I Crashed the Sales Assembly Summit 2018 and It Blew My Mind

Chicago Sales Assembly Event

If you haven’t heard about it, the inaugural Sales Assembly Summit 2018 gathered an elite crowd of some of Chicago’s most influential sales professionals. The attendees are the very best in the Midwest when it comes to all things sales. So what was I, a finance person (gasp!), doing there?

I guess if you look at it from a pure title standpoint, I was crashing the Summit. The Summit was rightfully designed for executive sales titles, CEOs, and the occasional CRO. However, like many of you, I work for a growing tech company and during these scrappy times, I am always selling on behalf of my company. I sell to investors, my network, bankers, brokers, vendors, neighbors, and any and everyone who will listen to me talk about my company.  

So whether I crashed or didn’t crash, I had just as much interest in learning how to sell better as anyone else there. Plus, I paid for my ticket.

What I Learned Changed How I Think about Sales

My guess was that the Summit content would hit on some of the key skills or characteristics needed as a modern salesperson. And just like the 1 million blog posts I’ve read on sales, I fully expected talks on these topics to be packaged up in nice little 5 step sales hacks that could marginally improve sales performance, which would be great!

But that’s not at all what I experienced. For me, the content from the Summit was not about how to sell but rather how to think about sales. I came away with a new perspective of how a salesperson can transform their way of thinking to become much more effective and authentic in the sales process.

The three key takeaways I highlight below may not seem new, but the speakers brilliantly presented the material and took these topics to a new intellectual level. We all know salespeople need to value sell and be storytellers. And oh yes, because buyers have more power now than ever, salespeople need to be transparent, too. But the Summit presenters made me think about these topics in new and profound ways.

I guess they sold me.

Sales = Context

This was the overarching message from the opening keynote speaker John Barrows, owner of JBarrows Consulting. Barrows grabbed our attention by highlighting super common sales speak and telling us why it was, quite frankly, stupid.

“Is this still a good time to talk?” even though the person picked up the phone at your scheduled meeting time, and “Does that make sense?” after you droned on for 8 minutes about your product features and realized you are actually asking yourself, “Did I just make sense?”

Like all good comedy, it was funny because it’s true! Beyond the comedic effect of these examples though, Barrows was highlighting an important issue.

Salespeople are at risk of becoming cookie cutter versions of each other. They open with the same lines, they talk about their products in the same way, they ask the same boring questions, and, ultimately, they don’t add any more value in their selling process than the next person. This is amplified by the fact that salespeople are becoming increasingly “templatized” (jury’s out on whether this is a real word, but I liked Barrow’s use of it).

By templatize, Barrows means salespeople, especially SDRs, are forced now more than ever to push out email templates. Even subject line optimization and email personalization can be automated. According to Barrows, this isn’t sales. This is actually marketing, and we should let marketing do what marketing does.

Marketing is content, and sales is context. – John Barrows

Sales has never been explained to me so eloquently. It struck me that Barrows was basically talking about value, consultative, and social selling all at once. But he simplified it by rolling all of the aspects of those methods up into “context.” Sales IS context, and context must be wrapped around content.

Barrows provided examples of where this was important: Onboarding/sales training, email/content strategies, social/brand building, and presentations/demos.

Sell the 20 percent by John Barrows

Don’t get caught up explaining 100% of the features offered in your solution rather than amplifying the 20% that customers will actually care about and use.

In his example of context for presentations/demos, Barrows explains that of the products you use daily, you probably only use 20% of their capability. He cited Excel and your cell phone as prime examples.

Barrows went on to explain that reps get caught up in explaining 100% of the features offered in their solutions rather than amplifying the 20% that customers will actually care about and use. Finding that 20% and tailoring your presentation to their priorities is context. In his blog post Sell the 20%, he states, “The problem with this approach (selling all product features) is that if everything you present is incredible, none of it will stand out.”  Find what is important to your customer and use that as the context for your sale.

Barrows ultimately took the stage as the opening keynote speaker and set the stage for the rest of the day about how salespeople can fit into this incredibly complex and evolving industry. He brought this home by asking the question, “What can you do that a computer can’t?” The answer is context.

Storytelling is Sales, But You Also Have to Believe the Story

In what was the most entertaining panel of the day, Genevieve Thiers, Founder of Sittercity.com, absolutely captivated me. Below is proof that I am not just saying that for this blog. You can check the date and time of my Slack message to my boss sitting next to me. The timestamp checks out.

I love her Slack message.She articulated that there are different strategies for growth depending on the type of business you create.

  1. If you are creating a Next Gen business, you are iterating and need to fully understand the 3 points as to why you are better than the versions that came before you.
  2. If you are creating a new category, first, your CEO must listen to sales and understand what barriers they are coming up against. It is your CEO’s job to knock down those barriers for sales and allow sales to then focus on selling the vision.

In both of these scenarios, telling the story is paramount. If you are iterating, you MUST know those 3 things that make you different and communicate those things better than your competitors. If you are creating a new category, your CEO steps up and knocks down barriers while you focus on telling the most elegant and impactful version of your story.

Thiers stressed that it is really that simple. You have to figure out how to tell the right story, and then run full steam ahead with it.

Again, salespeople as storytellers is nothing new. But knowing which story to focus on given which category of business your company falls into adds a different dimension.

Side note: Thiers’s interaction on the panel with Godard Abel, Co-Founder of G2 Crowd, was amazing. Someone get these two a reality TV show.  

While Theirs highlighted the importance of being able to tell your story, Brian Burkhart, Founder of SquarePlanet, evangelized that telling the story isn’t enough on its own, you have to believe it.

In a controversial move, Burkhart told the audience he had been bored for parts of the Summit because people were not pitching with passion. He unapologetically said all presenters had a fantastic opportunity on stage to sell everyone at the Summit on their beliefs but some had failed. While I don’t agree with his assessment entirely and while I do think he is a slightly frustrated person on this topic in general (watch his video, you’ll see why and also realize he’s pretty spot on when it comes to messaging and pitching), he did make a good point.

He made his point not by regurgitating Simon Sinek’s Start with Why (though it did come up), but by asking a man in the front row to please give him a $100 bill out of his wallet. When the man couldn’t produce it, Burkhart kept asking and the man kept giving him an emphatic no. Burkhart’s point was you can’t give something away that you don’t have, no matter how much you want to. You have to have the belief yourself in order to give it away when you are telling your story.  

An imperfect sales review is better than a perfect one.

Transparency (Real Transparency) is How to Build Trust in Sales

In the closing keynote speech, Todd Caponi, former CRO at Power Reviews and now author of the new book, “The Transparency Sale” (available in Sept 2018), spoke about the importance of being transparent in the sales process. According to Caponi, every interaction is an opportunity to either build or erode trust in sales. Seems pretty obvious, right? But he backed it with rock solid research.

From his time at Power Reviews, Caponi knows that 4.2 – 4.5 rather than a 5.0 is the ideal star rating for purchase probability. Why? Because the brain needs balance. We don’t believe something is perfect. If you don’t define what is imperfect about your product, people will do their homework and find the reasons it’s not perfect for them. If you embrace imperfection and are upfront about it with your prospects, they can decide then and there if those imperfections are something they can live with and won’t go digging to find them on their own.

Caponi gave a real-life example of a competitive situation where the prospect asked him to explain why his company was better than the competitor. But Caponi asked if he could actually start with where they weren’t better than their competitor and why. Caponi was transparent and upfront about what his company had given up so they could be really good in other areas. He took the burden off the prospect to figure out Caponi’s company’s shortcomings and simultaneously built trust. Caponi won the deal.

Once again, we all know today’s salesperson must be transparent. But when you are trying to grow your company as fast as you can and EVERY deal is important and the competition is so strong, I think it’s hard for salespeople to know exactly where to position themselves on the transparency spectrum. It’s never good to lie, but isn’t it smart to shine the best possible light on your product?

This is where Caponi’s take on transparency is so transformational. His research shows it is actually best to LEAD with the imperfections, which I think is a powerful thing for a salesperson. This idea gives salespeople a framework of when and how to speak about any shortcomings their product may have rather than dreading the difficult questions later in the process and grappling with how to handle those questions at some unknown future point in time.

Other Inspiration from Chicago’s Sales Assembly

I clearly walked away from the Summit inspired by what I had heard and these new ways of thinking about sales. There were a few other speakers who were truly inspirational who need mentioning.  

Wade Burgess, CEO of Shiftgig, was one of those people that you could just sit and listen to and write down quote after quote. He fielded questions from his Fireside Chat with common sense that made you take a step back and think, “Oh yeah, this really isn’t that complicated if you just think sensibly and stand by your principles.”

When asked about active listening, he simply said, “Active listening is really just caring about what the other person has to say.” Again, it was just another “Oh yeah – you are SO right moment” for me. Look him up on Twitter. Everyone in Chicago was tweeting Wade Burgess quotes. And this is my formal request to you, Mr. Burgess. Will you be my life coach?

lifecoachBrian Bar, Founder and CEO of Victory Lap, spoke about sales training. His methods are world class. But what stuck out to me was his emphasis on genuinely believing in your salespeople.

He referenced a famous study (the Rosenthal Effect) where researchers told school teachers certain students were high potential. These students were in fact not high potential students but they improved academically because of how their teachers interacted with them after they thought they were high potential students.

Bar explained the Rosenthal Effect works for sales teams. If a sales leader truly believes in his sales team, that leader will nurture their career and those team members will succeed. When there is so much discussion about how to ramp a salesperson, when to cut them loose, and how to manage millennials today, this wisdom stripped it all back to basically say, be a good person and believe in your people.

Closing Thoughts

Sales Assembly Summit 2018 was always going to be a standout event from the beginning because it was the first of its kind in Chicago. But the Sales Assembly team and all of the presenters took the opportunity to truly inspire and influence this growing community. Thank you.

To Jeff Rosset, Sales Assembly CEO and one of my newest LinkedIn connections, congrats on such an inspiring and transformational event. I’m truly sorry not sorry for crashing. Please don’t ramp up security next year.



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