The Power of the 5/15: A Simple Framework for Reflection and Growth

In leadership and in life, the tools that stick are often the simplest ones. They’re not the most complicated frameworks or the trendiest methodologies, but the ones that you can consistently return to, week after week, without friction.

The 5/15 is one of those tools. It is almost 3 years to the day since I wrote my first 5/15 in Groupon and I have loved writing them every week since. At its core, it asks just five questions that can be answered in fifteen minutes (it probably takes more than 15 minutes and it is my Saturday morning ritual. Five reflections. Fifteen minutes. That’s it. Yet over time, this small ritual compounds into clarity, alignment, accountability, and growth.

In this post, I want to explore the importance and power of the 5/15, why it works, how you can use it for yourself or your teams, and what it looks like in practice.

What is the 5/15?

The 5/15 originated as a leadership and management tool, first popularized in Silicon Valley and later adapted by leaders in tech, consulting, and startups around the world. The name is literal: five questions, fifteen minutes to answer them.

The five questions usually look like this:

1. What were your successes last week?
2. What didn’t get done, or what was a failure?
3. What’s the plan for next week?
4. What was the highlight of the last week?
5. What opportunities do you see ahead?

You can adjust the questions slightly depending on your context, personal reflection, team updates, or even project retrospectives, but the structure stays the same.

The key is that it is short, repeatable, and reflective. Anyone can fill it in, and it creates a steady rhythm of accountability without becoming a chore.

Why the 5/15 Works

The 5/15 works because it taps into a set of universal human and organizational needs:

1. It builds consistency

By keeping the format identical every week, you train yourself (and your team, if you’re using it collectively) to develop a rhythm. Over time, the questions themselves become triggers, you start noticing highlights in real time, or thinking proactively about opportunities simply because you know the 5/15 is coming.

2. It encourages honesty

Unlike long reports or dense presentations, the 5/15 cuts through fluff. Fifteen minutes is not enough time to spin stories, over-explain, or drown in metrics. You have to be concise and honest. That honesty is powerful.

3. It balances reflection with action

The structure forces you to look back (successes, failures, highlights) and look forward (plans, opportunities). Too often, teams get stuck in one or the other. The 5/15 ensures you’re doing both every week.

4. It scales from individual to team

One person can use a 5/15 to check in on themselves. A manager can use it with direct reports to keep alignment tight without micromanagement. A leadership team can use it to scan the horizon together. It’s simple enough to work at any scale.

5. It compounds over time

The first 5/15 might feel small, almost trivial. But look back at 20 weeks of them, (or me with 150 of them done) and you have a living journal of growth, accountability, and opportunity-spotting. This is where the compounding power shows itself, small weekly reflections add up to big change.

How Leaders Use the 5/15

When used well, the 5/15 becomes more than just a “status update.” It turns into a cultural habit. Here are a few ways leaders apply it:

• With teams: Instead of lengthy weekly reports, each team member fills out a 5/15. The manager scans them all in under an hour and gets a real sense of the ground truth.
• For projects: After every sprint or milestone, the team captures a 5/15. This is less about performance and more about lessons learned and opportunities to improve.
• For self-reflection: Many leaders use a 5/15 as a private journal, especially founders and executives who need to balance big-picture vision with day-to-day accountability.
• As a coaching tool: A mentor or coach can ask a client to bring their 5/15 to sessions, which makes it much easier to spot patterns and blockers.

The Power in Each Question

Let’s break down why each of the five questions matters.

1. What were your successes?

Celebrating wins matters. Big or small, taking a moment to notice what went right builds momentum. For teams, this creates visibility and morale. For individuals, it keeps you from overlooking progress.

2. What was overdue, didn’t get done, or was a failure?

This is the accountability piece. By putting unfinished work or failures in writing, you’re less likely to bury them or move on without reflection. The important thing is not punishment, but learning: why didn’t it get done? What can change next week?

3. What is the plan for the next week?

This question bridges reflection and action. It forces prioritization and ensures clarity of focus. Over time, it helps you see whether your actions are aligning with your goals.

4. What was the highlight of the last week?

Not every highlight will be a business metric. Sometimes it’s a breakthrough conversation, a team bonding moment, or even a personal win. This question humanizes the process and keeps motivation alive.

5. What are the opportunities?

This is the visionary piece. Opportunities might be new markets, creative ideas, partnerships, or simply noticing an inefficiency worth fixing. By asking this every week, you build a habit of looking up from the grind and scanning the horizon.

The 5/15 in Practice

Imagine a team of ten. Instead of everyone sending long weekly emails, they each complete a 5/15 in fifteen minutes. The manager reads them in an hour, highlights common themes, and brings just a few big discussion points to the team meeting.

The result?

• Everyone feels heard.
• The manager gets a real picture of progress and challenges.
• The team spends less time reporting and more time doing.
• Opportunities don’t get lost because someone was “too busy.”

For an individual, the practice is just as valuable. Looking back at your own 5/15s over six months, you can track recurring blockers, notice patterns in your highlights, and see whether your weekly plans are moving you toward bigger goals.

Why Now?

In 2025, when so much of work is distributed, fast-moving, and AI-powered, the human element of reflection is more important than ever. Tools can automate reports, generate insights, and track KPIs, but they can’t replace the personal act of reflecting on successes, failures, highlights, and opportunities.

The 5/15 is the antidote to both overwhelm and automation fatigue. It’s short, human, and powerful.

How to Get Started

If you want to try the 5/15 for yourself or your team, here’s a simple way to begin:

1. Pick a cadence: Weekly works best. Same day, same time.
2. Keep it short: No more than fifteen minutes per person. Bullet points are fine.
3. Share or store: Decide if this is private (a personal reflection journal) or public (a team alignment tool).
4. Review consistently: The real power comes from looking at patterns across time, not just one entry.
5. Adapt if needed: If your team wants to tweak the questions, do it, but keep the spirit of five short reflections.

Using AI to Write and Review 5/15s

One of the most exciting shifts in recent years is how AI can enhance simple frameworks like the 5/15 without taking away their humanity. At first glance, the 5/15 feels too personal to automate, but AI isn’t here to replace reflection. Instead, it acts as a companion that can make your 5/15 richer, more consistent, and easier to review.

Here’s how:

1. AI as a Drafting Partner

When you sit down to complete your 5/15, you don’t always remember the details. AI can help you by:

• Summarising your week: Pulling highlights from your calendar, emails, project tools, or chat logs.
• Prompting reflections: Asking clarifying questions (“What was the most energizing meeting this week?” or “Which task slipped twice in a row?”).
• Spotting small wins: AI can flag things you might overlook, like a resolved ticket backlog or a quick mentoring chat, and nudge you to celebrate them.

Instead of staring at a blank page, you get a structured starting point.

2. AI as a Reviewer

After you’ve written your 5/15, AI can analyze it to provide extra insight:

• Pattern detection: Spot recurring blockers (“You’ve listed documentation delays three weeks in a row”).
• Tone check: Highlight whether your reflections are overly negative or missing recognition of wins.
• Alignment mapping: Compare your weekly plans against quarterly goals or OKRs to ensure focus.
• Actionability score: AI can flag vague plans (“Work on project X”) and suggest more specific ones (“Draft outline for feature spec on project X”).

3. AI for Managers

For leaders reviewing multiple 5/15s, AI can compress the information into a single snapshot:

• Theme clustering: Grouping common challenges (e.g., “Four team members cited testing bottlenecks”).
• Highlight amplification: Surfacing the most inspiring wins across the team.
• Opportunity synthesis: Spotting new opportunities mentioned in different places that align (e.g., two engineers noticing similar customer feedback).

This doesn’t replace human reading, but it reduces noise and ensures nothing slips through the cracks.

4. AI-Enhanced Reflection Tools

With today’s AI integrations in tools like Notion, Confluence, or even Google Docs, you can set up workflows where:

• You write your raw 5/15.
• AI drafts a polished version for sharing.
• AI extracts themes and logs them into a longer-term journal.
• Over time, AI generates quarterly retrospectives automatically, using nothing but your 5/15s.

The end result: your fifteen-minute reflection becomes part of a much larger narrative of growth, without extra work.

👉 Adding AI into the 5/15 process doesn’t dilute its power, it amplifies it. You still do the reflecting. AI just helps you see patterns, sharpen your plans, and carry your reflections forward into action.

Conclusion

The 5/15 is deceptively simple. Five questions, fifteen minutes. Yet it has the power to transform the way you reflect, the way teams align, and the way organizations grow.

It gives space for celebration, accountability, planning, and vision, all in one lightweight ritual.

Most importantly, it’s sustainable. You can keep doing it week after week without burnout. And when you look back at months or years of 5/15s, you’ll see more than notes. You’ll see a record of growth, resilience, and opportunity.

So next week, when the week wraps up and the emails are still flying, carve out just fifteen minutes. Answer five questions. Start your 5/15.

You’ll be surprised at how powerful it becomes.

By Example

1. Successes

• ✅ Published and promoted multiple AI and LEGO weekly roundups (This Week in AI, This Week in LEGO).
• ✅ Created & continually improved the multi-platform content (LinkedIn, YouTube, X, Blog posts) with consistent imagery, branding, and summaries.
• ✅ Progressed LEGO museum storytelling with Wall of Fame inductees, stylised cartoon haul images, and family-centric posts.
• ✅ Strong engagement on LinkedIn with AI thought leadership pieces (Uncle Bob & Clean Code in the age of AI, Jira/Confluence Utopia).
• ✅ Continued building the 30 Days of AI relaunch momentum, framing the next wave of posts and demos.

2. Overdue / Failures

• ❌ Video consistency: Low audio quality, lip syncing on overlays and YouTube uploads lagged behind blog posts in pacing; some posts went out without aligned short-form video on darrenredmond.com
• ❌ Networking/admin: Follow-up on advisory roles could have been tighter.
• ❌ LEGO museum physical progress: contracts and planning permission is dragging and needs prioritization, plus organization, display cabinets, and plinth layouts slipped behind due to focus on content.

3. Plan for Next Week

• 🎯 Lock in video schedule: each blog post → short YouTube + TikTok/Instagram cut.
• 🎯 Prep deeply for advisary strategy & GenAI role with a clear 3-2-1 adoption framework narrative + case studies.
• 🎯 Advance Redmond’s Forge museum planning.
• 🎯 Relaunch Day 16 & 17 of 30 Days of AI, building on analytics + Airtable demos.

4. Highlight of the Last Week

🌟 The Epic Galway Trip, a 7-hour adventure with Luke & Rose, battling rain and traffic, Camile/food stops, and finally landing LEGO hauls. Turned into a brilliant family story + blog + video. This perfectly tied together the Forge’s family, LEGO, & storytelling vision. The advancements in the video creation over the week, from my voice having bad audio at the start of the week, to fades, underlay tracks, & tons of AI generation by the end of the week.

5. Opportunities

• 🚀 Use the AI avatar mini-figure video idea to scale content creation for both AI and LEGO channels.
• 🤝 Leverage advisory/consulting opportunities (company names redacted) as bridges between AI thought leadership and SMB enterprise transformation work.
• 📈 Position Redmond’s Forge as a unique hybrid brand (LEGO + AI storytelling), can it be a differentiator in both niches.
• 💡 Viral content potential with creative LEGO video ideas (publish the sad Death Star collapse video, stop-motion hauls, museum setup timelapses).
• 🎟️ Start teasing physical museum exhibitions and test audience willingness to visit via polls, or ticket pre-sales. Create a Groupon deal for the museum.