10 questions you need to ask to understand your customers’ pain points

We’ve talked about pain points before. Our blog post on pain points is one of our highest-performing, which tells us you might want to know even more about them.

The interest in this topic is encouraging: if marketers are searching for this term, they are aware pain points are vital to help attract, engage and delight customers.

So we’ve decided to break down the questions you need to be asking (as well as who to ask and when to ask them). These ten questions are for both prospects and customers, and will help you get to the bottom of what makes them tick.

What are the biggest problems facing your customers? Until you answer this question, you cannot fully position yourself as a solution, which means you’re potentially missing out on a whole chunk of business.


But first…

To understand customer pain points, you need to first acknowledge that these problems change over time. What worries your buyer persona before working with you will change in the early days of them becoming customers, and will change again once they’re an established customer. The aim, of course, is to eradicate pain points for your customers, but until that happens: always be asking questions.

If you see customers as ever-evolving, then you’ll be sure to keep up with their pain points along each stage of the buyer’s journey, and change your approach accordingly. This gives them a more personalised experience, and prevents you treating everyone the same. Different products and services, approaches and solutions will suit your customers at different times.

For the sake of this blog post, we are looking at customers in three stages:

  1. Prospects before they become customers

  2. New customers

  3. Long-term customers.

Questions to ask prospects before they become customers


These conversations are likely to happen on your website’s chatbots, enquiry forms, and through social media channels. These are places where people are testing you out, not wanting to commit too much before they decide if you’re a good fit for them.

If you’re lucky, you might also have Connect Calls between prospects and your salespeople, where you can ask questions that dig further into their pain points.

Learn more: Free Guide to Buyer Personas

What to ask

Before becoming customers, conversations with your prospects need to focus on taking their ‘blue-sky thinking’ desires, and condensing them into manageable solutions where you can really ‘wow’ them.

This is also the stage where you’re trying to get rid of tyre-kickers and work out whether this prospect is serious about buying. Asking the right questions now not only helps you create more marketing collateral around these pain points to gain more business in the future, but helps you decipher whether the prospect is a time waster or not.

Are you searching for a solution that will help you do more with the resources you have?

Productivity-based questions will make prospects’ ears prick up. What business doesn’t want to be more productive? To use the ESM Inbound mantra, who doesn’t want to be ‘better, faster, happier’?

Be ready with an answer though. If you’re promising your product or service will deliver increased productivity, make sure you know the best solutions to suggest, considering their budget, time and other determining factors.

What’s the biggest thing holding your business back from growth?

Who doesn’t want to grow? By showing you’re happy to discuss their business plans in these early conversations, it illustrates you’re taking them seriously, and don’t shy away from aspirational thinking.

Once they open up about where their business currently is and where they want it to go, you’ll be able to display your knowledge and expertise in helping them. Show them how your product or service could help them grow.

What does your boss spend most of their time thinking/worrying about?

In early conversations, you aren’t always guaranteed to speak to decision makers. So asking a question on their behalf can tell you two things: 1. What the boss’ primary concerns are, and 2. What people at the company perceive the boss’ primary concerns to be.

Hopefully these are the same thing, but it’s not always the case and can tell you a lot about the internal workings of the company, such as how goals are communicated from the top down. To work out what the boss’ pain points are, try to get them to join the conversation as soon as possible (after all, they’re more likely to be responsible for budget than the person you initially speak to).

What are the problems at your business that come up time and time again in meetings?

Finding out the long-lived, never-ending tasks that your prospects grind away at every day is the key to providing a quick win and proving your worth. If you can identify, then help minimise, these time-consuming, monotonous, irritating pain points, you’ll help them move from teetering on the edge of their decision to work with you, to leaping into your arms to sign up.

Asking these wide, big picture questions at the start is less intimidating and pushy than focusing on the minutiae of how their business operates. This feels less invasive for them, while actually providing you with a really clear picture of where the current problems are. You’re scoping out their needs and learning which goals to prioritise, but without over-promising.

Questions to ask new customers


These questions should increasingly happen via phone calls and video calls: now they’ve become customers, they will want far more direct contact with you – your team may even be visiting them on-site to have face-to-face consultations, training or implementation sessions.

It’s in your best interest to keep communication channels wide open. This is a crucial point in your relationship and a critical time to dig deeper into their pain points, so keep conversations as direct and personal as possible to build trust to share their pain points.

What to ask

Once a prospect has become a customer, the clock starts ticking, counting you down to getting your first 'win' under your belt. It isn't enough that they've merely signed a contract or made a purchase with you; you need to nurture that customer so that you build solid relationships and, ultimately, they become a long-term customer and evangelist of your brand.

The questions you ask at this stage need to revolve around finding quick solutions for their most painful pain points, proving that they made the right decision by choosing you.

What’s your current plan to tackle your problem and how is it working?

You need to know where you’re starting in order to get your customer to where they want to be. Don’t be afraid of asking direct questions like this now; it’s only through honesty – where the customer might have to reveal they either don’t have a plan, or that it isn’t working – that you can make a real start on a solution for them.

As a new customer, it’s important these more specific, tricky conversations start happening – while giving you an idea of typical pain points facing your customers at the start of their journey with you.

What’s your deadline?

To prevent scope creep, to manage expectations and lay down realistic goals, you need to know the time frames your customer is expecting from the start. If these aren’t possible, it’s better they know about it now than further down the line.

It could be that the time scales they want aren’t realistic, but you can still provide them with a faster, better-quality service than they’d get if they used another provider or tried going it alone. Make sure you show the value of your offering, in terms of productivity and time-saving capabilities.

Who is currently responsible for fixing this problem?

Whoever is currently working to fix the main pain point at the company – whether it’s issues with running over budget, loss of productivity, complicated processes, or lack of support – you need to be working closely with this person. They are your way to finding the best solution, and discovering more about what has and hasn’t worked in the past.

If you haven’t worked with this person during the sales process, ask someone to introduce you and plan a one-on-one interview between them and someone on your team. If you can ease this person’s day-to-day life, they will become your biggest support and advocate at the business.

Questions to ask long-term customers


Do you have regular reviews with your customers? Do you visit them or invite them into your offices? Do you pick up the phone for a chat about how things are going? Your oldest customers are the ones to nurture and care for better than anyone – and yet so often they get forgotten when competing with new business.

Make your contact with these customers as personal as possible – ask them what their preferred method of communication is for a catch up and work around them. 

What to ask

Your oldest customers are a goldmine of information – not just because they hold the potential to become evangelists and advocate for your business, but because they have so much experience of working with you that you can probe them for details about their pain points along each step of the way.

By the time your customers have stayed with you for a while, and made multiple purchases from you, you’ll have fixed a lot of pain points for them – otherwise, why would they still be with you? That doesn’t mean, however, that they aren’t looking forward, refocusing their goals for the future. You can help with these, but it can open up a whole new set of pain points.

Are you happy?

The question we should probably all be asking more. So simple, the ‘Are you happy?’ question can open up into a wide array of further questions, but on the surface feels straightforward to answer. 

The answer is win/win for your business: if they say yes, then you’ve got a happy customer who will likely make a great case study or give you a glowing testimonial – from there, you can find out the pain points they still have and work to help solve them. If they answer no, then you can ask more about where you might have dropped the ball or under delivered; this is your chance to show you’re listening and want to delight them.  

Are our solutions still meeting your needs? What could we be doing differently?

Leading on from the happiness question – which might focus on service and relationships – you can move the discussion to more action-based targets. Getting your long-term customers to focus on their future – and to see you in it – is a great way to illustrate their need to continue working with you.

Perhaps you’ve made changes to your offering since they signed up, which they don’t know about and might benefit from? Maybe they’re due an upgrade, training session or demo? This is the chance to showcase that they aren’t outgrowing your offering.

If you weren’t working with us, what might your alternative solutions be?

Phrased in this way, this important question doesn’t sound as blatant as ‘are you considering leaving us?’ which would make many customers wince! Depending on how accurately and quickly they can answer this question, you’ll get an idea of how serious they are about considering an alternative solution.

It’s a useful exercise to get customers to visualise a world without you and your products in it, which they may realise they don’t like the sound of. This question also gives you insight into your competitors – one of the most important factors when asking questions around pain points.

A final tip...

Not only can you be using these questions directly with prospects and customers, but find out from your sales team what the common queries are that come up on calls.

Finding out customer pain points isn’t just the job of the marketing department. To build an accurate, detailed picture of the problems affecting customers at every stage of their journey, it’s up to everyone who engages with customers at your business to contribute their experience – and to probe with meaningful questions.

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