Inspire the next step and win more deals

Show people how to use your product, get the technical win, grow faster

I met a Founder in the consumer space who created a marketplace that allowed people to order bespoke, custom products from artisans and creators who were among the best in the world at their craft. An example might be someone wanting a custom wooden table and willing to pay a significant amount for a one-of-a-kind piece. When the artisan asked the prospective customer what they wanted, the customer had no idea where to start. Eventually, the customer would bring inspirations from common higher end brands like Restoration Hardware, Pottery Barn, etc. 

What ended up happening? People would receive a handmade version of what they had envisioned for their homes, which delighted the customer but likely made the artisan cringe, knowing what could have been possible. This highlights a disconnect between the customer's vision and the true value of handmade goods.

What does this have to do with enterprise software? I see Founders and sellers asking customers to lead the discussion and it’s a backward way to run any customer engagement. If there’s only one takeaway from this post, let it be this: stop asking your customer, “So, what do you want to do with our product during this POC?” or “What do you think is a good next step?”

If you don’t inspire and guide your prospect in how they should engage with your business, expect scenarios and responses like but certainly not limited to:

• “Let me get back to you once I talk to my team. Can you send the recording?”
  (They didn’t talk to their team, and they probably forgot the recording existed.)

• “Hey, we really enjoyed the conversation, but we decided to evaluate [Competitor] because they have features X, Y, and Z.”
  (You’re frustrated because you have those features too, but the prospect didn’t get it. Now you’re spending time convincing them the competitor isn’t as good, and you never hear back.) You must demonstrate and inspire what’s possible at every step of the customer engagement process—from your documentation to your website to your sales approach.

  • Reminder: you must be objective. Do you have the features, and do you offer true differentiation compared to alternatives? If not, is this a “product issue” or a “sales issue”? It’s likely a combination of both, but good discovery will help you understand your true limitations in the deal.

So, where do you start? Begin by reviewing how you conduct discovery and pitch your product (avoid asking for pain, instead walk them into it). By the end of your first 1-2 calls, do you fully understand your customer’s workflow?

Start with the workflow

When it comes to workflow, the most successful teams present a diagram or workflow using tools like Excalidraw or FigJam to visually show the customer where their company fits into the value chain. This approach also helps uncover challenges in certain areas. For example:

Rather than relying on vague success criteria, guide your customers on how they should be using and testing the product. Encourage them to focus on your differentiators and unique features. Don’t assume they will immediately understand or appreciate these on their own.

For instance:

“We think your focus on ease of use is great, but let’s define this based on what you’ve shared with me so far. Specifically, what makes this easy?” “Great, so customers like ours use us because we automate that entire process end-to-end, whereas you're doing it manually. Let’s make sure you try that and compare it to how you’re doing it today.”

This approach helps you get more specific about their success criteria and highlights how your product stands out as a vendor.

Lastly, there are three key steps to earn a POC, win a POC, and ultimately secure a customer:

1. Deliver what people expect and want – This starts with strong positioning and a strong pitch. How often are people seeking clarification on what you do and why? 

2. Get the technical win – Prove the product’s value and demonstrate true differentiation (technical wins, win deals).

3. Sell roadmap – People aren’t just buying what you offer today; they need to be inspired by what’s possible and what they can expect from you as a long-term partner, so sell your roadmap.

Remember, people buy from people!