The Top 11 Questions Every Leader Should Ask Before Starting a Tech Project

Technology projects usually start with smart teams, ambitious goals, and the best of intentions. But far too many lose momentum, go over budget, or fail to deliver lasting impact. The frequently quoted Gartner statistic states that 70% of tech initiatives fail, not because of poor technology, but because of weak strategy, misalignment, and rushed execution. The root cause is often skipping the foundational questions that align people, clarify purpose, and reduce risk.

Starting a tech project is a business decision. A leadership responsibility and most importantly, a human-centered effort. Technology succeeds when it’s designed around people, with clear goals, shared understanding, and the capacity to support behavior change.

The following eleven questions help leaders focus on what matters before the first team meetings are scheduled. They help create alignment, momentum, and outcomes that last.

1. What problem is being solved, and who experiences it?

Every effective technology project starts with a clear why, a real problem that matters to someone. Too often, projects are initiated based on assumptions, trends, or executive preferences instead of real user needs.

Leaders should make sure the problem is grounded in lived experience. That means talking to front-line staff, customers, and impacted teams before jumping into solutions. This problem needs to be clarified at the beginning to save time and confusion later. Who is this for? What pain point are we addressing? If you or your team can’t articulate the user problem in plain language, you’re not ready to start.

Tips/Tools: Frame this as a user story around an identified user need. Here’s an approach: “As a [user], I need [function], so I can [benefit].” As an example: As a customer support agent, I need a dashboard that shows real-time metrics so I can prioritize tickets better.

2. What does success look like, and how will it be measured?

Success needs definition and a shape. Without it, teams and their projects drift. Metrics should capture business value and user outcomes not just a checklist of completed technical tasks. The point is to truly focus on what matters.

Whether it's a faster turnaround, reduced rework, improved satisfaction, or better data access, leaders should define what success looks like from multiple angles. Vague goals like “improve performance” or “modernize the platform” won’t cut it. Are we increasing speed, saving money, reducing errors, or delighting customers or constituents? The goal is to make the metrics meaningful, not just measurable.

Tips/Tools: Consider foundational metrics like a Net Promoter Score, system uptime, revenue impact, or adoption rate. The easier the metrics are to measure, the more likely they will be more than once.

3. What is in scope and just as important, what is not?

Scope creep kills momentum. Clarity around scope protects teams from burnout and misalignment. Leaders should be ruthless about defining boundaries, specifically what will be delivered (like a minimally viable product), what will wait, and what has been ruled out.

Scope should include both functionality and behavioral change. If new systems require new habits, that effort needs to be resourced and supported and not left to chance. Always ask if you are you solving an isolated problem, or stacking new tech onto legacy systems without addressing the root? If the foundation is shaky, even the most beautiful solution will wobble.

Tips/Tools: Use tools like a clear Product Requirements Document (PRD), a RACI matrix (who’s Responsible, Accountable, Consulted, Informed), or a simple “Must-Have, Should-Have, Could-Have” feature list.

4. Who are the stakeholders, and how will alignment be maintained?

Projects often involve more stakeholders than expected including users, IT, operations, legal, compliance, and others. Without a clear communication plan to keep them aligned, decisions get delayed and momentum stalls.

Stakeholder alignment should be intentional. This means clear roles, shared context, and consistent communication. Misaligned stakeholders lead to moving goalposts, confusion, and rework. Clearly identify how you will keep the stakeholder engaged, informed, and accountable. Alignment is not a one-time event; it’s a practice that must be sustained and done on-purpose.

Tips/Tools: Don’t confuse being “in the loop” with being “on the hook.”  Set up recurring stakeholder check-ins, use shared documentation on an easily accessible collaboration sites like Microsoft Teams, and appoint a strong product owner or project manager to keep things moving along. Outsourcing project management expertise can help this dramatically.

5. Do the team, tools, and resources match the project’s ambition?

Tech projects don’t run on ideas alone. They require skilled people with time to focus. Leaders should confirm that the right roles are in place, from technical leads to change agents and that those people have the bandwidth to succeed. If not, are you hiring, borrowing, or outsourcing? It’s also important to assess tools and infrastructure. If the existing environment can’t support the work, no amount of effort will fix it.

Tips/Tools: Do a reality check. If everyone is already at 100% capacity, this project is already at risk. Don’t overlook skills like DevOps, security, and data governance, which are often afterthoughts but critical to success.

6. What are the biggest risks, and how will they be managed?

Every project carries risk. These may be technical, operational, financial, and cultural. For each risk, ask: What’s our mitigation plan? Who owns it? When will we revisit it? The trick is to identify the most significant ones early and assign ownership to manage them.

Risks should include people dynamics. Will there be resistance to the change? Are key voices missing? Will already-busy teams take on too much? Assume yes to these questions to help manage the risk. Calling these risks out up front increases the chances of a smoother path forward.

Tips/Tools: Ask more questions: What’s our fallback if the tech doesn’t scale? What happens if we lose a key team member? Are we compliant with industry regulations? Managing risk is simply key to project success.

7. How will assumptions be tested before major investment?

Every plan is full of assumptions: that users want the feature, that data will integrate, that systems will scale. The earlier you test them, the cheaper the lessons. Leaders should push for early validation through prototyping, pilots, or user testing.

It’s far more efficient to learn what doesn’t work in a sandbox than to discover it after a full launch. Key questions like: Can we pilot it? Prototype it? Get quick user feedback? It’s better to “fail small” early than rebuild later. Early feedback helps avoid wasted effort and builds confidence in the approach.

Tips/Tools: Consider running a short discovery sprint or pilot project. User interviews and usability tests are inexpensive but extremely valuable ways to test in a more forgiving environment.

8. Is the timeline realistic, given the work and the change involved?

Ambitious timelines look good on paper, but unrealistic ones lead to often create unnecessary stress, rushed delivery, and long-term rework. Timelines should reflect not just the technical tasks but the learning curve, change readiness, and space for iteration.

Moving fast is good and moving smart is better. Realistic pacing supports quality, adoption, and sustainability. And remember: hitting a deadline means little after next quarter if adoption flops or the solution breaks.

Tips/Tools: Make it flexible. Plan in sprints, set short-term milestones, and leave buffer time for QA and deployment. Having ambitious goals is necessary, but ensure they can be met with more than just effort.

9. What happens after go-live?

Go-live is not the finish line. It’s the beginning of real-world use. Key questions include: Who will maintain the code or systems, onboard new users, fix bugs, and manage enhancements? Leaders should ensure there is a clear plan for ownership, support, training, and improvement.

Ongoing investment is required to keep systems relevant and effective. Without that commitment, even the best tools lose value quickly.

Tips/Tools: Don’t just think of this as tech support or IT’s job to maintain going forward. Build in documentation, training, clear ownership and a roadmap for improvement to help go-live move into “how we do it now.” This improvement outcome also needs a budget line item next year and beyond.

10. Does this project support the long-term vision?

Projects should connect to something bigger than the current task list. Zoom out. How does this project align with our larger strategy? Does it reinforce our competitive advantage? Or are we investing in something shiny that might distract from what matters? Leaders need to step back and ask whether the initiative supports long-term goals, builds new capabilities, or lays the groundwork for future innovation.

A technically sound project that doesn’t align with strategy becomes noise. The most valuable projects support mission, growth, and momentum. If it’s a foundational play, it’s great. If it’s an experiment, say so. But don’t pretend it’s a game-changer if it’s just a quick fix.

Tips/Tools: Do a vision check. Ask how this initiative will look in 12 months. It’s tempting to go further but do so with flexibility as the pace of technology change is staggering. Consider could this new technology help enable true differentiator? Will it scale as you grow? Will it help you reduce future risk?

11) The Really Important One: How will people be supported through the change?

This is the one of the most overlooked and critical questions to ask. This system change is really a people change. New tools bring new behaviors, new expectations, and new friction.

Leaders must consider:

• Who will be impacted?

• What do they need to succeed?

• How will the organization help them feel prepared, not disrupted?

Tips/Tools: Change management should not be seen as a soft skill or optional add-on. It is a core function of any successful transformation. Communication, training, and support should be built in from the beginning. The very beginning.

Final Thought: The real work starts before the work begins

Technology alone doesn’t deliver results, people do. Strong tech projects don’t just start with code; they start with clarity, collaboration, and the courage to ask the right questions. These eleven questions are more than a checklist: they’re a mindset and a leadership practice. The help create a foundation for transformation that lasts.