7 Essential Questions to Ask Yourself Before Calling a Sales Prospect

As salespeople, we‘ve all been there. You have a list of prospects to call, a quota to hit, and the clock is ticking. It‘s tempting to just pick up the phone and wing it, hoping that your natural charm and quick thinking will be enough to carry the day.

But according to John Smith, VP of Sales at Vitally.io, that‘s a recipe for disaster. "Too many reps waste time chasing prospects who were never a good fit in the first place," says Smith. "They show up to calls unprepared, missing key information and unable to address the buyer‘s needs. As a result, they struggle to build pipeline and close deals."

The antidote, according to Smith, is rigorous pre-call preparation, starting with determining if a prospect is even worth pursuing. "Salespeople need to qualify their prospects before investing time in a conversation. That means doing your research and asking tough questions about whether there‘s a mutual fit."

To help salespeople make that determination, Smith recommends asking themselves these seven essential questions before calling a new prospect:

1. What do I know about this company and industry?

It may sound obvious, but you‘d be shocked how many reps fail to conduct basic research on a prospect‘s company and industry before reaching out. According to LinkedIn‘s State of Sales Report 2021, 88% of B2B buyers expect salespeople to be knowledgeable about their company and industry. Fail to demonstrate that knowledge and you‘re fighting an uphill battle from the start.

Before picking up the phone, take 10-15 minutes to scour the company‘s website, press releases, social media, and sites like Crunchbase. Look for information on:

• What products or services they sell
• Who their target customers are
• How they position themselves in the market
• What their competitive differentiators are
• Any recent funding, expansions, or leadership changes
• Key metrics like revenue, growth rate, and number of employees

But don‘t stop there. Go a level deeper and research their industry as a whole. Set up Google Alerts for relevant industry keywords and scan trade publications. Identify emerging trends, market forces, and common challenges companies in this space face. Develop a point of view on the industry that allows you to speak from a place of credibility and authority.

For example, say you sell supply chain management software and your prospect is a logistics manager in the automotive industry. In your pre-call research, you might uncover:

• The company recently opened a new warehouse to expand its distribution capabilities
• They emphasize their use of automation and robotics as a key differentiator
• The industry as a whole is grappling with chip shortages and port congestion
• Many auto OEMs are exploring ways to improve supply chain visibility

Armed with those insights, you can tailor your outreach to highlight how your software helps automotive companies gain real-time visibility into their supply chain, automate manual processes, and mitigate disruption risks. You‘ll immediately differentiate yourself from other vendors who show up spewing generic pitches.

2. Who is the person I‘m calling and what is their role?

Another critical step in pre-call preparation is researching your specific point of contact. You need to understand who this person is, what their job entails, and how they fit into the broader organization.

Start by looking up their LinkedIn profile and any other online footprint. Pay attention to:

• Their exact job title and how long they‘ve held that role
• What companies they worked at previously and what they did there
• Their educational background and any certifications
• What groups or interests they list on their profile
• Any articles, posts or comments that give a sense of their perspective

If you have Sales Navigator, use the tool to map out their reporting structure and identify other key stakeholders. Understanding who they report to, who reports to them, and who else is on their team will give you valuable context for the conversation.

All of this research allows you to put yourself in the buyer‘s shoes and anticipate what‘s likely to resonate with them. For example, a Director of HR will have very different priorities and pain points than a Front-End Engineer or a Chief Financial Officer.

A CFO will care about high-level business outcomes like cost savings, revenue growth, and mitigating risk. An engineer will geek out over technical specs and integrations. An HR leader will want to know how your solution impacts employee experience and fits into their existing tech stack.

The onus is on YOU to understand what matters to each buyer persona and tailor your approach accordingly.

3. What does their typical buying process look like?

Another crucial factor to assess before engaging a new prospect is what their buying journey typically looks like.

According to Gartner, the typical B2B buying group for a complex solution involves 6 to 10 decision makers‚ each armed with four or five pieces of information they‘ve gathered independently. That means you‘re likely not dealing with a single buyer but a web of stakeholders, influencers, and gatekeepers – each with their own priorities and objections.

Before you pick up the phone, try to piece together the lay of the land. Ask yourself:

• Who are the key decision makers and what are their roles?
• How does this company typically evaluate and purchase solutions?
• What are their budget cycles and legal/procurement processes?
• How long do deals like this typically take to close?

Some of this information you may be able to uncover through online research – looking at past press releases about new vendor partnerships or analyzing job postings for clues about their tech stack and purchasing needs.

You should also tap into your internal resources like account executives, sales engineers, and customer success managers who may have worked with this account or similar companies in the past. Ask them about the buying process, key players, and relevant use cases.

If you don‘t have perfect information, that‘s okay. You can use your initial conversation to fill in the blanks, asking questions like:

• "In the past, how has your team decided to move forward with a project like this?"
• "Aside from yourself, who else would typically be involved in evaluating a solution in this area?"
• "What‘s your typical purchasing process and timeline for bringing on a new tool?"

Just be sure you have a basic understanding of what you‘re walking into so you can set realistic expectations and tailor your messaging appropriately. If you know they just started a new fiscal year, emphasize the ROI you can deliver this quarter. If you know their buying process involves security and legal review, come armed with relevant docs and certifications.

4. What are their potential pain points and needs?

This is perhaps the most important piece of pre-call preparation. If you can‘t articulate how your product or service will tangibly benefit the buyer and solve a real pain point – you have no business calling them. Period.

Before reaching out, take a step back and consider what challenges a person in this role at this type of company is likely facing that your solution can help with. What are the biggest thorns in their side or obstacles to hitting their goals?

If you sell marketing automation software, a VP of Demand Gen is likely struggling with:

• Generating enough qualified leads for sales
• Personalizing their outreach at scale
• Measuring campaign attribution and ROI
• Optimizing their tech stack and processes

If you provide IT service management, a Director of IT Ops likely loses sleep over:

• Resolving incidents and outages quickly
• Maintaining security and compliance
• Supporting remote and hybrid workers
• Implementing automation and self-service

Do your homework to understand what matters most to each persona you sell to. Look at your past deals won and lost for clues. Read industry analyst reports, surveys, and forum discussions to understand top priorities. Ask your customers what they care about most and what triggered them to buy.

The deeper you understand their world, the more powerfully you can connect your solution to their needs. For example, you can share a customer story about how you helped a similar company reduce average handle time for IT tickets by 50%. Or cite a stat about how much revenue the typical B2B company loses due to poor lead follow-up.

Doing your research allows you to speak to the insights and outcomes your buyers care about and positions you as an expert who can help them. Which brings us to our next question…

5. What is my objective for this call?

This may seem like Sales 101, but you‘d be amazed how many reps pick up the phone without a clear goal in mind. No two sales calls are the same – your objective should be dictated by the context of the buyer and where they are in their journey.

If you‘re cold calling a prospect who‘s never heard of your company, your goal might simply be to introduce yourself, pique their interest, and book a discovery meeting. Launching into a full-blown pitch or trying to close the deal on the first touch is premature and off-putting.

On the other hand, if you‘re calling an inbound lead who‘s already watched a demo and downloaded pricing info, they‘re likely much further along in their buying process. Your objective is to understand what‘s driving their urgency, assess where your solution fits into their priorities, and advance to a proposal or negotiation.

Regardless of the scenario, it‘s crucial to align your desired outcome with the buyer‘s readiness. Hubspot‘s 2021 Sales Strategy Survey found that salespeople make on average 8 touches with prospects before closing a deal. Very rarely does a deal happen in one conversation.

Before each touchpoint, get clear on what information you need to gather, what you want to communicate, and what commitment you‘re asking for. Have a list of discovery questions prepared, a loose agenda to guide the conversation, and clear next steps you‘ll be driving towards – whether that‘s a follow up call, a stakeholder meeting, or a signed contract.

Just remember to hold those objectives loosely. Selling is about meeting the buyer where they are, not rigidly adhering to your own timeline and process. Be prepared to adapt your approach based on what you hear.

6. How will I earn the right to ask questions and deliver insights?

Let‘s be real. We live in an age of empowered buyers and infinite information. Your prospects are not sitting around waiting for a sales rep to educate them about their business. They‘ve likely already done a ton of research on their problem and potential solutions. They may even know more about your competitors than you do.

To earn the right to their time and attention, you have to ditch the generic pitch and focus on delivering relevant value. How will you get this specific human to think or consider something they currently aren‘t? What‘s in it for them to explore this conversation?

Before each touchpoint, brainstorm ideas for how you could make the buyer smarter, better prepared to do their job, or armed to achieve their goals. For example:

• Sharing a relevant customer story or case study that highlights outcomes they care about
• Citing a new industry data point or trend they may not have seen
• Offering a fresh perspective or counterintuitive insight about their challenge
• Asking a thought-provoking question that gets them to examine the status quo
• Connecting the dots between a recent trigger event and your solution
• Name dropping a competitor or peer company who‘s seen success with your offering

The key is to tailor your approach to each individual buyer and what‘s likely to resonate with them. An IT director and CMO will respond to very different use cases, proof points and value propositions.

Do your homework and put yourself in their shoes. Role play how you‘ll respond to likely objections and pivots. Have a few different angles and conversation starters up your sleeve so you‘re ready to engage them, wherever the dialogue goes.

Remember, your goal in each interaction is to leave the buyer a little better off than before. Even if you don‘t close the deal in that moment, you want them to hang up the phone feeling like it was worth their time. That you understand their world and have valuable solutions to offer. Plant enough of those seeds and you‘ll earn the right to keep the conversation going.

7. How will I navigate the inevitable objections?

You could do everything else in this article right and still face pushback from buyers. That‘s just the reality of sales. Humans are naturally resistant to change and primed to see risk in any new purchase.

The key is to prepare for those objections ahead of time so they don‘t catch you flat-footed. Before each interaction, make a list of the reasons this buyer is likely to tell you "no." For example:

• They‘re too busy right now and want you to call back next quarter
• They don‘t think they have budget for your solution this year
• They‘re locked into another contract and aren‘t looking to switch
• They don‘t see how the problem you solve is a big enough priority
• They had a bad experience with a similar product in the past

For each likely objection, brainstorm a few ways you could reframe the conversation and unpack their concern. Maybe you foreshadow the objection proactively, so it‘s less powerful when they bring it up. Maybe you pivot and get them talking about the cost of not solving the problem. Maybe you share a customer example that challenges their assumptions.

The point isn‘t to strong-arm buyers into saying yes. It‘s to create an opening for a richer dialogue so you can better understand their hesitations. Objections are often opportunities in disguise – a chance to go deeper and position your solution as uniquely valuable to their situation.

Of course, sometimes objections are a sign that this deal isn‘t meant to be – at least not right now. In those cases, the best thing you can do is accept it graciously, keep the door open for future conversations, and use it as a learning moment. Feed those insights back into your qualification process so you get better at identifying true fit.

Bringing It All Together

At the end of the day, selling is both an art and a science. Yes, you need to have strong product knowledge, sharp communication skills, and a healthy dose of grit.

But the sellers who truly excel are those who take the time to prepare for each conversation like an athlete trains for a race. They do their homework, get in the buyer‘s headspace, and adapt their approach based on what they hear.

By methodically working through these seven questions before each new prospect interaction, you set yourself up for success. You‘ll weed out poor-fit buyers faster, craft more relevant messaging, and engage buyers in richer dialogues.

It takes more effort than winging it – but that‘s what separates the average reps from the superstars. As Vitally‘s John Smith advises, "Do the hard work to deeply understand your buyers and tailor your sales motion to what they care about most. Your pipeline and commission checks will thank you."

Now if you‘ll excuse me, I have some calls to make.