During our first year building Palabra our marketing strategy was exclusively organic, and our first sales came from 1:1 conversations with potential users.

But those sales didn’t come right away. After a month of difficult conversations and failed demos, I knew I had to do something different. That’s when I learned a very new and innovative approach to direct sales: actually listening to what people were saying.

Since then, I’ve talked to many founders and went through their demos. I noticed they were making many of the same mistakes I was before.

That’s why I decided to create this guide, hoping to share my experience and tips to talking less and selling more.


This is what helped me listen more and close more sales.

    1. Write down your list of three (3) key things you should ask and know before the call ends.
    2. Structure your conversation -introduction, questions and next steps.
    3. Doing enough background research to know possible use cases and questions.

As always, this guide is made with non-enterprise B2B software in mind. I speak from my experience and lessons handling sales as a founder of an early stage B2B SaaS solution.

This doesn’t mean it won’t be useful for other types of businesses, if it’s your first time handling sales you’ll probably get some actionable insights from this article.

📞 What a failed sales conversation looks like

Just because your sales call didn’t end in an actual sale it doesn’t mean you failed. You might be talking to someone who just doesn’t have a use case for your product, or is not ready to buy yet. It could also be because you’re not talking to the right person within a company.

But there are definitely some cases where everything seems to be right and you still don’t get to close a sale.

When I started getting into 1:1 sales calls I went through months where I had 5 to 10 weekly demos with little to no conversions. There was more than one reason for it, and some had to do with how immature our product development was.

But I quickly learned the way I was handling these calls had a lot to do with our poor close rate. And I found a few things I could do to improve. But first, let’s focus on how to identify a failed sales call.

My first lesson learned was this: it’s not always easy to know if prospects are interested in buying or just being nice.

Only a small percentage of prospects have told me truthfully why they don’t like our solution, why they think it won’t work for them. They usually listened patiently to what I had to say, and had a polite excuse when I tried to get them to commit to buying.

So how do we know if there’s room for us to improve our sales strategies? Here’s my short list:

  1. When there’s no clear commitment on their end after the call ended. It doesn’t have to be a subscription, prospects can commit to a follow up call, team mate introduction or giving more contact information. If you have no next steps including their time, money or information, they probably have no intention on moving forward.
  2. When you can’t give honest and obvious reasons on why your product will be useful for your prospects. This was specially dificult for me with an early product, since we didn’t have a defined use case or ideal customer profiles. If the sales call ended and you can’t describe a clear use case to your team, you probably weren’t asking the right questions.
  3. When you end up with a long list of feature requests that are not on your roadmap. Even if you’re early, you should have an MVP which adds enough value to allow you to sell it as it is. You’re not selling promises, and if those feature requests mean that your company needs to go on a different direction to what you planned, it could really hurt your developement and focus.

After finding this, I started taking notes on each of my demos on a spreadsheet. For each demo I wrote down what their use case was, what features they had requested, and what their commitment was. If I had a clear next step commited, I counted it as a win.

📞 How to be better at sales with an early product

Having an early product means most of your sales calls won’t end in an actual customer, and that’s ok. In early sales conversations, learning about your prospects and industry is as important as selling your product.

To be better at sales you first have to go through your sales conversations. Record every demo you have (of course, asking your prospects’ permission) and watch at least some of them.

Being a first time founder I didn’t have much time to rewatch my recorded calls, so I chose those that went well and those that went terribly poor.

I found I was usually making at least one of these mistakes:

In most poor demos, I was making all 4 mistakes at once.

So what to do once you know what’s wrong?

For me it was sitting down and finding strategies to stop making the same mistakes over and over again. The hardest one (by far) was learning to listen.

📞 How to talk less and sell more

Listening to prospects is not at easy as it sounds when you are worried about selling them your solution. Specially if you’re at an early stage and don’t have much experience selling software, it’ll be hard to keep a clear mind and dig into the most important answers you get.

But here’s the thing: selling isn’t about convincing people to try your product, it’s about identifying how your product can solve a problem for them.

In a direct sales conversation, you should have two take outs:

  1. Identifying if the person you’re talking to has a problem you could solve (the more details the better)
  2. Communicating clearly how your product is a solution to their problem.

If you fail at #1, you’ll end up trying to convince people who don’t actually have a problem you could help them with. Those are not your users, and there’s nothing you can do today to make their life easier. Even if you somehow convince them to sign up, they’ll probably cancel their subscription, making your churn go up.

Failing at #2 is usually connected to #1, because the only way of communicating a solution is to understand the problem perfectly. You have to listen really carefully to understand what those problems are.

Most of your conversations with prospects should be about #1. Make a lot of questions. Listen closely and follow up on what isn’t clear. Make the other person feel listened to. Worst case scenario, you end up with valuable insights about what problems people have and as an early stage startup, this information is crucial to find product-market fit.

Here are some lessons I learned while taking a direct sales approach to SaaS. Most of them came from reading The Mom Test, talking to awesome people and experimenting on my own.

1. Writing down what you want to get from the conversation

This list should be really short. My initial conversation guide had 15+ questions to get to understand the problem, and then a short demo. It worked kinda fine, but I usually got lost by question 5, and then started thinking about what to ask next instead of listening to the answer.

The Mom Test suggests you should “prepare your list of 3”. Three things you want to get from each conversation, depending on who you’ll be talking to.

In early Palabra demos, when I asked to have a quick chat to someone in a startup, I usually had three different scenarios:

I prepared three different notes to look at before each conversation, one for each buyer persona, and wrote down my list of three. I started asking questions that came to mind from listening to what people were saying, and spent almost no time looking at my notes. If I ever felt I was getting lost, I just glanced towards my list of three for that particular person and checked if I was missing something. Freedom.

2. Having a structured set of questions

This advice came from a great friend and the best UX designer I’ve met 👉 sofandrade.com👈 She knows all about user interviews, and since I was also trying to learn from our prospects, I knew it would help.

Her advice was to divide my questions into chunks or topics I wanted to know about. Give a structure to my script.

There are a few ways of structuring your conversations. I used and recommend two:

Having differentiated topics gives you flexibility to follow the conversation and not worry about what to ask after each answer. If you ask a question from the first topic and your user’s answer goes to a slightly different topic, you can go to that part of your guide and then come back after that’s done.

A smart move was to leave questions about pains for last. By then I usually had enough information about their problem and could offer a clear solution with Palabra.

If we had a solution, I’d briefly tell people why I thought this would work, and offered to show them in a demo. By focusing on their specific solution in the demo, I only showed one feature and not the whole product, which was a much better use of everyone’s time.

3. Doing some background research – but still ask people

You can’t go into a sales pitch without knowing who you’re talking to. For B2B sales you need to know about the company and the person you’re actually going to talk to. The key here is to use that information wisely.

I used to start conversations on what I’d learned from their landing page, to let people know I had done my homework. But this was actually making me start on the wrong foot – by talking too much.

Asking about their company and what they do there gives you inside information you wouldn’t get from LinkedIn or a landing page. And it also helps break the ice, since it’s an easy answer for anyone.

My solution was full transparency. I started each conversation by saying I had done a bit of research about them but still wanted to hear from them. Then I would ask what they usually do.

This was incredibly effective. Being honest took away all of my nervousness and allowed me to relax into the conversation. I felt like I had no secrets, I was just telling the truth and asking questions. And I think this works both ways: the person you’re talking to will probably trust you more if you’re honest about what you’re doing.

Just keep in mind the introduction should be short, and they should be doing all the talking. Trust that your discovery questions were enough to make people know they matter to you, and then focus on listening.

📞 Final thoughts

Since my first sales calls almost a year ago, I’ve found much better ways of handling these conversations.

First, I decided to hire a sales coach. This was probably the best business decision we made. Matt Wolach has years of experience and gave us actionable insights to help us improve our sales processes in just a few weeks.

Second, we learned A LOT from these early calls which allowed us to:

My script has changed many times since we first started, and now I’m able to get into sales calls feeling confident and knowing what questions to ask.

Selling an early product continues to be a challenge, but learning to listen to people allowed me to quickly improve and get insights for our business.

Start by creating a process you can trust, and take small steps to improve it.

If you’d like to gain control over your customer pipeline and feed it with real time information on how they interact with your product, Palabra can definitely help.

Book a call with me if you’d like to dig deeper.

Happy calling!