10 discovery questions MSPs should be asking prospects and clients

To increase your chances of closing a deal, you need to understand the customer and their specific needs. Why might they be seeking help from a managed services provider? What problems are they trying to solve? What challenges are they facing? How can your IT services help overcome these challenges?

While no prospect wants to be ambushed with non-stop questions, well-crafted inquiries can make all the difference when it comes to winning new business. If you have prospects or clients willing to engage in a dialogue with you, use these key questions to gain a better understanding of their needs and accurately prescribe your services.

For managed IT services:

1. What are you currently doing for IT in your business?

First off, you need to get a general sense or understanding of your prospects’ current IT environment. Do they have an in-house IT department? Are they already working with another provider? Knowing these elements will help you determine which angle you need to take with the rest of the conversation and the sale as a whole.

2. What are your goals for the next six months (business or IT-related)?

Asking this question is a great way to gain insight into the prospect’s business by looking at the future instead of the past. In fact, the future is exactly what you need to focus on in order to recommend services for their business and forecast potential issues they may face. And, knowing where they want to be in six-to-twelve months can help you position your services as a way to aid and support their business goals.

3. What are some of the roadblocks you’ve been facing with achieving your goals?

A question like this can help you uncover some of the pain points the client or prospect has been experiencing—whether directly related to IT or not.

Let’s say, for example, that the prospect’s company is growing, but they tell you that they’re having trouble retaining quality talent. How does this help you? Well, you now know that a remote help desk solution could be positioned as an alternative to building and/or staffing an in-house team. In this scenario, you’ve uncovered a challenge and are proposing a specific service that can act as a solution.

4. What’s been your approach to solving these problems so far?

In other words, how have they attempted to solve the problem, or do they already have a solution in place to address it? If they haven’t tried anything, that’s your in. If they have, ask follow-up questions to determine what they like or dislike about their current solution, as well as what factors would drive them to make a change.

5. Do you have a budget set aside to implement new solutions?

While talking about budget may seem a bit forward, asking this question can help you determine the level of financial commitment the prospect has to solving their problems. Equally, it will help you gauge whether the services you are offering will fit within their budget. If they can’t afford your services, knowing this beforehand can save you a lot of time and effort in the long-run.

6. What does a successful solution look like to you?

Do they define success by saving time or money? Are they hoping to rid their staff of the day-to-day burden of IT? Their answer to this question will help you pinpoint their vision of success. With this information, you can ensure you’re focusing on the right value proposition in your conversations to make that happen.

For managed security services:

7. What type(s) of data are you using and/or creating on a daily basis?

Similar to question number one, this question can help you better understand their general IT environment, but as it relates to data creation and protection.

How do they depend on data for day-to-day operations? How would they be impacted if they couldn’t access their essential data? What’s the level of risk they’re willing to accept? Additionally, this can help you uncover any major regulations (HIPAA compliance, PCI, etc.) they need to comply with.

8. Do any of your employees bring personal devices to work?

Do they recognize the security risk of the bring your own device (BYOD) trend in the modern workplace? If their answer is no, for example, it presents a perfect opportunity for you to propose a mobile device management (MDM) or other solution that protects endpoints.

9. What security risks are you most concerned about?

The answer to this question can help you determine exactly what your client or prospect is looking for protection against. Have they been hit with malware or ransomware before? Do they believe their employees need better security training? Are they worried about becoming the next major breach headline? Listen to their concerns, and then provide an ideal solution.

10. Are you equipped to handle all of these potential issues and risks on your own?

This is the zinger, and more of a hypothetical question than discovery question. Asking your client or prospect this can really put into perspective their need for enhanced IT security.