The Power of Legal Team Playbooks: Insights From The L Suite Community

I think of playbooks as an act of empathy for our future selves: The version of you who dreams of one day, maybe even soon, going on vacation. The iteration of your team that's expanding and taking on half a dozen new hires. Or, your company six months from now, navigating hyper-growth mode or a high-profile acquisition.

Playbooks can create continuity, efficiency, and more streamlined communication within your legal team and across departments, making them an essential tool for just about any sized organization. But that's not to say they're all-powerful — a playbook does little good if it ends up filed away somewhere gathering dust.

As the Chief Legal Officer at Gusto, I've experienced the power of well-crafted legal team playbooks and how they can help enable the business. Recently, I had the opportunity to discuss this topic with Peter Wei, head of legal at Octaura, in a panel facilitated by The L Suite. Read on for a recap of our conversation.

Key Takeaways:

• Identify specific pain points and goals at the onset. Ask pointed questions like "What problem am I trying to solve?" and "Who is my audience?" to ensure your playbook addresses real needs.

• Collaborate across teams when developing playbooks. Include stakeholders from relevant departments early and often to improve efficacy and boost buy-in.

• Treat playbooks as living, breathing documents by establishing clear processes for feedback, updates, and version control. Be sure each playbook has an "owner" in charge of maintenance.

• Track metrics like time saved on specific legal tasks to demonstrate ROI and justify the resources invested.

• Work out a system for deprecation, and keep in mind that different playbooks may require different levels of formality for this process.

The Playbook's Purpose

Playbooks provide structured approaches to repeatable challenges or high-stakes situations that recur regularly but infrequently, like annual SEC audits. They can be an incredible time-saver — but only when designed and implemented with intention and strategic thinking. On our legal team at Gusto, our plates are full every day, so the last thing we want to do is create a superfluous process for the sake of process.

In general, a playbook can serve multiple purposes, including:

1. Scaling operations: It allows you to amplify your team’s impact without increasing headcount.

2. Consistency: It ensures your business approaches recurrent legal issues in a unified manner.

3. Onboarding and knowledge transfer: It facilitates smoother transitions when team members join or leave.

4. Risk management: It helps you identify or mitigate potential legal risks more systematically.

For Wei, who leads a small team, playbooks are also crucial for running a legal department with limited resources. "The playbook is an essential tool in our repertoire to ensure we get as much coverage as possible, rope in stakeholders, and magnify the impact we bring to the table,” he said during our panel discussion, noting that at Octaura, it's helped his team move agreements faster, assess risks better, and build processes for other departments to ensure nothing falls through the cracks.

Specific Playbook Use Cases

Some playbooks focus on internal processes for common legal tasks or challenges like incident response. Others are more business-facing — a tool for collaboratively addressing contracts and deals, for instance. A playbook may even be something you share with the board to get everyone on the same page about cybersecurity or other critical issues. The way you design your playbook will largely depend on the people who will be engaging with it.

Below is an incomplete list of potential use cases and issues you can document or codify using playbooks:

• Contractual terms standardizations

• Agreement negotiations

• Litigation management strategies

• Incident response procedures

• Strategic deals and M&A processes

• Cybersecurity response plans

• Compliance procedures

• Product team collaborations

• Acqui-hire processes

• Outside counsel and vendor management

Make Your Life Easier With Auditors and Outside Counsel

In the event of regulatory scrutiny, a thorough playbook shows good-faith intent to comply, support customers, and do the right thing by the law.

On this note, keep in mind that playbooks are usually not privileged. They may be discoverable in litigation or subject to regulatory review, so ensure their content aligns with your company's policies and legal obligations.

Additionally, playbooks are a valuable tool for engaging with outside counsel. A comprehensive playbook is a place to keep an ongoing list of approved firms, processes for onboarding additional legal support, budget guidelines, and invoice review procedures.

Playbooks vs. SOPs

Playbooks are usually more flexible and actionable than standard operating procedures (SOPs). While SOPs tend to be more rigid, high-level policies that explain what a company or team does, playbooks provide practical, hands-on guidance. They can also cover both procedural and substantive topics, allowing for more diverse applications.

And unlike policies, which may not directly help employees perform their jobs, playbooks are designed to be immediately useful. As Wei put it, “Coming from the banking sector, when there was a policy and a procedure for everything, playbooks sort of fill in those gaps.” They can serve as educational tools, addressing business needs and evolving based on feedback.

The Playbook Planning Process: Ask Pointed Questions and Take Stock

The last thing you want to do is spend hours creating beautiful, useless documents. Before diving into creating a playbook, take stock of what already exists within your organization, and get clear on the main pain points a playbook will help solve.

A few core questions to ask include:

• What is this meant to do, and what problem are we trying to solve?

• Is this addressing a repeatable pain point?

• What's the most immediate or specific issue this can address?

• Who is the audience — e.g., is it the internal legal team, sales, product, marketing, or some combination?

• Who will “own” this playbook in terms of updates and maintenance?

• How much training will be needed to implement this?

From there, you can start to outline your playbook's structure, content, and logistics like where it will live. For instance, will it consist of fillable templates that provide quick, actionable guidance? Or will it be a more comprehensive guide? Will it live on Google Docs or third-party software your company already uses?

For routine, high-volume tasks like responding to customer complaints, a specific process or template might be more effective than a comprehensive playbook. In contrast, complex, strategic deals might necessitate a more detailed playbook covering multiple lifecycle stages.

Think Collaboratively and Get Buy-In

Designing playbooks usually requires working alongside other teams like product, privacy, commercial, or compliance. Connecting the dots across departments improves the playbook's potential effectiveness — and the likelihood that people will really use it.

Further, people absorb material differently when they're included in the process of creating it, versus simply being handed a document and told to comply. When crafting your playbook, include the audiences who will be engaging with it early and often — even make them part of the experience of writing it, if possible. This can also help ensure you're using language everyone understands (and avoiding legalese as much as possible).

This type of collaboration is also a chance to demonstrate the playbook's value from the get-go. If you're implementing a contract review process to streamline deals, for instance, having the head of sales on board from the start can showcase how the system will help them close new business faster. Or, for a comms compliance playbook, collaborating with the marketing team can illustrate how they'll be able to get campaigns out the door more efficiently.

For Wei at Octaura, the first playbook he developed was for the go-to-market team. Clear communication with the company's higher-ups and go-to-market team members helped ensure everything went off without a hitch. "I had buy-in from the leadership team, and they understood that the goal wasn't to offload important work," he said. "I made it very clear that I'd still be doing final reviews, but that there was a lot of initial back and forth that could be cut out." He also held a candid conversation with the go-to-market team to secure their support, emphasizing that the playbook would ultimately give them greater autonomy and speed up their processes.

Learn from Your Peers' Experiences

Wei started building his first playbook for Octaura shortly after becoming a member of The L Suite — he noted that the community's Braintrust forums were instrumental in this process. "I was able to easily search for the keyword 'playbook,' go through existing documents to understand the frameworks that were out there, and learn what my fellow peers were thinking about," he said, noting that his end playbook involved an amalgamation of several different templates suggested by others and documents from the company's own paper stack.

Implement, Maintain, and Iterate

A playbook isn't a static document — it's a living, breathing resource. To keep it useful and relevant, you need training and feedback protocols.

As part of this process, Wei recommended doing tabletop exercises with the tech team to test and refine the playbook. "I find that the tech folks are great at poking holes into a process and how you've structured something, and thinking of loopholes — it's part of their job. I sometimes think that's where the best documents come out of."

You should also implement regular reviews to ensure the content stays accurate and relevant. Establish a clear process for suggesting and making updates, and maintain a system for tracking changes and ensuring everyone has access to the most current version.

Measure Success and ROI

If you have data to support how a playbook actually helped make something better, faster, or stronger, it will help make that all-important organizational buy-in easier to secure in the future.

A few metrics you may consider monitoring include:

• Time saved on routine tasks

• Reduction in response times to legal inquiries

• Improved consistency in contract terms or negotiation outcomes

• Positive feedback from business partners

You can monitor these metrics through regular surveys, SLAs, and feedback sessions with your team and business partners. Consistently measuring and reporting on these metrics will help demonstrate the continuous value of your playbooks.

Define the Deprecation Process

Just as your team's goals and organization's larger business objectives change over time, your playbooks will need to evolve. It's important to have a formal process for retiring outdated elements or sections.

You can prioritize deprecation based on risk and impact. For high-level policies that impact the broader company and employees like a code of conduct, a formal deprecation process is critical. Further, for heavily regulated industries, documentation of policy changes is always a good idea. "For any institution that has regulators (or a threat of regulators) who come in annually, you better be able to explain how and why you decided a particular policy is no longer in play," said Wei.

Tactically, deprecated playbooks can include moving items to a specific folder or archiving them in a document management system; the most important aspect is ensuring people know which version is current.

As much as playbooks are an ongoing journey, they're also a testament to progress and forward momentum. Ultimately, they're part of your team and company's maturation process. Celebrate this maturity by making playbooks part of the culture. They'll ultimately drive huge benefits that extend far beyond legal — and that your future self will be incredibly grateful for.

For GCs and CLOs looking to connect with other legal professionals about the power of playbooks, The L Suite can offer helpful resources. Apply to join today.

About The L Suite

Called “the gold standard for legal peer groups” and “one of the best professional growth investments an in-house attorney can make,” The L Suite is an invitation-only community for in-house legal executives. Over 4,000 members have access to 300+ world-class events per year, a robust online platform where leaders ask and answer pressing questions and share exclusive resources, and industry- and location-based salary survey data.

For more information, visit lsuite.co.