Skip to content

10 Key Questions for CEOs to Test Tech Lead

10 Key Questions for CEOs to Test Tech Lead
5:26

Mid-sized firms are lagging in security and business transformation, risking their future in a competitive landscape. As a fractional CTO, I’ve seen tech leads overlook gaps that could cost millions, from hidden cyber threats to stalled digital initiatives. Recent data paints a stark picture:

  • A 2024 NAVEX report shows 46% of SMBs don’t use firewalls, leaving them exposed.
  • NAVEX also notes 59% of small businesses think they’re too small for cyber threats—a dangerous misconception.
  • Deloitte’s 2023 report highlights mid-market struggles with legacy systems and evolving cyber risks.
  • AHEAD’s 2021 study reveals 42% of enterprises face stalled digital transformations due to complexity.
  • X discussions in February 2025 point to outdated tools holding mid-sized firms back from growth.
    This blog uncovers 10 layup questions—5 on security, 5 on transformation—that 99% of tech leads at mid-sized firms likely can’t answer. Ask these to safeguard your firm’s success.

Security Questions

Cybersecurity isn’t just about firewalls—it’s about spotting hidden risks before they escalate. Here are five layup questions your tech lead likely can’t answer, exposing vulnerabilities that could cost your firm dearly.

  • How are you blocking email tracking pixels?
    Email tracking pixels are tiny, invisible spies embedded in emails, monitoring your every click. Most tech leads don’t even know they exist, let alone block them, leaving your firm’s data exposed to marketers and bad actors. Non-compliance with privacy laws like GDPR can lead to fines of $40,000 per breach, not to mention reputational damage.
  • What’s our Microsoft Secure Score, and how do we compare?
    Microsoft Secure Score measures your firm’s security posture across Microsoft 365, but many tech leads haven’t heard of it. Without knowing your score, you can’t benchmark against industry standards or address weak spots. A low score could mean unpatched vulnerabilities, risking breaches that cost millions in penalties.
  • How do we identify and handle at-risk accounts?
    At-risk accounts—those with weak passwords or suspicious activity—are a hacker’s entry point. Yet, most tech leads lack a process to identify or secure them, leaving your firm open to attacks. A single compromised account can lead to a data breach, with penalties averaging $4.35 million, according to 2023 data.
  • Can you share our security incident response process?
    A formal incident response process is critical to minimizing damage from breaches, but most mid-sized firms lack one. Tech leads often scramble reactively, delaying recovery and amplifying costs. Without a process, you risk regulatory fines and prolonged downtime, potentially costing hundreds of thousands.
  • What’s our plan for non-compliance penalties?
    Non-compliance with regulations like GDPR or HIPAA can lead to fines exceeding $100,000 per incident. Most tech leads can’t answer this because they haven’t planned for it, leaving your firm vulnerable to unexpected financial hits. Proactive planning is key to avoiding these costly penalties.

Business Transformation Questions

Business transformation isn’t just about new tech—it’s about aligning IT with growth and efficiency. Here are five layup questions your tech lead likely can’t answer, exposing transformation gaps.

  • What’s our tech debt’s impact on scalability?
    Tech debt—outdated systems and quick fixes—slows growth, but most tech leads can’t quantify its impact. Without this insight, your firm risks scalability issues, delaying expansion and costing opportunities. A clear assessment is crucial to prioritize fixes and ensure growth.
  • How are we automating to boost efficiency?
    Automation can cut operational costs by 30%, yet many tech leads lack a strategy for it. Without automation, your firm wastes resources on manual processes, stunting efficiency. Knowing what’s automated (or not) reveals critical gaps in your transformation journey.
  • What’s our cloud migration strategy for growth?
    Cloud migration drives scalability, but most tech leads can’t articulate a clear strategy. This oversight leads to inefficiencies and higher costs, with 60% of firms overspending on cloud due to poor planning. A defined strategy ensures your IT supports growth without breaking the budget.
  • How do we measure IT’s ROI on business goals?
    IT investments should drive measurable business outcomes, but most tech leads can’t connect the dots. Without ROI metrics, you’re flying blind, wasting resources on misaligned tech. This question uncovers whether your IT is truly supporting your firm’s goals.
  • What’s our plan to align tech with long-term strategy?
    Tech should support your 5-year vision, but most tech leads focus on short-term fixes. Lack of alignment leads to inefficiencies and missed opportunities, costing your firm in growth potential. A long-term plan ensures your IT evolves with your business.

Take Action Now

Keep security and transformation answers top of mind and readily available for your firm’s success. Don’t settle for a deer-in-the-headlights response or “let me get back to you” from your tech lead. Act now—schedule a consultation with me, a fractional CTO