Blog · Author
Sarah Smith
Head of Proposal Strategy · 76 posts.
The win-theme retirement ceremony
A quarterly ritual: which win themes we stop using, and why. This quarter, three retired. One we kept against better judgment.
The internal SME review cadence we kept
Weekly 20 minutes beats monthly 90. A year of iterating on our own SME review rhythm, and the cadence that finally stuck.
Section 2: the technical approach without jargon buildup
Why almost every technical approach section opens with the wrong sentence, what the right opening looks like, and a rewritten example from a real bid. The jargon buildup that kills evaluator attention in the first paragraph.
The compliance matrix revisited, one year in
What we wrote about compliance matrices in May 2025, what we've learned since, and the five corrections that change the recommendation. A one-year retrospective on a foundational RFP-mechanics piece.
The draft review heatmap: which sections attract edits
A year of reviewer edit data across hundreds of drafts. Which sections attract the most edits in pink, red, and gold review — and what that pattern tells us about where craft weaknesses cluster.
Executive summaries: the shortest high-leverage document in B2B sales
The canonical pillar on executive summaries. Why one page decides whether the proposal gets read, the five parts of a strong exec summary, two before-and-after rewrites, who signs off.
Federal FY Q2 RFP surge playbook
What federal-facing proposal teams should have ready by April 1 to handle the fiscal-Q2 volume surge — pre-approved content, capture-lead calendars, bid/no-bid discipline, and what breaks under load.
SME collaboration, the six-month update
Revisiting the September 2025 SME-collaboration series. Which patterns persisted in real teams, which ones had to be rewritten, and the one I was wrong about.
Mapping every response paragraph to the scoring rubric
The discipline that turns a 60-page response into an evaluator's checklist. Why every paragraph needs a rubric citation, and how to make the mapping visible without cluttering the document.
A grid for past-performance writeups
The table that turns 20 disorganized references into submit-ready past-performance prose. Four rows, six columns, and the discipline that makes every reference tell the same story from the buyer's angle.
Section 1: the executive summary nuances most teams miss
The executive summary is the section most teams write last, worst, and most generically. When you write it depends on the RFP's shape. Three shapes, three rules, and the nuances nobody tells you.
Win-loss, Part 5 of 5: the eighteen-month view
Eighteen months of running a win-loss program for ourselves. What we'd change if we started over today, what we wouldn't, and the one investment that compounded more than we expected.
Win themes, one year after we published the field guide
The field guide held up on most counts and was wrong on two. What I'd rewrite today, what I wouldn't, and the one test that keeps earning its place.
Win-loss, Part 4 of 5: closing the KB feedback loop
How a debrief finding becomes a block edit that ships into the next bid. The review cadence that makes it stick. The specific anti-patterns that break the loop.
Win-loss, Part 3 of 5: the five anti-patterns
Lessons logged and never applied. Themes that don't match answered questions. Five failure modes I see when a win-loss program looks healthy from the outside but isn't moving the win rate.
Win-loss, Part 2 of 5: debrief rituals that actually run
A 30-minute debrief format with four questions and one DRI. Why quarterly debriefs fail, why per-bid debriefs work, and the calendar discipline that keeps the practice alive past month four.
Win-loss intelligence, Part 1 of 5: what to capture and when
The 18 fields we capture on every bid, why each one matters, and why most teams skip twelve of them. Part 1 of a five-part series on running win-loss as a habit, not a quarterly ritual.
The proposal-team staffing playbook (3, 15, 50 seats)
Proposal-team structure is volume-driven, not culture-driven. What the three-seat, fifteen-seat, and fifty-seat functions look like. Named roles, named failure modes, when to jump tiers.
Past-performance writing voice: past tense, specific, humble
Three real awarded past-performance narratives, anonymized. Why present-tense past performance reads like marketing, and why the humble voice wins more than the confident one.
DORA compliance showing up in DDQs
The EU's Digital Operational Resilience Act shows up in a visible fraction of recent DDQs. What the regulation asks for, what buyers actually want, and how to structure the response without inventing posture.
The RFP kickoff, the 30-minute version
For small teams where a 90-minute Shipley kickoff is a non-starter. The trimmed agenda, what gets kept, what gets pushed to async, and the one artifact the kickoff still has to produce.
Hiring a proposal manager in 2026: what actually changed
The job description template we use, the interview questions that still work, and the three things that have changed since 2024 about what a proposal manager role actually requires. Written for hiring managers staffing up in Q1.
Annual planning for proposal teams: the three-sheet model
A three-sheet annual plan — bid forecast, capacity forecast, skill-gap sheet — that a small proposal team can build in a week and revise quarterly. Due by mid-January if you want it to matter.
The annual proposal-team retro template
The questions we ask at year-end and the format that surfaces what monthly retros miss. A 90-minute meeting that produces a durable artifact instead of a slide deck that gets archived and forgotten.
The security-questionnaire closeout list
Ten fields security teams should confirm before signing off on a DDQ. A single-page closeout checklist, written for the person whose name goes on the submission and whose audit exposure is real.
The end-of-year win-themes audit
Five prompts for retiring win themes that have lost discriminatory power, and promoting the ones that actually showed up in wins. A year-end ritual that takes an afternoon and pays out across the next twelve months of bids.
The minimum viable capture plan
Four questions, one table. Why most capture plans collapse under their own weight, and the stripped-down version small and mid-size teams actually use.
Three exec summaries I rewrote this week, part 8
The December installment of the rewrite series. A year-end DDQ-fronted RFP, a public-sector re-compete, and a managed-services renewal. Three rewrites and what each one was actually doing.
Year-end DDQ surge: how to staff it
The operational playbook for running 40 to 60 due-diligence questionnaires through a small security and proposal team in the last six weeks of the year, without losing the team.
Proposal post-mortems: the discipline, the template, the follow-through
The canonical long-read on proposal post-mortems. What a post-mortem actually accomplishes, the template that makes the discipline sustainable, how to get a debrief from the buyer, and the three follow-through patterns that work.
Discriminator vs. feature: which one moves the score
Two real RFP sections, same underlying win theme, different framings. Which framing evaluators picked, and the rule I extracted from comparing them.
The proposal post-mortem template: preview
A Wednesday teaser for next week's pillar. The fields that matter in a post-mortem template, and the one section most teams skip.
Past-performance library hygiene for year-end
Three questions that decide whether a past-performance entry stays in the library, gets rewritten, or gets retired. A December sweep that pays off in the Q1 pursuit wave.
DDQ answer voice: why consistency beats polish
Buyers forgive plain writing. They do not forgive a questionnaire that reads like it was stitched from eight different people. How to keep 300 DDQ answers sounding like one voice.
The security-questionnaire response team that actually ships
Three roles, one DRI, a 48-hour SLA. How regulated vendors staff the Q4 questionnaire wave without shipping stale answers or missing deadlines.
The five compliance-matrix mistakes that lose bids
Real patterns from real debriefs. The matrix mistakes that surface as scoring penalties on the buyer side, and the discipline that prevents each one. Citations to VisibleThread on the most common cause.
Discriminator tests: three worked examples
The APMP discriminator test is simple to state and brutal to apply. Three real-shape proposal sections, run through the discriminator filter, with the rewrites that survive.
SME collaboration, reconsidered
The 48% bottleneck hasn't moved in five years. Every playbook that attacks it via better communication has failed. The economic frame, three patterns that partially work, the one that fully works, what tooling must do.
SME collaboration, reconsidered: the preview
The async-first SME workflow we wrote about all year was half-right. Two hundred real interviews and a year of customer data later, here is what we got right, what we got wrong, and what the canonical post tomorrow will argue.
Three exec summaries I rewrote this week, part 6
The October installment of the rewrite series. A SaaS bid, a federal IT services bid, and a healthcare DDQ-fronted RFP. Three before-and-afters and what each rewrite was actually doing.
The RFP section priority matrix
Evaluator weight times effort hours equals where to spend the draft budget. A simple matrix that tells you which sections deserve gold-team review and which sections deserve a paragraph and a citation. With three worked examples.
SME collaboration, Part 4 of 4: a KB your SMEs will actually use
What makes an SME contribute to a knowledge base versus what makes them ignore the tool. Closing the four-part series — the structural choices that decide whether your KB compounds or rots.
The color-team review discipline, explained for modern teams
Pink, red, gold, white. The four-team review discipline most modern proposal shops know by name and don't actually run. This post reclaims it — what each team is for, why teams skip it, the rubrics, and how to run reviews async in 2025.
SME collaboration, Part 3 of 4: the 20-minute capture call
The synchronous meeting that saves four days of draft revision when the question is genuinely complex. The agenda template, the recording-and-transcript discipline, and what gets routed to a capture call vs. an async ticket.
The executive summary that fits on two pages, always
Length is a win-theme signal to evaluators. A two-page executive summary is a commitment; a six-page executive summary is a hedge. Six compression moves I run every time.
SME collaboration, Part 2 of 4: ticketed asks and response SLAs
Why 'just ping them on Slack' fails as an SME workflow, what a structured ticket form should contain, and the response SLAs that make the queue legible to engineering managers and proposal leads at the same time.
SME collaboration, Part 1 of 4: the async interview
Part 1 of 4 on SME collaboration. The async interview pattern: structured prompts, short turnarounds, an audit trail, and no scheduled meeting. Why it works when 'just ping them' doesn't.
A field guide to win themes that actually win
The canonical pillar on win themes. What they are, what they aren't, the swap-name test applied across six worked examples, and the discipline of constructing themes from capture and retiring themes that didn't earn their score bump.
Preview: the field guide to win themes that actually win
A teaser for tomorrow's win-themes pillar. Two worked examples — one theme that fails the swap-name test, one that survives it — and what the difference looks like in the response.
The DDQ review cycle you can actually finish
Two rounds, not four. The structure that keeps security questionnaires from missing deadlines, and what to drop when you cut the ceremony.
Section openings that earn the next paragraph
Six real section openings from winning proposals, annotated. What they did, why the evaluator kept reading, and how to write them yourself.
Discriminators: the word your evaluator was trained on
APMP calls them discriminators. Most teams don't write them. Three real examples from awarded proposals — what they did, why they worked.
The complete bid/no-bid scoring framework
The canonical bid/no-bid framework. Five variables scored 1–5, weighting, the rubric template, the bid-decision meeting, override discipline, and where the rubric is honestly wrong.
Bid/no-bid is a decision, not a vibe
A preview of Thursday's pillar piece. Why most teams score implicitly, what implicit scoring costs, and the meeting structure that turns a vibe into a decision.
Three exec summaries I rewrote this week, part 4
Continuing the series. Three before/after exec-summary passages from this week's bids, including a tabled structure that scored well in a state-government pursuit.
Good win themes are verbs, not adjectives
Adjective win themes — robust, scalable, frictionless — fail the swap test. Verb win themes describe what changes for the buyer. Three before/after rewrites of real proposal language.
Past performance that actually maps to the scope
Selecting which prior contracts to cite is a craft skill, not a database query. Three worked examples of past-performance selection — what to cite, what to omit, why the relevance map matters more than the impressive number.
Reading an RFP like the procurement lead who wrote it
RFPs are procurement documents written by named humans with known constraints, drafted from templates reused for fifteen bids. Read them that way and the response writes itself differently. The canonical long version.
Three exec summaries I rewrote this week, part 3
Field notes from the editing desk. Three illustrative before-and-afters of executive summary openings I cut down this week, and the pattern each one is fighting.
Reading the RFP the procurement lead actually wrote
RFPs are procurement documents written by named humans with known constraints, not sales documents. Read them that way and you respond 40 to 60 percent better. A preview of next week's pillar piece.
A bid/no-bid scoring rubric we actually use
Five dimensions, a 1–5 score on each, a written floor, and a no-bid decision that is as cheap to defend as a bid decision. The rubric I bring into every kickoff.
Win themes when you're the incumbent defending a contract
Defending a contract is a different proposal than winning one. The win themes that worked four years ago will lose you the renewal. Here's what changes when you're already inside.
The RFP kickoff meeting that saves two weeks
A 60-minute kickoff that decides ownership, win themes, the compliance scaffold, and the review calendar. Run badly, it costs you two weeks. Run right, it pays for itself by Friday.
DDQ Anatomy, Part 4 of 4: operations and vendor management
The closing section of a vendor DDQ. Incident response from the operational side, business continuity, vendor risk management, and the questions that decide whether you're a vendor procurement will renew.
DDQ Anatomy, Part 3 of 4: the security section
The security section is 60 questions long, mostly SOC 2-shaped, and it's where vendors most often ship answers that won't survive the buyer's actual security review. Here's what's asked and how to respond.
Three exec summaries I rewrote this week, part 2
Three illustrative before-and-after exec summary openings. The patterns that fail, the edits that work, and why the second sentence is where most exec summaries lose the reader.
DDQ Anatomy, Part 2 of 4: legal and privacy
The legal and privacy section of a vendor DDQ is where 45 questions repeat bid-to-bid. Here's what they ask, what evaluators check, and how to answer without losing a week to it.
The DDQ response playbook, end to end
A canonical playbook for due-diligence questionnaires. Seven stages from intake to post-mortem write-back, what each stage owns, where each one breaks, and why the same DDQ next year should take half the time.
DDQ Anatomy, Part 1 of 4: the finance section
What the finance section of a DDQ asks — SOC audit history, revenue recognition, debt covenants, parent-company financials. What evaluators want, where questions repeat, and what good answers look like.
Win themes and the swap-name test
If you can swap your company name with a competitor's and the win theme still makes sense, the win theme is fluff. Six examples of themes that fail the test, six that pass, and what evaluators actually score.
Red flags and the bid/no-bid gut check (Part 4 of 4)
Five signals an RFP is a wired bid, an unfunded wish list, or a procurement that was never serious. The closing piece in the Reading an RFP series.
Win themes are not value props
Six win themes — four that fail the swap test, two that survive it. The difference is the difference between a theme an evaluator scores and one they skim past.
The unwritten rules inside every RFP (Part 3 of 4)
Procurement leads write RFPs in a particular dialect. Once you can read it, the scoring rubric, the disqualifiers, and the actual priorities surface within the first 20 pages.
The compliance matrix you wish existed (Part 2 of 4)
The compliance matrix is the most consequential artifact in proposal work, and the one most teams build too late. Part 2 of Reading an RFP — what it is, how to build one in 30 minutes, and why it usually doesn't get built.
What 'reading an RFP' actually means (Part 1 of 4)
Reading an RFP isn't reading. It's six discrete passes — scope, compliance language, evaluation rubric, timeline and addenda, procurement signals, deal quality — each producing its own artifact. Part 1 of a four-part series.
The 8-stage RFP response pipeline, explained
A canonical long-read on how a mature proposal shop actually moves an RFP from the hand-off email through submission and the post-mortem that feeds the next bid. Eight stages, what each one owns, and where each one fails.
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