Blog · Pillar
Team & Workflow.
55 posts in this archive.
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.
The proposal team I wish we'd hired first
A year in, an honest look at the hiring order on our own proposal function — who we brought on in what sequence, and the reordering that would have saved us six months.
The Saturday KB hygiene drill
Thirty-five minutes of knowledge-base maintenance that keeps Monday's drafts from citing stale content. A year in, here's the drill that actually stuck.
Team rituals that stuck at one year
The three team rituals we kept after a year, the two we killed, and the one we reintroduced after thinking we'd retired it. A short field note on what a small company's process actually looks like.
The capture-lead role, reconsidered
The shape of the capture-lead role we started with, the shape it became, and why the difference matters for anyone hiring into the role in 2026.
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.
The Saturday review of outgoing pursuits
A 15-minute Saturday ritual for reviewing the week's outgoing proposal pursuits. Three questions, applied in order: what to kill, what to push, what to staff up. The cheapest pipeline discipline we run.
Team KPIs we stopped tracking
Two proposal-team metrics we killed this year. Why each one misread the work, and what we replaced them with. Short, opinionated, written from my own dashboard.
The Presidents' Day proposal stagger
Two RFPs due Wednesday, a federal team off Monday for the holiday. How we resequence the pipeline to land both bids without a Tuesday-night fire drill.
The Valentine's Day deadline drill
A weird pattern in our submission data: federal fiscal-year Q2 RFP deadlines cluster around mid-February. Here's the drill we run when three bids land in the same week.
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.
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.
The team we hired in year one, honestly
Roles we hired, roles we should have hired earlier, and one role we hired too early. A quick accounting of the first year of PursuitAgent headcount decisions, in the spirit of being useful to anyone about to make the same calls.
The capture-to-proposal handoff checklist
Seven fields the capture team has to deliver before the proposal team starts writing. Why most handoffs fail on three of them, and how to enforce the handoff as a gate rather than a courtesy.
The January past-performance backfill ritual
Two hours in mid-January to refresh last year's past-performance references so they actually carry the weight they need to for this year's bids. The shortlist, the edits, the re-approvals.
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 January proposal-pipeline reset
A 90-minute ritual for the first working Saturday of the year. Archive finished bids, retire dead opportunities, and prune the active list. The point is a pipeline that reflects what you will actually work on in Q1.
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.
Year-one numbers we can share
The product metrics we're willing to post publicly after year one, the ones we aren't, and the reasoning behind each line. An honest ledger instead of a slide deck.
The week between Christmas and New Year, for proposal teams
The slowest week of the year has a use. Five low-overhead rituals that cost an afternoon each, capture the year's learning, and set up the team for a clean January. What to do when nothing is landing.
The Christmas Day silent-inbox note
Nothing is shipping today. No buyer is responding. No clarification question is getting answered. This is the correct default, and here is why we built the system around it.
The holiday handoff runbook, part 2: the questions we forgot
Follow-up to the holiday handoff runbook. Four prompts we missed the first time — covering portal credentials, unsubmitted addenda, decision-of-last-resort authority, and the quiet bids you forgot you were still on the hook for.
The holiday handoff runbook
What to write so the on-call proposal lead isn't paged at 11pm on December 23. A 30-minute template that pays for itself the first time a portal deadline moves.
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.
The Cyber Monday color-team review
A field note on the unusual pattern of scheduling a pink-team review on a holiday long weekend. When it works, when it doesn't, and the one rule that keeps it from backfiring.
Thanksgiving week: how we staff three active pursuits
Our ten-minute Monday huddle that keeps the short week from collapsing. Three active pursuits, three owners, one rule about Wednesday at noon.
The rolling Q4 capacity plan for proposal teams
A five-week look-ahead that reallocates the proposal team twice. Why a static quarterly plan breaks in Q4, and what a rolling version does instead.
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 Halloween submit weekend triage
Operational note for proposal teams facing weekend deadlines. Three rules we run on every weekend submit. Short, written down so we can find it again next Halloween.
The Saturday backlog triage pattern
Thirty minutes on a Saturday morning, three buckets, and Monday is ready to go. A small operational ritual we use to keep the proposal backlog from compounding into chaos.
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.
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.
Our own proposal process, in public
How PursuitAgent responds to its own inbound RFPs. The intake, the bid/no-bid, the writing, the gold team, and the parts of the product that don't help us yet because we haven't built them.
The 20-minute proposal retro
The ritual we run after every submit. Five questions. One owner per action item. Twenty minutes. Why most proposal post-mortems don't happen and what makes this one stick.
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.
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.
The Monday-morning RFP triage standup
15 minutes, four questions, one decision. The weekly ritual that replaces inbox scraping and stops bid/no-bid from happening by drift.
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.
The SME draft packet, generated automatically
What we ship to an SME alongside the question so they can answer in five minutes instead of fifty. The packet's components, the retrieval that builds it, and the design choices that keep the SME out of our tool.
SME collaboration is a UI problem
An opinion piece. Why 48% of teams still cite SME wrangling as their #1 problem after five years of vendor promises — and why the answer is not another tool but a better surface for the SME.
In preview: SME-ask tickets with SLA timers
Every SME ask creates a ticket with a deadline derived from the bid date. Open tickets show on the proposal dashboard. Missed SLAs flag, they don't auto-chase. In preview alongside the Proposal Builder section-assignment surface.
The second-question rule for SME asks
A short field-note on how to ask SMEs for input. Ask one concrete question first; save the open-ended one for after you've got the first answer.
The SME Slack bot: architecture and boundaries
How the PursuitAgent SME bot asks for input, what it does with the answer, and what it deliberately refuses to do. A short tour of the boundary between the bot and the human.
The Saturday shuffle: reprioritizing the proposal queue
A 10-minute weekly ritual that reprices every active proposal against its actual deadline pressure and probability of win.
The Friday-afternoon submit is a code smell
When proposal teams routinely submit at 4pm on Fridays, the late-week pattern reveals capacity and capture-hygiene problems upstream. What the smell tells you and what to fix.
Stop CC-ing your SMEs, part 2
Six weeks after we said stop CC-ing your SMEs on every email, here are the patterns that have actually shown up in disciplined teams. The replacement was not a tool — it was a queue.
The Sunday night compliance check
A 15-minute habit before Monday's kickoff. Read the compliance matrix against the calendar. Find the four things that will hurt you in week three. Write the email Sunday night so Monday is not the day you discover them.
The proposal week bracketing July 4th
Federal buyers don't move. Commercial buyers don't move. Reviewers do. A short field note on the bid weeks bracketing the July 4th holiday and the four things to triage now.
Month two: the questions we got from readers
Two months into writing this blog daily. Six questions readers sent, paraphrased. What I learned from the questions, and where the blog is going next.
The Friday 4pm review is the wrong ritual
End-of-week color-team reviews are the default in most proposal shops. The reviewers are tired, the writers can't fix anything, and the meeting becomes a tracker entry instead of a review. There's a better cadence.
The shadow SMEs who should be on every proposal invite
Three roles answer the hardest questions on most proposals and aren't titled as experts. How to identify them in your org and why they belong on the kickoff invite.
The proposal backlog after a long weekend
Memorial Day Tuesday: 11 RFPs in the inbox, three SMEs back from PTO, and 90 minutes before standup. Three triage moves we use.
Stop CC-ing your SMEs
The 48% SME-bottleneck stat has held steady for five years. Most teams treat it as a people problem. It is a workflow problem. Replace the CC chain with a ticketed ask that has a deadline and a single owner.
See the proposal workflow
Take the 5-minute tour, then start a trial workspace when you're ready to run a real pursuit against your own source material.