operations administrationchief of staffexecutive operationsfounders officestartup ops
Complete evaluation framework
What to assess and how to score it
Review the evidence signals before interviewing. Then use the anchored descriptions—not instinct alone—to choose the score that best matches each answer.
01
Evaluation factor
Execution and reliability
35% weight
Check how they ran a founder's calendar, inbox and travel at pace: tools like Superhuman, Notion, Linear, board pack prep, investor update cycles, weekly priority tracking.
Evidence to listen for
Describes a workload they owned and how they kept it from slipping
Names the tools and systems they ran day to day
Can talk about volume: tickets, inboxes, orders, uptime
Nothing quietly falls through when they are busy
Five-point scoring guide
1
Poor
Cannot describe their own workload; things slip without them noticing.
2
Needs Improvement
Handles routine volume; drops work under pressure.
3
Satisfactory
Reliable on steady-state work; struggles when volume spikes.
4
Very Good
Consistently reliable at real volume with a system for staying on top.
5
Excellent
Names the founder's recurring rhythms they owned, cites turnaround times, and describes nothing slipping through during fundraise or launch weeks.
02
Evaluation factor
Improving the process
25% weight
Probe what they rebuilt rather than maintained: meeting cadence redesign, an onboarding checklist, expense flow in Ramp or Brex, dashboards replacing manual status chasing.
Evidence to listen for
Has changed a process rather than only following one
Can name what was slow or error-prone and what they did about it
Documents so the improvement survives them
Knows when a process is worth automating and when it is not
Five-point scoring guide
1
Poor
Follows instructions only; no sense that process can change.
2
Needs Improvement
Notices problems but escalates rather than solving.
3
Satisfactory
Makes small improvements; impact is local and undocumented.
4
Very Good
Has redesigned a real process with measurable effect.
5
Excellent
Points to a specific process they scrapped or automated, with hours reclaimed for the founder and a system others still use.
03
Evaluation factor
Judgement and autonomy
25% weight
Assess where they decided alone: declining meeting requests, reordering the founder's week, handling a vendor dispute, escalating a hiring or spend issue without waiting for permission.
Evidence to listen for
Knows what to decide alone and what to escalate
Handles an exception without freezing or improvising recklessly
Protects confidentiality and access appropriately
Asks a clarifying question rather than guessing on something costly
Five-point scoring guide
1
Poor
Either escalates everything or acts recklessly on their own.
2
Needs Improvement
Needs frequent direction; uneasy with exceptions.
3
Satisfactory
Sound judgement on familiar decisions.
4
Very Good
Clear sense of their own authority; handles exceptions well.
5
Excellent
Gives clear examples of acting on the founder's behalf, plus a case where they held back and explains the line they drew.
04
Evaluation factor
Communication
15% weight
Look for how they wrote on the founder's behalf: investor emails, all-hands notes, candidate rejections, and how they pushed back on senior people politely.
Evidence to listen for
Writes clearly enough that people act without a follow-up
Manages expectations before a deadline slips, not after
Handles a frustrated colleague or customer calmly
Works across time zones or async where the role needs it
Five-point scoring guide
1
Poor
Unclear written communication; goes quiet when things slip.
2
Needs Improvement
Communication needs chasing; raises problems late.
3
Satisfactory
Clear enough day to day; proactive updates are inconsistent.
4
Very Good
Clear, proactive, and calm under pressure.
5
Excellent
Shows concise written artefacts they drafted, handles discretion around confidential topics, and describes chasing executives without damaging the relationship.
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