The 2026 AI Planning Playbook: Key Considerations
Over the past three years, we’ve had the privilege of working with hundreds of organizations, family-owned businesses, nonprofits, and mid-sized companies across the Midwest. And the message is clear: AI success isn’t about having the biggest budget or the flashiest tools. It’s about being intentional, human-centered, and ready to learn.
The teams that are gaining traction right now are the ones that take a thoughtful, step-by-step approach. They aren’t trying to “do AI” everywhere. They’re identifying real pain points, empowering their employees, and creating space to experiment. They balance curiosity with structure, and excitement with accountability.
Here’s what success looks like in the organizations that are getting this right:
· They start small but start smart—one workflow, one team, one problem at a time.
· They invest in their people as much as their platforms. AI is treated as a skill set, not a shortcut.
· They build guardrails early, aligning AI use with their mission, values, and brand.
· They focus on habits, not hype—creating weekly learning rhythms that stick.
· And they share stories of progress, keeping their teams engaged and momentum high.
We’re watching this play out across every industry: AI is helping leaders and their teams reclaim time, streamline workflows, and spark creativity again. But more importantly, it’s helping organizations rediscover energy and optimism about the future.
2024 was the year most organizations woke up to AI.
2025 became the year of experimenting, testing tools, running pilots, and learning what works.
Now, 2026 is shaping up to be the year of scaling, the year when AI stops being a side project and starts becoming a core capability.
This playbook is designed to help business and nonprofit leaders think beyond the shiny tools and focus on what actually matters: strategy, people, and progress. Whether you’re a CEO, CFO, HR leader, or department head, these themes will help you align your 2026 planning and budgeting around long-term impact, not quick wins.
Use this as a discussion guide for your leadership team, a starting point for budgeting conversations, or a framework to shape your internal AI roadmap.
The em dashes “—” are provided by me. 😉
1. AI as a Strategic Line Item, Not a Tool Expense
AI is no longer something you “try.” It’s something you plan for.
The organizations that are seeing the most value from AI have stopped treating it as an IT experiment and started treating it as a business transformation initiative. That means moving AI from the “software” category into the strategic investment category on par with technology infrastructure, process improvement, and leadership development.
AI touches nearly every corner of an organization’s operations, HR, customer experience, marketing, sales, finance, and more. To manage it well, you need visibility, budget, and governance.
Consider:
Creating a dedicated AI strategy line item that covers advisory, pilots, and employee enablement.
Including AI governance and risk management in annual compliance or IT budgets.
Funding cross-functional collaboration—AI wins happen where teams intersect, not where they’re siloed.
💡 Mindset shift: You’re not “buying tools.” You’re building a smarter organization. Also, read my Stop Viewing AI as a Cost.
2. Upskilling & Habit-Building for Everyone
The biggest barrier to AI adoption isn’t technology, it’s human confidence.
Employees need space and permission to experiment without fear of doing something wrong. In 2026, leading organizations will treat AI learning as a core skill, not a side project.
Training can’t be a one-and-done webinar. It has to be an ongoing rhythm bite-sized, role-specific, and grounded in real work. The goal isn’t to make everyone an AI expert; it’s to make everyone AI-capable in their daily roles.
Consider:
Offering weekly AI learning blocks or “AI Hours” where teams explore new tools together.
Appointing AI champions or ambassadors within each department to guide peers.
Weaving AI discovery into existing professional development and staff meetings.
💡 Ask: How will we build a culture that learns as quickly as technology changes?
If you are in Ohio, apply for Tech Cred to get reimbursed for your AI training.
3. Workflow Transformation & Process Automation
True AI success comes from rethinking work, not just automating it.
As you plan for 2026, take time to evaluate which tasks consume time but don’t add strategic value. That’s where AI can help. The organizations that see the most return are those that integrate AI into workflows not as a gimmick, but as a genuine productivity partner.
Look beyond individual tools to the systems and processes that create bottlenecks. Even small wins automating reporting, email triage, or data entry can compound into major time savings.
Consider:
Mapping your most repetitive or manual processes for potential automation.
Starting pilots with low-risk tasks to build confidence and measure ROI.
Documenting improvements and reinvesting saved time into higher-value work.
💡 Ask: What would our team look like if we automated the 20% of work that slows us down most?
4. Data Readiness & Responsible Use
AI is only as good as the data it’s fed.
For many organizations, data cleanup isn’t exciting, but it’s essential. The quality, accuracy, and accessibility of your data determine whether AI helps or hurts.
Before adding new AI tools, audit where your data lives, who owns it, and how current it is. Organize your knowledge bases, CRMs, and internal documents so they’re searchable and secure. In 2026, leaders will prioritize sources of truth data as the foundation of any AI initiative.
Consider:
Cleaning up and tagging files, shared drives, and CRMs for easy retrieval.
Defining clear AI usage policies, what’s allowed, what’s not, and why.
Strengthening security and privacy protocols before connecting data to AI systems.
💡 Ask: If our AI learned from our current data, would we be proud of what it knows?
5. Pilot & Innovation Budgets
Innovation doesn’t happen by accident. It needs funding, time, and trust.
A small “innovation budget” can give teams permission to explore new ways of working without fear of failure. Treat pilots as learning investments rather than experiments with pressure to produce instant ROI.
Encourage each department to propose one AI-driven pilot that directly solves a pain point. Capture results, celebrate lessons learned, and share them across the organization. The real win is the learning curve you accelerate.
Consider:
Allocating an AI exploration fund to test new tools or processes each quarter.
Hosting AI hackathons or sprint weeks around real business problems.
Using pilot results to inform next year’s larger strategic investments.
💡 Ask: What’s one bold idea we can test in 2026 that could unlock breakthrough efficiency?
6. Tool Consolidation & Integration
AI tools are multiplying faster than most teams can track. The challenge now isn’t choosing the newest—it’s ensuring what you have works together.
A 2026-ready strategy focuses on integration, consolidation, and intentional use.
Before buying something new, review your current tech stack. Many existing platforms (Microsoft, Google, Salesforce, HubSpot) already have AI features waiting to be unlocked. Leaders who streamline their systems reduce confusion, costs, and change fatigue.
Consider:
Conducting an AI tool audit to identify redundancies or overlaps.
Prioritizing tools that connect departments rather than create silos.
Setting annual reviews to evaluate whether tools still meet your needs.
💡 Ask: Are we multiplying tools or magnifying impact?
7. Workforce Planning for the Human + AI Era
AI is changing the way people work.
Leaders who recognize this early will create more adaptable, future-proof organizations. As automation takes on repetitive tasks, employees will need to focus on creativity, decision-making, and human connection—the things machines can’t replicate.
2026 is the time to update job descriptions, workflows, and even org charts to reflect this shift. Introduce roles that bridge people and AI, and make sure employees understand how these changes benefit them, not threaten them.
Consider:
Adding AI-assisted responsibilities to existing job descriptions.
Creating new roles like AI Operations Lead.
Including AI proficiency in performance and development plans.
💡 Ask: How will we prepare our people to thrive alongside AI not compete with it?
8. Measuring AI ROI & Adoption
What gets measured gets improved.
Without metrics, AI initiatives risk fizzling out after the novelty wears off. Leaders need to define what success looks like both in performance and in culture.
AI ROI isn’t just dollars saved; it is also hours returned, decisions accelerated, lessening the mental load and employee confidence improved. Establish a few key metrics, measure quarterly, and adjust as you learn.
Consider:
Taking a baseline snapshot of current productivity and workflows.
Measuring both quantitative (time saved, accuracy improved) and qualitative (employee sentiment) impacts.
Using an AI scorecard to track department progress and share wins.
💡 Ask: What stories do our numbers tell about how AI is transforming our work?
9. Governance, Ethics, and Trust
As AI adoption grows, so does responsibility.
Customers, donors, and employees are paying attention to how organizations use AI. Transparency, fairness, and accountability aren’t optional, they’re essential for long-term trust.
Establishing clear governance now will protect your brand and reputation later. Whether you’re a nonprofit handling donor data or a business managing customer interactions, define how AI aligns with your organization’s values.
Consider:
Drafting a clear AI use policy that sets expectations and guardrails.
Forming a small AI council or review committee to evaluate new use cases.
Auditing systems regularly to ensure accuracy, fairness, and compliance.
💡 Ask: Does our use of AI strengthen trust with the people we serve or put it at risk?
Think of your AI journey as a maturity curve:
Awareness – learning what’s possible
Adoption – testing and building comfort
Integration – embedding AI into workflows
Optimization – measuring and scaling what works
2026 is the year to move confidently from experimentation to integration. Every small step you take now compounds into future readiness.
AI is not about doing everything faster; it’s about doing the right things smarter.
As you plan for 2026, ask yourself:
“How can we use AI to elevate our people, strengthen our mission, and make work more meaningful?”
That’s how you future-proof your organization and your leadership.
I can’t wait to hear about your AI planning and impact.
If this feels daunting, we can help you navigate this AI journey together!
2025 AI Adventures
November
November 12 Taste of IT in Dayton https://www.technologyfirst.org/toit
November 13 Cincinnati Game Changer AI session 1:15-2:45 at Paycor
November 19 Ohio AI Summit https://www.ohioaisummit.org/
December
December 2 CincyAI 3-5 at UC Digital Futures. In-person event. 1900 members and 160 people attend every month. https://www.eventbrite.com/e/1505087259509?aff=oddtdtcreator We just finalized our 2026 dates. See the CincyAI newsletter for all the details.
I love answering your AI questions. Feel free to message me.
Where AI and inspiration collide!
Kendra Ramirez
KendraRamirez.com
We provide AI Speaking and Training, AI Readiness, AI Strategy, AI Roadmap, Workflow Automation, and Implementation.
**For those new to my work, I have been in tech my whole career. Over 15 years of running my digital agency (website, social media, and lead generation) and 7 years of helping businesses navigate AI. Over the past two and a half years and, I’ve had the privilege of leading over 160 training and speaking sessions, empowering businesses to embrace the transformative potential of AI. My passion lies in simplifying complex technologies to help organizations grow, innovate, and thrive.
I am so excited that you are on this journey with me! Thank you! 🤗
I have been writing weekly about AI here for over two years. You can search all of my enewsletters here if you are looking to brush up on a certain topic. kendratech.substack.com