Looking to Master Sales Questioning?

In my current remote closing role, I've spent the past 10 months honing my questioning skills during discovery calls.

During this time, I've conducted 310 of these calls, and I can count on one hand the number of people who didn't want to progress to the next phase.

What I find even more interesting is that my second call show rate is 93%, and I achieve a 60% close rate on these second calls.

Want to know my secret?

I put it down to this straightforward 8-part questioning framework I originally got from Hubspot and refined through Cole Gordon's sales training.

I use this on every first call, so let's dive in:

Part 1: Uncover Their Challenges

The first step is to identify the problem because, without a problem, there is no sale. I always start with the same opening question:

On your form, you said (insert problem) was your biggest challenge. Why don’t you start by expanding on that?

I find this question demonstrates that I’ve prepared for the call and gets them talking about the most important thing straight away.

After that, I throw in some background questions to get a feel for their business health to see whether or not we can even help them.

I ask things like:

What marketing are you doing? How is that performing?

What's your monthly sales revenue/average order value/conversion rate etc.?

Once I have a clear picture of their challenge(s) and business stats, I move on to the next step.

Part 2: Explore Their Goals

Next, I want to understand what they want and why.

If prospects don't believe that achieving their goals will lead to a better future, they won't invest in your services.

So, I ask questions like:

Imagine we've been working together for 6 months. What does success look like in terms of monthly revenue?

What target return on ad spend (ROAS) or cost per acquisition (CPA) makes business sense for you?

Out of interest, what's the reason behind these numbers?

Now that I have quantifiable goals and the rationale, I move on.

Part 3: Discuss Their Plans

After hearing their challenges and goals, I want to talk about their plans for solving their issues.

Typically, I find out what options they're considering, for example:

Who else have you contacted about getting some outside help with this?

I follow up with questions like:

What do you like about them? How come you reached out to us?

What specifically are you looking for from an agency partner?

Towards the end of this phase, I also ask them to explain why their current approach isn't an option for them going forward.

I'll say something like:

Why not just keep doing this yourself/stay with your current agency?

I find this helps sidestep the status quo objection later on, which is so common in this space.

Part 4: Determine Their Timelines

Knowing when they want to start is crucial for predicting when deals will close. I ask questions like:

When are you looking to get help with this? Why then? Any other reasons why this is important now?

Now I know when they want to kick off, I proceed to the next phase of questioning, which can be a little trickier to ask.

Part 5: Explore The Consequences of Inaction

This phase can be challenging but essential. The prospect needs to believe that the problem is actually worth solving.

I help them realise this by inquiring about the duration of their problem and its impact:

You mentioned (insert problem) earlier in our call. Out of interest, how long has this been going on?

I see - what impact has that had on you/the business?

Can I ask you a difficult question? I hate asking this, but what happens if you don’t sort this out?

When prospects genuinely need assistance but are hesitant due to fear or uncertainty, questions like these can help reinforce their need for help and motivate them to take action.

Part 6: Delve Into the Implications of Action

Next, I want to find out what solving their challenges and achieving their goals actually means.

People usually have a "why", and if you can align with it, you maximise the chances of winning the client.

Let's say you crack (insert problem) – what's next? What's the long-term vision for the business?

I used to find asking this next question super awkward. Then I realised you can soften it by giving a heads-up and adding context.

I say something like:

Mind if I get a bit personal here?

The reason I'm asking is I'm all about helping people achieve not just business success but also the life they want.

So, how will achieving X change things for you personally?

Now they've told me their ultimate business goal and personal motivations behind all this they'll be more inspired to get help.

Part 7: Discuss Their Budget

Knowing that the prospect can afford your help and is on the same page on the level of investment required is vital.

After all, you can't help them if they can't invest in your solution, so I ask:

How much are you planning on investing in advertising per month to start with? Why that number?

From this, you get an idea if they can afford your agency fees without directly asking them.

If they say a tiny number here, I tell them the entry-level to ensure we don't waste time doing an audit and having another call.

Part 8: Identify Who Has Authority

Before transitioning into the closing part of the call, I find out who else has a say in the decision (if anyone).

I like to get everyone involved as early as possible to avoid hearing - "I need to speak with my partner" at the end.

I get this information by asking:

Who else is involved with you on this?

Is there anybody else who should be on the 2nd call? No husband/wife or business partner?

If they have a spouse or a business partner, I'll also ask:

What do they think about getting some outside help with this? Are they supportive?

If it's appropriate to get other people on the call, I'll also ask for their email addresses so I can invite them to the next call.

And that's it.

To Conclude…

I probe and ask more questions than this, and each call is unique, but these steps are the bread and butter of my questioning on discovery calls.

They help me understand if/how we can help a potential client and eliminate most objections before the second call.

Try this framework out, and let me know how you get on by replying to this email or messaging me on Instagram. Peace ✌️