Top 10 reasons founders fail at sales

Sales is hard.

A lot of founders underestimate what it takes to win deals.

There’s so much competition that exists. So many options for a buyer to choose from.

You really need to bring your A game consistently if you want this to work.

In this article, I’ll go through the most common reasons I’ve seen why founders can’t make sales work for them.

This might shed some lights on key areas where you can improve.

If you’re doing all of these well - keep going. All you need is time and perseverance.

Couple announcements:

1. Building up the waitlist for September group coaching. Have a few folks committed with a couple spots left. Let me know if you’re interested. More info about what we cover + membership cost here.

2. Upcoming community webinar on August 20 at 11 EST. Topic is How to do sales discovery. Start a free trial of the community to attend.

1. Your product isn’t solving a real problem

This is the harsh reality to face. Is your product solving a problem that’s worth paying for. The latter part is really important.

Companies need to make a bunch of tradeoffs on where they spend their resources.

They have 100s of problems they need to solve. Some large, some small.

Some have direct impact on revenue, cost, and culture. That’s where the money goes.

Anything that indirectly impacts this is considered a nice to have, and will almost always get pushed out.

There’s limited funds/resources that can be allocated to solving problems.

Are you in the top 5? If not, you’ll always struggle a bit with sales.

Product is the biggest driver to sales success.

2. You’re winging it

Can you explain your sales process start to finish? Can you write it down on a napkin? Do you know exactly what steps you need to take from a lead raising their hand to you getting paid?

If not, you’re winging it. Which doesn’t work well in sales.

Sales is an equation. Volume x Conversion = Results

The volume piece is pretty simple to get. The conversion piece needs to be broken down by each stage of your process.

The more consistent you are with running sales cycles, the more confident you’ll be in your conversion rates.

Once you have repeatability, then the game is all about fueling volume.

But you need a systematic approach to figuring out how you stabilize that conversion rate.

3. You’re running a wait and see approach

Which brings me to my next point - you’re running a wait and see approach to sales.

You have a free trial. You don’t reach out to book a call during this trial.

You have a demo link on your website that books directly in your calendar.

You run a training call that you call a demo.

You tell them to “let you know” if they’re interested.

And you wait.

4. You’re training instead of demoing

Let’s touch more on my previous point.

Many founders think that because they built the tech, they inherently know how to show it.

And what ends up happening is they train a prospect instead of demoing.

They show how to use the features.

That’s not a demo.

A demo puts the features in the context of the prospect’s world.

It has a formula to doing it right.

Context > Problem > Capabilities > Show Features > Ask

Demos are an editing exercise. You only show workflows that solve problems.

They aren’t a customer yet. You can’t train them on using your tech. They’ll just be confused.

5. You didn’t understand their pain

Which brings me to my next topic: pain.

Most deals are closed because pain exists for the prospect.

And in order to demo well, you need to understand pain.

You need to probe deep. What are their current workflows, what have they tried, why didn’t it work?

Where do they want to be? What’s holding them back from getting there?

How does this problem cost the business? What metric is suffering because of this?

What are the negative consequences on the business if this doesn’t get solved soon?

This stuff is important to winning deals. And for doing a great demo. But often gets missed.

6. You’re running a selfish cycle

Which brings me to my next piece - your sales cycle is about you, not them.

When you’re doing qualification, it’s about making sure they are right for you.

When you’re doing a training session instead of a demo, it’s about showing your functionality.

This needs to be flipped. Sales is about helping a prospect buy. They need to go through this thought process:

1. I have a problem
2. Do you understand my problem?
3. Do I trust that you can solve my problem?
4. How do I get started?

If you don’t help them get through this through our sales cycle, then you didn’t really make it about them.

7. You’re difficult to buy from

Your pricing/packaging is confusing.

Your sales calls aren’t resulting in a mutual outcome.

They have to do extra research and take extra steps to understand if you’re the right solution, because you’re not making it easy for them to do so.

The whole experience of landing on your website, booking a demo/starting a trial, understanding your process, getting help from you on calls, etc. The whole thing needs to be about making it easier for them to buy.

8. Your calls are all over the place

A sales call is designed to reach a mutual outcome.

You have a goal. They have a goal.

The meeting needs to get both of you there.

Which means that meetings can be blueprinted.

There are different meeting types. Know which ones you need in your cycle.

Then script the first 3 minutes of that meeting to make sure you get to a mutual outcome. That script should include:

1. Time check
2. People check
3. The purpose of the call, and ask permission to ask questions.
4. Their ideal outcome for the call
5. Then permission to discuss next steps if outcome is achieved.

9. You’re not using a simple sales methodology to help you

It’s hard to navigate sales cycles. You need to ask the right questions, which will lead to the results you want.

But these questions need to be carefully crafted. Usually somewhat on the fly (although some scripted questions like a Pain Funnel can work).

You can use the FOUNDER framework to help uncover the right information throughout your sales cycles, which will increase the chances of winning deals.

Facts - systems, tools, workflows, people

Objectives & Pain - where are these workflows breaking down, and where do they want to get to. This creates a gap in their business.

Uncovering Impact - how does this gap impact the business as a whole (think revenue, cost, culture, efficiency, risk)

Negative Consequences - what happens to the business if they don’t solve this?

Driving Events - what timeframe is driving a change now?

Reaching a Decision - what are all the steps and people involved to make a buying decision

You need to know this about every deal to maximize your chances of winning. It trickles into your entire sales cycle, from calls to follow-ups to proposals.

10. You’re not really doing sales

This is really the thing I’ve come across the most with founders.

They think they’re doing sales. But when you dig into the mechanics of it, they’re not really doing sales.

They’re letting sales happen.

Then they get frustrated at the results.

Easiest thing you can do to flip this around is to build a Minimum Viable Sales Process and start upskilling your sales skills.

There’s no real way around this.

Your current skillset is what’s stopping you from achieving your results.

Let that sink in.

Then do something about it.

This post first appeared in the Founder-Led Sales Newsletter on August 9, 2024. Subscribe to the newsletter here .

For more practical early-stage sales tips, connect with me on LinkedIn .

If you’re looking for more hands-on help implementing your first sales process, reach out for coaching packages .

P.S. Starting the waitlist for the next group coaching cohort starting in September. LMK if you’re interested. Package info here .