The Curious Engineer

All blogs / Engineering management / careers

Aviv Ben-Yosef

avivbenyosef.com

I help CTOs and VPs of Engineering make their orgs worth more than they cost.

Engineering management / careers

’18’19’20’21’22’23’24’25’26
Posts
433 from 28 Jun 2018 to 28 Oct 2026
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weekly (54 in the last year)
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personal blog
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2026 46

  1. The Manager's Schedule Is a Trap
  2. Shipping the Roadmap Is the Minimum
  3. Essays
  4. The AI Bill Is the Cheap Part
  5. Thoughts About Eng Leadership in 2026
  6. Software Factories Are a Local Maximum
  7. Be A Sponge CTO
  8. Maximizing Return-on-Feedback
  9. No One Innovates Their Way Out of a Delivery Problem
  10. Leveraging Fear of Commitment
  11. Nobody's Giving You a Quarter to Feel Clean
  12. Stealing Blame
  13. Nobody Is Coming To Tell You To Go
  14. Their Fault. Still Your Problem
  15. No Wind Is a Good Wind
  16. Can't Read the Label From the Inside
  17. You Didn’t Hire a Slow Team
  18. Stop Lying to Your Cofounder
  19. Axioms of Effective Leadership
  20. Default to Lazy
  21. Nostalgia Debt
  22. Leadership as a Supporting Role
  23. CEO-CTO Therapy Part 4: What Are You Even Doing?
  24. Margin Call: Getting Some Breathing Room
  25. Run the Leadership Diff
  26. Net-Positive Mistakes
  27. You Taught the Company to Overload You
  28. Stop Firefighting Better
  29. Auto-Pigeonholing Tech Leaders
  30. CEO-CTO Therapy (Part 3): Prioritization
  31. Manufacturing Creativity
  32. From Sinking to Shipping: Tackling Your Org’s Debt
  33. Internal PR: Fix Your Team’s Reputation
  34. Suffering Isn’t Leadership
  35. Tech Leadership Right Now: Experimentation, Not Answers
  36. Tech Capital Renaissance
  37. Personal Progress: Don’t Weigh Down Your Team
  38. Your Team Structure Is a Constraint
  39. Change Management in Tech Organizations
  40. Soft-Skill Upgrades for Tech Leaders
  41. Making Engineers Autonomous
  42. First-Principles Debugging for Leaders
  43. 180 Observations and Thoughts from 180 Days in Rome
  44. CEO-CTO Therapy (Part 2): Measuring Engineering
  45. OKRs for Tech Teams: Doesn’t Have to Suck
  46. 10 Observations from 2025 for Eng Leaders

2025 52

  1. The CTO Scrooge
  2. CEO-CTO Therapy (Part 1): Communication
  3. Deliberately Shaping Engineering Organizations
  4. The Shallow Leadership Crisis: Practical Steps to Lead With Depth
  5. Leadership Stances: Are You a No-Op Leader?
  6. Simple Leadership
  7. Flexible Code, Rigid Org
  8. Strategic Optimism
  9. Benjamin Button Software Engineers
  10. Stop Caring So Much About Your People
  11. Dumbest Default: Functional Teams
  12. Squeeze Failures Dry
  13. Business Thinking for Tech Executives
  14. Conveying Competency
  15. Gardening Organizations
  16. Foolproofing Teams
  17. Exploiting Mistakes
  18. Learning to Learn
  19. Hype Escaping Velocity
  20. Dump Others’ Metrics
  21. Actualization Levers
  22. Self Iterations
  23. When The Going Gets Tough
  24. Back to First Sight
  25. Your Title Is Holding You Back
  26. 10x Engineers as Double-Edged Swords
  27. It Takes Two To Tango
  28. Beware Sexy Projects
  29. Feedback Debt
  30. Making Leadership Work
  31. Raising the Bar Starts with You
  32. Excuse Exhaustion
  33. Fighting Momentum
  34. Leader Impostor Syndrome
  35. The Code is the Easy Part
  36. Org Martial Arts
  37. Stop Ad-Hoc Leading
  38. Lost Mortem: The Autopsy of Missed Opportunities
  39. Engineering-Enabled Velocity
  40. Fake It So You Make It—Becoming a Proactive Tech Leader
  41. Set Expectations or Set Up Failure
  42. Second Startup Syndrome
  43. Your Leadership Crutches
  44. How To Create a Brittle Engineering Organization
  45. Lies CTOs Tell (Themselves and Others)
  46. ROI Over Features: The Profitable Engineer’s Manifesto
  47. Costly Moments: Where “Move Fast” Fails
  48. Unpopular Defaults for High-Performing Tech Organizations
  49. Tech Debt isn’t Debt
  50. Leadership Isn’t One Size Fits All
  51. Solo Coaching
  52. Introduction to Impact Retrospectives

2024 52

  1. Coaching Inception
  2. Tech As a Strategic Factor
  3. What Are You Missing?
  4. Don’t Go with the Flow
  5. Tech Exec Yearly Assessment
  6. Coaching Exceptions
  7. Timing as Leaders
  8. Getting Help
  9. Tech Org Defaults
  10. How To Ruin an Engineering Organization
  11. Focusing Engineering Organizations
  12. On Purpose
  13. Tech Exec Growth Curves
  14. Career Complacency: Local Maxima and Low Motivation
  15. Breaking Autopilot
  16. Handling Executive-Startup Mismatch
  17. Igniting Insight: Accelerating Growth as a Leader
  18. Less Leadership Abstraction
  19. Planned Leadership
  20. Tech Leadership Maxims
  21. Communicating With Your CEO
  22. Mission Impossible
  23. Are You a CT-NO?
  24. Naming Matters
  25. 10x Engineering Teams
  26. Communicating Ambiguity
  27. CTO Agenda
  28. Tech Executive Alignment
  29. Team Rehabilitation
  30. Tech Leadership Skills for 2024
  31. Debugging Management
  32. Lifting Lethargic Leaders
  33. Fauxtonomy
  34. Retrospecting Retrospectives
  35. Bottlenecking
  36. Coaching for Sanity
  37. Talent Waste
  38. Debugging Leadership Growth
  39. Sucking Agency
  40. Creating Discomfort Zones
  41. Founder Defocus
  42. FinOps Flops
  43. Futility of Shortening Iterations
  44. Scaling Out Product-Engineering
  45. Tech Ahead of Business Fallacy
  46. Dropping Vanity Metrics
  47. R&D Innovation for Fun and Profit
  48. Profitable R&D Structure and Growth
  49. Making Profitable Software
  50. Highly Profitable Engineering Teams
  51. The Mediocrity Limbo
  52. Why The CTO Sucks: Part 2

2023 50

  1. Why The CTO Sucks
  2. Ego Paralysis
  3. Refactoring Feedback
  4. Leap or Sleep
  5. Sparing the Midnight Oil
  6. Leadership Debt
  7. Tech Agnosticism
  8. Product Mastery from the Operating Room
  9. Escaping Local Maxima
  10. Creating Autonomous Teams
  11. Product Engineering
  12. Reorg Pitfalls
  13. The Reset
  14. Impact Tuning: Tech Leadership
  15. Curing Reactivity
  16. The Grow Slow Guide
  17. Weaning Off Productivity Porn
  18. No One Needs Your R&D Metrics
  19. The Strategy Void
  20. Embracing Politics
  21. The Hired TechExec Pitfall
  22. On Scrappiness
  23. Swinging the Sword
  24. Gedanken Experiment: Your Purpose
  25. Startup Hyper Paralysis
  26. Conversation Catalysts: Embracing Shibboleths
  27. Spotty Connections
  28. High-Density Conversations
  29. Gilding Guilds
  30. Pathological Anxiety
  31. Evaluating Leadership: Beyond the Basics
  32. Startup Rollercoasters: Communication for Leaders
  33. Treating Lowered Expectations
  34. Communication Strength
  35. Individual Growth Plans
  36. Perpetual Leadership Motion
  37. Plagues of Mediocrity
  38. Self Leadership
  39. Reassess For R&D Success
  40. Leaps of Strategic Faith
  41. Sprints and Marathons
  42. Input, Output, Outcome
  43. Impact Alignment Checklist
  44. Belt-Tightening or Suffocation?
  45. Motivating Matters
  46. “My CEO Doesn’t Know…”
  47. Engineering Leadership Quick Assessment
  48. Thinking Bigger
  49. When Product Fails
  50. Making Space for Success in 2023

2022 50

  1. Your First Managers
  2. Strategic Superposition
  3. Tech Decelerators
  4. Surviving Startup Adolescence
  5. CTO Ergonomics: Stop Shrugging!
  6. The Bright Side
  7. Upstream Tech
  8. Feeling the Void
  9. Velocity or Acceleration
  10. Tech Exec—Cofounders Fit
  11. Time Crisis Dilation
  12. Leadership SLAs
  13. Optimism For Geek Leaders
  14. Stop Fretting
  15. Pushover Leadership
  16. Task Forces
  17. If Not Now, Then Never?
  18. Change Cadence
  19. Collaboration Patterns Part III: Hybrid
  20. Collaboration Patterns Part II: Remote Only
  21. Collaboration Patterns Part I: Colocated Teams
  22. Experience Acceleration
  23. Successful Team, Pointless Leader?
  24. Not A Family
  25. Objecting to Objectives
  26. Taking The Reins
  27. Questioning Axioms
  28. Motivational Pull
  29. Money-Mouth Distance
  30. Embracing Common Sense
  31. My Tech Exec Interview Checklist
  32. Aiming for Longer Tenures
  33. Instilling Urgency
  34. Catching Your Breath
  35. Processing
  36. The Case for Fewer Engineers
  37. Where Are You Headed?
  38. What Do You Do?
  39. What Are You Optimizing For?
  40. Miscommunication Plan
  41. Permission to Take the Lead
  42. Preventive Plans and Contingencies
  43. Forming Alliances
  44. Pop Quiz: Objectives Inspection
  45. People Over Processes
  46. Courage Over Fake Niceties
  47. The Void of Empowerment
  48. Team Empowerment Alignment
  49. Handling Talent Fear
  50. Tech Impact: Real-Life Examples

2021 52

  1. Suspension of Disbelief
  2. Assessing Engineering Managers
  3. Myopic Leadership
  4. Signs You’re Doing OKRs Wrong
  5. The Superposition Leadership Fallacy
  6. Bespoke Culture: Tailoring Your Organization
  7. Taking Empowerment Too Far
  8. Righting The Ship
  9. Choosing Your Battles
  10. Stop Focusing on Tech Debt
  11. Impact Without Burning Out
  12. Maintaining Urgency
  13. Time to Say Goodbye
  14. Personal Growth Targets for Senior Leaders
  15. Helping People Quit
  16. Refactor: Extract Team
  17. Leveling the Bar
  18. Yak Spotting
  19. Startups on Hard Mode
  20. The Founder vs. Hired Executive Gap
  21. Smartup
  22. The Origin of Innovation
  23. Using Executive Leverage
  24. Foster Executives
  25. Generating Effective Chutzpah
  26. Management as a Profession
  27. The Demise of Coaching
  28. Don’t Cultivate Snowflake Engineers
  29. Growing Growth Mindsets
  30. The Courage to Let Go
  31. The Self-Encapsulating CTO
  32. Double Your Impact-Per-Engineer
  33. Code: Our Biggest Sunk Cost
  34. Scale Up, Impact Down
  35. Leadership Risks
  36. Code Apes
  37. Intention, Inertia, and Introspection
  38. The Titles Zero-Sum Game
  39. The Fallacy of Meeting Expectations
  40. Ego Check: Tech for Tech’s Sake
  41. You Don’t Need a “Tech Strategy”
  42. Fast Iterations, Slow Progress
  43. Less Principal Engineers, More Product Engineers
  44. Transparency or Anxiety
  45. The Disagreement Quota
  46. Empowering Constraints
  47. Restoring Trust
  48. Are You Doing Good?
  49. Assuming Executive Position
  50. Taking the Initiative
  51. The Micromanagement Flywheel
  52. Stop To-Do List

2020 53

  1. Leadership Reserves
  2. The Roadmap to Mediocrity
  3. You Should Be Moving Faster
  4. HR: Hemorrhaging Responsibility
  5. Deadline Language Barrier
  6. No Perfect Reorg
  7. Traits of Successful VPs of Engineering
  8. Authentic Leadership: Embrace Uniqueness
  9. Controlling Your Time
  10. Forget It and Set It
  11. Promotional Material
  12. On The Catwalk
  13. Lowering Org Debt: Spotting Org Smells
  14. How Not To Get Fired As A CTO
  15. Growing Engineering: Resiliency Trumps Experience
  16. Communication, Gesticulation, Articulation
  17. Noticing Change
  18. It’s Not Your Team, It’s You
  19. CTO + VP Engineering: Needed or Redundant?
  20. The Traits of a Great Engineering Culture
  21. IC Growth Paths
  22. Own It
  23. Managing Non-Feature Work: Part 3—Suggested Approach
  24. Managing Non-Feature Work: Part 2—Guiding Principles
  25. Managing Non-Feature Work: Part 1—Failed Approaches
  26. The Professionalism Snowball
  27. Shoving Square Engineers in Round Holes
  28. Soliciting Upward/Chutzpah Feedback
  29. Stop Being a Floating Leader
  30. The Most Important Partnership
  31. Fostering Creativity In Engineering
  32. Moving Upstream
  33. The Habit of Challenging the Status Quo
  34. Strategy as a Tactic
  35. Lowering Your Doubling Time
  36. Balancing Safety and Productivity
  37. Increasing Your Executive Leverage
  38. Missed Opportunity Cost
  39. Thoughts on Team Productivity in Quarantine
  40. Your Managers Are Passing Their Time Cargo-Culting Important Work
  41. What Are You Waiting For?
  42. Never Hear an Excuse Again
  43. Over-Engineering Your Organization
  44. Fixing Your Decision Waffling
  45. Tech Leadership: The Work Is Not the Work
  46. Stop Mediating
  47. How to Demotivate Your Engineering Team in 10 Work Days
  48. What If You Never Hire Senior Engineers?
  49. Wishful Leading
  50. Stop Answering the Questions–Question the Questions
  51. Zero Trust Leadership
  52. Help Your Team Become Grown-Ups: Not Everything is Fun!
  53. Insanity Defined

2019 51

  1. Spontaneous Human Induction
  2. Don’t Shy Away or Risk Cowardly Management
  3. Stale Velocity
  4. Risky Business
  5. First Class 1:1s
  6. Executive Operating System: Tracking Personal Initiatives
  7. The Many Upsides of an Employee Leaving
  8. Destroying Comfort Zones
  9. It’s Not Just First Impressions
  10. Watch Your Language
  11. Using the Power of a Tech Executive for Good
  12. A Team Can Deliver 100% of Every Sprint and Still Be Underperforming
  13. Leadership Isn’t Waiting for Stars to Align
  14. Why Your Managers Suck
  15. R&D Has Too Much Power in Startups
  16. Stop Thinking of R&D as a Cost Center
  17. Do Your Managers Really Want Agility?
  18. Expectation Setting
  19. Putting Your People in the Spotlight
  20. The Executive Mindset
  21. Different Archetypes of Organizations
  22. The Management Bit
  23. Feedback Timeliness
  24. Idempotent Reviews
  25. The Pat on the Back
  26. Drowning in a Fountain of Knowledge
  27. You Can’t Sharpen a Saw You Don’t Have
  28. Dead-Letter Meetings
  29. The Debate Club
  30. Not All Seniors Are Created Equal
  31. Know Your Place
  32. Stop Whining!
  33. Peter Pan Employees
  34. Guidelines, Not Solutions
  35. The Success of a Process
  36. Straw-man Architecture
  37. So You Had to Go Uphill Both Ways
  38. The First Investment
  39. Co-Responsibility Is No Responsibility
  40. Reducing Daily Interruptions is on You
  41. Long Term vs. Next Sprint
  42. Leaving Developer Experience for the Experienced
  43. No One Likes Surprises at Work
  44. What Is Your Job Here?
  45. 1-on-1s with Skips
  46. Setting Up New Managers to Succeed
  47. Missing Autonomy Case Study: Useless Architecture
  48. Decision Awareness
  49. Growing as a CTO
  50. What’s on the Agenda
  51. Blitz Mode

2018 24

  1. My System for Choosing Tech
  2. Of Hero Coders
  3. Overwhelm
  4. Maintaining an Outsider Perspective
  5. Limiting Technical Debt
  6. Making It Easy to Supply Feedback
  7. Keeping The Rust At Bay
  8. The “Just Checking” Manager
  9. Busy is Easy
  10. Tailoring A Hiring Strategy
  11. Avoiding the “Big Guns” Stack
  12. Avoiding Surprises: Employee Career Management
  13. Alone at the Bridge of a Rocketship
  14. Growing Teams Too Quickly
  15. Managing Overly Optimistic Developers
  16. Keep Internal Changelogs
  17. The Rambo CTO
  18. Yes, They Are Looking At You
  19. Don’t Outsource Common Sense
  20. Don’t Be Too Nice
  21. Sometimes It’s Good To Be Unremarkable
  22. A Bad Apple Can’t Lead The Orchard
  23. Don’t Rush to the Keyboard
  24. Remember how you first learned to code?

Undated 3

  1. Work With Me
  2. The Tech Executive Operating System The field manual for running an engineering org like the business function it actually is. Get the book →
  3. Capitalizing Your Technology Turn engineering spend into defensible advantage — and make the value legible to the rest of the C-suite. Get the book →