Gregor Ojstersek
@gregorojstersek.bsky.social
CTO | Founder of Engineering Leadership newsletter (165k+ subscribers) - Helping you become a great engineering leader!
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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!
Managers have been vibe coding forever 😂
November 7, 2025 at 3:44 PM
Managers have been vibe coding forever 😂
Most teams obsess over prompt engineering but the wins come from context engineering:
Prompt Engineering = wording the question.
Context Engineering = designing the inputs, constraints, and examples the model uses to think.
When you control the context, you control the outcomes.
Prompt Engineering = wording the question.
Context Engineering = designing the inputs, constraints, and examples the model uses to think.
When you control the context, you control the outcomes.
October 30, 2025 at 10:28 AM
Most teams obsess over prompt engineering but the wins come from context engineering:
Prompt Engineering = wording the question.
Context Engineering = designing the inputs, constraints, and examples the model uses to think.
When you control the context, you control the outcomes.
Prompt Engineering = wording the question.
Context Engineering = designing the inputs, constraints, and examples the model uses to think.
When you control the context, you control the outcomes.
Underrated leadership skill:
Naming trade-offs out loud.
When people see the cost, they respect the decision.
Naming trade-offs out loud.
When people see the cost, they respect the decision.
October 25, 2025 at 6:29 PM
Underrated leadership skill:
Naming trade-offs out loud.
When people see the cost, they respect the decision.
Naming trade-offs out loud.
When people see the cost, they respect the decision.
5. Tools used.
Jira leads usage across organizations.
Homegrown dashboards rank second at 23%, reflecting increased internal analytics.
Jira leads usage across organizations.
Homegrown dashboards rank second at 23%, reflecting increased internal analytics.
October 24, 2025 at 12:32 PM
5. Tools used.
Jira leads usage across organizations.
Homegrown dashboards rank second at 23%, reflecting increased internal analytics.
Jira leads usage across organizations.
Homegrown dashboards rank second at 23%, reflecting increased internal analytics.
4. How metrics are tracked.
Common methods include retrospectives, customer feedback, and surveys.
Teams also reference automatically derived operational metrics (e.g., DORA) via existing tooling.
Common methods include retrospectives, customer feedback, and surveys.
Teams also reference automatically derived operational metrics (e.g., DORA) via existing tooling.
October 24, 2025 at 12:32 PM
4. How metrics are tracked.
Common methods include retrospectives, customer feedback, and surveys.
Teams also reference automatically derived operational metrics (e.g., DORA) via existing tooling.
Common methods include retrospectives, customer feedback, and surveys.
Teams also reference automatically derived operational metrics (e.g., DORA) via existing tooling.
3. Metrics teams try to avoid.
Respondents flag vanity or gameable measures:
• PR counts.
• Days worked.
• Ticket counts.
• Lines of code.
• Story points totals.
Focus shifts from volume to outcomes in these responses.
Respondents flag vanity or gameable measures:
• PR counts.
• Days worked.
• Ticket counts.
• Lines of code.
• Story points totals.
Focus shifts from volume to outcomes in these responses.
October 24, 2025 at 12:32 PM
3. Metrics teams try to avoid.
Respondents flag vanity or gameable measures:
• PR counts.
• Days worked.
• Ticket counts.
• Lines of code.
• Story points totals.
Focus shifts from volume to outcomes in these responses.
Respondents flag vanity or gameable measures:
• PR counts.
• Days worked.
• Ticket counts.
• Lines of code.
• Story points totals.
Focus shifts from volume to outcomes in these responses.
Activity counters also rank highly:
• Pull requests.
• Days worked.
• Lines of code.
• Tickets closed.
• Story points completed.
• Pull requests.
• Days worked.
• Lines of code.
• Tickets closed.
• Story points completed.
October 24, 2025 at 12:32 PM
Activity counters also rank highly:
• Pull requests.
• Days worked.
• Lines of code.
• Tickets closed.
• Story points completed.
• Pull requests.
• Days worked.
• Lines of code.
• Tickets closed.
• Story points completed.
This is how engineering orgs are measuring performance in 2025:
October 24, 2025 at 12:32 PM
This is how engineering orgs are measuring performance in 2025:
Most 1:1s drift.
CLEAR turns them into decisions.
Here’s the framework I use to turn 20 minutes into real progress:
CLEAR turns them into decisions.
Here’s the framework I use to turn 20 minutes into real progress:
October 22, 2025 at 12:27 PM
Most 1:1s drift.
CLEAR turns them into decisions.
Here’s the framework I use to turn 20 minutes into real progress:
CLEAR turns them into decisions.
Here’s the framework I use to turn 20 minutes into real progress:
5 phrases that build trust fast:
1. Tell me more.
2. I might be wrong.
3. Help me see it your way.
4. Here’s what I can do today.
5. Thank you for pushing on this.
1. Tell me more.
2. I might be wrong.
3. Help me see it your way.
4. Here’s what I can do today.
5. Thank you for pushing on this.
October 21, 2025 at 12:31 PM
5 phrases that build trust fast:
1. Tell me more.
2. I might be wrong.
3. Help me see it your way.
4. Here’s what I can do today.
5. Thank you for pushing on this.
1. Tell me more.
2. I might be wrong.
3. Help me see it your way.
4. Here’s what I can do today.
5. Thank you for pushing on this.
This is the reason why many engineers and engineering leaders believe AI is impacting the industry negatively.
October 19, 2025 at 2:48 PM
This is the reason why many engineers and engineering leaders believe AI is impacting the industry negatively.
Rotating Tech Leads can save you six figures in churn and weeks of delivery drift.
Keeping one fixed TL looks efficient until:
• Growth stalls
• Bottlenecks appear
• Knowledge walks out the door
Why rotate instead of appointing one forever TL?
Keeping one fixed TL looks efficient until:
• Growth stalls
• Bottlenecks appear
• Knowledge walks out the door
Why rotate instead of appointing one forever TL?
October 18, 2025 at 12:31 PM
Rotating Tech Leads can save you six figures in churn and weeks of delivery drift.
Keeping one fixed TL looks efficient until:
• Growth stalls
• Bottlenecks appear
• Knowledge walks out the door
Why rotate instead of appointing one forever TL?
Keeping one fixed TL looks efficient until:
• Growth stalls
• Bottlenecks appear
• Knowledge walks out the door
Why rotate instead of appointing one forever TL?
You can burn six figures while shipping the wrong thing.
Here’s how a strong Tech Lead saves you from that:
1/ What is a Tech Lead and what do they do?
A Tech Lead owns the technical implementation of a specific project.
Here’s how a strong Tech Lead saves you from that:
1/ What is a Tech Lead and what do they do?
A Tech Lead owns the technical implementation of a specific project.
October 17, 2025 at 10:57 AM
You can burn six figures while shipping the wrong thing.
Here’s how a strong Tech Lead saves you from that:
1/ What is a Tech Lead and what do they do?
A Tech Lead owns the technical implementation of a specific project.
Here’s how a strong Tech Lead saves you from that:
1/ What is a Tech Lead and what do they do?
A Tech Lead owns the technical implementation of a specific project.
What you tolerate becomes your culture.
Standards are your daily choices:
Standards are your daily choices:
October 16, 2025 at 12:27 PM
What you tolerate becomes your culture.
Standards are your daily choices:
Standards are your daily choices:
If winning the meeting matters more than winning the market, you’re losing.
Every. Single. Day.
Every. Single. Day.
October 15, 2025 at 12:26 PM
If winning the meeting matters more than winning the market, you’re losing.
Every. Single. Day.
Every. Single. Day.
Indecision is the most expensive decision.
It burns time and trust:
It burns time and trust:
October 14, 2025 at 12:28 PM
Indecision is the most expensive decision.
It burns time and trust:
It burns time and trust:
People don’t quit “companies.”
They quit managers:
Good managers are multipliers.
Bad managers are black holes.
They quit managers:
Good managers are multipliers.
Bad managers are black holes.
October 13, 2025 at 12:28 PM
People don’t quit “companies.”
They quit managers:
Good managers are multipliers.
Bad managers are black holes.
They quit managers:
Good managers are multipliers.
Bad managers are black holes.
20,000 lines of the wrong code is negative velocity.
Maintenance makes it a debt snowball:
Maintenance makes it a debt snowball:
October 12, 2025 at 12:31 PM
20,000 lines of the wrong code is negative velocity.
Maintenance makes it a debt snowball:
Maintenance makes it a debt snowball:
Most “slow teams” aren’t slow.
They’re interrupted:
They’re interrupted:
October 11, 2025 at 12:27 PM
Most “slow teams” aren’t slow.
They’re interrupted:
They’re interrupted:
AI can write code faster.
But that was never the bottleneck:
But that was never the bottleneck:
October 10, 2025 at 12:27 PM
AI can write code faster.
But that was never the bottleneck:
But that was never the bottleneck:
You can always buy tools later.
But you must start earning trust now.
That’s where real productivity comes from.
But you must start earning trust now.
That’s where real productivity comes from.
October 9, 2025 at 12:27 PM
You can always buy tools later.
But you must start earning trust now.
That’s where real productivity comes from.
But you must start earning trust now.
That’s where real productivity comes from.
AI isn’t “plug and play.”
It’s plug and pay:
It’s plug and pay:
October 8, 2025 at 12:33 PM
AI isn’t “plug and play.”
It’s plug and pay:
It’s plug and pay:
Want to unlock $1M–$10M in productivity without buying another AI tool?
Fix your culture first:
Fix your culture first:
October 7, 2025 at 12:31 PM
Want to unlock $1M–$10M in productivity without buying another AI tool?
Fix your culture first:
Fix your culture first:
I'll be speaking at the Codemotion, Milan, Italy, on October 15.
The talk is called: Tech Lead Rotation in Your Engineering Team.
I'll be sharing:
The talk is called: Tech Lead Rotation in Your Engineering Team.
I'll be sharing:
October 3, 2025 at 12:02 PM
I'll be speaking at the Codemotion, Milan, Italy, on October 15.
The talk is called: Tech Lead Rotation in Your Engineering Team.
I'll be sharing:
The talk is called: Tech Lead Rotation in Your Engineering Team.
I'll be sharing: