Yes, you have a point
Success with AI is not about the technology itself. It is about how the tool supports your people and advances your strategy.
In this 5-part series, I’m sharing how to use the ALIGN framework to troubleshoot friction in your AI implementation and turn AI into a genuine strategic advantage.
The Absorb phase was about gathering data to understand the current situation. The Legitimize phase is about respecting the people who shared their experiences and perspectives by responding with a clear, prioritized roadmap.
The Reality Check
Launching an AI initiative is an achievement. While we all want projects to go off without a hitch, sometimes we just don’t know things until we start. If outcomes aren’t lining up with expectations, consider it an opportunity to learn rather than a setback. Use this phase to identify gaps and recalibrate.
Gather the feedback you received during the Absorb phase and organize it into these three sources of friction:
Strategy (The "Why"): Feedback regarding high-level goals.
Is the AI helping you move the needle on your core mission, or has it become a distraction?
Execution (The "How" and "When"): Feedback regarding the daily reality.
Is the tool reliable, useful, and credible? Does it fit the workflow, or is it creating "shadow processes" and just too messy to be useful?
Culture (The "Who"): Feedback on how the technology impacts your people.
Is it shifting how you live out your values or how you serve your customers and staff?
Do customers and/or staff feel undervalued, or ignored. Do staff staff feel like their jobs are threatened?
Make clear the Gaps
Use this simple audit for each major feature to highlight exactly where the project is falling short of the vision:
The Reality Gap:
What we planned: AI reduces administrative burden by 30%.
What we observed: Staff are spending 40% more time "babysitting" the AI's output.
The Verdict: The tool is functioning, but the data is unreliable.
Individually Review the data
Each leadership team member should review on their own the data collected during the Absorb phase. This includes insights from:
Direct Conversations with project teams and users.
Note on Responsibility: Use discretion regarding names in the report. People can become fixated on "Who said that?" rather than "What is the problem?" If the culture has a tendency toward this, the person compiling the report should keep the findings focused on high-level themes.
Feedback from impacted staff and customers.
Data Trends and technical performance metrics.
Direct Observations of the tool being used in daily workflows.
Reviewing this individually first allows leaders to process the "unfiltered truth" before the pressure of a group meeting begins. Some folks may feel "under fire," so it is best not to do this as a group initially. If the Project Sponsor is not on the senior leadership team, I recommend they be included in the review from the beginning. If that is not congruent with current practices, bring them in as soon as possible.
Lead with a desire to understand and empathy
The Empathy Filter: Appreciate the role and status of the person who shared the data. It may be anonymous, or it may be clearly identifed. Consider that each person is offering their “truth” their perspective informed by their experience. Their position, the level of that position, their time with the company, their comfort with AI, their comfort with change all are factors in their responses.
Take an Initial Pass: Mark each item:
✅ This sounds accurate to me.
❓ I need more information.
✖ I don't see this.
THe leadership gut check
“Change starts at the top” is a common refrain. I used to think that simply meant needing a strong sponsor to decree a project’s existence. Now, after years of organizational development and project management, I see it differently.
Leaders are often the primary obstacles to an initiative, sometimes unconsciously, and sometimes consciously as they protect their territory. The tragedy of leadership misalignment is that the staff are always the ones caught in the crossfire.
An effective leader must be brave enough to ask themselves hard questions before walking into the leadership team alignment meeting:
Commitment: How committed am I, truly, to the success of this AI implementation?
The Unspoken: What concerns have I been harboring that I haven’t shared?
Vision: What does success actually look like from the perspective of my specific role?
Self-Reflection: On the whole, am I helping or hindering this implementation?
Leadership Alignment Check: Four Essential Conversations
After the individual team members have had time to digest the information, the leadership team will begin a series of meetings with four distinct conversations to avoid "decision fatigue" and ensure raw data is fully understood before decisions are made or work is prioritized.
Conversation 1: The Pulse (Review the Summary)
Goal: Capture initial reactions without discussion. Look for "Small Wins", the parts that are working, to lead with when you eventually communicate to the organization.
Conversation 2: The Context (Fill in Missing Details)
Goal: Address items marked "Need more information." If the data doesn't exist, establish the metrics you need to track.
Conversation 3: The Reality (Validate Assumptions)
Goal: Compare initial project assumptions against the lived experience of the staff. What did we get right? Where were we blindsided?
Conversation 4: The Alignment (Identify Priorities & Root Causes)
Goal: Reach consensus on the "Why" we are doing this AI implementation and why we are having these issues. If leaders disagree on either the purpose or the root cause of problems, the resulting roadmap will be disjointed and the staff will get caught in the middle.
The Technical Reality Check: AI Recalibrations
Before prioritizing, apply a technical lens to determine if the friction is a human, data, or tool problem. This ensures your roadmap is grounded in reality:
Instruction vs. Tool Failure: Is the AI failing, or is the "prompt" simply missing context? If it’s an instruction issue, the fix is better templates, not a new tool.
The "Fabrication" Audit: Identify where the AI is generating confidently incorrect fabrications or "Logic Breaks." These are non-negotiable risks. Move them to "Stops" or "Mystery" immediately.
Data Foundation Debt: Is the AI underperforming because internal data is messy? You may need to prioritize "cleaning the house" before the technology can deliver.
The Prioritization Filter
Now, filter the remaining feedback and technical requirements through the lens of Strategic Impact vs. Effort. At this stage, our goal is stabilization. We must address areas of frustration quickly so that people don't disengage from using the AI.
The "Maintains": Start by identifying what is working well. These "Bright Spots" build confidence and provide a stable baseline for the team to lean on while other areas are fixed.
The "Stops": Features causing enough friction to degrade the customer experience or data integrity. Once you've acknowledged the wins, you can objectively decide what to pause or pivot immediately to stop the "bleeding."
The "Nuance Gaps": Manual workarounds necessary because the AI doesn't understand the job. These require training or process adjustments to eventually move them into the "Maintains" category.
The "Mystery": Issues where you aren't sure of the root cause; give these more time with guardrails before deciding their permanent home.
The Responsive Roadmap
A roadmap in the ALIGN framework is a commitment.
Immediate Fixes: Address the top 1–2 "Blockers" to show momentum and build trust.
Strategic Adjustments: Realign the AI’s role to support the actual nuances of the work you identified in the Absorb phase.
The Commitment: Explicitly state what you are not doing right now, so the team knows where to focus their energy.
It is really important to attach a high level timeline to the roadmap so that people know relief is on its way.
The Strategic Project Sponsor: Anchoring the Realignment
When the C-Suite recommits to the priorities, it is a good time to take a look at the project sponsor. It is common to appoint the CTO as the default Sponsor for AI just to get it off the ground, but as the project’s impact becomes clearer, you may realize the true owner should be the person who "owns" the specific strategic pillar the AI is meant to support.
The best Sponsor is the person who has the most to lose if the strategic goal isn't met. If the AI's goal is to reduce customer churn, the Head of Customer Success should likely be the Sponsor, with the CTO as a key Strategic Partner.
The Immediate Focus of the Strategic Sponsor:
Before the roadmap is finalized, the Sponsor brings it to the project team for a "sanity check." By seeking their input on potential technical hurdles or "tweaks" before the final stamp of approval, the Sponsor demonstrates respect for the team’s expertise and ensures the plan is actually executable.
They serve as the vital link between leadership’s vision and the project team’s reality. They ensure the C-Suite understands the technical "cost" of strategic pivots, while ensuring the project team understands the "why" behind shifting priorities.
They ensure the "Stops" actually stop and the "Maintains" are protected.
They protect the Project Manager and technical team from "scope creep" and competing departmental "asks" while the system is being stabilized.
Communicating the Road Map and Next steps
Legitimize is the practice of validating your team’s feedback, aligning leadership around immediate priorities and creating a prioritized roadmap to swiftly address concerns and limit frustration.
Staff will want to to know if they were really heard, and what is going to be done about it.
Deciding who communicates “Yeah - you have a point” is a strategic decision that depends on the level of disruption to customers and to staff. If this project resulted in High-Stakes Disruption to customers and/or to staff, breaking the trust of the customer, causing deep frustration, the CEO needs to be the one to step up. When the CEO validates the team's lived experience, it provides the psychological safety needed for everyone to re-engage.
If the issues were caught before things went entirely off the rails, then the project sponsor can likely communicate the priorities and road map with high level next steps to the staff. It is something you are going to want to thoughtfully consider to ensure a continuation of trust and buy-in.
The Goal: A Calibrated Ecosystem
If people must overextend themselves to meet a technology, the system is not correctly calibrated. In a well-calibrated ecosystem, technology supports the strategy and the people. When we align these elements, we fix a project and we build an organization capable of turning any disruption into a new way to thrive.
Next Post: Integrate. We will explore how the project team and impacted staff turn these priorities into actionable steps and daily practices.