Startup sales - why so scared?

You have built something you believe in. You can explain how it works, why you created it and what you hope it will become.

Then comes the moment to contact a potential customer.

Suddenly, improving the website feels urgent. There is another feature to finish, another market report to read or another version of the pitch to prepare.

If that sounds familiar, it is worth asking what you are putting off.

Selling can feel personal when the business is yours. You are asking someone to consider something you have invested time, money and a great deal of yourself in. A lack of interest can be difficult to separate from a judgement about you.

But customer conversations are part of finding out whether the business works. You need a way to have them, even when they feel uncomfortable.

What is making sales difficult for you?

Before deciding you are “bad at sales”, get specific.

Are you worried about bothering people? Being asked a question you cannot answer? Hearing that the product is too expensive? Or discovering that the problem matters less to customers than you hoped?

Perhaps you associate selling with pressure and persuasion, and you do not want to behave that way.

Each of these concerns needs a different response. Writing another sales script may do little if the real difficulty is asking someone to pay.

Try finishing this sentence honestly: “The part of selling I most want to avoid is…”

That gives you something concrete to work on.

Start by understanding the customer

You do not need to begin a conversation with a polished performance. Begin with a relevant reason to speak and an interest in the other person’s situation.

Ask how they currently handle the problem you believe you can solve. Find out what is difficult, what they have already tried and how important it is to change.

For example:

• What happens when this problem comes up?

• Who does it affect?

• What does it prevent you from doing?

• How are you dealing with it now?

• What would make you consider a different approach?

Listen to the answers before explaining your product.

Your enthusiasm matters, but it cannot substitute for understanding whether someone needs what you offer.

Be clear about why you are getting in touch

If you are asking for research input, say so. If you would like to explore whether someone could become a customer, be honest about that too.

Avoid presenting a sales approach as a request for impartial feedback.

Keep your invitation specific and easy to understand. Explain why you thought of them, what you would like to discuss and how much time you are asking for.

You might say:

“I’m building a service to help small teams manage customer handovers. I’m interested in how you handle that as your team grows. Would you be open to a short conversation to see whether what we’re developing could be useful?”

Relevance gives someone a reason to consider the conversation. They still get to decide whether it is worth their time.

Talk to customers before trying to automate everything

Early conversations can reveal questions your website and sales materials do not yet answer.

You may discover that the person you expected to buy does not control the budget. That implementation is a bigger concern than price. Or that customers value a part of the product you rarely mention.

Meet in person when it is useful and practical. A video call or phone conversation can also give you valuable insight. Choose a format that suits the customer and the discussion.

As the business grows, stay close enough to hear how customers’ needs are changing. Even when someone else owns sales, those conversations can help you make better decisions about the business.

Make an offer and agree a next step

Listening is essential. So is recognising when there is enough understanding to discuss working together.

Founders can become comfortable collecting feedback while avoiding an actual offer.

When there appears to be a fit, explain what you can provide, what it costs and what getting started would involve. Be honest about limitations, particularly with an early product.

Then ask a clear question: “Does this look useful enough to explore a paid trial?” or “What would you need to decide whether to go ahead?”

If they are interested, agree a next step with an owner and a date. If they are not ready, understand what is missing without assuming that more persuasion will solve it.

Make it easier to find relevant people

Start with a clear description of the person or business you want to reach.

That makes it easier to ask existing customers, former colleagues, friends and advisers for introductions. “Do you know anyone who runs customer support in a growing software company?” gives people more to work with than “Do you know anyone who might buy this?”

Events and professional communities can also help you meet people with relevant experience.

Choose them for the conversations they make possible, then contribute and follow through.

For practical ideas, read The importance of meeting people in real life and how to maximise your time.

Keep a simple record of your sales conversations

Memory becomes unreliable surprisingly quickly.

Use a CRM system, or a simple structured tracker while your needs are small, to record:

• Who you spoke to and their role

• The problem they described

• Whether your offer appears relevant

• What you agreed to do next

• When to follow up

• Why an opportunity progressed or stopped

Choose a tool you will actually maintain. Start with the information that helps you act, then add complexity when there is a clear reason.

The purpose is to understand the conversations and avoid losing commitments you have made.

Follow up thoughtfully

There is no useful universal number of times you must contact someone before they buy.

Follow up in line with the conversation. Refer to what they said, provide what you promised and explain why another discussion might be worthwhile.

If the timing is wrong, ask whether they would welcome contact later. If they decline, respect that.

Persistence is more useful when it is informed by the customer’s circumstances. Repeated messages without a relevant reason can make it harder to build trust.

Review what you are learning

Set aside time each week to look at what happened.

Which people responded? Which problems mattered enough to discuss? Where did conversations lose momentum? What did customers misunderstand?

Separate what you know from what you are guessing.

One rejection does not tell you the whole offer is wrong. Repeated feedback about the same issue deserves attention.

Use those patterns to improve your audience, message, offer or sales process. That gives your next round of conversations a clearer purpose.

What could you do this week?

Choose a small action you have been avoiding.

Contact a relevant prospect. Ask a customer why they chose you. Make a clear offer to someone who has already expressed interest.

Prepare enough to have a useful conversation, then notice what actually happens. You may still feel uncomfortable, but you will have something real to learn from.

When sales brings up a bigger founder question

Avoiding sales can connect to wider concerns about confidence, pricing, focus or the possibility that your plans need to change.

I coach and mentor founders through these questions, making room for both the commercial decisions and how you are experiencing them.

If you would value someone alongside you while you work out what is getting in the way, explore how we can work together.

Cheers,

Duncan