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How to Manage 15+ Direct Reports Without Losing Your Mind
Big Tech gutted middle management. Now you're managing 20 people instead of 5. Here's how to scale yourself without burning out.
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The email landed in my inbox last Tuesday:
"Dave, my team just went from 8 to 18 people overnight. Three other managers were laid off and their teams got folded into mine. I'm drowning. HELP!"
The quiet middle management purge over the last couple years has left thousands of leaders managing spans of control that would have been unthinkable five years ago.
The “more of the same” playbook doesn't work when you're managing 15+ people.
Most leaders try to do everything they used to do, just faster.
That's a playbook for burnout.
The answer isn't working harder. It's redefining management.
And leveraging AI to do it excellently.
Do Less: Slow Your Cadence
Let's do the math:
8 people × 30-minute weekly 1:1s = 4 hours
18 people × 30-minute weekly 1:1s = 9 hours
Layer in some basic prep and switching time, and that's nearly half your week.
The Fix:
Weekly 1:1s become bi-weekly for solid performers
Monthly team meetings become quarterly
Daily check-ins become weekly summaries
Frequency isn't quality. Better to have meaningful bi-weekly conversations than rushed weekly check-ins.
Take Risks: Vary Your Distance
Strategic attention allocation:
Close Management: New hires, critical projects, performance issues
Medium Management: Solid performers, skill development
Distant Management: Top performers, subject matter experts
This isn't neglect. It's wise resource allocation.
Deputize Others: Distribute Leadership
You need to ensure your team gets leadership.
That doesn’t mean you have to do it all yourself.
Identify 2-3 lieutenants to review work and coach others
Create peer review processes for routine decisions
Teach "What do you recommend?" as your default response
Leverage AI: Your Management Force Multiplier
AI helps you manage more people better than you managed fewer people before.
AI-Powered 1:1 Preparation
Upload team work samples and notes to Claude or ChatGPT:
"What patterns do you see in Sarah's recent work?"
"What development areas should I focus on?"
"What questions should I ask based on their challenges?"
Automated Performance Insights
Feed team dashboards into AI to identify:
Who's trending up or down
Which projects need attention
What obstacles are blocking multiple people
Smart Meeting Summaries
Record meetings and use AI transcription to:
Generate action items automatically
Track who committed to what
Monitor follow-through
Broadcast More: Scale Communication
One-to-one doesn't scale. One-to-many does.
Record Loom updates instead of explaining things 18 times
Create shared dashboards for performance tracking
Use group 1:1s for people in similar roles
Bundle and Standardize
Standardized Expectations
Create common templates for similar roles. Use AI to generate:
Role-specific expectation cards
Decision-making frameworks
Escalation criteria
Group Similar Activities
3-person 1:1s for similar roles
Batch approval sessions
Skill-based coaching groups
Be Explicit: Communicate the New Reality
What You're Stopping:
Reviewing every piece of work
Weekly 1:1s for everyone
Being the go-to for every problem
What You're Starting:
Strategic planning and obstacle removal
Developing senior people as leaders
Building systems that scale
Updated Values:
From "manager approval required" to "use your judgment"
From "escalate problems" to "bring solutions"
The New Operating System
Your job shifts from:
Reviewing work → Setting standards others can apply
Solving problems → Teaching others to solve problems
Making decisions → Creating decision frameworks
With AI as your co-pilot, you can:
Prepare for conversations faster
Spot patterns you'd miss manually
Personalize development at scale
Generate insights from team data automatically
Your people don't need more of your time. They need clearer direction, better systems, and confidence to operate without you.
A well-designed team of 18 can outperform a micromanaged team of 8.
The question isn't whether you can manage this many people.
It's whether you're willing to lead them differently.
Our Sunday AM posts:
📌 Wise Advice from A Nine-Figure CEO (Dave on LI)
📌 How to Measure a Life Well-Lived (Mar on LI)
📌 How to Use Psychometric Tests Effectively (Dave on X)
And here are our most popular posts last week:
🔥 7 Red Flags You’re About to Make a Bad Hire (Dave on LI)
🔥 Use AI to Land Your Next Job Faster (Dave on X)
🔥 11 Life-Changing Lessons (Mar on LI)
Our goal is to build a community of 1 million thoughtful, curious leaders.
You can help us by reposting anything that resonates with you.
Thank you for reading. Appreciate you!
Dave
Ways To Work With Us
MGMT Accelerator - Eight 90-minute sessions over four weeks plus 3 group coaching session starting October at 7 11:00 AM ET. Perfect for experienced leaders with 3-10 years of experience who want to refine their systems to deliver more impact and level up as a leader.
MGMT Fundamentals - Eight one hour sessions over two weeks. Perfect for managers with 0-3 years of experience who want to quickly build the skills and systems to lead their team effectively from Day 1.
Customized Leadership Programs - Bring our MGMT Accelerator or MGMT Fundamentals in-house for a tailored, intensive workshop. Ideal for 15+ leaders.
1:1 Executive Coaching - My sweet spot is solving real problems to help leaders scale with a common sense Management OS. Growing companies with 50-250 employees.
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