2026-01: First 5 Wins For Busy Leaders
How to Use This Guide
This guide is not about becoming proficient with AI. It’s about helping experienced leaders begin thoughtfully, in ways that:
> reduce friction
> preserve accountability
> and do not change how decisions are made or defended
The examples in this guide are defensible starting points. They are places where AI supports preparation, clarity, and thinking without introducing new risk or authority confusion.
You do not need to use all five.
You do not need to move quickly.
And you do not need to explain or justify using AI in these ways.
One thoughtful use is enough to build confidence.
The Boundary Rules (Read Before You Begin)
Every example in this guide follows four simple rules. If an AI use case violates any of these, it doesn’t belong here.
1. AI prepares, the leader decides
AI may help organize, surface, or structure information. It doesn't make judgments, conclusions, or recommendations on the leader’s behalf.
2. AI drafts, the leader reviews
All output is provisional. Leaders remain responsible for accuracy, tone, and intent.
3. AI supports thinking, not authority
AI may assist how leaders think, not what they stand behind.
4. AI output is always optional
Nothing produced by AI is required to be used, shared, or followed. If AI use doesn’t reduce friction without introducing new risk, it isn’t a win.
Win #1: Clarifying Messy Information Before You Act
What this is
Using AI to organize unstructured inputs: emails, notes, or documents before forming a position or opinion.
A familiar Situation
A leader opens their inbox before a meeting and finds multiple email threads, a shared document with tracked changes, and notes from a prior discussion. There isn’t time to read everything closely, but there is responsibility for understanding what’s going on before weighing in.
Why this is a win
Leaders are constantly absorbing fragmented information. This use of AI reduces cognitive load without outsourcing judgment.
What to watch for
> Summaries that reframe emphasis or priority
> Language that sounds confident but removes nuance
> Missing context that only lived experience would catch
Where leaders use this effectively
> Preparing for meetings
> Reviewing long email threads
> Synthesizing notes from multiple sources
Where leaders should not use this
> Final decisions
> External communication
> Performance evaluations
Safe-use prompt (example)
“Summarize the key points and themes in this content without adding interpretation or recommendations.”
Leadership check
Does this summary reflect what I already know to be true? Or, did it introduce anything I need to question?
Win #2: Improving the Quality of Your Own Draft Thinking
What this is
Using AI as a thinking mirror to surface gaps, assumptions, or weak logic in your own draft ideas.
A familiar Situation
A leader drafts a short internal note outlining a proposed direction, but something feels unfinished. The idea is mostly there, yet it’s unclear whether the reasoning is complete or if important considerations have been missed.
Why this is a win
Leaders already think and draft. AI can help test clarity without replacing authorship.
What to watch for
> AI reinforcing initial assumptions instead of challenging them
> Polished logic that skips uncomfortable trade-offs
> Gaps that feel “too clean” for real-world decisions
Where leaders use this effectively
> Early drafts of internal memos
> Outlining ideas
> Stress-testing reasoning
What this is not
> Ghostwriting
> Final messaging
> Speaking for the leader
Safe-use prompt (example)
“Review this draft and identify unclear assumptions, missing considerations, or logical gaps.”
Leadership check
Would I be comfortable explaining how this thinking was developed?
Win #3: Preparing for Conversations, Not Replacing Them
What this is
Using AI to anticipate questions, objections, or perspectives before a conversation takes place.
A familiar Situation
A leader is walking into a conversation where opinions are likely to differ. The topic isn’t controversial, but there are competing priorities, and the leader wants to be prepared to listen without being caught off guard.
Why this is a win
Preparation improves listening and responsiveness without scripting people.
What to watch for
> Over-preparing that limits real listening
> Questions that steer instead of invite
> Mistaking anticipation for understanding
Where leaders use this effectively
> 1:1s
> Team discussions
> Stakeholder conversations
Where leaders should be cautious
> Emotional topics
> Sensitive performance discussions
Safe-use prompt (example)
“What questions or concerns might someone reasonably raise about this topic?”
Leadership check
Am I using this to listen better or to avoid thinking in real time?
Win #4: Identifying Trade-offs Before Making a Decision
What this is
Using AI to surface possible trade-offs, risks, or second-order effects. Not using AI to choose among them.
A familiar Situation
A leader is considering two reasonable options under time pressure. Both seem defensible, but each carries implications that may not show up immediately once a decision is made.
Why this is a win
Time pressure causes leaders to miss downstream consequences. AI can widen the lens without narrowing responsibility.
What to watch for
Risks framed too generically to be useful
Second-order effects that are plausible but irrelevant
Analysis that expands without clarifying the decision
Where leaders use this effectively
Early-stage decision framing
Comparing options
Explicit boundary
AI does not decide.
AI does not recommend.
Safe-use prompt (example)
“List potential trade-offs, risks, and second-order effects associated with each option.”
Leadership check
What am I still personally responsible for deciding?
Win #5: Reducing Friction in Repetitive, Low-Stakes Writing
What this is
Using AI to draft routine internal language that the leader reviews and edits.
A familiar Situation
A leader needs to send several routine updates that don’t require deep judgment but still need to be clear and professional. Writing them isn’t difficult, it’s just time-consuming and repetitive.
Why this is a win
It saves time without risking credibility.
What to watch for
Language that subtly shifts tone or authority
Over-neutral phrasing that avoids responsibility
Text that sounds “right” but not like them
Where leaders use this effectively
Status updates
Internal summaries
Routine documentation
Where leaders should avoid this
External communication
Sensitive messaging
Anything requiring judgment or nuance
Safe-use prompt (example)
“Draft a neutral, professional summary of the following information for internal use.”
Leadership check
Would this sound appropriate if attributed directly to me?
What These Wins Have in Common
Each example in this guide:
> operates before decisions, not instead of them
> preserves review, accountability, and authorship
> reduces friction without increasing exposure
None of these require:
> rollout
> permission
> adoption programs
> explanation
They are small, contained, and defensible.
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How This Fits with Strategic AI Briefing
This guide covers starting behaviors.
The newsletter exists to help leaders:
> interpret what’s changing
> recognize patterns
> make sound judgments over time
The vault exists to give leaders reusable frameworks they can return to when similar situations arise.
Each plays a different role. Together, they form a coherent system.
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In closing, we're striving for confidence, not momentum.
One thoughtful use, applied consistently, builds confidence faster than broad experimentation.
The goal isn’t to use AI more. It’s to lead well in situations where AI exists.
Quick Links to the 5 Wins