Chapter 8: The First 90 Days — A Tactical Playbook

The Clock Starts Now

The first 90 days in a Legal Ops role are critical to building momentum and establishing credibility. Stakeholders — the GC, CFO, business leaders — form their assessment of Legal Ops' value within the first quarter. A clear plan, disciplined execution, and visible results in Days 1-90 establish the foundation for sustained influence and budget approval.

This playbook divides the 90 days into three phases, each borrowing from a proven methodology: Design Thinking for discovery, Lean Startup for strategy, and Agile for execution. The phases are sequential — each builds on the outputs of the prior phase.

Days 1-30: Design Thinking (Discovery)

The Objective

Understand the current state with empiricism, not assumption. Gather data on how the legal function actually operates, where it creates value, where friction exists that slows business outcomes, and what the rest of the business perceives about the legal function.

The Empathy Interview Circuit

Schedule 30-minute interviews with every key stakeholder who interacts with the legal department. The target list:

• GC / Chief Legal Officer: Strategic priorities, pain points, political landscape, budget constraints
• CFO / Finance Director: Views on legal spend, accruals quality, budget forecasting reliability
• Head of Sales / Commercial: Contract cycle time experience, legal bottleneck perceptions
• Head of HR: Employment law support quality, policy maintenance, tribunal preparedness
• Head of IT / CTO: Technology stack, integration points, data governance, security requirements
• Head of Procurement: Vendor management overlap, billing systems, ALSP relationships
• 2-3 lawyers on the legal team: Day-to-day workflow reality, tool frustrations, process pain points
• 2-3 paralegals / legal support: Administrative burden, system gaps, knowledge access

The interview format is structured but conversational. Three core questions drive every conversation:

"What does legal do well for you?" This reveals the function's perceived strengths and existing value that must be protected during any transformation.

"Where does legal slow you down?" This surfaces opportunities for improvement — and the answers will cluster around predictable themes: contract turnaround time, approval workflow complexity, responsiveness timelines, and self-service capability gaps.

"If you could change one thing about how you interact with legal, what would it be?" This is the diagnostic gold. The single-change question forces prioritisation and reveals the highest-impact improvement opportunity.

The Dark Data Audit

While conducting interviews, simultaneously audit the legal function's data landscape. "Dark data" is the institutional information that exists but is inaccessible, unstructured, or unknown:

• Matter data: Where is it stored? Is it in a matter management system, spreadsheets, email folders, or individual lawyers' personal files?
• Contract data: How many active contracts exist? Where are they stored? Is metadata (party names, key dates, value, governing law) structured and searchable?
• Spend data: Is external counsel spend tracked centrally with standardised coding? Or is it distributed across individual cost centre budgets with no aggregation?
• Knowledge assets: Where do templates, playbooks, and policy documents live? When were they last updated? Who owns them?

The Dark Data Audit produces a heat map of information accessibility: what you can find, what you know exists but cannot access, and what you suspect exists but cannot confirm. This heat map directly informs technology and data strategy in Phase 2.

Deliverable: The Discovery Report

At the end of Day 30, produce a concise (5-7 page) Discovery Report summarising:

• Key themes from stakeholder interviews (anonymised where appropriate)
• The Dark Data heat map
• The top 5 pain points by frequency and impact
• Initial observations on the maturity baseline (referencing the CLOC/ACC frameworks from Chapter 3)
• A preliminary list of "Quick Win" candidates — improvements that are high-impact, low-effort, and achievable within 60 days

Share this report with the GC. It demonstrates rigour, establishes a shared fact base, and creates accountability for the strategy phase that follows.

Days 31-60: Lean Startup (Strategy)

The Objective

Translate discovery findings into a prioritised strategy and roadmap. Define what to do, what not to do, and in what sequence.

Strategy Formulation: The Priority Matrix

Map every identified opportunity and pain point onto a 2x2 matrix:

The Priority Matrix is a communication tool as much as a planning tool. Showing the GC and CFO that you have systematically evaluated opportunities and consciously decided what not to pursue builds confidence in your judgment.

Strategic Deferral: The "Not Yet" List

The "Not Yet" list is the most underappreciated output of the strategy phase. It explicitly names initiatives that will be pursued after Months 1-12 rather than immediately, and explains the sequencing logic. Common "Not Yet" candidates include:

• Technology deployments that require process design first (CLM after contract processes are mapped and optimised)
• Enterprise-wide rollouts that benefit from pilot validation first (organisation-wide AI deployment after a controlled proof of concept proves value)
• Projects inherited from prior leadership that do not align with current strategic priorities
• Vendor relationships that carry political importance but lack economic justification

Documenting the "Not Yet" list protects the Legal Ops leader from scope creep and provides a defensible basis for sequencing initiatives effectively. It communicates strategic discipline: you have chosen which battles to fight first.

Process Mapping Sprint

Select the top 2-3 processes identified in Phase 1 and conduct the process mapping exercise described in Chapter 6. The output is a documented "as-is" and a proposed "to-be" for each process, with a clear articulation of the time, cost, or quality improvement the redesign will deliver.

Technology Assessment

Based on the process maps and the Dark Data Audit, assess whether existing technology is under-utilised (a common finding) or whether new technology is genuinely required. The assessment framework:

1. Do we already own a tool that does this? Many legal departments have technology licences that are partially or entirely unused. Check existing licences before issuing RFPs.

2. Can we solve this with configuration, not acquisition? Often, the existing tool can be configured or extended to address the requirement. A SharePoint site with a decision tree may fully address the knowledge base need without requiring a dedicated platform.

3. If we need new technology, what is the minimum viable deployment? Start small. A CLM pilot with one contract type and one business unit proves value faster and at lower risk than a full enterprise rollout.

Deliverable: The 12-Month Roadmap

At the end of Day 60, present a 12-month roadmap to the GC and, ideally, the CFO. The roadmap should contain:

• 3-5 Quick Wins to be delivered in Days 61-90
• 2-3 Strategic Projects to be scoped and initiated in Months 4-6
• The No-Go list with rationale
• A preliminary budget (or resource request) for Months 4-12
• Success metrics for each initiative

Days 61-90: Agile (Execution)

The Objective

Deliver visible, measurable results. The Quick Wins identified in Phase 2 are the vehicle.

Quick Win Selection Criteria

A genuine Quick Win meets all four criteria:

• Visible: The improvement is noticed by stakeholders beyond the legal team
• Measurable: The benefit can be quantified (time saved, cost reduced, satisfaction improved)
• Achievable: It can be delivered within 30 days with existing resources and authority
• Low-risk: Failure does not create a worse situation than the status quo

Common Quick Wins

Standardised NDA template and self-serve workflow. If the organisation processes more than 50 NDAs per year and lawyers are reviewing each one individually, a standardised template with a self-serve intake form can be deployed in 2-3 weeks. The visible impact — business users getting NDAs in hours instead of days — is immediately noticed by the commercial team.

Legal intake portal. Replace the multi-channel request chaos (email, Slack, phone, hallway) with a single intake form that categorises, routes, and tracks requests. Achievable with existing tools (Jira, ServiceNow, or even a well-structured Microsoft Form) within 2-4 weeks.

Spend dashboard. Aggregate existing e-billing or invoice data into a single visual dashboard showing spend by firm, practice area, and matter type. Even a basic Excel or Power BI dashboard, produced in 1-2 weeks, transforms the CFO conversation from "we think we spent about $X" to "here is exactly where the money went."

Outside counsel billing guideline enforcement. If OCBGs exist but are not actively enforced, select the three most common violations, communicate the enforcement standard to panel firms, and begin flagging non-compliant invoices. This can be done manually as a bridge to automated e-billing enforcement.

The Feedback Loop

Agile execution requires a tight feedback loop. For each Quick Win:

• Define the success metric before launch
• Measure weekly during the 30-day execution window
• Conduct a brief retrospective at the end: what worked, what didn't, what to adjust for the next initiative
• Communicate results to stakeholders explicitly — do not assume they will notice

In the Trenches

The 90-Day Turnaround

Anika Singh was hired as the first-ever Head of Legal Ops at a 600-person Australian professional services firm. The legal team of four lawyers operated with minimal technology infrastructure (Microsoft Office only), no documented processes, and spend visibility limited to annual budget allocation. The GC who hired her set a clear expectation: "The CEO expects us to demonstrate the value of this role within the first quarter."

Anika ran 18 empathy interviews in her first three weeks. The most consistent theme: the sales team waited an average of 11 days for contract turnaround, which translated to lost sales cycles. The Dark Data Audit revealed a significant asset: 2,400 contracts existed in a shared drive but lacked structured metadata, obligation tracking systems, and template standardisation — a foundation ready to be organised and leveraged.

Her 12-month roadmap included a CLM deployment (Strategic Project, Month 6), a panel rationalisation (Strategic Project, Month 8), and a legal analytics programme (Strategic Project, Month 10). Her No-Go list explicitly deferred AI tools until the data foundation was in place.

For her Quick Wins, she chose three: (1) a standardised services agreement template with pre-approved deviation ranges, deployed through a simple Word template with a one-page user guide; (2) a legal intake form on Microsoft Forms, connected to a shared Planner board for queue visibility; and (3) a monthly spend summary sent to the CFO, built from manually aggregated invoice data.

The services agreement template alone reduced average contract turnaround from 11 days to 4 days for standard deals. The intake form gave the legal team visibility into its queue for the first time — and revealed that 30% of incoming requests were duplicates or could be resolved with a policy FAQ (which became the foundation for a knowledge base in Month 5). The CFO received her first-ever monthly legal spend report and, in Anika's words, "looked at me like I had performed a magic trick."

The CEO renewed the Legal Ops mandate at the 90-day review. The role was made permanent, and the budget for the 12-month roadmap was approved.

The Monday Morning Checklist

• Schedule your first five empathy interviews this week. Start with the GC, CFO, and Head of Sales. Use the three core questions. Take notes, not recordings — the informality builds trust.
• Start the Dark Data Audit. Open your legal team's shared drive, matter management system, or email archive and answer: Can you find every active contract? Can you determine total external spend for last quarter? Can you locate the current version of every template? The gaps you identify are your data strategy priorities.
• Draft your Priority Matrix. Even before completing all interviews, begin mapping what you already know about pain points onto the 2x2. This gives you a working hypothesis to test and refine as you gather more data.
• Identify one Quick Win you can deliver in 30 days. It should meet all four criteria: visible, measurable, achievable, and low-risk. Commit to it, resource it, and communicate it. Your credibility depends on delivering at least one tangible result before Day 90.