you, the Chief of Staff. If this is the case, you’ve become a single point of failure, which can be detrimental for any business. I even like to include a Batman/Robin pairing for each playbook: one person who is responsible for the process and a secondary who is there to support and ready to step up if the first person is unavailable.)
🌊 Test the Waters: A playbook untested is a strategy unproven. Once you have an initial draft, start to share it with relevant parties who will be using the playbook. Foster open communication channels, encouraging team feedback for refinement before full-scale implementation. As mentioned before, a playbook should not be a new document that people see for the first time during its roll out. While writing and before launch, you should be continuing to check in with the users of the playbook to make sure processes haven’t changed since you last spoke or if there is new information that is now important to include. Getting team members’ feedback early on will help with adoption down the line and will make people feel included in building the scaffolding and foundation of the company.
🚀 Implement the Playbook: Once the playbook is in a place where the team feels like it can be followed and repeated regularly, it’s time to announce the playbook to the rest of the team. Depending on your company’s communication cadence, identify the right place and time so that the playbook is well received and acknowledged. Shoutout team members who helped you write the playbook and get ready for things to get more efficient!
(Additional Note from Clara: When I worked at AngelList, whenever a playbook was completed, the author would announce it like a “feature roll out.” Because the culture there was heavily engineering, announcing it like so would help our operations team members be noticed by our engineering teammates and helps foster stronger culture between cross functional teams and departments.)
🔋 Update Accordingly and Regularly:
A Chief of Staff should conduct pilot tests, gather feedback, and iterate on playbooks regularly. This iterative process not only refines the content but also fosters a sense of ownership among team members, making the playbook a collective achievement.
A great time to do this is when new team members are onboarded and experiencing the playbook for the first time. Ask them for feedback on what was unclear or could use more detail and incorporate those changes for the next reader.
(Additional Note from Clara: At the end of each playbook, document when the playbook was last updated and by whom. That way, there is a running tracker of when the playbook was last edited and those dates can be a relevant reminder on when it’s time to revisit this process.)
In Conclusion
Playbooks can be a powerful tool in the Chief of Staff’s arsenal to get more done, more efficiently. An informative, navigable, and inclusive playbook becomes the compass that guides the team through uncharted territories, turning challenges into opportunities. Don’t feel pressure to have all your playbooks written at once. Start with the most urgent and by leading by example, you’ll inspire other team members to write their own playbooks that can be integrated into your company’s centralized resource hub.
🙏🏼 Special thanks again to Fatema for helping co-author this issue of the newsletter. You can learn more about Fatema and her work, as well as get access to additional Chief of Staff templates here: Inclusive Innovative Templates.
🎥 Upcoming Events and Workshops:
February 1st: Upping Your AI Prompting Game as a Chief of Staff
February 7th: [IN-PERSON] NYC Chief of Staff Happy Hour (approval required for non AaCoS members)
February 15th: Feedback as a Catalyst
February 15th: [IN-PERSON] Chicago Chief of Staff Dinner Party
February 27th: Defining the Chief of Staff Role
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Additional Chief of Staff Related Reads:
The Chief of Staff Role: How To Find the Right Fit in the Interview Process
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