3 Questions Startup Founders Should Be Asking Clients to Secure Sales, According to StartupSales’ Adam Springer

Landing a B2B client is an exciting moment for an early-stage startup.  But sometimes founders make the mistake of not asking the right questions and pushing too hard during the sales process, which can derail the deal. Labs mentor Adam Springer, founder of StartupSales, held a session to discuss the three questions all founders should be asking during the sales process to secure deals without coming on too strong.

Question #1: Why us?

One of the most fundamental questions founders should be asking inbound contacts, meaning potential clients who reached out to you, is why they’re interested in your product. “You don’t want to make assumptions. You want to understand what problem the customer is having and let them speak about it,” Springer says.  Asking potential clients why they’re interested in your product will allow you to tailor your sales pitch to their specific pain points later in the sales process, but be careful not to be too aggressive. “It's important to be curious and keep your ears open. Even though you're trying to sell your product, your job isn’t to sell them at this time. Your job is to investigate and consult,” Springer says. “At this stage, you also want to make sure that your product is the right fit for them.”

For potential clients that you’re reaching out to, also known as outbound contacts, your approach should be very similar. For example, if you have a cloud-service startup, “you could approach the CTO of the company and say, you’re in charge of this section of infrastructure for your company.  How are you currently handling it?” Springer says. “When you approach clients from the perspective of doing market research, it really opens the door to asking insightful questions.”

It’s important to know exactly which businesses you’re going to be reaching out to early on. “Part of that is defining your ideal client profile. If you know who you're going after from the beginning, then you can start asking the right things,” Springer says. But be sure to not only target your ideal client, but also the right person within the company.  “Let’s say you’re looking for the head of marketing for a tech company. That's really vague. Sometimes the structures of companies vary widely, so you’ll want to know exactly who you need to be contacting and what they're in charge of.”

Learn more about ideal customer creation and inbound/outbound contact.

Question #2: Are you using our competition’s product?

It may feel a little awkward  to ask an inbound contact that question, but figuring out if they’re using a competing product can give you a huge advantage when it comes time to negotiate. “A good question to ask is why they’re leaving them. What is it that they don't like? You want to make sure that you don't have the same negatives as your competition does. Otherwise, they're going to adopt your product and churn, and that's really bad for you,” Springer says.

With outbound contacts, you’ll want to start the conversation by speaking about the product they’re currently using. For example, if you have a blogging software startup, you can approach the client by praising the content on their site. Then, follow that up by asking how they publish their content. “That way, you make it all about them. It's a very personal and curated conversation. They know it’s not a canned, copy and pasted message,” Springer says. If they mention any pain points with the product they’re currently using, take that as an opportunity to introduce your solution, but don’t force the conversation. “If they take it to the sales side by talking about pain points, then it’s fine to transition the conversation. But let them take it there, not you,” Springer says. “You should always go into these conversations with the purpose of investigating and learning.”

Question #3: What’s your timeline?

For both inbound and outbound contacts, being aware of timelines is important so that you know not to try to sell your product at the wrong moment. “One way to find out their timeline is by asking them what stage they’re currently in. Are they just looking to see what options are out there or are they ready to test different products?” Springer says.

Once they let you know what their timeline is, you can begin to plan accordingly. “Let's say your target tells you they're with your competition and they want to adopt a new product. You can ask them when their contract is over with them,” Springer says. “Now you know exactly what your timeframe is to go through all the relevant sales processes with them.”

Regardless of where you are in the sales process, and whether your target is inbound or outbound, you always want to approach every conversation with open ears. “Be a good listener. Try to really understand what the client is saying,” Springer says. “And don't look for what to say next, let the conversation flow naturally.”

Learn more about sales for early-stage startups.

This post is based on content from a WeWork Labs programming session.

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