Questions to Ask Your IT Leader

Questions to Ask Your IT Leader

Keeping your company cyber-secure entails knowing what questions to ask technology leaders in the organization. With the ever-growing threat of cyber-attacks, questions about your security posture shouldn’t remain unasked. The questions you ask about technology create awareness about your risks and the actions that should be taken to protect your organization’s servers, sensitive data, and services from breaches and attacks.

Indeed, most C-suite executives and other decision-makers aren’t trained in technical IT security or risk management. However, since they are the heartbeat of any organization, they need to know about the right IT manager questions to ask. If you’re a decision-maker in your company, you need a checklist of cybersecurity-related questions you may want to bring up during your meetings with the business technology team:

The Role of IT Leaders in an Organization

IT leaders are high-ranking individuals responsible for managing a company’s IT infrastructure, resources, software, and applications. IT manager questions are often directed to these individuals. Your organization’s business technology and IT security strategies depend on their decisions and expertise. They ensure operational stability and the execution of your business strategy, besides spurring innovation.

IT leaders keep abreast of new trends and technologies that give your organization a competitive advantage in the market. While at it, they look out for vulnerabilities and risks that can disrupt the organization’s IT strategy and overall profitability. In today’s business world, IT-related decisions must be made all the time. These could be related to vendor selection, cybersecurity strategies, and data securities.

Your organization’s IT leadership plays a vital role in these decisions. The team helps to strike a balance between meeting the organization’s IT demands and incompatible business priorities. IT leaders also help to negotiate decisions relating to budgets and expenditure. Therefore, when figuring out questions to ask leaders in your company, IT leaders should also be in the mix.

Questions to Ask Technology Leaders

It’s clear to see that the IT department is an indispensable component of your organization. As a decision-maker, you’ll know you’re getting the best out of the team if you have the right questions to ask technology leaders during your engagements. Here are the critical questions to ask the IT manager, whether you have an in-house IT department or receive managed services from a partner provider:

How Responsive Are We to Downtime?

One of the critical questions to ask technology leaders during your board meetings is whether your organization has an incident response plan. When faced with a breach or an attack, normal business operations may grind to a halt. There should be a recovery plan during downtimes to help you resume normal operations while mitigating damage.

Your IT team’s ability to answer this question demonstrates preparedness. For instance, if there’s a multi-resource recovery plan to help the company recover from a breached IT system, business processes will stay intact. The breach response and recovery plan should also be swift and available for deployment.

How Are You Keeping Our Business Secure?

IT leaders should be asked to provide information on the company’s cybersecurity strategy. As recently as the mid-1990s, the only IT-related threat that companies worried about was someone finding their way into buildings housing critical IT hardware and stealing the equipment. Today, cybercriminals are smarter and don’t even target your company’s hardware. Instead, they’re more concerned with your data.

Threat actors can monetize your company’s data in dozens of ways. Whatever their motivation, your IT team needs to ensure you’re fully protected at all times. When formulating questions to ask CTO, inquire about the cybersecurity strategies in place. These may range from firewall protection and strong encryption to hardened IT resources. Implementing these measures goes a long way in protecting you against attacks.

One of the critical questions to ask technology leaders pertains to data encryption. Most companies store their data in the cloud or use cloud-based vendors and service providers. Securing your cloud data is of the utmost significance, and it starts with encrypting your cloud data. Although cloud data is typically stored in an encrypted form, it’s best to secure it further.

The encryption built into the cloud storage systems you use may not be sufficient because experienced hackers know how to unlock certain algorithms. One of the most crucial IT manager questions to ask is whether additional encryption measures are in place. The security of your cloud environment is guaranteed if military-grade encryption standards such as Advanced Encryption Standard (AES) and Rivest-Shamir-Adleman (RSA) are in place.

Does Our IT Strategy Align with Our Overall Business Plan?

IT teams should focus on cybersecurity and business performance. For this reason, they should utilize an IT-business alignment model. Key among the questions to ask CTO is how they plan to streamline IT business processes to ensure faster response times and a more efficient supply chain.

The IT team should work towards common business goals and also be aware of and support what other departments are doing to attain those goals. Remember there’s no competitive advantage in simply using technology in today’s dynamic business world. Using technology strategically in alignment with your organization’s business goals gives you a competitive advantage.

Does Our Technology Track Benefit or Impede Productivity?

Technology is meant to improve productivity. On the flip side, it could also be a stumbling block to attaining your business goals. With the right technology, supply chains, businesses processes, employee recruitment, and other essential aspects of the business will get streamlined.

In a business that leverages technology, the dependence could also impede productivity. For instance, with inevitable glitches such as power failures and bugs, it will be challenging to perform simple tasks such as credit card processing. In this case, one of the questions to ask technology leaders is whether there’s a strategy for ensuring technology doesn’t impede business productivity.

Do You Have the Right Resources for What You’re Doing?

During your meetings with IT leaders, one of the questions to ask about tech is whether you have adequate resources for what they’re undertaking. The question touches on the budget you have and the human resources and expertise at hand. By asking this question, you’ll also want to know about the ROI of different technologies.

With the right resources, your IT team will have everything needed to implement the necessary technologies while mitigating risk. An IT team that can produce a balanced scorecard for the resources it needs knows its goals and how they align with the organization’s overall objectives.

Should We Consider Outsourcing Anything?

Sometimes, you need the expertise of an outside team to manage your IT infrastructure. Outsourcing IT services isn’t an admission of failure. It shows you recognize the expertise an outside team brings to the table. A good in-house IT team recognizes that sometimes, it needs to get complemented by an outside team.

IT professionals know too well that managed service providers bring in new skills, technologies, and expertise that could be useful to your organization. During your engagements with the IT department, you need to ask whether an outside team should be brought in.

Are We Staying Compliant?

Businesses need to comply with various regulations, from the California Consumer Privacy Act to the GDPR privacy policy. Key among the questions to ask tech leaders in your company is whether you’re compliant with these regulations. Generally, the compliance standards that apply to you depend on your industry.

Your IT department should outline the standards relevant to your industry and determine whether your data practices are compliant. Maintaining compliance proves you’ve implemented the best data security practices and helps you avoid hefty fines if a breach occurs.

Where Will Technology Be in Five Years and How Will We Adapt?

Technology keeps changing, and companies can only survive if they stay abreast of these changes. As drivers of tech innovation in your company, the IT department should forecast how current technology trends will pan out in the future.

The IT department should advise your organization’s decision-making team on the technologies to invest in to boost productivity. Indeed, you don’t want to invest in a technology that will be obsolete in five years. For this reason, the CIO and other IT leaders should be able to forecast where the current technology will be in the coming years and recommend how to adapt to the changes.


Decisions made by IT leaders don’t apply to your organization’s technology alone. It also affects other aspects of the organization, including business efficiency, growth, and innovation. As a decision-maker within your organization, make sure you get the answers to these IT manager questions whenever you engage with the IT department.

Since IT is a mission-critical resource for your organization, you shouldn’t miss the opportunity to ask the right questions. If your organization appreciates the expertise of a managed IT and cybersecurity service provider, you need partners like IT Authorities. We’re here to improve how you do business by helping you become more secure, agile, and productive. Contact us today to book a free consultation.