“You haven’t been happy with him for a while now. Why don’t you just rip the band-aid off and end the relationship? You’ve been complaining about him for over a year. And you’ve voiced your needs to him. Repeatedly.”

“But, I don’t think you realize. He’s different than other guys I’ve been with. What if I’m able to get him to change? I see huge potential in him. I think I can get him to make some headway. I really feel we could be something magical.”

This conversation between girl friends could be happening over mimosa brunch in San Francisco’s Marina district. Or over cappuccinos in Tribeca, New York. Over red wine in Paris’ Latin Quarter. Or over Pad Thai in Bangkok’s Thonglor neighborhood.

It’s such a common quandary that it transpires in many places across the globe every single day. The universal wisdom we’d be giving our friend is this: we never end relationships early enough. And that: change comes from within.

And yet, these are lessons we need to learn for ourselves. We often feel like our situations are unique. That they’ll work out differently, or that we can somehow pull things off despite the conventional wisdom. The fact of the matter is: we’re fooling ourselves.

The same applies in startup sales.

Surprise, surprise…founders and startup operators don’t follow all common knowledge. At times, even great advice.

And that’s okay. (It’s something I’ve come to accept as a coach. It’s my duty to be in my clients’ corner whether or not they follow what I offer them.)

So, you might ask, what great sales/GTM recommendations don’t get adhered to by startup people? What are the tried and true rules of the game that often only get absorbed thanks to lived experience?

Don’t over-rely on your network.

Folks in StartupLand will often tell me, “Paul, we’d like to sell to our network first. It’ll just be easier to book introductory calls and start sales conversations.”

“Of course…take big bites out of that low-hanging fruit. Go ahead and reach out to folks in your network. Your YC batchmates, your fellow portfolio companies. Get warm intros to key targets. But we should also get started building a sturdy go-to-market. Each week you put this off is a week you’ll add to finding message-market fit. And unlocking that can take 6, 9, or even 12 months if you dedicate yourself seriously to the exercise. Even the largest networks get depleted over time. Finding a scalable way to get in front of customers is crucial to the survival of your startup. Not only that, but the feedback you’ll get from friendlies is not the input you want. You should seek out the harshest reactions from customers. The brutal truth from the market.”

What usually happens after this little exchange? Startup operators choose not to carve out the time to do the grimy work of prospecting. They’ll rely on their networks to garner free trials, pilots, and even early sales. Only to realize a few months later that they have an issue getting in front of customers once they’ve worked their relationships. Now comes the difficult work of finding message-market fit. And instead of being on a sweet month-over-month trajectory, we’ve got a startup that plateaus for months revenue-wise. This leads me to my next point.

Intellectually, it’s not hard for startup operators to understand that without doing top-of-funnel activities, they’ll lack sales. After all, opportunities are the gas for your sales engine. However, developing the no-nonsense discipline to block out sizeable chunks in one’s calendar and executing effectively day in, day out is altogether another matter. It’s far from glamorous. But veteran sales leaders will tell you: the leading reason sales teams don’t hit their number is a sparse pipeline.

With all that being said, you wouldn’t believe how much this gets put aside for other tasks. The excuses from intelligent, capable startup employees abound. “I had to put out so many fires the last two days. I wasn’t able to get to it.” Or “We had a product feature we needed to deliver to a new customer last week. I was coding a ton of the time. I just couldn’t get around to it.” Or even, “I was busy closing two big deals. I had my hands full with our current pipeline.” This last one is my favorite. As it compartmentalizes deals being closed from them being sourced through prospecting. Overfocusing on closing deals without creating new opportunities in your pipeline only sets you up for a rollercoaster ride. You prospect until you fill up your pipeline. Only to focus on closing. Only to realize that you’re lacking pipeline. Only to do it all over again. Meanwhile, your revenue growth is a series of fits and starts. Making it impossible to maintain healthy month-over-month growth.

Only then will clients ask, “Paul, we’re not growing fast enough. With this trajectory, I don’t think I can raise our next round. What gives?”

“Ahhhh…” I’ll answer. “We’ve hit a roadblock. Let’s focus on feeding our pipeline consistently. A scalable go-to-market motion. But it’s going to take discipline…”

Products don’t just sell themselves.

“Paul, we’ve been in market for the past 3 months, and we haven’t closed any deals. I’m not sure we built the right thing from the get-go.”

“You know, product-market fit is a function of both your product and your go-to-market execution. You need a sufficient amount of both to achieve it. You could have the best product. But if you don’t properly get it to market, you’ll have zero sales. You could also have the best go-to-market motion. But with a terrible product, you wouldn’t be able to score a single customer. You need both ingredients. I can help you with one of those two variables. If we level up your ability to execute in sales, one of two things happens. Your revenue goes up and to the right, which is our favored outcome. Or, a bright spotlight gets shined on your product. And if we execute properly, we have some clarity there. Something like: If we build out these two features over the coming 3 months, we’ll be able to close $275K worth of pipeline we’ve built up.”

“Yeah, yeah, but if we present our product correctly, people should want it. I feel like we do a really good job demoing the platform…showing them all of the bells and whistles. And yet, we have a huge amount of deals dropping off post-demo. I think we should consider pivoting and building something completely different…that people will buy.”

“You’re welcome to go ahead with that. But I would hate for you to waste all of this great product work because you didn’t know how to sell or go to market properly. We can figure this out together.”

One of two things occurs at this point. Founders will decide to pivot (in most cases, prematurely). Or they’ll decide to hunker down to figure out their sales.

If they choose the latter, there might be some thrashing about before I get tapped on the shoulder. “Paul, we’ve tried a ton of different things. We’ve established what we feel is a sturdy sales process, but we’re still not closing a lot of our qualified opportunities. And we need to start closing a lot more if we want to raise our A in the next 12 months. What’s going on?”

“It could be a bunch of issues…including poor qualification, not selling next steps, conducting a subpar demo…let’s take a deeper dive…I’d like to help you unlock this.”

Those are just a few illustrations that emerged when I started thinking about earned wisdom. There are a ton I’m missing, I’m sure. The list is surely huge in our startup ecosystem. With that, what’s some advice you’ve gotten that you wished you’d taken when you first heard it? And what did you have to go through for that wisdom to finally sink in?

I always want to hear more stories. With those, I’d love to continue figuring out ways to reach founders and startup operators before they acquire their scars.