5 Common Sales Mistakes Founders Make (and How to Fix Them)

Welcome to Sales Skills For Founders, a weekly newsletter with one actionable skill for sellers who are tired of tips, tricks, and scripts. AI isn’t going to close deals for you so let’s master sales, one skill at a time.

Today’s Skill: Awareness

Learning to sell as a Founder comes with unique challenges, and chances are, you're making mistakes without even realizing it.

We can learn new skills all day long but if we aren’t aware of our blindspots, it can get us into trouble. Founders normally don’t have someone reviewing these things with them consistently. (It’s one of the reasons I started doing Sales Call Roasts.)

Sales reps have managers reviewing their calls, pipeline meetings, and are provided ongoing training. But as a Founder, you don’t have that luxury.

So here are five common mistakes I see and how you can avoid them to tighten up your sales game.

1. Knowing the Product Too Well

Mistake: Relying too much on your product’s features to sell and letting your product be a “crutch”.

Fix: Stop talking in features, start speaking in stories. Use specific client use cases or “Win stories” to craft a “day in the life” narrative. How does your solution fit into their world and make their life easier?

Client stories should relate to areas of your product or service so the more of these you have the better you can tell a “before and after” story instead of showing a feature you offer.

Your product might be great, but real impact happens when you frame it around solving their problem in a way they truly relate to.

2. Fear of Talking About Money

Mistake: Getting nervous about pricing and offering discounts too quickly.

Fix: Prepare your pricing strategy in advance, make it simple, and stand by it. Set clear boundaries around your pricing and confidently explain why you charge what you do. There is a value to what you provide and it’s also not for everyone. The right audience will pay you what you’re worth.

Discounting too soon signals doubt in your ability to solve their problem. If you don’t believe in your value, why should they?

3. Trying to “Close” on the First Interaction

Mistake: Thinking that people will buy after one call or assuming one good demo means the deal is closed

Fix: Get curious about their buying process. Ask questions like:

• "Who else needs to be involved in this decision?"

• "How does your team usually evaluate solutions like this?"

• "Would a separate call with just your Finance team be helpful?"

Not all buyers follow the same process and if you try to “go for the close” too quickly it will put your buyers back on their heels. You may not understand their problem fully after the first call, don’t rush it!

Be flexible, adapt, and collaborate with them instead of forcing them through an artificial sales funnel.

😂 As a bonus, here is a 2-min video to one of the best responses Gary Vaynerchuk has ever given to a question that will prove this point

4. Getting “Happy Ears”

Mistake: Mistaking vague enthusiasm (e.g., "This looks great!" or “I definitely think this could fit”) as a buying signal.

Fix: Everything isn’t always roses. Most of us have some hesitations but we might be afraid to expose them. Get ahead of any issues before it’s too late by asking something like, “Do you have any concerns or hesitations about what we’ve discussed?”

Many Founders avoid creating tension because they are afraid of coming off as confrontational. But the friction it creates is good because it exposes weak spots and opens up an honest dialogue. Lean into it.

👉 If you missed last week’s newsletter on Creating Tension, read it here

5. Over-Reliance on Email

Mistake: Trying to close deals via email alone.

Fix: Prioritize live conversations and always schedule next steps before ending a meeting. A prospect who agrees to a next meeting is showing real interest.

Also, we shouldn’t be going back and forth through email answering questions. It’s okay to say, “Can we talk for 10 minutes about your question. It might be easier to chat about it so I can explain further.” You don’t have to do this for every question but if they are continuing to ask questions then they are interested. Don’t lose the chance to go deeper.

Sales isn’t about convincing, it’s about understanding.

Face-to-face interactions (which are mostly virtual these days) build trust and connection. And please, turn your camera on!

Final Thoughts:

You’re not going to get rid of all the mistakes and as you improve your skills new ones may creep up. What’s important is to build awareness with your sales interactions and recognize when something isn’t working.

You should be recording all of your sales calls so you can review them often by yourself or with a coach. You’ll start to recognize patterns and pick up on areas that get you stuck.

Practice is about building your strengths and weaknesses. Don’t avoid looking for those blindspots. They might be the very thing preventing you from closing more deals!

Action Item:

Which of these mistakes sounds familiar?

Take 15 minutes to reflect on how you can adjust your approach so when you encounter one of these situations you are prepared.

What’s one thing you can change in your next client interaction to improve your results?

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