Ask Astra

What deals are stuck in my pipeline?

Stuck deals identified, blocker diagnosed, next action drafted — every Monday.

Business insightSalesWeekly Monday 9am. Mid-week follow-through check. 14-day unstick rate report.

Try this with Astra See all things to ask

Free to startNo credit card requiredUpdated Apr 2026

You'd think this needs a sales ops hire — Astra runs the pipeline hygiene scan from chat in 5 minutes, with a recommended action per deal.

The short answer

Astra scans your HubSpot pipeline every Monday morning and identifies stuck deals using stage-time benchmarks calibrated to your historical sales cycle. A deal is 'stuck' if it's been in stage longer than the 75th percentile of similar-size won deals. For each stuck deal she pulls the last touchpoint (Gmail thread + Granola call notes), identifies the blocker (waiting on legal, ghosted by champion, pricing objection, technical question unanswered), and drafts the specific unsticking action — a 4-line email, a discovery question, a CFO talking point, or a 'should we disqualify' call. Top 10 stuck deals land in a Lark message Monday 9am with deal value, days stuck, blocker, and recommended next move. You spend 20 minutes reviewing and approving. Most teams unstick 30-40% of stuck deals within 14 days of running this loop.

How Astra actually does it

1
Pull HubSpot pipeline + benchmark stage times
Compute 75th percentile time-in-stage for won deals by ACV bucket. Flag any open deal exceeding that benchmark as stuck.
HubSpot
2
Diagnose the blocker per deal
Pull last 7 days of Gmail thread + Granola call transcripts + HubSpot notes. Classify blocker: legal, champion-gone, pricing, technical, decision-maker-needed, or unknown.
GmailGranolaHubSpot
3
Draft unsticking action per deal
Specific next move: 4-line nudge email, discovery question, ROI proof point, or 'recommend disqualifying' rationale. Each is copy-paste ready.
4
Send Monday brief
Lark message 9am Monday with top 10 stuck deals: deal value, days stuck, blocker, recommended action, one-click approve. Total review time: 20 min.
Lark
5
Track follow-through
Wednesday + Friday: re-check which actions you took, which moved the deal forward. After 14 days she reports unstick rate and which blocker types are most fixable for your team.

What it looks like in chat

What deals are stuck in my pipeline this week?

Astra

Top 10 stuck deals (sorted by value × stick risk): 1. **Acme Corp — $48K ARR — 47 days in 'Demo Done'** (benchmark: 18d). Blocker: champion (Sarah) hasn't replied in 3 weeks. Last call: she said she'd loop in CFO. **Action: send a 3-line check-in to Sarah with a bypass — 'happy to brief your CFO directly, here's a 5-min Loom of the ROI calc.'** 2. **Beta Industries — $32K — 31 days in 'Proposal Sent'** (benchmark: 11d). Blocker: legal review. Their procurement team wants SOC2 docs. **Action: send our SOC2 report + DPA + a Stripe Atlas-style FAQ. I have the template ready.** 3. **Gamma — $28K — 22 days in 'Trial'** (benchmark: 14d). Blocker: nobody from their team has logged in for 8 days. **Action: probably dead. Recommend disqualifying with a 'reopen anytime' email.** [7 more deals listed] **Reply 1 to ship Acme's email, 2 for Beta's SOC2 packet, 3 to send Gamma the disqualify, etc. I queue everything in Gmail drafts for your final approval.** Total pipeline value at risk: $186K. Realistic unstick: 30-40% = $55-75K back in motion.

What you get back

Monday 9am Lark message with top 10 stuck deals, blockers diagnosed, unsticking actions drafted as Gmail drafts ready for one-click approval.

Cadence

Weekly Monday 9am. Mid-week follow-through check. 14-day unstick rate report.

Ask Astra this right now

We'll spin up your workspace, hand the prompt to Astra, and you see the answer in 60 seconds. Free.

Try this with Astra

Frequently asked questions

What if my CRM isn't HubSpot — does this work with Salesforce or Pipedrive?

Yes. She works with Salesforce, Pipedrive, Close, Attio, or any CRM with deal-stage history exposed via API. Setup takes 10 minutes (auth + field mapping). The benchmarks recalibrate to your data automatically.

I don't record sales calls — can she still diagnose blockers?

Less precise but still useful. Without call data she falls back to email thread analysis + HubSpot notes + last-activity timestamps. Diagnosis confidence drops from ~80% to ~55%, so she'll flag uncertain cases as 'investigate' vs prescriptive actions. Connecting Granola or Gong takes diagnosis to 80%+.

What if I don't have enough closed-won deals for benchmarks?

Below 30 closed deals she uses category benchmarks (SaaS sales cycle medians by ACV). Above 30 she uses your actual data. The threshold for 'stuck' starts loose and tightens as she learns your team's real cycle. First 4 weeks expect more false positives.

Can she actually send the emails or just draft them?

Default is draft-only — emails land in your Gmail drafts folder for review and one-click send. You can flip to auto-send for low-risk actions (SOC2 doc requests, calendar nudges) by saying 'Astra, auto-send the standard SOC2 packet on those.' Strategic comms always stay draft-only.

Run your one-person company.

Hire your AI team in 30 seconds. Start for free.

Free to start · No credit card required · Set up in 30 seconds