30-60-90 Day Plan for New Enablement Leaders (Book Guide)

Stepping into a new enablement leadership role is both exciting and daunting. You’re tasked with driving adoption, improving performance, and influencing revenue outcomes, often without a clear roadmap for how to start. That’s exactly why this guide exists.

This 30-60-90 day playbook is built on the research, frameworks, and best practices from Just-in-Time: The Future of Enablement in a World of AI. Each recommendation in the plan ties back to proven concepts and strategies outlined in the book, ensuring you’re not just following a checklist, but applying a science-backed, field-tested approach to building a modern enablement function.

Throughout the guide, you’ll see references to specific chapters and page numbers, so you can dive deeper into the full context as you execute.

By anchoring your first 90 days in these practices, you’ll avoid the pitfalls of “reactive enablement” and instead position yourself as a Sales Performance Architect (pp. 152–153), someone who designs systems that drive lasting results, not just one-off programs.

This playbook is not meant to replace the book; it’s designed as a quick-reference companion. Use it to guide your actions in the first 90 days, while turning back to the book for stories, examples, and deeper insights into why these strategies work.

First 30 Days: Listen, Learn & Build Trust

🔑 Priorities: Understand the landscape, build credibility, and uncover productivity killers.

Establish relationships with sales, marketing, and product stakeholders — you’ll need them aligned for your roadmap.
Influence leadership through insights (p. 159): Begin by listening to sales calls (1–5 per week). Share weekly trend emails with sales leadership — competitive intel, objections, and suggested enablement actions. This positions you as a trusted advisor early.
Meet with Managers 1-1 and Shadow your reps (p. 161): Sit with 1–2 reps weekly. Observe workflows, ask about prospecting approaches, and identify workarounds outside of the CRM. These insights will uncover hidden enablement gaps and help you build trust.
Run a time-and-click study( p.62): Shadow a rep preparing for a call, measure the number of tabs opened, clicks made, and time wasted. This quickly uncovers productivity barriers.
Gather feedback (p. 162): Use bite-sized surveys (<5 questions, <2 minutes) to capture rep perspectives on onboarding and training. Feedback should shape your early roadmap.
Audit content & tools (pp. 167–168): Begin mapping where outdated or duplicative resources live. Look for “shiny object” tools that add more friction than value.
Dive into your current enablement platform: Assess adoption rates (daily active usage), feature usage, content quality and freshness. Talk to your sales leaders, marketing peers and reps to get a pulse on it. If you want your enablement programs to be successful, they need to like it and use it.

✅ Deliverables by Day 30:

A short “State of Enablement” briefing with leadership.
Initial trust and credibility with reps through shadowing.
A prioritized list of enablement gaps (onboarding, content decay, tech complexity).

Days 31–60: Design & Align

🔑 Priorities: Co-create strategy, set up structures, and secure buy-in.

Create a "Sales Excellence" champions council (pp. 164): Include top reps, managers, and skeptics. This group tests initiatives, shares best practices, and builds cultural momentum.
Embrace feedback loops (pp. 161): Establish a cadence of lightweight surveys and informal coffee chats with reps to continuously refine onboarding and content.
Architect, don’t just deliver (pp. 152–156): Avoid the “content hamster wheel.” Move toward a Sales Performance Architect mindset, focusing on systems, not just one-off requests.
Build repeatable change enablement (pp. 120-123): Adopt a T-shirt sizing framework (S/M/L/XL) to roll out changes consistently.

✅ Deliverables by Day 60:

Enablement strategy & roadmap aligned with exec sponsors.
A documented assessment of whether your current platform is meeting your team’s needs, and a recommendation to either optimize usage, retrain, or if necessary reconsider your tech stack (see the bonus section).
Launch your sales champions council and meet biweekly. Use them to validate what’s working, surface gaps, and evangelize new processes.
Change enablement framework drafted and shared.

Days 61–90: Execute, Reinforce & Scale

🔑 Priorities: Deliver quick wins, reinforce through managers, and prove impact.

Once you understand your needs, evaluate whether your current enablement platform is serving you. The
Lead through your leaders (pp. 165–167): Plan reinforcement with the same rigor as kickoff events. Enable managers to reinforce key skills in 1:1s and team meetings. Use Slack channels for reps to share examples and gamify adoption.
Executive reinforcement (pp. 165–167): Encourage leadership to champion enablement by modeling tool usage, dedicating meeting time, recognizing reps, and collaborating closely with you.
Quick win execution (pp. 66): Roll out one high-impact initiative — e.g., embedding contextual content shortcuts in CRM, improving data hygiene, or streamlining onboarding steps.
Measure & communicate impact (pp. 167–168): Track early outcomes (CRM adoption, ramp time, content usage). Share results with leadership and reps to reinforce progress.

✅ Deliverables by Day 90:

Visible quick wins that reduce rep friction.
Reinforcement rhythm embedded in manager cadences.
First enablement impact metrics shared with execs.

Bonus section: How to Evaluate Whether Your Current Enablement Platform is meeting your team's needs

Once you’ve shadowed reps, met with your Sales leaders, gathered feedback, and clarified your enablement needs, the next step is to evaluate whether your current enablement platform is serving you. Too often, organizations get dazzled by feature-rich tools that promise everything but fail to drive adoption or impact in the field.

Ask yourself:

Does the platform reduce cognitive load and context switching for reps (Ch. 4, pp. 80–85)?
Does it provide analytics and feedback loops that help you measure adoption, usage, and performance outcomes (Ch. 9, pp. 144-148)?

📖 For deeper guidance, see Chapter 2, where I highlight the importance of evaluating whether your enablement platform is actually enabling, not hindering.

Pro Tip: Avoid the Shiny Object Trap in Evaluations

As you evaluate platforms, beware of the “shiny object trap”—the tendency to chase new tools because they look impressive in demos or claim AI-powered magic. New platforms can easily become more noise in an already cluttered tech stack.

Instead:

Focus on solving the top 2–3 productivity killers you identified in your first 30 days (pp. 160–161).
Anchor platform evaluations to rep workflows and adoption ease, not feature checklists.
Treat new technology as an insurance policy: it should amplify your investments in CRM, onboarding, and content—not replace them (Ch. 8, pp. 140–142).

It's easy to get dazzled by flashy features and slick demos when evaluating software. To stay focused on your actual needs, create a simple evaluation grid before you embark on demos. Your grid should include:

Top three problems: Clearly define your biggest enablement challenges.
Must-haves: List the non-negotiable capabilities the software must have to address those problems.
Nice-to-haves: Identify any desirable features that would be beneficial but aren't essential.
Top three evaluation criteria: Determine your most important evaluation factors (e.g., ease of use, integrations, pricing, support).

During your evaluation, have each person on your team rank the solution against this criteria on a scale of 1-5. The scores will help provide an objective view on each potential product's effectiveness