Getting Past The First Meeting

Hey folks 👋

Today I’m drilling down on first meetings. Specifically, from an outbound sales and business development perspective.

Why? Despite a ton of enthusiasm shared between both parties in many first meetings, they notoriously lead nowhere a lot of the time. No sales. No partnerships. Nada.

This adds up to a significant waste of time. Which, is super precious as an early-stage founder.

Increasing the rate at which you convert first meeting prospects into customers or partners will massively help compound your growth over the long term. It’s an important part of keeping a sales flywheel well oiled. Particularly for B2B startups.

That’s why I have paid close attention to this metric over the years. And, have devised strategies to constantly improve it over that time. I’ll break this down into five actionable takeaways next.

1. Filter Targets With Laser Precision

Absolutely vital to improving the conversion rate of your first meetings is to heavily filter and qualify who you are meeting in the first place.

To do this, be specific and nail your ideal customer profile. Which is:

If you calibrate your ideal customer profile too broadly, you risk wasting a ton of time pursuing prospects that won’t convert, or, maybe they will, but the relationship won’t be optimally mutually valuable. This has a huge compounding effect since your ROI from each relationship is used to build and acquire the next.

Be ruthless, and continually adjust your ideal customer profile as you build and scale your product.

2. Frictionless Discovery

Here’s a common sales misconception: ‘meetings mean momentum’ and ‘calls create closers’.

Why? Real-time face-to-face communication often *feels* like it has a higher chance of converting a target customer into a paying customer.

But, it’s often unsubstantiated without the right foundation in place. That’s partly to do with the perception of establishing social currency, and, partly to do with the satisfaction of delivering the ‘full pitch’.

What is dangerous about this belief system is that it calibrates outbound sales efforts to push for meetings, not sales.

In reality, a meeting is actually a friction point to closing a sale. So, erasing it from your sales process altogether is the ideal objective. The most productive first meeting is not to have one.

For B2B SaaS startups selling low ticket packages that do not require much internal dialogue to drive a purchasing decision, this is entirely possible. You should be able to ‘close’ them on your sales assets alone—website, videos, social presence, etc.

In order to achieve that, having a website or other online resource that clearly communicates product benefits is critical. Like, crystal clear. 

This also applies to B2B SaaS startups selling complex or high ticket packages, since it will make first meetings way more productive.

Common mistakes I see—that go against clarity—are the use of jargon, grandiose claims, complicated language, or just plain information overload. All this does is confuse prospects.

Keep it straightforward, simple.

As a guide, imagine you are explaining your solution to John Tuld, the infamous CEO antagonist in 2011’s Margin Call. 👇

When faced with a situation that was highly complex ‘under the hood’—one in which he had to grasp the fundamentals of urgently—John Tudd said to an associate:

Picture John opening your website. He needs to understand why your service will benefit him in three seconds. Flat.

This is the bar in a time-constrained world, where sales prospects are super busy and have a million distractions pulling them in other directions.

Short one-sentence pitches that clearly and measurably deliver a result work well.

✅ Good: Increase your organic search traffic by 43% in 90 days. 

❌ Not so good: The leading peer-to-peer digital marketing platform, utilizing AI to drive next-generation SEO optimization that finally meets your incremental uplift goals.

How to tell if your sales messaging isn’t crystal clear?

Prospects do not ‘get’ the product until you’ve taken them through a real-time walk-explanation via a meeting. This is a powerful signal that your website collateral needs tweaking.

If you are in this position, good-fit prospective customers drop away because they didn’t identify a perceived solution match for their problem.

And, bad-match sales leads request meetings because they *think* your solution could help them, but in reality, it can’t. This yields lost sales opportunities and a ton of wasted time.

If they are ‘sold’ on your sales assets alone, you can close them through self-serve functionality or over async communication like email or chat applications (more on that next).

3. Zero Barriers

I generally advocate ‘zero barrier’ customer onboarding process as an idealistic goal, so that it drives simplicity in approach. Even if it’s not possible in reality.

For example, what is the fastest and most seamless way to get the product in the hands of a paying customer?

Things like admin (forms, contracts, documents), payments, end-user education, process compatibility, and technical integrations are barriers.

For example, instead of pushing for a meeting, the ability for prospects to take action and onboard themselves as a customer via self-serve functionality on your website is way more productive.

No need for a call first, they can just open an account and get up and running straight away. This is particularly relevant for low-ticket purchasing decisions.

At my first B2B startup, an audience exchange tool for web publishers, we made this process seamless after hitting product-market-fit:

1. Enter email (create account, agree to terms)

2. Grab HTML code (auto-generated) 

3. Customize widget (no code)

4. Install on your website (copy and paste into HTML)

5. Instant results (real-time traffic uplift reported in dashboard)

If you are at an MVP or v1 stage and consider self-serve onboarding unrealistic, you may be able to conduct this async over email or chat applications.

I launched my first B2B startup purely over email correspondence, which proved to be very time-effective. This involved coordinating around 20 website owners to install and live our solution on the same day.

For B2B startups that sell high ticket, bespoke, or complex packages at an enterprise level, there are naturally more barriers and moving parts. Plus, longer sales cycles with numerous stakeholders, etc.

A common compromise for a self-service approach is website lead collection—'request a call’.

But, that alone is a wasted opportunity. If a prospect has entered their contact details, they are probably prepared to go further!

Take them as far into the sales process as possible. This will make your first meeting more productive. And, you will have ideally removed some conversion barriers along the way, increasing the likelihood of follow on dialogue and an eventual sale.

You want them to become emotionally invested as soon as possible. Try to trigger a sensation of value creation and ‘sunk cost’ into your onboarding process. Collect nuanced details or provide a tool or resource. Let them play around, or, calibrate something which can be shared internally.

4. Simple Next Step

You’ve hit the end of your first meeting. What next?

Next steps! Simple, actionable. The nature of this will depend on where they are in your sales cycle and the complexity of your offering.

For simplicity, this can be broken down into three segments:

• Discovery. Discovering the benefits of your offering.

• Evaluation. Evaluating if it makes commercial sense.

• Action. Adopting your solution.

Whatever segment your prospect is in, it’s generally helpful to walk them through the next steps within that segment. Where appropriate, an overview of all three.

This should be done with an emphasis on one simple, not scary immediate next step. This leads to the next step, and so on. Progressive activation.

Next steps can be reconfirmed via email afterward, which puts actionable information at your prospect’s fingertips.

And, depending upon what you are selling, this may also involve dissecting into numerous touchpoints at the same company—tech, finance, marketing, business development, legal, product departments, etc.

5. Intent Segmentation

Even when you have nailed all of the above perfectly, sometimes prospects just don’t want to commit to using your product *right there and then* after the first or subsequent meetings.

There’s a basket of reasons why—conflicting internal politics, priorities, or business logic inertia to go up against.

That’s fine—an optimum sales and marketing operation drives relationships, not transactions.

In effect, you can increase the conversion rate of your first meetings by thinking longer-term, keeping prospects engaged, and closing them later.

This means segmenting post-first meeting leads into at least two distinct groups that you service differently:

1. Action takers. They accelerate down your sales funnel quickly and become customers right away.

2. Deliberators. They lurk around in the second phase of your sales funnel—interest—(after awareness and discovery) until they are ready to take action.

The deliberator group is often suboptimally serviced. At worst, completely ignored. This can be a competitive edge. Keep them engaged. Build trust and confidence.

At a minimum, through a newsletter. Even better, through providing value in other ways. Tools, reports, introductions, event invitations.

As an example, at my last B2B startup, we provided a free analytics tool. This was a fantastic touchpoint to drive continued dialogue with our deliberator prospects. Eventually, driving many to convert into revenue-generating customers months and even years later.

Another example is a company I previously covered in this newsletter, Cyrex, a cybersecurity firm focused on the video game industry. They experiment with this really well by regularly running hacking webinars that attract hundreds of game developers in various stages of their sales funnel.

The net result is fewer ‘wasted’ first meetings.

To receive more newsletters like this, subscribe below.👇