The Secret to Winning More Big Deals

We want to close big deals. Big customers want better solutions, lower prices, and their problems solved. Bingo! That’s what we do! And lucky for us, we do it better, cheaper, and faster than our competitors.  

So then, why aren’t we closing more big deals?

We aren’t closing more big deals because we’re not making the buying process more emotional.

In big deals, we think big dollars means big logic. It doesn’t. The bigger the deal, the bigger the emotion. While we’re zigging with features, benefits, price discounts, savings ROI, and contract concessions, buyers are zagging with how they feel about change.

Buyers have much more emotion about our solution, product, or service than we recognize. Especially in a pandemic world.

Mostly that emotion is doubt.

Perhaps they doubt your ability to execute. They doubt your pricing is competitive. They doubt they will get the budget approved. They doubt this switch will help their career. They doubt this is worth their time. They doubt your company is the right long-term partner.

To oversimplify this, they doubt something, and it’s stalling you from winning the deal.

When we sense doubt, we need to meet emotion with emotion. The secret is to give the buyer fewer spreadsheets and more confidence, excitement, or peace of mind about your solution.  

The Puppy is just too cute to send back

In solution-oriented sales today, the best way to help the buyer feel something is the modern version of the puppy dog close. Let them take it home and try it out.

In other words, let the customer engage meaningfully with the people delivering the service. This can take on a lot of different shapes. This isn’t is teeing up your A- list referrals – it’s much more than that.

Bring the person or team responsible for delivering the service into work directly with the customer on a short trial basis. Perhaps it’s a proof of concept. Maybe it’s letting the customer shadow another project or customer solution. Maybe it’s something else the customer suggests.

This also does not mean giving the deal away for free (all finance folks can sigh now).

Instead, think of it as free VIP backstage passes.

Ask…How can we bring the customer further into our process to make them not just a customer but a fan? If it works for Justin Bieber, it can work for you.

By making them a fan, the buying process becomes more emotional and less logical. And people do crazy things based on emotion (perhaps they even buy your product).

To oversimplify this, give a little to get a lot.

The Buyer’s Perspective

About 2 years ago, I led a $1M+ software and services vendor selection. This purchase was part of a strategic business case I had developed. Besides the money involved, I felt like I had invested substantial career capital in this initiative, and the wrong decision wouldn’t just be professional. It’d be personal too.

We were deep into the buying process, but I doubted we had the right guys selected. I was scared of making the wrong choice. What would that mean for my career advancement if this blew up?

The Salesperson sensed my pace slowing and took the initiative. He connected me with the leaders and teams responsible for delivering our solution. I spent a lot of time with them. I knew what he was doing, but it didn’t matter. The more time I spent with them, the more I liked them, and the more confidence I gained that they could deliver.

And we closed the deal.

But Brian, that won’t work for my situation because…

  • Objection #1: There’s no way I can put the person responsible for operations delivery in front of a customer.
    • Handling Response: Level up internally. If the deal is worth it, bring in a more senior leader with similar growth targets and will be supportive.
  • Objection #2: There’s no way the person responsible for delivery will want to engage with the customer.
    • Handling Response: Level up internally. If the deal is worth it, bring in a more senior leader that has similar growth targets and will be supportive.
  • Objection #3: There’s no way the customer will commit the time to engage in a short term, non-committal engagement/ trial/ backstage tour.
    • Handling Response: A quick no is better than a slow maybe. If the client pushes back, you missed something earlier in the sales cycle, and you aren’t as close to closing as you thought you were.

Wrapping Up

If you’re in business, then your company has a growth target. If you have a growth target, then there’s a pipeline with big deals in it.

How can you make one of those big deals a fan, not just a customer?

The 3 Little Pigs of Digital Leadership

Photo Cred from Disney Archives

Digital Transformation isn’t just for companies; it’s for leaders too. A company’s need to digitally transform has been well documented, but the need for its leaders hasn’t.

So what does becoming a Digital Leader even mean? 

Becoming a Digital Leader means becoming more data-driven than you are today. 

When you use data to become a Digital Leader, you become more insightful.

And that insight helps you transform your company to withstand the winds of change. You become the little pig building the brick house

It’s important to clarify – becoming a Digital Leader does not mean you have to become a techie. Instead, it means using technology to make smarter and faster business decisions. It’s about using technology to run a more agile operating model.

The next 10-20 years have been referred to by many as the technology deployment age. There will no longer be the have and the have nots. It will be the use and use not – until the use nots go out of business.

Technology is shifting from differentiator to equalizer. 

Large corporations will use technology to more cheaply reach into secondary and tertiary markets to access customers previously too fragmented or expensive for them to serve.

Small and mid-size companies will use technology to punch up in customer experience, target marketing, and solution design.

(To dive deeper into this concept, check out this podcast with PE Investor @Tracy Graham of Graham Allen Partners about investing in overlooked businesses and modernizing their operating model to unlock value.)

This creates a huge opportunity and risk for both sides…so who wins? 

The little pig building the brick house wins. 

Which leader little pig are you? Let’s find out. 

Little Pig in the Straw House

Most of us, myself included, are building straw houses. We’re building straw houses because we’re relying too much on our tribal knowledge to make decisions.

Tribal knowledge cements us in the past, like using MapQuest to drive to your Florida vacation.

Suppose you’ve been in your industry or your job a while. In that case, you’re likely using your well-earned experience and “gut feel” to fill in data visibility gaps and make (outdated) insights.

Recently we acquired a company that brought new talent into our organization. The new leader, let’s call him Tom, and I began working together to integrate our businesses. Tom started asking data-driven questions such as:

“How do you know how much client work is in your backlog at any point in time?”

When I went to show him our reporting and respond to his question, it hit me: I had been building a straw house. I was relying too heavily on my tribal knowledge. There was no way this data alone was sufficient to make the right resourcing decisions.

The biggest problem the little pig building the straw house has is thinking their tribal knowledge is an asset to the company.

 In truth, it rarely is as valuable as we believe it is.

Little Pig in the Stick House 

The little pig building the stick house recognizes the need for change but gets it wrong. 

In business today, this little pig is an “add more people leader” when solving a problem or gaining access to the data they need.  

I.e.

“Our systems don’t integrate the way we need them to. Let’s create roles and hire people to manually perform a process, and give us the reporting we need.” 

In truth, we should be spending our time being ruthless about systematizing access to the cold hard data. 

Little Pig in the Brick House 

The little pig building the brick house spends his time systemizing the data in his business, department, or team. His objective is to make it visible and usable for himself and the other little pigs across the enterprise. 

By systemizing the data you need, other leaders in your business begin to benefit from that visibility too. You help other leaders start to see customer change happening earlier than they previously would have. 

This is how digital transformation begins in a company. 

So, which little pig are you? And what can you do next to start building a brick house?

The Most Powerful Word in Goal Setting

141 million Americans will be setting New Year’s goals this year. Unfortunately, only 8% of us will be keeping them. What if you knew you would reach your goal? What if you were guaranteed to achieve it? 

This one little word can make that happen for you. It can change your fortune in 2021 and beyond. Please use it wisely. The word is: yet.

Continue reading “The Most Powerful Word in Goal Setting”

The Question We’re Asking, or Being Asked

A New Year has begun, and we’re off to the races executing new strategies, launching new products, and building new teams. Wouldn’t it be nice to have a bigger budget, more resources, and deeper bench strength? Sure it would. Sadly, the question we’re all asking, or being asked, is “how do I do more with less?” The answer: You outsource. 

Continue reading “The Question We’re Asking, or Being Asked”

The Problem with Predictability


As a business leader, I love predictability. Arguably all of my daily efforts go into capturing it. I want predictability in our sales process. In our financial forecast. In our production throughput and quality measures. I want predictability in my morning coffee.

But the problem with predictability is that we chase it instead of creating it.

And that matters because when we chase predictability, it runs away, just like my 3-year-old when it’s time to leave the park. 

Continue reading “The Problem with Predictability”

Planning Your Strategy: How To Have It All

Much of today’s strategy development is about eliminating risk and reducing uncertainty. Maximize upside and minimize downside. Heavy emphasis on minimizing the downside. But what if we shifted our thinking to maximize upside by maximizing downside? There will always be a downside. What if we used it?

Enter antifragile thinking.  

Continue reading “Planning Your Strategy: How To Have It All”

Why You Want To Hire Your Replacement

Is this how you’ve felt when new talent comes into the company?

New Talent Arrives

On October 28th at 12:24 AM we had our 2nd daughter. Her Big Sis, a high-octane, “I do everything myself” three year old was so excited that when we brought her home from the hospital she was shaking on the couch. Holding her, she kissed her and said “I love you baby Avery” and “You’re so cute.” Disclaimer – she also tells ants and bugs “You’re so cute” too.

Nonetheless, her reaction and mindset to being a Big Sis has amazed me. Much different than Big Bro’s reaction when I showed up re: picture above.

So which one are you? Big Bro or Big Sis?

Continue reading “Why You Want To Hire Your Replacement”

The Collaborator’s Guide to Giving Feedback

Collab is all the rage right now. And it should be. One of the things I miss most from our pre-COVID world is a whiteboard, my team and ordering in lunch. That combination is magic.

But collaboration has a dark side. And if you’re not careful, it will have you completely lost in the woods. The dark side grows darker every time we prioritize harmony over debate. Comfort over clarity. Conformity over curiosity. The magic runs out when we go along to get along.

Continue reading “The Collaborator’s Guide to Giving Feedback”

How to Create a “Fake Work” Culture

We have a problem with employee engagement in the U.S. It’s increasing.

According to a 2018 study by Gallup, 34% of U.S. employees are engaged in their job, tying the highest this number has ever been. Employee engagement is the second pandemic of our generation, and it’s time we do something about it. That something is more fake work.

Continue reading “How to Create a “Fake Work” Culture”

Failure to Fail: What I’ve Learned from Playing it Safe

“The greatest danger for most of us is not that our aim is too high and we miss it, but that it is too low and we reach it.” – Michelangelo

In poker, I hate going bust. The few times I do push all in, I make sure it’s with a hand that can’t lose. Then the new guy hits an inside straight on the river and Snap! I’m watching from the sidelines for the next 2 hours. My preferred approach is to die a slow death. Little bets and bluffs until my chips vanish like the picture of Marty’s brother in Back to the Future.

But here’s what I’ve learned from playing it safe: when we aim too low we never unlock our potential.

Continue reading “Failure to Fail: What I’ve Learned from Playing it Safe”