AI has secured a meaningful place in the leadership toolkit, helping to expand and pressure-test strategy, but widely used AI tools usually struggle with Priorities and KPIs unless they are given the right context.
When used well, AI accelerates thinking. It helps pressure-test ideas, surface alternatives, and tighten language. Used poorly, it creates polished output that sounds confident, but doesn’t translate into meaningful execution.
Closing that gap requires feeding the tool the right inputs so it understands how your business runs and can give you feedback that actually helps you and your team execute the plans you’ve put so much time into designing.
When AI Falls Short
You start with a new chat, eager to solve a problem. You paste in a paragraph about a challenge, maybe a strategic draft, or a quick list of priorities. Sometimes it’s a KPI list pulled from a slide deck or your full strategic plan presentation.
Regardless of what you give it, the inputs are almost always situational, not structural.
A tool like ChatGPT can help you brainstorm, reflect on ideas, organize your language, or suggest options you haven’t considered. Sometimes you give it context, like a description of the company and industry or a strategy document or planning slide, but most don’t go this far.
Very few companies give their AI tool a clear picture of how decisions are made, how priorities cascade, or how execution is reviewed week to week. The tool is asked to reason without being taught how the business actually runs. This is why AI tools usually struggle with priorities and KPIs
The prompt usually sounds like, “Can you clean this up?” or “What am I missing?” or “Help me think through this.”
It’s a generic question, so the output feels generic, too. In turn, the user tries to feed in more background.
They explain why certain ideas won’t work.
They clarify constraints after the tool has suggested them.
Prompting becomes longer and more detailed, but still episodic. Each conversation feels like a one-off, and the user has to re-teach the same context again and again.
This is the point where many teams conclude that “prompting is the hard part.”
In reality, what’s hard is that the uniqueness of your business lives in your head, not in a form that the AI can consistently reference.
The tool will ask questions that feel helpful, but they aren’t useful. They don’t reflect the tradeoffs you’ve already made or the constraints your company operates under. They sound like questions someone would ask if they had just been introduced to your business five minutes ago.
That’s because, in a very real sense, they have.
AI tools don’t know your business unless you teach them. And most leaders underestimate how much of their strategy lives outside formal documents.
AI Only Works With the Inputs You Give It
There’s an assumption that AI struggles because prompts aren’t specific enough.
That assumption is partially true, but incomplete.
The deeper issue is that AI lacks access to the experience CEOs and leaders bring. It doesn’t know why certain initiatives were abandoned, which metrics caused past distractions, or where execution consistently breaks down.
OpenAI CEO Sam Altman has emphasized that AI systems operate based on the data and input they receive, and that they do not inherently “understand” user intent beyond what is made explicit in prompts. In reporting on his remarks, The Guardian summarizes Altman’s point that large language models “operate on pattern recognition rather than understanding,” and they are “only as good or as accurate as the information with which they are provided.”
That matters at the executive level with regard to strategy, and the priorities and KPI’s that drive it.
Strategy is not a set of instructions. It’s a set of choices made over time. AI can reason extremely well, but it cannot infer which choices matter most without being told.
Why Prompting Becomes a Leadership Problem
Prompting issues become most visible when CEOs and leaders use AI for priorities and KPIs.
These aren’t brainstorming exercises. They are mechanisms for focus, accountability, and execution. A priority that lacks grounding becomes a theme. A KPI without context becomes a number that gets reviewed and ignored.
When AI doesn’t understand your strategic intent, it defaults to safe assumptions. It optimizes for balance. It tries to be comprehensive with it’s suggestions.
Those qualities sound responsible. However, in practice, they dilute focus.
The AI output improves the language of priorities but weakens their impact. The words get prettier, but the decision gets softer.
The Continuous Suggestion Problem
Many CEOs notice the issue when AI starts pushing back.
The tool might ask clarifying questions about goals, stakeholders, timelines, or success metrics. At first, this feels helpful. On closer inspection, it’s a sign the AI is still orienting itself.
It doesn’t know which constraints are fixed and which are flexible. It doesn’t know which outcomes matter more. And it doesn’t know what “good enough” looks like in your operating reality. It’s designed to continually suggest.
So it keeps circling.
The conversation becomes iterative because context is missing. Leaders either over-prompt, pasting in long explanations every time, or under-prompt and accept output that feels polished but shallow.
Neither approach scales.
The Hidden Cost of “Getting Better at Prompting”
Some leaders respond by investing significant effort into prompting.
They upload strategy decks. They explain past decisions. They correct assumptions. They restate priorities again and again, hoping to anchor the conversation.
And it works—to a point.
AI becomes more informed. Outputs improve. The questions get closer to the mark.
But there’s a cost most leaders don’t account for.
The leader becomes the system.
Every new prompt requires re-anchoring. Every new session risks losing context. Insight improves, but consistency depends entirely on the leader’s attention. Instead of saving time, AI begins to demand it.
Prompting turns into another time thief for executives.
Inputs Matter More Than Clever Prompts
When AI does deliver value for leaders, it’s rarely because the prompt was clever. It’s because the inputs were grounded.
Effective AI interactions tend to include three types of signals.
First, explicit tradeoffs. Not aspirations, but decisions already made. What the company is prioritizing instead of something else.
Second, ownership clarity. Who owns the outcome when progress stalls. Not the department, but the role or individual accountable.
Third, execution rhythm. How priorities and KPIs are reviewed, challenged, and adjusted over time.
Without these inputs, AI can help articulate ideas, but it can’t help leaders execute them.
Why Execution Context Changes Everything
The power of AI is far more useful when it operates inside an execution system rather than alongside it. When strategy, priorities, and ownership already exist in one place, AI no longer has to infer how the business works. It can reason within constraints that actually reflect reality.
This is where leaders realize that the core issue isn’t AI capability. It’s fragmentation:
Strategy lives in a document. KPIs live in a spreadsheet. Meetings are held live or via Zoom, with various versions of notes being taken. And AI sits outside all of it, trying to reconstruct reality from a text box.
That’s an impossible job.
How AI Tools Can Reduce Friction
The most impactful AI tools are designed to operate where execution already happens. Like Align’s AI Priority Creator, they don’t require leaders to re-explain their business every time they want insight. They work within a system that already reflects priorities, ownership, and cadence. And it starts with a SMART priority framework, cutting out the need for continual iteration.
That’s where the time savings you’re looking for come from.
Instead of spending hours finessing prompts, you can focus on the decisions that matter. A SMART priority creates a shared understanding of what success looks like, who owns it, and how progress will be judged. The AI inside the platform exposes misalignment because ownership is visible. It pressure-tests assumptions because priorities are explicit. It sharpens focus because tradeoffs are already defined.
And it allows leaders to spend less time re-explaining intent and more time managing progress.
A Better Standard for AI at the CEO Level
The question isn’t how AI aids in your strategic execution. It’s whether the AI you’re using understands your business well enough to help you lead it.
If your AI tool requires constant explanation to stay relevant, it’s adding friction. Execution improves when AI-powered insights live within the system that runs the company.
Explore how Align’s AI tools provide clarity without the constant prompt evolution, making smart moves today for big wins tomorrow.
