Unhold the security-engineer req and carry it to Greg in conversation rather than clicking approve

September 23, 2026 at 4:09 PMstrategymedium

Situation

Seven days after telling Bjorn to hold the security-engineer ask for a couple of months, Peter reopened it when Steve Wallace asked whether it was still on hold. His answer was depends on your definition of on hold - it is something we can start moving - and he specified the route rather than just the verdict: get the requisition in front of Peter first, and then Peter works to shepherd it through. His stated reason for not simply approving it is that Greg will kick it back if it arrives as a bare approval, so he will sit down and have a conversation with him instead. On learning the req was already sitting in his queue he said if it is waiting with me, it is in a great place. In the same conversation he asked Steve to send the IT headcount analysis, explicitly so he would have the numbers when advocating for the role.

Reasoning

The 9/16 hold was about sequencing against Bjorn rather than doubt about the role, and Peter had already told Bjorn that the Wallace org is not over-staffed and may need to grow. With that settled, the remaining obstacle moved from is this justified to will Greg wear it - a different problem needing a different instrument. A bare approval has a known failure mode here: it converts a conversation Peter can win into a rejection he then has to reverse, which is more expensive than waiting. So the req sitting in his queue is not delay, it is deliberately keeping it out of the system until the ground is prepared, with the IT headcount numbers as the evidence he intends to bring.

Additional Context

Steve had just closed out the pen test with criticals and highs remediated, had SOC 2 evidence accepted, and had ISO 42001 called done - and has an ISO 27001 surveillance audit roughly six weeks out. That gives the security-engineer ask fresh supporting evidence it did not have a week earlier. Supersedes the hold half of the 9/16 decision.

Observed Evidence

Direct quotes from the 1:1. Peter confirmed in review that the hold was about Greg reception rather than the justification of the role.

Matching Patterns

74%
Switch Instrument, Not Intensity(treats the known failure of the formal channel as the trigger, changes channel from approval to conversation rather than pushing harder)
51%
Reclassify to Route - Decide Who Owns It, Then Give a Criterion Not a Verdict(reclassifies the blocker from justification to reception and takes ownership of that lane)
48%
Measure, Commit Publicly, Then Execute(asks for the headcount numbers first because the number is what makes the argument)

Confidence Breakdown

32/35
Evidence
26/30
Pattern
18/20
Source
7/15
Corroboration

Reasoning Depth Analysis

Org Signal:A requisition sitting in Peter queue is where advocacy gets built, not where it stalls - his directs should read waiting with me as progress.
Who Affected:Greg Kurtzer, who gets a prepared conversation rather than a form; Bjorn, who was told two months a week earlier; Steve org and the ISO 27001 surveillance audit.
Precedent:Approvals that would fail as approvals get converted into conversations before submission, with the evidence assembled first.
Consequences:Real - the req moved from held to in-flight with Peter owning the next step.
Timing:Prompted by Steve asking, and enabled by the audit and pen-test results landing in the same week, which supply the evidence the ask lacked on 9/16.

Source

reflection

AI Confidence

83%

Related Context

🎥
Steve <> Peter Weekly 1:1, 2026-09-18

fathom

Either you or I can kick that forward. Let us get it in front of me first. Approval. And let me work to shepherd it through. If I just hit approve on it, Greg is going to kick it back, but I will sit down and have a conversation with him.

🎥
Steve <> Peter Weekly 1:1, 2026-09-18

fathom

I had a conversation with Bjorn last week and made clear your org was not undersubscribed, but in advocating for like a security engineer, having those numbers specifically to show would be super valuable.

Outcome

No outcome recorded yet.

Decision ID: caba9ea6-cf06-486e-9572-4c59a0187035