When interviewing prospective IT support partners, it can be helpful to approach the conversation with some knowledge of IT Management Strategy. If you like, you can read our full article on how to Build an IT Service Management Strategy

When thinking of IT support, most people think of “reactive” support, i.e. password changes, troubleshooting problem printers, et cetera. To keep your systems secure and IT costs low, it is important to think “layered” and “proactive”.

  • Layered Security can make the difference in whether your organization experiences a breach or not. Hackers will look for multiple ways of getting access to your data so that they can sell it or hold it for ransom. For this reason, it’s important to take preventive measures to ensure that your data is securely backed up and protected from every angle. Some examples of elements in a layered security strategy include:
    • Automated Cloud Backup
    • Cloud Monitoring
    • Remote Monitoring and Maintenance of servers, workstations, and other devices
    • Security Awareness Training for staff
  • Proactive support is an invisible but important factor to consider because effective proactive support will reduce your overall support needs, thus reducing both risk and cost. Some examples of proactive support include: 
    • Patching of operating systems and business applications
    • Active monitoring and remediation of antivirus software
    • Active firewall monitoring and maintenance
    • Timely system upgrades to ensure the latest software versions are in use, instead of legacy systems
  • Reactive Support is the type of work that most non-IT folk are familiar with. To measure how effective the reactive support that you receive is, you will want to look at response time and resolution time, as well as customer feedback stats. Some examples of reactive support include:
    • Password changes
    • Workstation setups
    • Making changes to access permissions
    • Dealing with problem printers

With this approach to IT Management Strategy in mind, below we have outlined some questions to ask prospective IT partners when you are deciding who you want to work with. We hope this is helpful to you and your organization!

Proactive Support

Effective proactive support will save you time and money.

Question to ask: How frequently do you roll out patch updates for the devices that you support?

A patch is a set of updates, changes, or corrections to a program or operating system. This can include security updates, fixing bugs, and code additions that improve your device’s functionality. When you ask this question, you are listening for a systematic approach to patching. 

By staying a step ahead of updates, your organization will need less reactive support, which will keep your IT costs under control.


Question to ask: What actions do you recommend and implement to prevent data breaches?

When you ask this question, you are listening for proactive actions with a layered approach. For example, at AccountabilIT we recommend a combination of backup and disaster recovery solutions, remote monitoring and maintenance to identify and repair vulnerabilities before they turn into issues, and a robust Security Awareness Training for you and your staff because, statistically speaking, organization staff are the number one security vulnerability in an organization. These are just a few of the approaches to security that we recommend, all of our recommendations are tailored to the individual client. For more ideas on security measures to take, check out our free Security Checklist download. (link)

Question to ask: Tell us about your approach to remote monitoring and maintenance.

Again, with this question, you are listening to a systematic approach to remote monitoring and maintenance. As mentioned above, the purpose of remote monitoring and maintenance is to identify and correct vulnerabilities and bugs before they become actual problems. This will reinforce your organization’s data security as well as reduce IT costs by resolving issues while they are small and less time-consuming to address.

Question to ask: What safeguards do you recommend for data loss prevention?

When you ask this question, you are listening for proactive actions with a layered approach. This is a similar type of question to the one above about preventing data breaches. By asking similar questions from multiple angles, you are evaluating the breadth and depth of expertise of the person you are interviewing. You want to be sure to work with an IT partner with consistent, systematic approaches to layered, proactive security and disaster recovery.

Reactive Support

No matter how much amazing proactive support you have, the truth is that sometimes issues will arise. Effective reactive support will get you back up and running quickly with minimal time lost.

Question to ask: What are your current average response and resolution times?

When you have a problem, how quickly does your IT team respond to your challenge? How quickly can they resolve the problem once they are aware of it? By the time issues are brought to the attention of your IT support team, you and your staff have already lost valuable time and productivity. Whether you are working with an in-house IT support team or a managed service provider, these measurements are relevant.

Layered Security

Effective security is more than installing antivirus software, though many small and medium-sized businesses and organizations stop there. Unfortunately, hackers do not stop there. According to IBM, the average cost of data breach is currently at $137,000 and small and medium-sized businesses are particularly vulnerable to hackers because they often do not take the same security precautions that larger companies take. 

Question to ask: What kind of security awareness training can you provide my staff?

Lack of security awareness is the number one reason for data breaches. You want to work with an IT partner who can provide comprehensive security awareness training to you and your staff. You are listening for a formalized security training program with measurable results, testing, and point-of-failure follow-up training to ensure that your staff absorbs the information thoroughly and effectively.

Question to ask: What are your breach prevention strategies and what is your policy and process for when a breach occurs?

This is a repeat topic covered by another recommended question above. By focusing on data breach prevention, you are communicating that this is a top priority for your organization, which sets the tone for your working relationship with your new IT partner. Again, you are also learning more about the breadth and depth of the person’s expertise by asking about the topic of security from several different angles. 

Question to ask: What is your approach to security concerns raised by remote workers?

If your organization has a remote workforce, it is crucial to take additional security precautions to address this extra layer of vulnerability to your organization’s data. Here are some sobering statistics to give you an idea of the scale of this issue:

  • The FBI has reported a 300% increase in reported cybercrimes since the beginning of the Covid-19 pandemic (IMC Grupo)
  • 1 in 5 organizations have experienced a security breach caused by remote workers (Malwarebytes)
  • 47% of employees identified “distractions” as the reason for falling for a phishing scam while working from home (Tessian)

When interviewing a prospective IT partner, you want to be sure that you are working with an organization that recognizes the unique security challenges presented by remote staff.

Bonus Question 

In addition to proactive support, reactive support, and layered security, you want to make sure that you are working with an IT partner whose knowledge, experience, and professionalism you can trust. Here are some ideas for questions to help you assess these qualities in a prospective IT partner.

Question to ask: How much experience do you have in providing IT support? 

AccountabilIT has been providing IT support to small to medium businesses and organizations for over 18 years.

Question to ask: What Industries to you typically support?

At AccountabilIT, we support a variety of service-based industries. This broad experience helps us stay agile in the ever-changing landscape of IT security and support.

Question to ask: How long do your customers typically work with you?

At AccountabilIT, we are proud to build long-term relationships with many of our customers. We find that by tailoring our services to the needs of each organization, our working relationships are productive, rewarding, and lasting.

Question to ask: How do you track customer satisfaction and what are your most recent stats on this?

We send customer surveys with each support ticket to ensure that we are always providing the best possible service. We take pride in our consistently positive feedback.

Looking for an IT Support Partner?

We help our customers with their day-to-day support needs and we also help them improve all areas of security with scalable solutions so that they can attain high productivity levels for their teams while keeping costs under control.

For a free consultation and IT security assessment, please contact us today. We know what it’s like to run a business, and we know your time is valuable.  

We can:

  • Learn about your business
  • Give you some ideas on what improvements you can make right away
  • Provide free advice on your approach to IT security

And if you’d like, we can show you where and how we can help.