Top Qualifying and Technical Discovery Questions to Engage in a Cloud Discussion

You’ve landed a slot on your customer’s agenda to discuss the cloud and how Microsoft 365 provides a quick and easy entry point. Now what?

How you handle the next steps will be pivotal in determining how successful you are in moving to the next stage and, ultimately, towards a cloud roadmap for your customer.

The most vital tactic during this phase is to go to your meeting with the right questions, and with the right people from your team to ask those questions and manage follow-up. The information you gather during the discussion is the first step on the path to a cloud roadmap. If you’re concerned that you don’t have the in-house expertise to handle technical aspects that might arise, don’t be afraid to invite outside experts to the conversation. AppSmart can help with that if you need support.

We’ve compiled a list of questions that you can bring to the discussion. They cover a number of topics, including solutions your customer already has, their cloud readiness, and a number of technical discovery questions.

Before your meeting, remember these important tips:

  • Ask open-ended questions—Avoid yes/no questions that yield little usable information. Your questions should be framed so that they require your customer to provide the details you will need in your follow-up response.
  • Be prepared to handle objections—You’ll find a list of top objections, and helpful responses in our blog post Conversation Starter—Getting Your Customers to the Cloud.

The best approach to getting the information you need from your customer is to split your questions into two phases—qualifying questions and technical discovery questions.

14 Qualifying Questions

Ask these questions to learn more about your customer’s current business and technology challenges. You’ll get detailed information about solutions they already have, and will be able to assess their cloud readiness.

1. What current collaboration and communications challenges are you currently facing within your company?


  • What impacts are those challenges having on your company?

2. Describe any challenges that you experience related to Microsoft 365 support

3. Which office productivity and collaboration tools are your employees currently using?


  • If Microsoft, which product are you using?
  • What is your licensing situation?
  • Do you have direct agreement with Microsoft, or through a CSP, or do you have an Enterprise Agreement with Microsoft?

4. How many different office solution vendors do you need to manage and pay every month?


  • If you could streamline your invoice management and payment processing efforts, what impact would that have on your organization?

5. Do you have any on-premises servers?


  • What type?
  • Who manages them?
  • How much data do you have stored on them?

6. What are you using for Email today?


  • How are you procuring your mail licenses today?
  • When was the last time you looked at your mail licenses and asked the following questions:
    • Do you have the right number of licenses?
    • Are you leveraging all the features that are included in your subscription?

7. What advanced email capabilities, like archiving, data loss prevention (DLP), and encryption, do you have in place?

8. How many mailboxes or users do you have?

9. Microsoft and Google don’t back up your email, so if you delete emails, they can’t be recovered. Do you use an email backup service?


  • If yes, which one?

10. Where are data files stored in your organization?


  • How do you back them up?

11. What backup system are you using to protect company records and data?

12. What other cloud software are you using—for example, DocuSign, Salesforce, Adobe, or Quickbooks Online?


  • You can use connectors to link Microsoft 365 with any of your other software—for example, email can be linked to Salesforce. Do you use connectors to link applications?
  • If yes, which ones?

13. What is your cloud strategy?


  • Are you planning on migrating to a cloud hoster like AWS (Amazon Web Services) or Microsoft Azure to eliminate servers altogether?

14. As you consider updating your office technology, do you have specific quantitative or qualitative results in mind?


  • What are they?

10 Technical Discovery Questions

In this phase, you dive into more technical topics that are critical to company operations and the overall IT health of the company. The information you gather will help you make technology recommendations that align with your customer’s business challenges and requirements, and to demonstrate that you have the knowledge to support them in meeting their objectives.

Ask these questions to dive into more technical topics that are critical to the overall IT health of the company. The information you gather will help you make technology recommendations that align with your customer’s business challenges and requirements.

1. What service level agreements do you have with your customers?


  • What are they?

2. What are the financial impacts to your company if you don’t meet SLAs?

3. What disaster recovery or business continuity plan do you have in place?

4. What is the maximum downtime your company can afford before facing bankruptcy?

5. How do you routinely test and measure your business continuity strategy to ensure that you meet compliance requirements?

6. What strategies or systems do you have in place to restore any or all of your critical business data if it’s lost, stolen, or the subject of ransomware?

7. How do you use, retain, and store PCI and HIPAA personal health information to ensure compliance?

8. What security awareness and phishing training do you have in place today?

9. What cybersecurity insurance policy do you have in place today, if at all?


  • What security measures does your insurance company require you to have? (e..g, Multi-factor authentication, data loss prevention)

10. When was the last time an annual security audit or compliance assessment was completed?


  • What were the findings?

Enjoy this read? Make sure you check out our guide that will provide you with a blueprint on how to start or scale your cloud strategy using Microsoft 365. Access the guide 'Why Microsoft 365 Should Be Part of Your Cloud Strategy—And Best Practices to Get You Started' today.