I’ve been reflecting a lot recently on the power of expectation setting.
Let’s say there’s a founder who, by hustling for a month, can raise $500K on Wefunder from their customers and community pretty easily. But if she wants to raise $2 million, that’s going to be really really hard. If I chat with her ahead of time and say “Oh yeah it should be super easy to raise $2 million! No worries!” — when she only raises $500K in the first month, she is going to be very very disappointed in her experience of Wefunder. Net detractor. Bye bye referrals. Bye bye growth.
But if I chat with her ahead of time and say “Well that sounds like a stretch. But maybe shoot for $250K starting out, and then you can always increase that if you are over-subscribed” — when she raises double what I had set her expectation at, she will be over the moon! Delighted customer. NPS of 10. Referral-driven growth!
And the only thing that was different in those two scenarios was that I set different expectations in each one. She raised the same amount of money in each scenario. She put the same effort in. But because of a difference in expectation setting, she shifts from an irate net detractor, to a delighted net promoter.
Shout out to Justin Renfro on Team Wefunder for really embedding this principle of “conservative expectation setting” on our BD team over the last couple of years. I think it’s awesome.
But despite this rather meandering preamble, I am going to completely ignore everything I just wrote, by emphatically declaring that this podcast interview with Rory Billing is the greatest hour of content about “how to be awesome at sales” ever recorded on a microphone, in the history of the universe.
How’s that for conservative expectation setting???
Rory Billing is the Founder and CEO of The Fan’s Place, in Rory’s words “the non-alcoholic beer of sports betting”. And before starting The Fan’s Place, Rory had a number of sales roles, which we dive into.
If you want to get better at sales, I really would recommend listening to the entire interview! But here’s the synopsis of Rory Billing’s principles for sales success:
(1) The power of silence. When you ask a question, and the person you’re talking to responds. It can be incredibly valuable to just let their words sit for a second. To really make sure you “hear” them. And that they sink in. It’s also a great signal to the customer — that you are deeply listening. And can sometimes even provoke another thought, or follow-up, often deeper point — which might otherwise have been missed.
(2) Write well. As a History undergraduate student, I wholeheartedly endorse this point :) Obviously, spelling, punctuation and grammar as a given — everything is a touchpoint, and an opportunity to gain or lose credibility. But are your emails clear, concise? As Rory put it, “when I get a bad email from someone, it just turns me off immediately”. I couldn’t agree more.
(3) Ask questions. A pretty basic one here. But one specific tactic I really liked here — Rory mentioned that he used to track the percentage of time that he was talking, vs. the customer was talking, especially at the start of sales calls, which is a great forcing function on this point.
(4) Focus on the key points. As Rory put it: “If you’re on a phone call with someone for 30 minutes, they’re only going to remember 2 or 3 things you said”. So it’s critical to focus, and often reiterate key points — which you probably take for granted, because you’ve regurgitated them hundreds of times. But the customer might be hearing them for the first time on this call.
(At this point of the podcast, we made an impassioned request to Rory’s mum to send Rory shorter emails. It was funny. Me: “This is the new goal of the Closing Time podcast. To convey passive aggressive messages to the parents of the guest.”)
(5) Use your demo as a presentation, not an exploration. i.e. Too much clicking and scrolling in the demo can both risk losing your audience, and also risk something going wrong! So keep things tight, and keep the flow of the demo simple and consistent.
(6) Eagerness to learn. I reflected on this principle when I chatted with Mike Jue, the VP of Demand at Doorvest earlier this week (that episode dropping in a few weeks!). Mike framed it as “practice”, whereas Rory talked about an “eagerness to learn” — but in both cases, the key is this — how do you improve the gradient of your line? So that you can keep improving your results, not just by working harder, but by working smarter as well. And getting better and better at the job with every passing day?
(7) Be honest. If you obfuscate things that you think might deter a potential customer earlier on in your conversations, there are two obvious problems. Firstly, if and when those things come to light lower down the funnel, the customer might drop — either because those things you were hiding are dealbreakers, or potentially because your deception totally undermined their trust in you. And secondly (and maybe even worse!), if the customer does end up buying, and then is surprised by the bad things about your product that you were hiding, they are going to be really annoyed. Again, not rocket science here. But be transparent, honest and do the right thing. It really does massively pay off in the long run.
(8) Care more about the implementation than the sale. i.e. You should only want to sell something to a customer if you really believe it’s going to add value for them. Another way of putting it, as Rory did: “Your customer NPS ends up being the most important thing for you down the road. You can't sell a $4 million per year piece of software if you don't have other customers who that person can call.”
(9) The power of saying “No”. To Rory, “No is the most powerful word in the entire sales vocabulary”. It’s very tempting to acquiesce to every customer demand. But that leads you down a dark path. In Rory’s experience, super counter-intuitively: “You actually sell more when you start telling people No”.
And Rory’s answers on the rapid fire questions I asked him at the end:
What do you look for when you’re hiring sales people?
“Are they selling me in the interview process?” And not just the interviews themselves, but the follow-ups, cadence, tone, persistence, etc. I had honestly never really thought of this before, but I liked it! Meta!
A memorable deal?
Relationships was a central theme. Rory mentioned that one of his customers was actually in his wedding! I don’t think that was a ploy to close the deal, but you never know — maybe Rory had an ulterior motive in groomsman selection??
Biggest mistake you’ve made?
A lack of patience with his team-mates. (And also maybe a lack of self-awareness that went along with that). A pretty interesting story on this one!
A controversial opinion you have about sales?
“I don’t think sales training works at all”. Spicy. I like it. To build on that: “I just don't think anything works nearly as well as getting a bunch of at-bats, really taking your learning into your own hands, and having ownership of that process yourself.” Strong stuff!
The best sales person you know?
Combine Jim Holt, Jerry Baughey and Rachael Youngman into one sales person to rule them all! Jim was the product expert, super technical. “Didn’t need a Solutions Architect”. Jerry was your best friend in every sales cycle. And you just knew he cared so much. Rachel was the consummate enterprise sales person. “Her touchpoints were unbelievable”. Every time she was in town, she would know exactly who to reach out to, and go out for lunch with. The relationships she build were incredible.
And there you have it folks. Episode #7 in the book. And a bunch more in the works.
Big thanks to Rory for coming on the podcast — was genuinely one of the richest and most fun conversations I’ve had.
You can find him on LinkedIn here. And check out his startup, The Fan’s Place, here.
See you next time!
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