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My Biggest Proposal Horror Story (and how to avoid the same mistake)

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On a random November Wednesday many years ago I learned that a rainy day in Vegas is not the same as a rainy day in the Midwest.

That particular Wednesday was the due date for the largest proposal I had worked on up until that point. Estimated at $20 million per year with 4 optional renewal years (a total of five years), it was a lot of money, and a lot of work. 

We had spent two months straight working exclusively on this proposal. The team included myself plus another writer, 3 sales reps, countless technical engineers, and two partners – one for products and one for services. It was a giant proposal with a lot of moving pieces. 

By this point we had already had a moment of panic as the original due date neared with only half of our content written. Thankfully, it was extended by a week, giving us some breathing room.

We spent the extension writing and rewriting our content, holding team reviews for key sections and then for the final proposal, strategizing our pricing approach, and signing on the dotted line for the 10+ forms (if you don’t work on government RFPs, count yourself lucky). 

Once we received final approval, we printed out our one original and eight copies, hole-punched every page, and gently placed them in the appropriate binders. Everything was safely enclosed inside the FedEx box and sealed shut before being dropped into the shipping box to arrive at 10am the next day, a cool four hours before the deadline. 

When I arrived to work the next day, my teammate had sent me five frantic emails.

“The package is delayed,” she said. “It rained in Vegas last night.” 

Okay, it rained? I thought, not understanding the significance. 

“It’s not scheduled to go out until tomorrow. The city is shut down,” she explained over the phone. 

Our potential $100 million proposal was delayed because of a downpour and would miss the deadline.

We started contacting everyone we could who might be able to help.

Thankfully, a local team member on the account was nearby and willing to deliver the proposal. 

This was a good option, but there was one issue: FedEx wouldn’t release the package to him.

By this point, every manager and director in our department was on the phone with FedEx trying to authorize the package, but we were running out of time.

We decided to print the entire proposal at a local print shop where he could compile it all together and hand deliver it to the customer. 

At 1:35pm, he had the proposal in hand and was on his way to the customer.

We anxiously waited for an update, every new email alert teasing us that it might finally have made it. 

2pm, the deadline arrived and we still hadn’t heard from him. 

“Any update?” My teammate messaged me.

“Not yet,” I said.

At 2:15pm, we got an urgent invite from the local rep. 

I joined the call and angry shouts were already on the line.

“They wouldn’t accept the package,” he said. “I got there at 2:03pm. I was too late.” 

He tried to explain the circumstances, that the weather caused the delay and our package would have arrived on time, but the customer refused to accept it. They already had four proposals that arrived the day before and would not make any exceptions.

My stomach twisted as I thought about all of the hours we had spent perfecting our content, pricing, and overall approach. All of it wasted.

A $100 million opportunity down the drain with the surplus water in Vegas. 

It was a lot to process.

Later that day, we learned that fifteen other proposals arrived on the 4:30pm delivery from FedEx (including our original shipment). The customer returned all of them unopened. 

I still cringe when I think about that day and our proposal that was rejected for being three minutes late. 

But I learned a critical lesson: 

When submitting hard copies, always mail the proposal at least two days before the due date. 

Proposal teams tend to want to work up to the deadline. There’s always something else that can be tweaked, a new way we can present information, or someone else who needs to review the proposal. 

But when you’re up against that deadline, decide if that tweak or final approval is worth potentially losing the entire opportunity. 

We know we would have been invited to the next round if our proposal had been reviewed, but it never was. 

If you’re considering waiting until the last minute on your proposal, learn from this mistake, and give yourself extra time to submit, just in case. 

Note: This applies for electronic submissions too! Portals go down, emails bounce, and countless other technology issues can happen. I always submit electronic proposals the day before, just in case. 

Do you have a proposal horror story? Let me know in the comments! 

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