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I’m sure you know the discovery questions you ask during the first call with a lead can make or break a sale.

You want to uncover a lead’s IT needs and determine how your MSP can help them (if at all).

But I bet you struggle to find the right questions to ask.

That’s why I’ve put together 14 questions every MSP should include in discovery calls with new potential clients.

You’ll learn exactly the discovery questions to ask to help you put together a quality proposal and close the deal.

Sound exciting? Then let’s get into it.

Use These Discovery Questions to Uncover The Client’s IT Challenge(s)

I’m sure one of your biggest goals during a discovery call is to figure out exactly what problems your potential client needs to solve.

And you may start by doing a little research to give you a general idea of the common problems for a business of their size.

For example, here’s a look at the top technology challenges facing U.S. small businesses in 2017:


I’ll admit, that’s a great place to kick things off. But ultimately, it’s the discovery questions you ask that will really uncover your lead’s biggest IT challenges.

Here are a few to get you started:

#1. How has your business changed in the last year?

Even though this question asks nothing specific about technology, a lead’s answer can tell you:

  • If the business is growing or not
  • Whether the person you’re talking to truly knows the business
  • Whether the lead is proactively or reactively seeking help from an MSP

It’s true you might not get a direct explanation of IT issues with this question, but I’m sure your expertise can help you easily determine where problems might exist.

(And if not, it’s completely okay to ask specifically about IT as a follow-up.)

#2. What are your big goals for the next six months? What are some of the roadblocks you’re facing to get there?

Here’s a great way to get business insights by looking at the future instead of the past.

That’s exactly the perspective you need to forecast potential issues the business will face (even if the client’s answer isn’t explicitly IT-focused).

Take this example:

The client says their company is growing, but has trouble retaining quality talent.

Of course, that response doesn’t tell you anything directly about their IT challenges.

But for you, that might mean including a remote help desk solution in your proposal as an alternative to building an in-house team.

Here’s the other benefit of a question like this:

You learn how self-aware the client is about their own problems.

And as I’m sure you know, the more mindful the client is of their own challenges, the further along they are in the buying process.


#3. What’s been your approach to solving IT problems so far?

You don’t want to propose a solution the client tried previously and found ineffective.

Doing so stalls the buying process and damages your authority.

And that’s what makes this discovery question essential early on in the call:

You protect your reputation while also making sure you fully understand the customer’s needs.

#4. What led you to make a change now?

I’m sure you want to know the problem that prompted the lead to research your business and take your call.

Well, that’s exactly what this question will tell you.

And don’t forget this:

You’ll want to make the client’s response to this question the main focus of your proposed solution.

That’s because even if you think they have several other more pressing issues, whatever they say here is the challenge that’s top-of-mind for them.

And that’s the piece you want to be sure you address before anything else.

Here are 4 Discovery Questions to Determine Authority and Budget

While the days of BANT may be behind us, you still need to establish the role of the person you’re speaking with and their budget.

As Pete Caputa – CEO of Databox – explains over on Hubspot: easy access to online research means you’re not likely speaking with a decision-maker in the early stages of the sales cycle.

“In a world where prospects are busy, buying committees are formed to find solutions and lower level non-budget-wielding, non-people-managing employees are sent to search the internet for the latest and greatest goal-achieving, challenge-overcoming solutions.”

With that in mind, try these 4 questions to figure out who you’re speaking with (and if they can afford your services):

#5. What are you currently spending to solve your IT problems?

I’m sure you’ll agree with me here – knowing how much (if anything) your lead currently invests in IT gives you a lot of leverage.

Here’s why:

Let’s say, for example, they currently spend $1,000/month for a solution that isn’t working and they come to you for help.

That means a couple things for you:

  1. They’re ready to make a change.

Clearly they moved on from giving their current provider any chances to help and have moved on to exploring other options.

  1. They’re able to spend more than $1,000/month to make it happen.

If they weren’t, they’d likely just stick with their current provider.

Of course, if they’re not spending anything currently, you’ll need to ask a more direct question…

#6. What’s your budget for this project?

I’ll admit it seems a bit forward, but you often just need to ask outright about budget to make you and the client are even in the same ballpark.

There’s no sense in dragging out the conversation (or worse, putting together a proposal only to have it shot down) if the client can’t afford your services.

#7. What does the budget sign-off process look like?

This is the easiest way to determine whether you’re actually talking to a decision-maker or not.

Of course you’re hoping to be on the phone with the person who signs the contract.

But don’t make the mistake of dismissing someone who’s not – they can be an internal champion for your solution (and that’s just as valuable).

#8. Who else would would love to see this problem get solved ASAP?

A question like this helps you figure out other stakeholders who might need to get involved in the sign-off process.

But it’s also just a good question to understand the reach of the problem in need of solving.

If the client responds with “I think a everyone would love to solve this problem,” then you know it’s a big pain point for the entire business and that your solution would be universally welcomed.

Try Asking These Discovery Questions to Determine The Lead’s Stage in the Buying Process

#9. What happens if you do nothing about the problem?

The answer to this question tells you exactly how serious the customer is about taking on their challenges.

And that should be a big indicator of whether they are truly a viable prospect for your business.

#10. How do you feel about the way we compare with other solutions you’ve explored so far?

You’ll learn a lot about where the lead stands in the buying process with this question, including:

  • Whether they’ve done any research at all yet into competitors.
  • Whether they’ve done any research at all into you.
  • If a current customer referred them.

#11. When do you see yourself actually putting a solution in place?

Much like #9, this question tells you the customer’s timeline. But it actually takes things a step further than that.

If you weren’t able to figure out the buying process in earlier questions, this one should pull back the curtain a bit on stakeholders and next steps to move things further down the pipeline.

Always Close With These 3 Questions

#12. Are you available to meet again on “X day” at “Y time”?

Plenty of salespeople make the mistake of taking a passive approach for solidifying next steps.

If everything on the call points toward them being a viable lead, be assertive about getting time on their calendar within the next few business days.

#13. Who else needs to be on the call to hear more about what we discussed here today?

If you haven’t figured out your stakeholders yet, this question will tell you everyone you need to involve in a buying decision.

Try to get as many of them as possible on the call, with a particular emphasis on the decision-maker.

#14. What do you want to include on the agenda for our next call?

You need to know exactly what the client wants to see from you the next time you connect.

That includes demonstrations, pricing, case studies and any other relevant information that can help ease the buying decision.

And Don’t Forget…

Always wrap up your discovery call with a summary of everything discussed and an agreement on the major points from the client.

For example:

“It was really great learning more about you and your business today. I feel confident there’s great potential for our partnership. Just to recap everything I heard: you’re a 25-person startup looking to grow to 100 people in the next year. You’ve seen 230% growth in the last year and can’t keep up with the IT demands associated with such rapid growth. Your current solution isn’t working, so you’re looking to spend a little more than the $3,000/month you currently spend with X competitor for a more long-term solution. Next steps are to get me on the phone with you and your CTO next Wednesday to talk through our solution. Did I get all that right?”

If you ask the right questions and close with a strong recap like that, you’re bound to see an increase in your conversions (and as a result, more closed deals).

Good luck!