Selling skills
Reviving lost sales opportunities: How I turn them into closed-won using Gong

Brian LaManna
Enterprise Account Executive
Published on: February 25, 2025

Most sales reps treat lost deals like a breakup — painful, awkward, and something they never want to revisit. But that’s a huge mistake.
Every company wants to understandwhya deal went south. The best ones don’t just analyze the loss, they mine insights to re-engage and turn “no” into “not yet,” and “not yet” into yes. Gong included. Over$1.1M of my 2023 closed-won revenue came from deals thatalready existed.Not new inbound, not cold outbound — just opportunities left for dead.
Common mistakes reps make chasing old opportunities
Reviving closed-lost deals isone of the easiest ways to build your pipelinebut almost everyone messes it up by:
- Taking closed-lost at face value.Most deals don’t die because of price or value — they stall because the buyer couldn’t get internal buy-in. That means there’salwaysa way back in.
- Skipping the research.Context is everything. But without a way to pull insights together from emails, calls, text, video meetings, and CRM, most reps rely on guesswork – and that doesn’t get you very far.
- Sending lazy, generic messages.A weak message never converts. If you’re not crafting contextually-relevant, personalized messages, you’ll never get a response.
But it doesn’t have to be that way. Reps just need to get their hands on the right tools to support their success.
If you follow me on LinkedIn , you already know I’m such a Gong power-user, that I wouldn’t work in sales for any company that doesn’t use our platform. So, let me show you how I bring dead deals back to lifefastand turn them into closed-won using Gong.
The struggle of reconnecting with prospects before Gong
Most sales reps and AEswantto follow up on lost deals but the process is slow, manual, and frustrating. You know you should personalize your outreach, but the time it takes to gather relevant insights makes it feel impossible to do at scale.
Here’s what that looked like for me before I used Gong:
What I had to do
Why it was limiting
Dig through CRM(Salesforce, Hubspot, Dynamics — take your pick) to find the account.Open 5+ different tabsto review past opportunities.
No easy way to get the full picture — just a mess of disjointed info.
Sift through old notes(if they even existed) and/orSlack the previous repfor insights about what actually happened.
Notes were incomplete, outdated, biased, or missing altogether. Slack responses? Either“no opportunity there”or zero response.
Attempt to write a compelling messagethat would actually re-engage the prospect.
No easy way to tie past conversations into relevant, personalized outreach — just guesswork and gut instinct.
All this tookwaytoo many clicks and wastedwaytoo much time. It made no sense to drop a prospect into a brand new sequence and pretend we’never spoken. I knew past conversations held critical information that could help me land a new opportunity.
But those insights?Gone.Flushed down the drain.
My three-minute playbook for resurrecting lost deals using Gong
Thankfully, reconnecting with past prospects is no longer a time-sucking, multi-tab nightmare. What used to take several hours, now takes meless than three minutes— all insideone platform.
Here’s my step-by-step process using Gong:
1. Instantly access an account’s full history
- Search and select an account from my Gong homepage
- Review the complete picture, including every interaction and intent signal —calls, emails, texts, web meetings, and even the content they engaged with (decks, proposals, case studies)
- Filter interactions by specific people (e.g., perhaps I just want to review conversations with the Head of RevOps)

🚀Why it’s a game-changer
No more hunting for detailsacross sources, no missing pieces, no noise. I get the most relevant data on the people who matter.
2. Surface unique insights with AI-generated answers
- Use Gong’s “Ask Anything” to instantlygenerate sharp insightsthat will make my outreach stand out
- Example prompt:
- “I’m writing a prospecting email to re-engage this person.Provide three compelling bullet pointsthat highlight their keypain points, thevalue they’ve seenfrom our solution, and thechallenges or prioritiesthey’re currently facing. These should be sharp, persuasive, and easy to copy and paste into my email.”

- If needed, I can take a deep-diveinto specific calls and emailsfor proof and extra context. But honestly? I rarely have to. I’rather spend that time reaching out.
🚀Why it’s a game-changer
- No moresifting through notesorwaiting on teammatesfor context. No moreguessing about what mattersand getting it wrong. Ask Anything gives me a crisp summary of pains, value seen, and priorities.
3. Craft a hyper-relevant, personalized message
- Move to the Gong Engage sidebar (no extra tabs)
- In my “to-do’s,” Icopy and paste the AI-generated insightsand personalize my email in seconds

🚀Why it’s a game-changer
- No moregeneric email sequences. Every message isrelevant, and built to convert.
- Seamless workflow:From insights ➡️ to messaging ➡️ to outreach — all in one place.
Win more from existing pipeline
The highest performing reps don’t just chase new leads — theymaximize the pipeline they already have. Our data shows a direct correlation between time spent with buyers and quota attainment. Reps who exceed 130% of quota spend 60% of their time on customer-facing activities.

That’s why reviving lost deals is a necessity. But only if it’s efficient and gets you back in front of your buyer with the right message.
That’s exactly what Ask Anything helps you do. Instantly understand customer challenges, so you can craft compelling outreach — without getting stuck in research mode. It’s how elite sellers work smarter, not harder. Quarter after quarter. Year after year.
Your success – and your company’s long-term business growth – depends on leaving no stone unturned and knowing exactly which ones to flip. Lost deals don’t have to stay lost forever.
Take Ask Anything for a test drive and bring them back to life today.

Enterprise Account Executive
Brian LaManna is an Enterprise Account Executive and 6x President’s Club winner known for his tactical, data-driven approach to sales.
He founded Closed Won to help SDRs and AEs build repeatable systems for success and regularly shares actionable prospecting, discovery, and execution strategies with thousands of sellers on LinkedIn.
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