Gregor Ojstersek
@gregorojstersek.bsky.social
CTO | Founder of Engineering Leadership newsletter (165k+ subscribers) - Helping you become a great engineering leader!
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If 7 teams build the wrong thing, that’s a leadership issue, not an engineering issue.
Learn the business.
Aim the effort.
Learn the business.
Aim the effort.
November 15, 2025 at 7:30 PM
If 7 teams build the wrong thing, that’s a leadership issue, not an engineering issue.
Learn the business.
Aim the effort.
Learn the business.
Aim the effort.
Slow decisions sink momentum.
Ship a good decision now, refine with data later.
Ship a good decision now, refine with data later.
November 15, 2025 at 4:30 PM
Slow decisions sink momentum.
Ship a good decision now, refine with data later.
Ship a good decision now, refine with data later.
Trust looks like:
• Early risk calls
• Unfiltered status
• Volunteers for hard work
• Early risk calls
• Unfiltered status
• Volunteers for hard work
November 15, 2025 at 1:30 PM
Trust looks like:
• Early risk calls
• Unfiltered status
• Volunteers for hard work
• Early risk calls
• Unfiltered status
• Volunteers for hard work
You can’t own every fire.
Build leaders who prevent them.
Build leaders who prevent them.
November 14, 2025 at 7:30 PM
You can’t own every fire.
Build leaders who prevent them.
Build leaders who prevent them.
Build credibility in your teams by:
• Helping peers
• Owning outcomes
• Communicating early
• Doing what you promised
• Helping peers
• Owning outcomes
• Communicating early
• Doing what you promised
November 14, 2025 at 4:30 PM
Build credibility in your teams by:
• Helping peers
• Owning outcomes
• Communicating early
• Doing what you promised
• Helping peers
• Owning outcomes
• Communicating early
• Doing what you promised
3 signals your meetings work:
1. Agenda in the invite
2. Owners + deadlines are captured
3. Decisions written before the next meeting
1. Agenda in the invite
2. Owners + deadlines are captured
3. Decisions written before the next meeting
November 14, 2025 at 1:30 PM
3 signals your meetings work:
1. Agenda in the invite
2. Owners + deadlines are captured
3. Decisions written before the next meeting
1. Agenda in the invite
2. Owners + deadlines are captured
3. Decisions written before the next meeting
What it’s like moving from vibe coded app into a well-structured, scalable architecture 😂
Happy Friday and have a great weekend!
Happy Friday and have a great weekend!
November 14, 2025 at 1:23 PM
What it’s like moving from vibe coded app into a well-structured, scalable architecture 😂
Happy Friday and have a great weekend!
Happy Friday and have a great weekend!
Micromanagement is a symptom.
The cause is unclear outcomes.
Define done and trust will follow.
The cause is unclear outcomes.
Define done and trust will follow.
November 13, 2025 at 7:30 PM
Micromanagement is a symptom.
The cause is unclear outcomes.
Define done and trust will follow.
The cause is unclear outcomes.
Define done and trust will follow.
Velocity isn’t more tickets.
Velocity is fewer handoffs, faster feedback, and smaller batches.
Velocity is fewer handoffs, faster feedback, and smaller batches.
November 13, 2025 at 4:30 PM
Velocity isn’t more tickets.
Velocity is fewer handoffs, faster feedback, and smaller batches.
Velocity is fewer handoffs, faster feedback, and smaller batches.
Micromanagement fades when “done” is defined:
1. Write the outcome.
2. Name the owner.
3. Agree on the check-in.
1. Write the outcome.
2. Name the owner.
3. Agree on the check-in.
November 13, 2025 at 1:27 PM
Micromanagement fades when “done” is defined:
1. Write the outcome.
2. Name the owner.
3. Agree on the check-in.
1. Write the outcome.
2. Name the owner.
3. Agree on the check-in.
Leaders remove ambiguity, blockers, and fear.
In that order.
In that order.
November 12, 2025 at 7:30 PM
Leaders remove ambiguity, blockers, and fear.
In that order.
In that order.
5 phrases that raise safety:
1. You decide.
2. I could be wrong.
2. Show me the draft.
4. Let’s try a small test.
5. Thanks for flagging this.
1. You decide.
2. I could be wrong.
2. Show me the draft.
4. Let’s try a small test.
5. Thanks for flagging this.
November 12, 2025 at 4:30 PM
5 phrases that raise safety:
1. You decide.
2. I could be wrong.
2. Show me the draft.
4. Let’s try a small test.
5. Thanks for flagging this.
1. You decide.
2. I could be wrong.
2. Show me the draft.
4. Let’s try a small test.
5. Thanks for flagging this.
High standards aren’t pressure.
They’re precision:
- Clear definitions
- Fair expectations
- Predictable results
They’re precision:
- Clear definitions
- Fair expectations
- Predictable results
November 12, 2025 at 1:30 PM
High standards aren’t pressure.
They’re precision:
- Clear definitions
- Fair expectations
- Predictable results
They’re precision:
- Clear definitions
- Fair expectations
- Predictable results
5 questions that unblock teams:
1. What would we cut first?
2. What does “good” look like?
3. Who owns this by end of day?
4. What’s the smallest shippable?
5. What’s the risk we’re not naming?
1. What would we cut first?
2. What does “good” look like?
3. Who owns this by end of day?
4. What’s the smallest shippable?
5. What’s the risk we’re not naming?
November 11, 2025 at 7:30 PM
5 questions that unblock teams:
1. What would we cut first?
2. What does “good” look like?
3. Who owns this by end of day?
4. What’s the smallest shippable?
5. What’s the risk we’re not naming?
1. What would we cut first?
2. What does “good” look like?
3. Who owns this by end of day?
4. What’s the smallest shippable?
5. What’s the risk we’re not naming?
Your leverage shifts:
• 1 team → context & clarity
• 3 teams → delegation & coaching
• 5+ teams → structure & strategy
• 1 team → context & clarity
• 3 teams → delegation & coaching
• 5+ teams → structure & strategy
November 11, 2025 at 4:30 PM
Your leverage shifts:
• 1 team → context & clarity
• 3 teams → delegation & coaching
• 5+ teams → structure & strategy
• 1 team → context & clarity
• 3 teams → delegation & coaching
• 5+ teams → structure & strategy
3 signals you’re ready for multiple teams:
1. You coach weekly
2. You empower leads
3. You measure outcomes, not effort
1. You coach weekly
2. You empower leads
3. You measure outcomes, not effort
November 11, 2025 at 1:30 PM
3 signals you’re ready for multiple teams:
1. You coach weekly
2. You empower leads
3. You measure outcomes, not effort
1. You coach weekly
2. You empower leads
3. You measure outcomes, not effort
3 signals you’re faking certainty:
• Vague language
• Random fixes
• No questions
Switch to clarity: logs, metrics, timelines.
• Vague language
• Random fixes
• No questions
Switch to clarity: logs, metrics, timelines.
November 10, 2025 at 7:30 PM
3 signals you’re faking certainty:
• Vague language
• Random fixes
• No questions
Switch to clarity: logs, metrics, timelines.
• Vague language
• Random fixes
• No questions
Switch to clarity: logs, metrics, timelines.
Make “ask great questions” your unfair advantage.
Clarity beats confidence theater.
Clarity beats confidence theater.
November 10, 2025 at 4:30 PM
Make “ask great questions” your unfair advantage.
Clarity beats confidence theater.
Clarity beats confidence theater.
3 mistakes I made as a first-time engineering manager:
1. Involved in every detail
2. Doing too much myself
3. Focusing on things I couldn’t control
Fix: define outcomes, delegate, narrow scope.
1. Involved in every detail
2. Doing too much myself
3. Focusing on things I couldn’t control
Fix: define outcomes, delegate, narrow scope.
November 10, 2025 at 1:31 PM
3 mistakes I made as a first-time engineering manager:
1. Involved in every detail
2. Doing too much myself
3. Focusing on things I couldn’t control
Fix: define outcomes, delegate, narrow scope.
1. Involved in every detail
2. Doing too much myself
3. Focusing on things I couldn’t control
Fix: define outcomes, delegate, narrow scope.
3 senior phrases:
• “I’m not sure yet.”
• “Let’s explore together.”
• “X might know.”
• “I’m not sure yet.”
• “Let’s explore together.”
• “X might know.”
November 9, 2025 at 4:31 PM
3 senior phrases:
• “I’m not sure yet.”
• “Let’s explore together.”
• “X might know.”
• “I’m not sure yet.”
• “Let’s explore together.”
• “X might know.”
Promote the behaviors you want repeated, in public.
Coach the rest, in private.
Coach the rest, in private.
November 9, 2025 at 1:29 PM
Promote the behaviors you want repeated, in public.
Coach the rest, in private.
Coach the rest, in private.
Two engineers say “I don’t know.”
One follows with silence.
One follows with a plan.
Only one builds credibility.
One follows with silence.
One follows with a plan.
Only one builds credibility.
November 8, 2025 at 7:30 PM
Two engineers say “I don’t know.”
One follows with silence.
One follows with a plan.
Only one builds credibility.
One follows with silence.
One follows with a plan.
Only one builds credibility.
Conway’s Law in practice:
Messy leadership → messy architecture.
Clean up communication first.
Messy leadership → messy architecture.
Clean up communication first.
November 8, 2025 at 4:28 PM
Conway’s Law in practice:
Messy leadership → messy architecture.
Clean up communication first.
Messy leadership → messy architecture.
Clean up communication first.
If you fear looking junior, you’ll stay junior.
Trade ego for learning speed.
Trade ego for learning speed.
November 8, 2025 at 1:28 PM
If you fear looking junior, you’ll stay junior.
Trade ego for learning speed.
Trade ego for learning speed.
Interview tip: show your approach.
“I’d check A, confirm B, experiment with C.”
Reasoning beats recall every single day.
“I’d check A, confirm B, experiment with C.”
Reasoning beats recall every single day.
November 7, 2025 at 7:30 PM
Interview tip: show your approach.
“I’d check A, confirm B, experiment with C.”
Reasoning beats recall every single day.
“I’d check A, confirm B, experiment with C.”
Reasoning beats recall every single day.