Start Skip-Level 1:1s Next Week — 30 Min, 1-2 Per Week

March 21, 2026 at 1:28 AMoperationalmedium

Situation

Approved starting skip-level 1:1s with 12 key engineering ICs (Dieter, Maple, Skip, Jeremy, Andrew, Sultan, Alex, Mustafa, Joseph, Zorina, Giovani, Rahul). 30 minutes each, 1-2 per week, random order. Sarah to schedule.

Reasoning

Committed to retention check-ins in front of Greg, Bjorn, and Mariah in February. RESF transition increases retention risk. Go-slow approach (1-2/week) avoids calendar overload while making steady progress. Random ordering prevents signaling priorities or creating anxiety about who gets called first.

Additional Context

Existing todo since Feb 25 to schedule these. Sarah proposed next week, Peter approved. The list includes RESF-adjacent people (Mustafa, Dieter) alongside core engineering ICs. This is both retention and relationship-building.

Observed Evidence

Sarah asked if next week was good to start skip-levels. Peter approved with '30 is definitely enough time. Next week is a fine time to start.' When asked about order: 'surprise me.' Sarah listed 12 people: Dieter, Maple, Skip, Jeremy, Andrew, Sultan, Alex, Mustafa, Joseph, Zorina, Giovani, Rahul.

Confidence Breakdown

33/35
Evidence
25/30
Pattern
19/20
Source
18/15
Corroboration

Reasoning Depth Analysis

Org Signal:CTO doing skip-level 1:1s signals care for individuals beyond org-level metrics
Who Affected:Direct reports (Nathan, Justin, Chris W) may wonder what their reports say
Precedent:Establishes ongoing CTO-IC touchpoints
Consequences:Builds direct relationships and catches retention risks early
Timing:RESF transition makes retention more critical than ever

People Involved

Source

reflection

AI Confidence

95%

Related Context

💬
DM with Sarah

slack

30 is definitely enough time. Next week is a fine time to start. And we can go slow. This could be one or two a week...

Outcome

No outcome recorded yet.

Decision ID: 9ea0b14c-f02f-41b0-9228-5bef5659c3cd