7 Creative Plays to Resurrect a Deal Without “Just Checking In”

Most deals in a seller’s pipeline are, by default, dead.

That’s plain to see because world-class win rates hover around 30%. Even with a team of Account Executives trying their very best to get every single deal done.

This is particularly true if your product isn’t the clear and undisputed market leader, you’re selling into the enterprise, or you’re focused on an outbound sales motion.

The question, then, is how do you bring new life to a dying deal?

When you send three “checking in” emails with no reply. When it’s the end of Q1 and a buyer says, “Let’s revisit in Q4.” How do you delight your prospects to re-engage them in the deal?

Here are seven creative plays I’ve successfully used to resurrect dead deals. Steal them.

A note before we dive in.

These will require more time than a quick “checking-in” email. But in all my selling experience, the more creativity I invested, the more contracts I closed.

Plus, you can re-purpose each idea across multiple deals. It becomes faster and easier with every deal you use them for. Pick your favorite play, and test it on a few accounts this quarter.

Related: Sales Follow Up Email Templates (+12 Tips for Smart Salespeople)

1. Draft a “Future State” Press Release.

Get your buyer’s entire team energized by building a press release. Make the headline a future breakthrough that’s a result of working together.

Look for “Press” or “News” in their website footer. Mirror the format, and insert a new narrative. (I once bought a $10 domain — companyname-wins.com — to host the press release on it.)

If you try this, remember that executives and key employees think big. Really big.

For example, this week, I met the team at Demandwell. They help marketers drive organic traffic. Managers may like “easy keyword research,” but CEO’s and CMO’s think bigger, like:

“$110M Series C Backed by Sequoia, Driven By Efficient, Organic Growth”

You see, organic traffic means lower customer acquisition costs. That’s attractive to a big-name VC. So, Demandwell’s future-state press release might read more like this one.

2. Ghostwrite an All Staff Email From Their CEO

This play is similar. It helps your buyer visualize a future state.

But this time, it’s wholly focused on a single contact — like the prospect you’re working to convert into your champion.

Help your prospect taste a personal win by ghostwriting an email from their CEO.

Copy and paste their email signature into a new email. Update the name and title as if it came from their CEO, with a “Forward” stamp below.

In the body, write an update focused on an achievement you can help enable.


Ghostwrite CEO Email Image


3. Send an ‘Idea’ Email With a Genuinely Helpful Tool

This one works because it gives your prospect something that helps them do their job (regardless of whether or not they buy), tailored to them.

The mantra is: “Help me get my job done now. Later, I may be back to talk about your product.”

Shoutout to Will Allred for his collab on this with me.

You’ll want to adapt this to your industry, too.

For example: when I sold fundraising software, I’d make a $10 donation and forward the gift receipt with this email framework.

I’d attach a checklist with some notes on ways to improve their online giving flow and thank-you letter content. It helped my buyer do their job, regardless of whether or not they bought our product.


ideal email tool - image


4. Line Up a Guest Interview For Them

Who doesn’t love to showcase their smarts?

If you’re working with a senior-level prospect, ask to feature them in a new piece of content your marketing team is working on.

You’ll want to check in with marketing first, of course. But chances are good they’d like an industry voice in their content.

It’s a small step toward working together, and meeting others around your company.


Guest Interview Email - Image


5. Ask For an Internal Doc to Build Their Business Case

Even if you’re multithreaded, buyers have internal meetings about you, without you. Since you can’t be in all meetings, influencing your message when you’re not around is key.

Instead of kicking over case studies or your own marketing materials, camouflage your sales message inside one of their own internal documents.

Buyers love it, because it saves them time and it looks familiar. Most teams have a standard deck or document template. Some use Google Docs. Others, PowerPoint.

To maximize the chance your message gets through, ask for a copy. Then translate your business case — problem statement, its cost, your approach, the payoff, etc. — to their format.

Internal Doc Business Case Image


6. Do What You’re “Not Supposed” To Do

Reciprocity is real. When buyers see you going to bat for them, they’re likely to show up for you.

Work with your manager to create some type of exclusive offer. Something you can keep in your back pocket for when you hit a wall.

It needs to be something you’re not technically supposed to do — and couldn’t do for every account — but you’re able to get away with it for a large deal or a key logo.

This might look like opening a sandbox account, running a sample report, or anything that helps your buyer experience your value, de-risk their decision, and gain access that’s not available to everyone.

7. Send a Gift You Couldn’t Send to Anyone Else

Work to learn what makes your prospect “them” on a human level. Then, send a gift that speaks to that. No mugs, no notebooks. It should scream, “I see what makes you, you.”

For example, discover your prospect loves Chinese takeout? Send them a ‘Make Your Own Fortune Cookies Kit.’

That would be a pretty weird gift to send to any other prospect, right?

By the way, if you’re reading this and managing a sales team, try creating a budget for gifts. Give each Account Executive a fixed amount they can spend each quarter, without extra approvals.


If you’ve read through each idea, you’ll notice there’s a theme. Going the extra mile to surprise and delight your prospects. To bring them an extra shot of life during their week.

While it may sting if you invest your time and creative energy into testing one of these ideas, and you don’t see any immediate results, keep at it. You won’t be let down.

You’ll see stalled deals come back to life. You’ll boost your win rate. All without sending a single email that says “just checking in.”

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