The review-prep one-pager that turns the meeting on its head, the H1 tax-loss harvest most operators miss, Claude as your performance-review rehearsal partner, the 8-week post-review pivot, and what Q1 SaaS earnings mean for your 2026 RSU.
← New Money  ·  Issue 011  ·  The Sunday Brief Sunday, May 17, 2026
◆ Issue 011 · May 17

Performance
review
week.

What to walk in with, what to walk out with.

From the editor

Replies on Issue 010 leaned 02 and 05 — the offer-letter audit and entry-level collapse. Same anxiety, two surfaces. Both are downstream of the same thing: the comp conversation is structurally tilted toward the company, and the once-a-year window where it tilts back is happening this month.

Q2 mid-cycle reviews are in flight at most BigCo orgs through the next four weeks. Per McKinsey’s 2025 talent ops survey, only 23% of senior ICs prepare a written self-assessment more than 48 hours before the meeting. The 23% net +2.4× the comp adjustment of the other 77%. The prep is the leverage. Five plays this week to use the window properly.

01 Labor Repricing

The review-prep one-pager that turns the meeting on its head.

The default review meeting is your manager telling you what they thought of your year. The version that pays is you arriving with a one-page memo that makes the conversation about outcomes, comp-band positioning, and next-half scope — in that order. Per Levels.fyi Q1 2026 comp band data, the median delta between the 50th and 75th percentile inside the same level is $48k. That delta is decided on the prep, not the year.

The 5-block one-pager

1. Three outcomes. Each with a dollar, a point, or an hour saved. No activity.

2. One artifact link. The doc / dashboard / PR that proves outcome #1.

3. Comp-band ask. Specific number, anchored to a verifiable comp source. Not “a raise.”

4. Next-half scope. The two projects you’re proposing, sized to the next-level promotion criteria.

5. One risk. Something your manager probably doesn’t know about. Earns trust.

What to do this week

Write the one-pager today. Send it to your manager 48 hours before the review with one sentence: “Wanted to anchor the discussion — happy to talk to any of this.” The pre-send is the unlock; it shifts you from defending to setting agenda.

02 Capital & Assets

The H1 tax-loss harvest most operators leave on the table.

Tax-loss harvesting is treated as a December problem. It isn’t. The H1 window — now through June 30 — is where the cleanest losses sit, because the year’s gainers haven’t fully run and the laggards aren’t yet washed out. Per IRS Publication 550 rules, a realized capital loss offsets capital gains dollar-for-dollar, then up to $3,000/year against ordinary income, with the rest carrying forward indefinitely.

Practical: scan your taxable brokerage for positions down >8% from your cost basis. Sell, log the loss, buy a similar-but-not-identical replacement to dodge the 30-day wash sale rule (e.g., VTI → ITOT). A reader who did this in March banked $31k of realized losses against her concentrated-stock unwind from Issue 005. Net tax saving at her bracket: $7,440.

What to do this week

Open your taxable brokerage. Sort holdings by % gain/loss. For every red position deeper than −8%, calendar 20 minutes this week to execute the swap. Mark the wash-sale clock on your phone (Jul 1). The 20 minutes is most readers’ highest-paying hour of the year.

03 AI Leverage

Claude as your performance-review rehearsal partner.

Most senior ICs prep the substance and skip the rehearsal — then the meeting goes sideways because the manager asked the one question they didn’t expect. Claude Projects fixes this in 25 minutes. Drop your one-pager + a one-paragraph sketch of your manager’s priorities + your last two perf-cycle ratings into a project. System prompt below.

SYSTEM PROMPT
You are my skip-level manager in a performance review meeting. You have read my one-pager and you know my history. Be skeptical, fair, and quick. Ask the 8 hardest questions you’d ask in this meeting, one at a time. After each answer, push on the weakest claim.

You’ll find your two weakest claims inside the first three rounds. Those are the questions you’ll get in the real meeting. Tighten the one-pager, run the simulation again. Two passes = roughly 90% of the upside.

What to do this week

Spin up the Claude Project. Run two full simulations. The first will reveal the gaps; the second will harden the answers. 25 minutes total. Better prep than 95% of operators get for the meeting that resets their year of comp.

04 New Paths

The 8-week post-review pivot — if the conversation goes badly.

A bad review is information, not a verdict. The 8-week sequence that turns it into option-value: Weeks 1–2: ship the productized $3k offer from Issue 001 Play 04. Weeks 3–4: convert it to a $5k retainer with the same buyer. Weeks 5–6: add a second retainer. Weeks 7–8: document the production stack so a $25/hr VA can run delivery while you handle scoping. End of week 8: $10k MRR, ~6 active hours/week.

You don’t quit. You keep the W2 and run the holding co (Issue 002 Play 04) in parallel. Two months from now, you’re back at the same review meeting with optionality. The recursive part: knowing you have it changes the conversation.

What to do this week

Whether or not you expect the review to go well: write the 3-line productized offer this Sunday. Don’t send it. Save it as a draft in your email. Optionality you haven’t exercised is still optionality — and the act of writing it changes how you sit in the meeting on Monday.

05 Macro & Timing

What Q1 SaaS earnings just told you about your 2026 RSU.

Q1 2026 earnings wrapped last week. Per Bloomberg aggregates and individual 10-Q filings, the top-30 public SaaS names guided FY2026 revenue down a median 4.6% from their January outlook. NDR contracted from 109% to 102% on average. The cause is consistent across calls: budget reallocation from horizontal SaaS to AI tooling.

The career math: if your RSU is denominated in a Q1-guidance-cutter, the headline value on your offer letter is now ~12–18% optimistic on a forward basis. Don’t price your next 12 months against the grant-date number. Use the post-guidance market quote and discount another 10% for volatility. The honest read is your equity is worth less than your manager will reference next week.

What to do this week

Re-mark your unvested RSU at Friday’s close, not the grant-date price. If the value dropped >15%, ask in this week’s review for an off-cycle refresh tied to the original headline value. About 28% of asks get granted. The asks that don’t happen get nothing.

◆ Chart of the Week

The loyalty tax: 8% raise vs 25% switch.

Median comp change · operators 2 yrs into role · 2026
Stay · standard merit raise+8%
  
Stay · internal promotion+12%
  
Switch · lateral move+18%
  
Switch · level-up move+25%
 

Source: Levels.fyi + JOLTS separations-vs-pay cuts. The gap is the comp the market pays to people who interview. The review meeting is the cheapest way to ask for it before having to.

◆ The Tape
$48K
50th → 75th in same level
2.4×
Comp adj · prepped vs not
$7.4K
H1 tax-loss reader case
One favour before you go

Reply with one number: 01, 02, 03, 04, or 05 — which play you’d run first this week.

I read every reply. They shape what shows up in Issue 012.

Go run something. See you next Sunday.

— The Operator

still at McKinsey, still building

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