The Types Of Technology Leaders Who Won't Want to Complete the StackUp Assessment

When it comes to assessing your technology function, transparency is critical. Yet, not every technology leader will be enthusiastic about completing a thorough review.
‍
Most great technology leaders love the opportunity to learn something new, and to showcase their achievements - and StackUp's assessment supports that - in just 30 minutes, it can shine a light on the areas that need attention.
‍

But some technology leaders will avoid it at all costs, and this can be a red flag for CEOs, board members, and investors.
‍

Below, we explore the types of technology leaders who shy away from this kind of accountability and what that signals about their leadership.

1. Scared of Finding Out the Truth

These leaders fear what a comprehensive review of their technology function might reveal. They might appear defensive when questioned about their operations and avoid discussing specific challenges. They know that cracks are there but are too afraid to confront them.

• What they look like: They deflect questions and provide vague assurances. When pressed, they might say everything is “fine” but fail to back it up with evidence.
• Why it needs attention: A leader who fears transparency is dangerous. If they can’t face the reality of their technology function, they can’t make the improvements necessary for long-term growth.
• How to identify them: Ask, “What’s the biggest technology challenge we’re currently facing?” If their answer is general or evasive, they might be hiding from the truth.

2. Incompetent, and Know It

These CTOs are aware that they don’t have the skills or knowledge to effectively lead a technology function. Rather than seeking help or improving their skills, they choose to mask their incompetence by avoiding scrutiny.

• What they look like: They avoid complex discussions and often rely on others to cover for their weaknesses. You’ll find them consistently delegating tasks without showing personal accountability.
• Why it needs attention: Incompetence at the top means poor decisions get made, and those decisions ripple through the company. This puts the entire organization at risk.
• How to identify them: Ask, “What’s your approach to solving technical debt or optimizing system performance?” Watch for reliance on jargon without clear action steps.

3. Have Something to Hide

Leaders in this category may be deliberately concealing problems within their technology operations. Whether it’s covering up missed deadlines, inflated budgets, or unresolved issues, they’re selectively sharing information to maintain control.

• What they look like: They’re highly secretive about projects and resist providing updates unless specifically requested. They may also seem overly focused on controlling narratives in meetings.
• Why it needs attention: Deception leads to poor decision-making at higher levels. If your technology leader isn’t being transparent, the business can’t properly assess risk or opportunities.
• How to identify them: Ask, “Can you walk me through the key challenges we’ve faced in technology over the last year?” A leader who’s hiding something will either gloss over or minimize significant issues.

4. Selective with Information

Some technology leaders provide their CEO or board with only the information that serves them. They withhold details about projects that have stalled or budgets that have been exceeded to maintain a façade of control.

• What they look like: These leaders often present an overly optimistic picture and avoid digging into the weeds of any problems unless forced to.
• Why it needs attention: A CEO or board relying on incomplete information can’t make informed decisions. This lack of transparency can create blind spots that threaten the business.
• How to identify them: Ask, “Can you share a detailed breakdown of where we’ve exceeded our technology budget this year and why?” If they stall or provide only partial data, they may be cherry-picking the facts.

5. Think They Know It All

These leaders are often unconsciously incompetent. They believe they’re fully equipped to handle everything thrown their way and dismiss the need for assessments or external input. This arrogance blinds them to areas of weakness.

• What they look like: They’re dismissive of new ideas and reluctant to listen to feedback. They often say things like, “We don’t need to worry about that” without providing a solid rationale.
• Why it needs attention: Overconfidence without justification can lead to missed opportunities and ignored risks. A leader who doesn’t recognize their own limitations is a liability.
• How to identify them: Ask, “When was the last time we did a full technology audit, and what were the key findings?” A dismissive answer reveals a leader unwilling to self-assess.

6. Satisfied with the Status Quo

Leaders who are satisfied with mediocrity pose a real threat to growth. They believe that “good enough” is enough, resisting efforts to innovate or improve. They may have had some early success and now coast on that momentum.

• What they look like: They avoid any initiative that involves change. Instead, they focus on maintaining what already exists, even when it’s clear that updates or innovation are needed.
• Why it needs attention: In today’s rapidly evolving technological landscape, stagnation is dangerous. A business that isn’t actively pushing for improvement will be left behind.
• How to identify them: Ask, “What’s your vision for our technology function over the next 12 months?” A lack of ambition or innovation points to someone who’s stuck in the status quo.

7. Too Busy

The “too busy” leader might claim they don’t have the time to complete an assessment. In reality, it’s more a matter of priorities. Any leader who can’t make time for a 30-minute assessment that could improve their entire function is waving a red flag.

• What they look like: They’re constantly over-scheduled and seem to thrive on being overwhelmed. However, they rarely achieve meaningful progress, using busyness as an excuse to avoid critical tasks.
• Why it needs attention: A leader who’s too busy for strategic initiatives is a leader who doesn’t understand priorities. If they can’t carve out time for essential assessments, they’re not serving the company effectively.
• How to identify them: Ask, “If you can’t spare 30 minutes for a technology assessment, how do you prioritize other critical business functions?” This question will often expose their inability to focus on what matters.

Conclusion

A technology leader’s resistance to completing the StackUp assessment says a lot about their leadership style and priorities.

As a CEO, board member, or investor, spotting these red flags early can prevent deeper issues from taking root in your organization.

‍

If your CTO can’t spare 30 minutes for something as important as assessing the state of your technology, it’s time to ask some tough questions.