Deals Have Been Stuck in "Proposal Sent" for Two Months — Now What?
A proposal that has been open for two months is not automatically dead.
But it is definitely asking for a decision.
Small businesses often leave old proposals sitting in the CRM because closing them feels like admitting defeat. The deal could still come back. The prospect seemed interested. They said they needed to check with a partner or wait for their busy season to end.
All of that can be true. It still should not remain in "Proposal Sent" with the same expected close date week after week.
A proposal is not a stage where work happens. It is a moment in the buyer's decision process. If nothing has changed for 60 days, the CRM needs to reflect that reality.
The average can fool you
Say you have six open proposals:
- Two sent this week
- Two sent 18 days ago
- Two sent 70 days ago
The average time in proposal is around 29 days. That may sound acceptable.
But it hides the two deals that have been sitting there for more than two months. Those two are not a minor detail. They are usually the reason the pipeline looks stronger than the month actually is.
This is why averages alone do not help much. What matters is the spread: are most proposals moving at roughly the same pace, or are a few deals lingering far longer than the rest?
Sort your proposals by the date they entered the stage. Then focus on the oldest ones first.
Diagnose the stall honestly
For each old proposal, answer these questions in writing:
- Who can say yes?
- What problem did they agree they needed to solve?
- What happens if they do nothing?
- What was the agreed decision date?
- What has changed since the proposal was sent?
If you do not know the decision-maker or the decision date, the deal was probably not fully qualified before the proposal went out. That is common. It does not make the prospect bad; it means the proposal became a substitute for a sales conversation.
A proposal should not be the first time a buyer sees your price, scope, timeline, or recommendation. By the time you send it, they should know what they are choosing and what the next decision looks like.
Use a direct re-engagement message
Do not send another "just checking in" email. That gives the prospect an easy reason to ignore you.
Instead, make it easy to choose a path. For example:
Hi Maya — when we spoke, you were aiming to decide on payroll support by July 15. Is that still the timeline?
If the project is still active, I can hold 15 minutes this week to answer questions and confirm next steps. If timing changed, no problem—I can close this out for now and reconnect when it makes sense.
This message is respectful, clear, and useful. It does not pretend the delay is invisible.
If they reply with a real date and a real next step, keep the deal open and update it. If they say timing changed, move it to a nurture or deferred stage. If they do not respond after your defined follow-up sequence, close it as lost with a reason.
Closing an old deal is not deleting a relationship. It is making room for an honest forecast.
Fix what created the stuck proposals
After you clean up the old deals, look for the pattern.
Maybe proposals go out before budget is discussed. Maybe the person on the discovery call cannot approve the purchase. Maybe your scope is too broad, pricing is unclear, or proposals take a week to send after the conversation.
Choose one change. For many small teams, the best first change is adding two required fields before a proposal can be sent:
- Decision-maker confirmed
- Target decision date confirmed
You can also require that every proposal have a follow-up meeting scheduled before it leaves your inbox. A proposal with a calendar event attached has a much better chance of becoming a decision than one sent into silence.
Key takeaway
Do not let a few very old proposals disappear inside an average. Treat each one as a real decision: advance it, defer it, or close it.
Next step: In the next hour, sort open proposals by age. Send a direct decision-focused follow-up to the five oldest, and update each record with a next step or a realistic status.