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You're aligned with the CEO's vision. Your team respects your approach. You feel at home in the culture. |
But your direct boss? |
Different story. |
Maybe they optimize for speed while you optimize for quality. Maybe they're results-focused while you're people-focused. Maybe they love the details while you think strategically.
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Here's what most leaders do: Complain, become a chameleon, or fight every battle. |
Here's what smart leaders do: |
Use their boss's strengths strategically to achieve their own goals. |
Welcome to leadership Jiu Jitsu. |
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The Three-Layer Boss Analysis |
Before you can influence up effectively, you need a high-fidelity picture of your boss across three dimensions: |
Layer 1: What They Optimize For |
Mission-driven: Social impact, company purpose, long-term vision Money-driven: Revenue, profit, personal financial success Power-driven: Influence, recognition, career advancement Process-driven: Efficiency, systems, operational excellence
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Layer 2: How They Operate |
Communication style: Direct vs. diplomatic, data vs. stories Decision-making: Fast vs. thorough, collaborative vs. independent Feedback preference: Frequent vs. periodic, public vs. private Stress response: Micromanage vs. delegate, push harder vs. step back
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Layer 3: Where They're Strong (and Weak) |
Superpowers: What they're genuinely excellent at Blind spots: What they avoid or struggle with Preferences: What energizes vs. drains them
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If you watch them carefully, the 80/20 of this picture will emerge. |
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The Jiu Jitsu Framework |
Instead of fighting your boss's style, redirect their energy toward your objectives. |
Technique 1: The Strategic Redirect |
The Setup: Your boss complains about something you can't directly control. |
The Move: Make it their problem to solve, using their unique position. |
Example from the transcript😀 |
Instead of: "Compliance is slowing us down, but I'm doing my best." |
Try: "All this compliance is holding us back from hitting our targets. I've pushed as far as I can at my level. Could you use your strategic influence with the compliance team to help us find ways to take more calculated risks here and here?" |
Why it works: Appeals to their ego and position while getting them to solve your problem. |
Technique 2: The Fingerprint Smear |
The Setup: You need buy-in for a decision or approach. |
The Move: Get them to co-author the solution so they can't later criticize it. |
Two variations: |
For Detail-Oriented Bosses: Bring a rough draft and ask for their expertise on specific elements. |
"I've got the framework, but I think your experience with [their strength] could really improve the [specific section]. What am I missing?" |
For Big-Picture Bosses: Bring a well-developed plan but highlight 2-3 strategic decisions where their judgment is crucial. |
"I feel good about this plan, but a couple strategic calls will determine success. Given your experience with [relevant area], can I get your to weight in on these decisions?" |
Why it works: They can't tear apart something they helped create. |
Technique 3: The Language Translation |
The Setup: You need to communicate progress, problems, or requests. |
The Move: Frame everything in their "love language." |
Translation Examples: |
If they optimize for money: |
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If they optimize for speed: |
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If they optimize for recognition: |
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Advanced Techniques |
The Preemptive Strike |
When you know your boss will ask for something unrealistic: |
"I know you're going to want us to move faster on [project]. I've been thinking about how we could accelerate this. If you could help me get [specific resource/decision], we could cut the timeline by [specific amount]. Worth exploring?" |
The Strength Deployment |
When facing a challenge outside your expertise: |
"This [problem] is exactly the kind of thing you're brilliant at. I've done the groundwork, but I think your [specific skill] could unlock the solution. Could you take a look?" |
The Strategic Alliance |
When you're aligned with your skip-level manager: |
Don't: Go around your boss or create obvious triangulation
Do: Use skip-level insights to better understand your boss's pressures and motivations |
"If I'm reading the situation accurately, I think [skip level] values [specific outcome]. Here's a plan I believe will let us hit our goals while also hitting their goal." |
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Common Mistakes to Avoid |
The Adaptation Trap: Changing your entire leadership style to match theirs
Fix: Adapt your communication, not your core approach |
The Complaint Spiral: Venting about their style to peers or team
Fix: Channel that energy into strategic influence |
The Direct Challenge: Fighting their preferences head-on
Fix: Redirect their energy toward your goals |
The Assumption Error: Thinking they should work like you
Fix: Accept their optimization function and work with it |
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Quietly Measuring Success |
Leading Indicators: |
Your boss asks for your input more frequently Fewer of your proposals get shot down You spend less time managing up, more time leading
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Lagging Indicators: |
Your team gets more resources and support Your initiatives move faster through the organization Your boss advocates for you in rooms you're not in
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Your Next Move |
This week: |
Complete the three-layer analysis of your boss Identify one current challenge where you could use their strengths Practice one Jiu Jitsu technique in a low-stakes situation Observe how they respond and adjust your approach
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Remember: The goal isn't to manipulate your boss. It's to create conditions where both of you can succeed by leveraging each other's strengths. |
Great leaders don't just manage down. They strategically influence up. |
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What You Missed This Week |
Our Sunday AM posts: |
📌 20 Questions To Attract (and Keep) Top Talent (Dave on LI)
📌 11 Lessons to Shift Your Habits (Mar on LI)
📌 Complex Decision-Making Made Easy (Dave on X) |
And here are our most popular posts last week:
🔥 How to Speak Your Boss' Language (Dave on LI)
🔥 Why The 9-Box is The Worst HR Tool Ever (Dave on X)
🔥 Why You Should Invest More in the Team You Have (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. |
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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 February 18th 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 starting January 17th 12:00 PM ET.. 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 50-500 employees. | Speaking - We're now booking keynotes for Spring of 2026. Hit reply on this note, and we can set up a time to discuss topics and pricing. | MGMT Playbook - If you're here because someone forwarded this email, please subscribe before you leave. | |
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