Startup Myth: “Our product sells itself.” 1 Myth, 1 Home Run & 1 Lesson – 2nd Installment

Founders and startup operators often say to me, “Our close rate isn’t as high as we’d like. Our demos appear to be going well, but a lot of our prospects don’t convert after that.” Post-demo drop-off is a widespread problem. If it’s happening to you, take a deep breath.

The phenomenon is befuddling. You clearly heard excitement from your prospect on your last Zoom. “This could be a great thing for us!”, they’d said. You could taste the sweetness of a landed deal. The contract went out for signature. But when it came time to sign on the dotted line, all you got was silence. The most frustrating part? Having zero visibility into what happened. You’re oblivious to the inner workings on the other side of the table. And you’re stuck on the fact you had an enthusiastic prospect that suddenly went dark on you.

Here’s what usually happens when you go from excited prospect on a demo to him ghosting you. More often than not, you dropped on their “to do” list. When you’ve got a prospect on the phone or Zoom, they’re your captive audience. Because they explicitly agreed to the demo, there’s strong built-in intent and interest. They are primed and hungry to find out about your product and how it might make their problems disappear. When they get off the Zoom with you, they might actually be convinced that you have something they absolutely need.

But then, life happens. Their dog gets indigestion and needs immediate attention. They’re in the midst of an all-hands on deck product launch that could change their company’s fortunes, and are expected to help out with QA for the next forty eight hours. Their kids arrive from school elated about a new take home project. What was once a Top 3 item on their to do’s slides down that list. And quickly. Buying a software product starts to feel like a distant priority behind the other tasks piling up at home and at the office.

The lesson here is this:

It’s not enough to just sell your product or service.

You need to earn your prospect’s time and attention through the sales process.

That means that you should be constantly selling the next step.

When I coach my clients on this, I suggest they ask themselves, “What will the prospect get from attending the next call? What will they get from reviewing the contract? What value will they get from sitting through your demo? What can you promise they’ll get by going through an onboarding call with you?”

If you’re able to answer these questions with real benefits — not to you — but to your prospect, then you’ve got something. It becomes about unveiling that value to them in an enticing way.

Here’s how we sold our onboarding call when I ran sales at Whitetruffle. At the end of our introductory call, I’d say, “In our upcoming account optimization (fancy way of saying “onboarding”) call, we’ll make sure that you’re properly set-up on the platform so you can make the most of your 14-day trial with us. We’ll not only take you through all of the bells and whistles available to you in the product, but we’ll also put together your first few job reqs in such a way that you get the most qualified candidate matches on a daily basis. Lastly, we’ll give you tips on how to put together your company profile, so that you’re putting your best foot forward in attracting candidates.” Now, how does that sound, if you’re a prospect? Sounds like you’ll get a lot from the onboarding call, right? The tangible value of attending the call is crystal clear.

My first sales guy at Whitetruffle initially got a lot of no shows for this onboarding call. Once we brushed up his delivery of this end of intro call transition and made sure he was selling the account optimization properly, people started showing up to these calls in higher numbers. Those led to a ton more free trial conversions and more paid customers.


Home run: Epsilon3 founders went from thinking they had product market fit issues to 50X’ing their ARR in 12 weeks. That included closing the biggest deal in company history with a space company we’ve all heard of. 

I can still remember it. Our engagement was just a few weeks old. Epsilon3’s founders — Laura and Max — were downtrodden. They were doubting their product. Would the market accept it? They had been selling it for several months but hadn’t gained much traction. They told me, “Maybe we should build something else. Maybe this is a sign that the market wants something different.” The thought of scrapping their entire product had crossed their mind. I responded, “Guys, I think it’s a bit premature. I’d like us to have more market evidence before making such a sharp turn. What we have here could either be a product issue or a sales execution issue, or a combination of the two. I can help you remove the sales execution issue. And we can continue learning about the market’s reaction to the product. We owe ourselves that, before redirecting the ship in a brand new direction.”

Deep down, Laura and Max agreed. After all, they had invested close to a year in product development. They needed to give their baby a fair shake in the market.

I got to work on diagnosing the sales execution issues. A few things were broken. For one, free trials were extended indefinitely. They were rarely time boxed. And a lot of our free trial users weren’t converting to paid customers. We were hoping that folks would like the product enough during a loosey goosey trial period to then decide to pay us. We also had no way to figure out what constituted success in our trials/pilots. It was impossible to paint a picture as to what our trial users might expect during this phase. We desperately needed a way to control the sale.

Laura and Max pulled up their sleeves and implemented a ton in very short order. We installed a 14-day credit card activated free trial. We combined it with an onboarding call, which was a forcing function for our customers to enter in their credit card info. We instituted a sturdy qualification process, which ensured we wouldn’t demo to folks that didn’t match our ICP. We also worked to find out about the buyer journey in great detail early in the process. This enabled us to get in front of the decision makers quickly and therefore shorten our sales cycle. We got better at selling next steps, and booking the next call/meeting on the call we’re currently on. In conjunction with that, we stopped relying on email follow ups to book upcoming calls. Lastly, we figured out what success looked like during our trial and started setting those expectations for our trial customers.

Laura and Max’s efforts paid off quickly. We 4X’d MRR in the first month of working together and we’re on pace to do even better in subsequent months. A sweet culmination came with the closing of a game-changing six figure deal with a space company we all know. When working on the opportunity, I told Laura and Max that if they got it across the line, I’d travel down to LA to take them out to a celebratory dinner. At the time of this writing, I’m packing my bags for a trip to Tinsel Town.


Lesson: The more I am attached to the outcome, the less effective I can be as a coach. 

I have a confession to make.

I get emotionally invested in my clients’ success. (And this isn’t some form of humble brag, I promise).

Too much so, at times. It can eat away at me when we’re not moving as fast as we could. Or when I feel like my message isn’t landing the way it should. Or that I haven’t done a good enough job communicating a lesson that I learned the hard way. When I brought this issue up to my own coach — the fact that I was really struggling with the powerlessness of my coaching role — he put forth the advice above. I thought it so good, I even took it into therapy.

Everything starts with acceptance. If I can’t accept that my client is stuck, I won’t be able to help them shine the right light on their blockage, and consequently have it melt away. The more a client feels my need for their success or a certain outcome, the more they will resist any change I’m trying to impart. Trying to impart change, in the first place, isn’t the right method. Change must come from within. I can only help my clients look at an issue that might be causing them to get in their own way. I can suggest a way for change. Or a different way to look at things. The client — who is the player out on the field — must actually perform the change. There’s a ceiling to what I can do. I can offer the advice, the insight, the lesson, or even a path to change. But I can’t act on it. I have to be okay with my powerlessness at the end of the day.

If I become too attached to the outcome, I’ll force things. I won’t be able to meet my clients where they are, and help them where they might be stuck. I’ll most likely end up pushing them too hard, and they’ll resist even more. David Hawkins talks about this in his book “Letting Go”. Human beings resist change if they feel they’re being pushed into it. As my therapist has told me on several occasions, you must “join the resistance”. It is important to shine the light of awareness as to why someone might be resisting. Only then can someone make a true change about how they act. Understanding and seeing the blockage is the catalyst to change. Seeing the contours and shape of the resistance will in most cases dissolve it. But the person doing the self-examination must actually want to be different.

Once you understand that, you can see that wanting success for your client is about you. Not the client. If helping your client is about meeting them where they are and not pushing them towards change, then being attached to an outcome is not only counterproductive. It’s also putting yourself ahead of the client’s progress and needs. In order to best serve my clients, I need to put their needs to be supported over my need to be a “successful” coach. In essence, I need to get over myself in order to be at my most helpful to others.