Why IT leaders need better questions

No one needs reminding that IT leaders are expected to deliver results with precision, speed, and a sixth sense for what the business truly needs. Yet, most requirements-gathering sessions still end in misalignment, missed opportunities, or a flurry of generic wish lists. The real problem isn’t a lack of expertise or intent. It’s that most conversations start with the wrong questions or, worse, no clear questions at all.

How can IT leaders extract the truth from busy department heads who often feel just as pressured, misunderstood, and risk-averse? It comes down to asking the right questions—ones that cut through surface-level requests and reveal what actually matters to the business, the team, and the bottom line.

This isn’t about running a checklist. It’s about building trust, uncovering root causes, and translating messy, real-world pain points into actionable IT requirements. A well-structured interview with the right questions can save months of rework, budget headaches, and late-night escalations.

Here are 10 questions you can ask internal stakeholders or department heads to get a clearer understanding of the requirements necessary.

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1. If we could automate one process this quarter, which would save your team the most time?

What does this question help you understand about the department?

This question exposes the real bottlenecks that silently erode productivity. It pushes teams to identify their most repetitive, time-consuming task—the process everyone grumbles about but rarely escalates. The answer surfaces where manual work is draining hours and morale, whether it’s mindless data entry, approvals stuck in email, or endless spreadsheet wrangling. This isn’t just about convenience; it’s about seeing where inefficiency quietly undermines results and drains resources every week.

How will the answer help you better define requirements?

The response gives IT leaders a concrete starting point for automation—one with clear business value. It translates vague complaints into measurable pain points, quantifying the hours lost and the teams affected. Now, requirements become specific: what the process looks like, where it breaks down, what “done right” would mean for users. Defining requirements from this perspective makes automation projects more targeted, defensible, and impactful, ensuring that solutions drive real ROI instead of chasing the latest technology fad.

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2. What tasks or reports do you dread most each month and why?

What does this question help you understand about the department?

This question digs beneath the surface to uncover the work that employees resent, not just tolerate. It reveals recurring tasks or reports that are mentally exhausting, error-prone, or simply wasteful. These are often legacy processes that remain unchallenged because “that’s how it’s always been done.” The answer exposes the emotional and operational toll these tasks take, offering insight into where frustration simmers and productivity suffers. It’s not just about inefficiency—it’s about morale, retention, and the subtle, accumulative costs of bad process design.

How will the answer help you better define requirements?

When stakeholders describe what they dread, they’re giving IT a high-resolution map of where workflow optimization or redesign is most urgently needed. Their explanations reveal the underlying causes—broken handoffs, unclear ownership, compliance overkill, or outdated tools. These specifics help IT leaders write requirements that address root problems, not just symptoms. Prioritizing the elimination or automation of these dreaded tasks means solutions that are immediately meaningful, improve job satisfaction, and quickly demonstrate the value of IT partnership.

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3. Are there any manual processes that often result in errors or delays?

What does this question help you understand about the department?

This question uncovers the weak spots where manual intervention is still the norm and where mistakes or slowdowns are quietly costing the business. It highlights processes that are fragile, inconsistent, or prone to human error—often the same ones that lead to late nights, compliance headaches, or customer complaints. Departments may reveal recurring issues in data handling, approvals, reconciliations, or information transfer, pointing directly to the pain points that hurt both operations and reputation.

How will the answer help you better define requirements?

Clear examples of error-prone or delayed manual processes turn abstract pain into actionable requirements. The details—what’s breaking, how often, and with what consequences—allow IT to map out where automation, validation, or smarter workflows can make a measurable difference. Requirements become sharper: they specify not just what to digitize, but the controls, checks, and user experience needed to eliminate errors and speed things up. This approach ensures that solutions target the highest-risk areas, improving accuracy, reducing rework, and ultimately making the department more resilient and reliable.

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4. What’s the single biggest obstacle slowing your team down right now?

What does this question help you understand about the department?

This question forces a moment of clarity. It cuts through minor complaints and focuses attention on the one barrier that’s really holding the team back. Whether it’s a broken workflow, a missing integration, outdated software, or an approval bottleneck, the answer highlights where frustration peaks and momentum stalls. It also reveals what the team sees as their top priority—what, if fixed, would unlock the most progress.

How will the answer help you better define requirements?

By isolating the primary obstacle, IT leaders can avoid spreading resources too thin across dozens of issues and instead zero in on the change that will make the biggest impact. The answer provides a focal point for requirements: what the obstacle is, why it matters, who it affects, and how success should be measured. This clarity enables a targeted solution with real business value, sidestepping the trap of “boiling the ocean” and ensuring that IT is seen as a catalyst for meaningful progress, not just incremental fixes.

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5. If your team had 10% more capacity, what would you tackle next?

What does this question help you understand about the department?

This question reveals the ambitions, unmet needs, and strategic priorities that linger just out of reach due to current constraints. It uncovers the projects and improvements that staff consider important but have postponed, not because of lack of vision, but because bandwidth is maxed out. The answer exposes what the team values most—be it innovation, customer experience, process improvements, or overdue system upgrades—and where they believe the next leap in performance or value could come from.

How will the answer help you better define requirements?

Understanding what teams would do with just a bit more capacity helps IT leaders anticipate future demand and align solutions with growth opportunities, not just current pain points. The specifics provided in the answer give shape to requirements that are forward-looking and strategic. This means requirements can be designed to not only solve immediate bottlenecks but also enable the next wave of business progress, ensuring solutions are scalable, adaptable, and directly tied to the organization’s evolving goals.

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6. Have there been any recent setbacks or frustrations in serving customers or meeting regulatory requirements, and where do you think technology could make a difference?

What does this question help you understand about the department?

This question brings to light the real-world incidents where technology gaps have directly impacted customer satisfaction or compliance. It exposes the moments when the department felt vulnerable—missed deadlines, audit findings, or customer complaints—and where existing systems failed to protect against these outcomes. The answer reveals not only the practical obstacles but also the underlying anxieties about risk, reputation, and regulatory exposure that shape department priorities.

How will the answer help you better define requirements?

By grounding requirements in recent, tangible setbacks, IT leaders can ensure that solutions address business-critical issues rather than hypothetical scenarios. The specifics shared—what happened, why it mattered, and how technology could have helped—provide a clear blueprint for solution design. Requirements become sharper and more defensible: they focus on closing actual gaps, preventing repeat incidents, and building resilience where it’s needed most. This approach ensures IT investments are justified by real business impact, driving both trust and accountability in technology decision-making.

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7. What systems or tools do you wish ‘talked’ to each other better?

What does this question help you understand about the department?

This question exposes the integration gaps and data silos that quietly undermine efficiency and decision-making. Departments often wrestle with multiple platforms—CRMs, ERPs, finance systems, project trackers—that don’t share information cleanly. The answer highlights where double entry, manual reconciliation, or context-switching wastes time and increases the risk of error. It also uncovers the frustration employees feel when technology stands in the way of a smooth workflow.

How will the answer help you better define requirements?

Responses here guide IT leaders to the specific integration or interoperability issues that matter most to the business. Instead of chasing generic “system consolidation,” requirements can target the data flows and connections that will deliver meaningful improvements. The answer provides details on which systems need to connect, what information should be shared, and where automation or API development can reduce friction. This clarity ensures integration projects are focused, technically sound, and deliver visible value to the end users.

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8. How do you measure success in your department and what’s hardest to track?

What does this question help you understand about the department?

This question gets to the core of what the department truly values. It uncovers the key performance indicators, goals, and metrics that drive behavior and define achievement. Just as importantly, it reveals the blind spots—the data points or trends that are important but difficult or time-consuming to capture. The answer exposes both the department’s definition of success and the reporting pain points that hinder effective management and strategic decisions.

How will the answer help you better define requirements?

When IT understands both what is measured and what is difficult to track, requirements become more precise and relevant. Solutions can be designed to automate data collection, streamline reporting, and surface insights that matter most to stakeholders. This leads to dashboards, analytics, and reporting tools that do more than check a compliance box—they actively empower departments to manage and optimize performance. The result is technology that closes information gaps, supports decision-making, and directly aligns with business objectives.

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9. Where do you feel the most risk or exposure in your day-to-day operations?

What does this question help you understand about the department?

This question uncovers the department’s critical vulnerabilities—the areas that keep leaders up at night. It brings to light operational, security, or compliance risks that may not always be visible on the surface but have the potential for significant business impact. Whether it’s data breaches, system downtime, regulatory lapses, or single points of failure, the answer reveals where anxiety is highest and safeguards are weakest.

How will the answer help you better define requirements?

By identifying specific sources of risk, IT leaders can prioritize solutions that address the most serious threats first. Requirements become anchored in real business concerns, specifying the controls, redundancies, or monitoring capabilities needed to reduce exposure. This targeted approach ensures that investments in technology aren’t just about new features but about protecting the organization’s reputation, continuity, and compliance. Thoughtful risk mitigation, driven by direct stakeholder input, transforms IT from a cost center into a strategic protector of business value.

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10. If you could improve one thing about your team’s work experience, what would it be?

What does this question help you understand about the department?

This question goes beyond process and technology, tapping into the human side of work. It uncovers the everyday friction points, frustrations, or opportunities for improvement that affect morale, engagement, and retention. The answer reveals what matters most to the team—whether it’s clunky tools, lack of recognition, communication breakdowns, or a need for better training and support. It’s a direct line to the experiences shaping job satisfaction and performance.

How will the answer help you better define requirements?

Insights here guide IT leaders to design solutions that actually make work better for real people, not just for the business. The requirements that emerge are grounded in empathy and usability, focusing on the changes that will genuinely improve daily life for users. Whether it’s simplifying interfaces, speeding up support, or enabling remote work, the focus shifts to delivering technology that people want to use—solutions that foster loyalty, productivity, and a healthier workplace culture. In the end, these improvements drive adoption and maximize the return on every IT investment.

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