Jigsaw Comparison – The value of "why" in your proposals

“About us.” “The strategy.” “The idea.”

Shuffle through the pages of any proposal and you’ll see these “what” headlines, followed by words and images that explain those headlines.

The problem is, “what” doesn’t sell. “How” and “why” sell. Your proposal needs to go beyond content and provide context to your buyer. Yes, put the “what” somewhere on the page, but ensure you’re reinforcing it with more benefit- or context-driven language.

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Jigsaw Overview Graphic – How to sell an idea

One of the things I’m always baffled by is how people confuse the “sale” with the “product.” Too often, we go into pitches and presentations touting the greatness of our product, etc./blah/etc.

That’s not how people buy.

In a B2B scenario, people buy from people. The fact your product or service is great is a given. What they want to know is how you’ll nourish them, how you’ll add to the connection and the experience, and how you’ll make them better beyond that service.

There are three direct, powerful ways you can do that…

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What the Leafs' big moment can teach you about winning your next pitch.

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The day before the biggest pitch of his life, Kyle Dubas did the exact right thing – he hung out in L.A.

For the non-sports-aware among you, Kyle Dubas is the newly minted General Manager of the Toronto Maple Leafs. For the past half century, the team has mostly been a sad sack imitation of a once mighty sports franchise. In those 50 years, there have been no championships, rare runs deep into the playoffs, and a culture that could easily be described as “complacently mediocre."

Less than a half decade ago, Toronto decided to do something about that, dismantling the old culture, installing a smart front office and chasing one vision – win. Things have been moving in a hopeful direction. Drafts have yielded some of the league’s most exciting players. The team posted its top regular season total in 2018. And the Toronto Marlies – the farm team – just dominated its way to the developmental league’s Calder Cup. 

The General Manager of that team? A 32-year-old whiz kid named Kyle Dubas, recently elevated to the same position of the big club at a pivotal time.

Every July 1, the National Hockey League (NHL) opens the floodgates for veteran players with expiring contracts. “Free agency” gives those players the chance to choose a new team with which to sign. In the past, big fish free agents have avoided the Leafs. After all, this was a team that seemed like it wasn’t going anywhere in a hurry.

This year was different.

Perhaps the biggest free agent in the history of NHL free agency was slated to hit the market. John Tavares is a centre that spent his entire career with the New York Islanders. His contract was up, and he’d decided to explore free agency. He decided to talk to six teams, including the Toronto Maple Leafs. All they had to do was head over to the CAA offices in L.A. and make their pitch.

And boy, oh boy, from all accounts, it was one hell of a pitch. It must have been. The team landed Tavares, and the rumour is that they did it at a lower annual salary than some of the competing bids.

I’ve been keeping my eye on all sorts of articles about the pitch itself, and from what I’m reading, Dubas put together a textbook winning pitch – something any leader can do when they’re trying to win the next landmark piece of business.

Here’s what Dubas and his team did right – and what you can aopply to your next pitch.

They started with the buyer.
Want to know how to notpitch – check out Tom Cruise trying to convince the young quarterback in Jerry McGuireto make a deal. He spends all his time talking about his agency and what’s great about his city.

Dubas knew better than to do that with John Tavares.

Winning a pitch means understanding who your buyer is, how they buy and what’s important to them. It’s not what yousell, it’s how they buy.

Dubas knew that Tavares grew up inToronto, idolizing the Leafs. But it was going to take more than misty-eyed nostalgia to get Tavares to head north from New York. Money wasn’t going to be a deciding factor – every suiter was going to back up the Brinks truck. What would truly sway Tavares was the potential to win the coveted Stanley Cup while he was in his prime. When the puck drops in October, Tavares will be just 28. 

Your lesson? The first move in your pitch is to know the buyer.

They tailored the pitch to show “how” they’d activate the buying trigger.                        
Tavares'' biggest interest wasn’t just playing for a winner – it was howteams would build and sustain that winner.

So Dubas developed a pitch that addressed the “how.”

Media reports that the Leafs meeting stretched for three hours, involving Tavares, his agents and reps from Toronto. What the hockey team did during those three hours was lay out a specific roadmap towards the Stanley Cup. Ultimately the team believed that this focus was what it would take to win Tavares most of all.

Make your pitch about something – something that moves the audience.

They built a team ready to handle objections.
Those three hours weren’t spent blasting the player with information – they were spent holding a conversation.

A big part of that conversation meant being ready for lots of questions and objections. 

Who am I going to play with? What pieces are missing after you sign me? How are you going to keep this team together when young players want new contracts? 

By all accounts, the Leafs were very prepared. Dubas brought the Leafs coach and President along for the pitch, and gave them specific roles to pitch and handle Q&A. The team chose to answer Tavares with a depth of knowledge and insight into what the future looks like.

Your client will have objections. Figure out what they’ll be, and answer them before they even ask.

They did something unexpected.
The team made a video to back up its sales strategy.

Given the fact that Toronto is Tavares' hometown, it would have been easy to lay on the syrup with a 90-second, music laden piece featuring local kids in Tavares jerseys.

But that wouldn’t fit Tavares’ buying trigger. There certainly was some level of “come home and win a Cup, and you’ll be a hero.” But that wasn’t the focus.

Reports are that the Leafs went back to their home area, re-laid the ice and made a video featuring one of Tavares' future linemates to demonstrate how they’d play together. The effort, the involvement of the player and the production were impressive – but most importantly, the way the extra laddered up to the focus of the sale was critical.

Make your pitch memorable. Do something interesting that makes a powerful connection to your audience.

The GM went to L.A. early and did this one super important thing.
He rehearsed – for an entire day. By himself.

Tavares wanted to know that this wasn’t the Leafs of the bad old days. This was a team that had their stuff together, and seamlessly presenting and answering questions was an absolutely must do. 

So Dubas headed directly from the NHL draft in Dallas to an L.A. hotel room. He used the rehearsal to create a polished, confident veneer for the organization.

Your learning? Rehearse. Rehearse more. Rehearse the right things. 

One more thing – they drew on influencers to keep selling.
The Leafs were the first of the teams to pitch, meaning Tavares was going to hear loads of promises, ideas and numbers in the ensuring days.

The Leafs needed something to keep their message front and centre. Their answer was “influencers.” Specifically, they got out of the way and ensured that actual Leafs players could keep the conversation going. 

There are reports that a player the Leafs signed last yearwas very effective. Patrick Marleau has come to Toronto from San Jose last summer and shared his experience. Others gave straight talk on the culture, the coach and the path forward.

Influencers are the secret weapon in B2B and intenrnal marketing communications. Don’t underestimate the power of perspective from someone else who counts. It can mean the difference in your pitch.

In the end, Tavares signed, and Dubas – and new GM about who the fan base was hopeful but unsure, had impressed in the biggest possible way. 

Know the buyer. Understand what it takes to win. Be ready for objections. Do something surprising. Rehearse. Keep selling. That’s a blueprint for wooing a great player to a building team – it’s also a pretty good playbook for any business serious about winning.




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Jigsaw Overview Graphic – The 8 sins of proposals

I probably hate your proposals.

Why? Because they're milquetoast, word-laden documents that avalanche me in content – instead of lighting me up and getting me engaged in what you're selling.

There's a new eBook coming on this one – here's the first step. The 8 sins of proposals.

See. Solve. Sell – Jigsaw 416 220 4430 –

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Jigsaw Checklist – Reduce the amount of information on your slide.

Stop it.

Stop using your slides as a personal comfort monitor and start using your slides the way they're meant to be used – as a tool to reinforce your concepts and to help your audience navigate. This checklist helps.

So does the all new Jigsaw eBook The 8 since of PowerPoint. Want a copy of your very own? Drop me a line at and it's yours for the asking. 

See. Solve. Sell – Jigsaw 4126 220 4430.



The 8 sins of PowerPoint

Almost all PowerPoint I see is terrible – and it's not (just) the design that doesn't work. There's no thinking as to what the role of slides, visuals and words are.

But there should be. 

Fix any of these 8 sins and your PowerPoint will benefit – more importantly, the value of whatever your presenting goes up, up, up.

Jigsaw 7 Laws of Really Great PowerPoint - Overview Infographic - 2jt.png