How to ask sales leads smart questions about pain points and goals

Have you ever pitched at a prospect who didn’t buy? Of course, you have. Every salesperson has done pitches, calls and proposals that fall flat. It isn’t fun.

Business pain points questions screen share

Prospects don’t go ahead for a wide number of reasons. But when it comes to what distinguishes top-performers from mid to average sales agents, it often comes down to the questions being asked.

Sales team members who ask smart questions about pain points and goals are often far more effective than those who don’t.

When prospect needs are identified early on, then solutions and services can be tailored accordingly. It’s also the best way to pre-qualify (e.g. ensure a lead is Sales Qualified) a lead.

The top questions to ask leads to discover pain points:

  1. What’s holding the company (or division) back from growth?
  2. What is causing some of your biggest headaches?
  3. What does your boss/CEO obsess about?
  4. What challenges has Covid-19 caused?
  5. What issues are recently discussed across the company?

Why are pain points essential for sales?

Buyers need the following things for them to become customers: Authority (to say yes to a new product/service), a budget, and pain points.

Potential customers have a problem and you are providing the solution. Without pain, there isn’t a need, and when buyers don’t need anything, there isn’t a chance of a sale.

Money won’t be spent unless a business needs something. That’s the same the world over whether an airline is buying a new Boeing aircraft, or an accountant is getting a new monthly software subscription.

In this article, we look at a list of pain point questions you can ask. We’ve covered plenty of others in previous articles, so here are a few you might not have considered.

5 Pain Point Questions to Ask Prospects

Pain points are rarely “nice to have” purchases. Pain points are usually integral to a process, service, or product a company offers.

Or they’re an integral operational or capital expenditure.

In many cases, they can also be a new problem that requires a new solution (e.g thanks to Covid-19, restaurants need hand sanitizer and protective screens or equipment to keep customers and staff safe).

1: What’s holding the company (or division) back from growth?

This is a classic and mission-critical question. Providing what you offer has some relationship with how clients grow, then you are diving straight into a potentially crucial pain point that directly links with what you are selling.

Now more than ever, business pain points are going to fall around customers, winning more customers (revenue/growth), employees, products/services, or capital and cash flow.

Nothing gets a prospect more engaged than talking about what they are doing, and the issues they’re having preventing them from achieving goals.

2: What is causing some of your biggest headaches?

Headaches usually center around one of several core worries: customers, winning more customers (revenue/growth), employees, products/services, or capital and cash flow.

Find out where the headache areas are, and then use this to see how you can solve these problems. Tailor, as best you can, your product/service around providing a solution to one or more of these headaches.

3: What does your boss/CEO obsess about?

For salespeople talking directly to a CEO/Founder, you can ask them directly. Depending on what you are selling, and the size of the prospect, you may be talking to a decision-maker further down the chain.

Does it matter what someone’s boss is worried about?

When it comes to sales, yes it does. Decision-makers may not necessarily have their own budget, so a proposal may need to go further up for approval.

In that case, you need to know whether this is something that will get a senior leader interested, and therefore approve the budget.

Providing it’s a priority or immediate concern to those in positions of authority, then it should make it easier to secure a budget.

4: What challenges has Covid-19 caused?

Covid-19 has caused challenges for companies across a wide range of sectors. Some more than others. Many companies have gone under, and others have had to downsize. Naturally, that’s had a knock-on impact across supply and value chains.

For many companies, that’s where the challenges are coming from. As clients struggle, budgets have shrunk or vanished, and sales pipelines have dried up.

Businesses need help getting sales leads back in the pipeline. For some, this is a golden opportunity to prove value and support the growth of their clients.

In other cases, with companies struggling, new suppliers need to be sourced, which is another unexpected growth area following the impact of Covid-19.

5: What issues are recently discussed across the company?

One of the most obvious right now, in companies across the world — of every size — is because of Covid-19. Whether this has forced a work-from-home (WFH) policy that’s still in place or revenue loss, action needs to be taken.

What’s being discussed depends on the size of a company, of course.

Senior leadership in a large company is going to discuss a different set of issues than managers in a mid-size, or startup. Businesses often have layers of challenges that are directly proportional to their size.

Immediate pain points need quick solutions. If you can solve a problem a prospect is having, within a budget they can afford, then that should help you convert them into a client.

The only way you’re going to know is to talk through various pain points they’re having and problems that need solving.

Identifying pain points is the key to offering tailored solutions. This way, you aren’t simply pitching at hoping for the best. You are actively identifying challenges, then providing a way to solve them.