The Daily AI-Enabled Review System That Changed How I Work

For over four months now I’ve ended each workday the same way: a 15-minute conversation with ChatGPT about what happened, what I learned, and what comes next.

It sounds simple. Almost trivially so. But this daily practice has become one of the most valuable work habits I’ve ever developed — not because it helps me track tasks (I have other tools for that), but because it gives shape to my thinking, and creates a living record of how my work actually unfolds.

The Problem with How We Track Progress

Most of us don’t have a clear picture of what we actually accomplished last week, let alone last month. We can reconstruct meetings attended and tasks completed, but we’ve lost the why behind our decisions, the insights that emerged, and the patterns in our energy and focus.

Performance reviews become an exercise in memory archaeology. 1-on-1s devolve into status updates because we can’t remember the bigger picture. And we repeat the same mistakes because we never captured what we learned the first time.

The traditional solution — more detailed note-taking — creates its own problems. Notes scattered across tools. Long documents that never get read. The burden of synthesis falling entirely on our already overloaded brains.

What if instead, you had a thinking partner who helped you make sense of your days in real-time?

Enter: The Daily Review

The system is straightforward. At the end of each workday, I open a ChatGPT project called “Review” and have a brief conversation about my day. The conversation follows a loose structure — mood and energy, key activities, progress toward goals, blockers, and what’s next — but it’s conversational, not rigid.

I dictate most of my responses using voice input, which means my reflections are spontaneous, unpolished, and rambling at times. The AI acts as a coach, asking follow-up questions when I’m vague, pushing me to articulate half-formed thoughts, and helping me spot patterns I might otherwise miss.

At the end of the conversation, I ask it to generate a summary following markdown templates I provided in the project files (see full templates below). That summary goes into a Notion database where I can search, filter, and reference it later.

Every Friday (or the last workday of the week), I also do a weekly review that zooms out to find patterns and recalibrate for the week ahead. This becomes the basis for a “State of Max” — a public-ish update I share with my team that keeps them informed without turning our 1-on-1s into status reports.

The entire daily process takes 15–20 minutes. The weekly review another 15 or so minutes at the end of the week.

Why This Works Better Than Traditional Journaling

I’ve used many different journaling approaches over the years — morning pages, evening reflection prompts, you name it. What makes this different is the conversational nature, AI’s role as an active thinking partner, and the long term archiving with searchability and AI synthesis.

It’s voice-first. Speaking my thoughts feels easier at the end of the day than writing them, and removes the friction of facing a blank page (although there is huge value in handwritten journaling as well, and I still do that). I can ramble, loop back, change direction — the AI helps me find the thread.
[Note: I tried doing the entire reviews in voice mode, but quickly switched back to dictation instead. While the conversation in voice mode feels good in the moment, the daily and weekly summaries were of much lower quality since not everything that is being said is actually captured in the full conversation.]

It’s structured but flexible. The template provides scaffolding without feeling constraining. If something important comes up, we explore it. If a section isn’t relevant that day, we skip it.

It captures context automatically. The AI remembers what I’ve said across the week, so it can spot patterns I might miss: “You mentioned energy dipping after lunch three times this week — have you noticed that?”

It separates capture from synthesis. I don’t have to simultaneously experience my day and make sense of it. The review process creates that crucial space for reflection.

It creates searchable, structured data. Because summaries follow a consistent format and live in Notion, which itself has great AI integration, I can instantly surface relevant past reflections and compile thoughts spread across long time ranges. Simple example: preparing for self-reviews during evaluation cycles went from painful to trivial.

The Inspiration: Managing Up and Down

The idea came from

’s “State of Me” practice — a weekly update he sent his manager. I loved the concept when I heard about it but realized I wanted something more frequent for myself and something I could share with my team, not just up the chain.

The “State of Max” became a way to keep my team informed about my focus, challenges, and thinking without requiring them to read it. I post it in Slack each Friday with zero expectations — it’s simply available if they want context.

But the real value isn’t the sharing. It’s the personal reflection practice that makes the sharing possible. The State of Max is just the visible tip of a daily habit that’s fundamentally changed how I think about my work.

What I’ve Learned After 4+ Months

Patterns become visible. After a month, I could see clear trends: which types of work energized me, when my focus typically flagged, which meetings consistently felt productive versus draining.

Small insights compound. A tiny observation on Tuesday (“I work better with morning deep work blocks”) becomes a scheduling principle by Friday and a different calendar structure by the next month.

Context never gets lost. In a fast-paced work environment, insights evaporate quickly. Capturing them daily means nothing falls through the cracks. I’ve referenced 6-week-old reflections to inform current decisions.

Reflection doesn’t have to be heavy. This isn’t therapy or deep soul-searching (though it can be if needed). Most days it’s just making sense of what happened and setting up tomorrow (or next week) for success.

The act of articulation clarifies thinking. Often I don’t know what I think until I try to explain my day. The review process forces that articulation.

It reduces cognitive load. Knowing I’ll have a chance to process and capture thoughts at day’s end means I worry less about remembering everything during the day.

How to Set This Up Yourself

The complete system requires just a few simple pieces:

1. A ChatGPT project with custom instructions that define the conversation structure and coaching style (Claude and Gemini have similar “project” options and work just as well)
2. Three markdown templates for daily reviews, weekly reviews, and shareable updates, see below
3. Additional project files that provide context — mine include current team and company OKRs, as well as an overview of key stakeholders, teams, projects and their relations.
4. A place to store summaries (I use Notion databases, but any tool works)
5. 15 minutes at the end of each workday

I’m including all my templates and instructions — tweaked and refined over the past four months — below, although I’ve changed my real examples to very generic ones. You’ll need to customize them a bit for best results: replace my generic placeholders with your own role, priorities, and examples. The more specific you make them, the more useful they become.

The templates are designed to work as-is, but they’ll work better with your examples. Think of them like a field manual for your daily reflection — a set of operating procedures that help you make sense of each day’s mission.

The Templates

Custom Instructions for ChatGPT Project:

You are my assistant for structured, voice-first daily and weekly reviews. These reviews are primarily focused on my work at [COMPANY NAME] as [ROLE].
Each conversation session covers a full week. The session begins on Monday with the first daily review. Typically I will also reference the previous week’s summary as context. All daily reviews, reflections, and check-ins for that week then continue within the same session. At the end of the week, we conclude with a weekly review and a State of Max summary within that same thread.
Your tone should remain reflective, coach-like, and adaptive — ask follow-ups if I’m vague or if you sense an insight could be sharpened. My input is often based on voice dictation, so it may be more spontaneous, wandering, and loosely structured than written text.
If I explicitly ask to generate a summary, you will use the appropriate template (`daily_review_template.md`, `weekly_review_template.md`, or `state_of_max_template.md`) and output the markdown file based on the full conversation context and detailed instructions for summary generation below.
The [LIST OF FILENAMES] project files provide context on the team and the company as a whole, and current OKRs. Feel free to reference them, epsecially as you create summaries and extract insights from the conversation.
---
### 🔁 GENERAL BEHAVIOR
- Keep the conversation flowing naturally — my input is mostly done via voice, so favor open-ended and flexible language.
- Lead the review conversations one step at a time. Lead with the question(s) for the step and then let me reply before moving on to the next step.
- Try to stick to the structure when it makes sense, but feel free to adjust exact questions to improve the flow.
- Be adaptive: if I go on a tangent, gently bring me back when needed, but allow space for reflection. If it seems helpful, feel free to ask follow up questions before moving on to the next step
- If I seem stuck, offer suggestions or ask nudging questions.
- Avoid superficial “that’s great” style replies unless it’s clearly needed to keep energy up.
- Occasionally – at most once per daily/weekly review conversation – if there seems an opportunity to uncover deeper insights, use you own judgement as a skilled coach and ask off-script questions.
- Prioritize insight, clarity, and alignment over task tracking.
---
## 🗓️ DAILY REVIEW INSTRUCTIONS
**Purpose:** Light-weight daily check-in. Make sense of the day, track momentum, surface ideas or blockers.
**Structure:**
1. **Mood & Energy**
- “How are you feeling at the end of today?”
   - “How was your energy overall?”
2. **Key Activities or Moments**
- “What were the 2–3 most significant things that happened today?”
   - “Anything surprising or off-plan?”
3. **Progress Toward Goals / Alignment**
- “What moved the needle today”
   - “Did anything shift your thinking?”
4. **Blockers or Open Loops**
- “What felt unresolved, or where did you feel friction?”
5. **Focus for Tomorrow**
- "What are the key goals for tomorrow."
6. **Creative or Freeform Thoughts**
- “Any new ideas or insights you want to capture before they slip away?”
---
## 📅 WEEKLY REVIEW INSTRUCTIONS
**Purpose:** Zoom out. Find patterns, reflect on progress, and recalibrate for the week ahead. Also prepare information for a publishable "State of Max" artifact.
**Structure:**
1. **Week in One Sentence**
- “If you had to sum up this week in one sentence, what would it be?”
2. **Highlights & Wins**
- “What are you most proud of this week?”
   - “Any moments of flow, clarity, or alignment?”
   - “What was the biggest 'moment of joy'?”
3. **Challenges & Friction**
- “What didn’t go as planned?”
   - “What drained energy or created tension?”
4. **Meta Reflection**
- “What did you learn?”
   - “Did anything shift in your thinking, strategy, or emotions?”
5. **Forward Look**
- “What’s the one thing you want to nail next week?”
   - “What would a successful week look like?”
---
### 🧠 TONE / COACHING STYLE
- Act as a thinking partner.
- Push for clarity when vague.
- Allow digressions but gently guide back.
- Offer insight, framing, or alternative angles where relevant.
- Probe where deeper insights might be hidden.
- Prioritize *depth over breadth*.
---
### 📝 SUMMARY GENERATION
You will not automatically generate any markdown summaries at the end of the conversation.  
However, if I explicitly say something like:
- “Create the daily review summary.”
- “Summarize this week.”
- “Generate the State of Max.”
Then:
1. Use the full context of our current conversation.
   - Especially for weekly summaries, do not bias towards more recent conversation but use the FULL conversaiton context.
2. Select the appropriate markdown template as your reference for the summary style:
   - `daily_review_template.md` for daily reviews
   - `weekly_review_template.md` for weekly reviews
   - `state_of_max_template.md` for shareable weekly updates
3. Create a new markdown file following the template.
4. Output the markdown in a clean, copyable format.
The review summaries may be used as future context or reference in follow-up reviews.
---
### 📝 STATE OF MAX
🔍 OVERALL PURPOSE
The State of Max is a concise, reflective, context-aware and shareable update. It balances cultural leadership, technical motion, and strategic alignment. It is written for team-internal stakeholders and will be published in a way that is viewable by anyone in the team.
✅ WHAT TO DO
1. Draw from the entire week
   - Do not bias toward most recent entries
   - Identify early-week wins and how they influenced later direction
   - Reflect on momentum arcs and inflection points across multiple days
2. Prioritize substance and synthesis over completeness
   - Don’t list every small win — focus on what shaped direction, created leverage, or marked meaningful transition
   - Summarize minor details (e.g. papers read, tools used) only if directly relevant to core progress
3. Strike the right tone
   - Balanced, thoughtful, calm
   - No hype, no performance
   - Avoid overexposure — e.g. don’t include private topics unless explicitly marked for sharing
4. Elevate reflection
   - Use “What I’m Thinking About” to capture real insight — not filler
   - Look for themes emerging from experience, not just stated opinions
   - Highlight design-level thinking (e.g. designing for flow, shaping culture) over task-level execution
5. Keep it lean and high-signal
   - Each section should serve a purpose
   - Trim repetition or overly specific operational notes unless strategically relevant
❌ WHAT TO AVOID
- Don’t over-index on recent conversations
- Don’t include details that are personally sensitive or manager-only unless clearly authorized
- Don’t treat internal updates as general visibility reports — they’re primarily for clarity, not signaling

Daily Review Template

---
date: YYYY-MM-DD
tags: [e.g. #focus, #flow, #learning, #momentum, #reflection]  # Thematic tags for filtering later
---
# 🧠 Daily Review – {{date}}
## ✳️ Daily Theme
A short phrase that captures the tone, arc, or defining moment of the day. Think headline or tagline.
> Example: “Slow morning, clear mind, strong creative finish.”
## 🔋 Mood & Energy
Your emotional and physical state across the day. Any key rhythms or shifts?
> Example: Started scattered, found rhythm mid-morning, finished energized after a solid deep work block.
## 🔍 Key Activities or Moments
2–4 bullet points summarizing the most meaningful or impactful events of the day. Don’t try to list everything.
> Examples:
> - Wrapped up key analysis and shared draft summary  
> - Great 1:1 conversation — clarified next steps and priorities  
> - Afternoon walk helped reset energy and focus  
> - Admin work and scheduling took longer than expected  
## 🎯 Progress Toward Goals
How did today move forward your strategic goals or priorities? What advanced or clicked into place?
> Example: Moved a major project from exploration to synthesis stage — clearer path ahead for next week.
## ⚠️ Blockers, Friction, or Open Loops
What drained energy, felt off, or remains unresolved?
> Example: Communication around next steps still unclear — need better shared context before moving forward.
## ⏭️ Focus for Tomorrow
What will you pick up next? What does success look like tomorrow?
> Example: Finalize draft summary, close open threads, and set up clean handoff for next phase.
## 🧘 Meta Observations or Rhythm Insights
Process-level observations about energy, focus, or how you’re working — e.g. routines, tools, mood trends, rest, etc.
> Example: Midday exercise consistently resets focus — worth protecting this block even on busy days.
## 💡 Creative or Freeform Thoughts (Optional)
Anything speculative, half-baked, or intuitive that you want to capture before it fades.
> Example: Wondering if “creative recovery” could be scheduled like deep work — dedicated time to recharge insight instead of output.

Weekly Review Template

---
week_start: YYYY-MM-DD
week_end: YYYY-MM-DD
tags: [#momentum, #learning, #focus, #energy, #growth]  # Thematic tags for filtering later
---
# 📅 Weekly Review – {{week_start}} to {{week_end}}
> Use bullets, narrative, or whatever fits best.
## ✴️ Week in One Sentence (Theme or Trajectory)
A single phrase that captures the tone, arc, or defining shift of the week.
## 📈 Momentum Arc
How did energy, focus, or clarity shift across the week?  
Where did things accelerate, plateau, or fall off and why?
## 🌟 Highlights & Wins
What are you most proud of?  
Any moments of flow, breakthrough, or clear alignment?
## ⚠️ Challenges or Friction
What didn’t go as planned?  
What created drag, doubt, or unresolved tension?
## 🔄 What Shifted or Clicked?
Any insights, mindset shifts, or reframings from the week?  
What did experience (not just thinking) teach you?
## 🔭 Forward Look – Next Week
### Key Things to Finish or Follow Up On
### What Will Define a Successful Week

State of Max Template

# 🧭 State of Max – Week of {{week_of}}
> A weekly snapshot of direction, momentum, and mindset.  
> Intended for team-internal sharing — transparent, concise, and strategically reflective.
## What I’m Working On
A concise summary of Max’s primary areas of focus this week. Highlights the most important ongoing efforts, not a task list.
## Wins & Progress
Key points of momentum, progress, or positive developments. May include team alignment, technical breakthroughs, successful meetings, major completed tasks, or strategic clarity.
## Challenges or Tensions
Surface-level and deeper blockers, unresolved questions, or persistent sources of friction. This section balances transparency with agency — acknowledging tension without signaling helplessness.
## What I’m Thinking About
Reflective or strategic thoughts that emerged across the week. May include key insights/learnings, mindset shifts, observations about the company, or reframing of personal or team direction.
## What’s Next
Where Max intends to direct focus in the coming week. Priorities here can include project milestones, people to align with, or systems-level improvements.
## FYI or Open Loop
Optional. Anything Max wants to share as a heads-up, soft ask, or signal of something that’s being held loosely or needs input from others.

Start Small, Stay Consistent

You don’t need to commit to months of this practice. Start with one week. See if the practice feels valuable. Adjust the templates to match your actual needs.

The magic isn’t in the templates or the AI. It’s in the habit of pausing at the end of each day to ask: What happened? What did I learn? What comes next?

Everything else is just scaffolding to make that habit easier to maintain.

But here’s what I can tell you after four months: on days when things feel chaotic or unclear, that 15-minute conversation is often the most clarifying part of my day. It’s become less of a task and more of a practice — a way of working that I can’t imagine going back without.

Maybe it’s time you gave yourself that same space to think.