7 Crucial Questions to Ask Prospects Throughout the Buyer's Journey, According to HubSpot's Former Sales Director

Welcome to "The Pipeline" — a weekly column from HubSpot, featuring actionable advice and insight from real sales leaders.

Sales is an increasingly consultative profession. You could go so far as to say we're in the age of the "Always Be Helping" salesperson. That means reps need to provide prospects with helpful and specific resources as opposed to stuffing irrelevant information down their throats — but you can't get there if you don't understand where your prospect is coming from.

The sales rep-prospect relationship cuts both ways — as your prospects qualify you, you need to qualify them back. You have to be prepared to meet them at every stage of the buyer's journey and frame yourself as a knowledgeable, reliable, trustworthy resource.

That starts with asking the right questions at the right time. Here's a list of some of the most effective ones you can ask and when to ask them.

Awareness and Education Stage

Here, your prospect is realizing they have a problem — but they're struggling to articulate exactly what it is and, in turn, have no sense of how to solve it. This stage is very top-of-funnel, so your marketing team is likely going to handle these leads.

I don't always engage prospects at this stage, but if I do, I use a very light touch.

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1. "What were you looking for help with?"

Your company's CRM should be able to clue you into what piece of content your prospect engaged with or downloaded. You can leverage that information to dig a little deeper. Again, if you go this road, you need to keep it light. Just try to get them talking about their business pain and how the content they converted on relates to it.

2. "Is there anything else I can do to help you out right now?"

Keep this question vague. You want to stay in educational mode during the awareness stage — letting your prospect know that you're there to help and they can ping you whenever they have questions. But be careful here. You want to keep things low-touch, and there's a fine line between helpful and pushy at this point in the journey.

Consideration and Evaluation Stage

When prospects reach the consideration stage, they have a better understanding of their pain points. If I've connected with them during the awareness and education stage, then I've already started to educate them on the best way to solve their problem.

During this stage, they’ll be internally setting budgets and priorities, and it's the best time to get your foot in the door.

3. "Where are you in the budget-setting process? / Are you looking for proposed solutions now? / Is there a timeframe for finding a solution to your problem?"

These are some of the classic BANT questions — and you need to cover every element. A prospect could be an amazing fit on paper, but if they don't have the budget or leadership isn't considering vendors at the moment, you don't want to waste too much time on them.

If you do, you run the risk of souring your relationship with a prospect by pushing them to act before they're ready. I said it at the beginning and I'll say it again — this is the era of the "Always Be Helping" salesperson, and you can't help someone who doesn't want you to.

4. "When do you need to achieve [X] goals by? When do you need to implement the solution by?"

Prospects will often say, "yesterday" to this one, and how you follow up is key. Get specific with them — ask about their process, their goals, and their timeline. What are they hoping to accomplish, and when does that need to happen?

By personalizing the sale like that, you can get your prospect thinking about their purchase in terms of the benefits — how their specific pain points are going to be addressed — as opposed to things like features or price.

Your product becomes valuable to a customer the day they start seeing benefits — not the day they purchase it. Focus on the solution, not the purchase, and your product will begin to seem a lot more attractive.

5. "How can I make this process easy for you?"

In this day and age, you're probably going to have to deal with multiple stakeholders to close a deal. This question lets you get some perspective on where everyone involved is coming from — giving you insight that allows you to get everyone on the same page and see what a collectively agreeable solution for all the decision-makers could look like.

Decision and Purchase Stage

By this point, you’ll know whether your product is a good fit for your prospect and understand what needs to happen for a deal to close.

6. "How are you doing?"

I know what you might be thinking — "How are you doing?" How could such a generic question do anything for you this late in the game? And as you can probably assume, this question isn't some secret, magical, "hiding in plain sight" deal-sealer.

In truth, I use this question to read my prospect's trust in me. Buying a new product isn't traumatic, but there's still risk involved. Sales is, in large part, the art of building trust within a tight window — how a prospect answers this tells me where I stand with them.

If they say, "We’re behind," I ask if there’s anything I can do to speed up the process.

If they say, "We’re on track, I brought it up to my boss and we’re meeting about it on Friday," I know things are going well. If they say, "Well … " or "I don’t know … ", then I know we have a problem.

If they don’t want to tell me, it’s a sign that things aren’t going well and they don’t trust me. If they can’t tell me, it’s usually because they don’t know — and that means that I’m speaking with the wrong person.

7. "Have you gone through a similar purchasing process before?"

This question will give you a sense of how much hand-holding and educating you're going to have to do. If your prospect has gone through a similar process before, great — you can expect to put in less legwork with them when getting to purchase.

If they haven’t, the help you offer your prospect can make or break the sale. I always offer to walk my prospects through a first-time decision-making process — after all, I’ve done this a million times, and I understand how to help get executive-level buy-in.

I will also occasionally offer up a "Godfather" — a senior executive at the company who will check in with a customer once or twice a year to make sure things are going well. I’ve made this offer hundreds of times, and only a few customers have actually taken advantage of it.

The offer itself is often more valuable than the actual resource — prospects feel their risk is reduced if they know help is just a phone call away.

These questions have served me well throughout my career in sales, and I frequently use them to glean important information from my conversations. And while they might not amount to a hypnotic, "sure thing" sequence that always closes, they still can help you build trust and give you valuable perspective to see things through.