Many small-business owners confess to me that they’re worried they’ll say the wrong thing and totally blow that first sales meeting with a prospect from a large or enterprise company.

In my experience, this fear stems from lack of preparation. Large organizations are not alien species, after all. And no one knows your product or service better than you do. The likelihood of them asking you a question you don’t have the answer to is pretty low. With a little pre-meeting prep, you’ll be able to confidently navigate that first sales meeting.

There are three specific questions that I think you should prep for. Not because they’re curveballs — but because you might feel put on the spot if they come up. So let’s address those three questions and build that superstar sales confidence…

What do I say about the size of my business?


The size of your business matters much less than you might think. If you can solve a customer’s problem, the size of your company isn’t a concern.

In the rare circumstance when a prospect from a large organization asks you about the size of your company, don’t panic — and don’t lie. If you lie, you will eventually get found out…and your credibility will be smashed to smithereens.

You’re a small business and you likely have a small team. That’s okay! Don’t underestimate yourself. When you talk about the size of your business, include all staff — full time, part-time, and contractors.

This isn’t dishonest because — believe it or not — it’s exactly what enterprise companies do. It’s incredibly common for enterprise companies to have people who work for them on contract. And when the company talks about headcount, those contractors are included.

So mentally prepare yourself for the question (even though it’s an unlikely one) by adding up your entire team. You don’t need to be specific about who has what employment status, part-time status etc. — just have the total number handy and state it with confidence. And don’t forget to count yourself!

Showcase’s headcount, for example, is 12 people. That includes our employees, and it also includes regular contractors such as a bookkeeper and a copywriter. So when I tell a prospect that we have 12 people, I am both confident and truthful.

What’s more likely to happen is that the prospect won’t ask about the size of your company. Then, after working with you for a while, they’ll pleasantly remark, “Oh, there’s only six of you! It’s amazing what a great job you’re doing with such a small team.”

What if I work with their competition? How should I address this?

The longer you’re in business, the higher the likelihood that you have worked or are currently working with your prospect’s competitor.

How to handle this is specific to the type of work you do, of course.

If you’re selling a product, your prospect probably knows and accepts that their competition may have purchased it, too. This doesn’t always make it easy for your prospect to swallow, though, so come prepared to soothe them a bit.

Take Showcase, for example. We are delivering a platform (a vessel, really) for our customers to use at their discretion. We don’t control what goes into the Showcase app, we just make sure it gets into the hands of the right people. So we do work across competitors — and here’s how we frame this:

Our product is like Microsoft Word: All your competitors use it, but it’s what you do with it that matters.


Our product is like banking services: Your competitors probably use the same bank as you, but the bank provides a level playing field.

Exclusivity will probably be expected if:

  • Your offering involves work that would be considered strategically important to the company
  • You’re doing creative/original work designed to set the company apart from the competition
  • Your work together includes gaining access to confidential information regarding your customer’s business

In these cases, your prospect will probably expect you to sign a non-disclosure agreement — and they may expect you to sign a non-compete agreement as well.

You DO have rights, here, even as a small business doing business with a large organization. Don’t sign anything you’re not comfortable with, or that will limit your ability to do business in the future. Ask to negotiate the terms that don’t work for you. The worst they can say is “no.”

As you gain experience, you’ll know what is typical for your industry and your customer’s industry. If you suspect that the prospect may want your offering be exclusive to them, and you’re already working with one of their competitors, address this at the first meeting. Wasting the prospect’s time when you know you won’t be able to honor the terms like this is a fast way to burn a bridge.

Here’s my final thought on this subject: Always be open and honest. If you do currently work with your prospect’s competitor, answer honestly if they ask you about it. But never, ever show them confidential or otherwise private information about what their competitors are doing with your product or service. If the information is public (e.g. it’s on their website), it’s fair game unless your contract states otherwise — but sharing anything that’s not public just will make your prospect wonder about your discretion.

You said I don’t have to have an exact offer prepared yet — but what if they ask me about prices?

If you’re worried about being put on the spot about your prices, let me reassure you. Enterprise prospects know that the cost of your product or services is likely made up of a number of factors — factors which you are just now learning in your first meeting with them — and an on-the-spot quote is an unreasonable request.

Of course, this might not be the case if you’re selling a highly commoditized product such as bathroom supplies. But my bet is even if you’re selling toilet rolls, your enterprise customer understands you’ll have to crunch some numbers after your first meeting.

That said, your prospect may ask for a general or average cost for the purpose of figuring out how to prepare the budget on their end. To answer this perfectly understandable request, it’s okay to give them a ballpark figure.

Here are two ways you might word this:

1. “In the ballpark of $10,000.”

2. “For projects of similar size and scope, this typically falls into the $8,000 - $12,000 range.”

You’ve Mastered the Meeting. Now What?

At this point in our Small Fish, Big Fish series, you’ve made it through the first meeting with your prospect from a large or enterprise company. Congratulations! Not every small business makes it this far.

The rest of the articles in this series are going to focus on the ins and outs of the actual sale. So stay tuned!

Read the next article in the Small Fish, Big Fish series: Understanding Reporting Lines and How to Work With Them

Read past articles in the Small Fish, Big Fish series:

Get the whole series as a free e-book, Small Fish, Big Fish: A small-business guide to selling to large and enterprise companies.