60+ strategic questions to ask your team (with examples)

Strategic questions can unlock your team’s collective intelligence and drive meaningful progress toward shared goals. Going beyond surface-level check-ins, they reveal insights about alignment, innovation opportunities, and engagement levels that traditional status updates often miss.

The right questions at the right time can transform how your team thinks, collaborates, and executes. And whether you’re leading a remote team, managing through organizational change, or simply looking to elevate performance, strategic questioning creates the foundation for breakthrough conversations and sustainable results.

In this guide, we provide examples of more than 60 categorized questions designed for all different contexts — from one-on-one meetings to strategic planning sessions. Each question is crafted to generate actionable insights that move your team forward, not just fill meeting time.

Why strategic questions matter to team performance

Strategic alignment has a tangible impact on business. As research from LSA Global shows, highly aligned companies grow revenue 58 percent faster and are 72 percent more profitable than their misaligned counterparts. Aligned organizations also experience 16 percent higher customer satisfaction and 30 percent greater employee engagement.

Yet significant gaps remain. Workplace communication studies show that 52 percent of employees experience higher stress levels due to poor communication, while 44 percent fail to complete projects and 25 percent miss performance goals.

The gap between strategy formation and execution often lies in the quality of communication. When leaders ask generic questions like “How’s everything going?” they usually receive generic answers in return. But strategic questions probe deeper into the thinking, challenges, and opportunities that shape team performance.

Strategic questions serve as diagnostic tools. They can reveal where alignment breaks down, where innovation opportunities exist, and where engagement gaps threaten performance. They also transform routine conversations into mini strategy-building sessions that compound over time.

A framework for asking strategic questions: timing, intent, format

Effective strategic questioning requires intentional design across three dimensions: timing, intent, and format.

Timing determines impact. Strategic questions work best during natural reflection points, such as quarterly planning sessions, project retrospectives, one-on-one meetings, and team offsites. Avoid heavy strategic discussions during sprint crises or when teams are heads-down on urgent deliverables. The best strategic conversations happen when people have the mental space to think beyond immediate tasks.

Intent shapes outcomes. Clarify whether you’re  looking for alignment (“Are we all moving toward the same goal?”), exploration (“What opportunities are we missing?”), or reflection (“What can we learn from this experience?”). Mixed intent creates confusion that can dilute responses.

Format influences participation. Open-ended questions generate rich qualitative insights but may require more processing time. Quantitative questions allow for quick pattern recognition across larger teams. Live discussions build energy and real-time collaboration, while async formats give introverts and deep thinkers space to contribute meaningfully. Anonymous formats reduce political filtering and encourage honest feedback.

Consider using different format combinations, depending on the context. For example, start strategic planning sessions with anonymous pulse checks to surface issues, then use live discussion for collaborative problem-solving. Follow up complex strategic conversations with structured forms that capture individual reflections and commitments.

60+ strategic questions to ask your team

We’ve organized more than 60 strategic questions here by context and purpose. Use them as starting points, adapting the language and focus to match your own team’s culture and current challenges.

Avoid missteps when asking strategic questions

• Don’t use blame-y phrasing: Instead of “Why didn’t we hit the goal?”, try “What barriers did we encounter?”
• Avoid yes/no traps when you need more depth.
• Be mindful of timing, skipping the heavy questions during a sprint crisis.
• Always follow up: Questions without action tend to erode trust.

1. Strategic vision & objectives

These questions help teams connect daily work to bigger-picture goals and identify alignment gaps before they become performance issues.

• What does success look like for our team six months from now?
• Which of our current initiatives would you double down on, and which would you pause?
• How do our team’s priorities connect to the company’s top three strategic objectives?
• What would it take for us to exceed our current goals by 25 percent?
• If you had to explain our strategy to a new team member in two minutes, what would you say?
• Where do you see the biggest gap between our stated priorities and how we actually spend time?
• What assumptions about our market or customers are we making that might not be true?

Questions like these have the most impact during quarterly planning sessions and strategic retreats. They help reveal whether your team truly understands the “why” behind their work and indicate strategic misalignment early on.

2. Market awareness & competitive positioning

These questions can help your team maintain an external perspective and identify opportunities or threats that an internal focus might otherwise miss.

• What trends in our industry should we pay closer attention to?
• Which competitor’s recent move surprised you most, and what does it tell us?
• What are customers in our space starting to expect that we don’t currently deliver?
• If we were starting our business today, what would we do differently?
• What adjacent markets or customer segments represent untapped opportunities?
• How has our competitive advantage evolved over the past year?
• What external changes could make our current strategy less effective?

Incorporate these types of questions into monthly business reviews and customer feedback sessions. They will keep teams externally focused and opportunity-aware.

Consider also using Jotform’s End of Day Report AI Agent to continuously collect market reports from your team. The information you collect can help identify emerging trends and competitive intelligence.

3. Team collaboration & work habits

These questions can uncover collaboration friction and lead to process improvements that will directly impact your team’s overall effectiveness.

• What’s one thing we do as a team that we should stop doing immediately?
• Where do handoffs between team members create unnecessary delays or confusion?
• Which meetings add genuine value, and which could be eliminated or restructured?
• How do we make decisions as a team, and where does that process break down?
• Is there information you need to do your job well that you don’t currently have?
• When do you feel most productive and engaged during the workweek?
• What’s one process change that would save our team five hours per week?
• How do we handle disagreements, and what could we improve about that process?

For best results, use these questions during team retrospectives and process improvement sessions. They will help surface operational inefficiencies and collaboration gaps that strategy alone can’t fix.

4. One-on-one check-ins

These questions can transform routine one-on-one sessions into strategic development conversations, helping to align individual growth with the greater team needs.

• What project or responsibility would you love to take on that you haven’t had the chance to yet?
• Where do you see your biggest opportunity for impact in the next quarter?
• What skills are you developing that could benefit the team more?
• What’s one thing I could do differently as a leader to help you be more effective?
• Which of your strengths do you feel the team underutilizes?
• What concerns you most about our team’s direction, and what excites you most?
• How do you prefer to receive feedback and how often?
• What would need to change for you to feel more ownership over strategic decisions?

5. Customer impact & feedback loops

These questions make sure the customer perspective remains central to strategic thinking and operational decisions.

• What’s the most important thing we could do to improve our customers’ experiences?
• Which customer feedback themes keep appearing that we haven’t fully addressed?
• How do we currently measure customer satisfaction, and what are we missing?
• What would our best customers say is our biggest competitive advantage?
• Where do we create friction in the customer journey that we could eliminate?
• How quickly do customer insights reach decision-makers on our team?
• What would customers be willing to pay more for that we don’t currently offer?

Integrate these questions into product reviews, customer success meetings, and strategic planning sessions for maximum impact. They’ll help your team maintain customer-centricity amid internal operational focus.

6. Tactical & execution-level strategy

These questions bridge the gap between high-level strategy and daily practice, ensuring that plans translate into effective action.

• What’s stopping us from executing on our strategy more effectively?
• Which of our current tactics are working better than expected and why?
• Where do we need clearer decision-making criteria or processes?
• What resources or capabilities do we need to achieve our strategic goals?
• How do we know if we’re making progress on our most important objectives?
• What early warning signals should we monitor to catch problems before they escalate?
• Which strategic initiatives require more attention or different approaches?
• How do we balance short-term performance with long-term strategic investments?

Use these types of questions during monthly business reviews and project check-ins. They help keep strategic plans grounded in operational reality.

7. Innovation & opportunity scouting

These questions cultivate innovative thinking and help teams identify breakthrough opportunities beyond incremental improvements.

• What’s an idea you’ve been curious about but haven’t had time to explore?
• If we had unlimited resources for one experimental project, what would you propose?
• What’s working well in other industries that we could adapt to our context?
• Where do we see emerging technologies or trends that could reshape our approach?
• What assumptions about “how things work” in our field deserve more scrutiny?
• What would we attempt if we knew we couldn’t fail?
• Which of our constraints are real, and which are just habitual thinking?
• What adjacent problem could we solve that would create new value for customers?

Incorporate these types of questions into innovation sessions, strategic offsites, and brainstorming meetings. They’ll help generate fresh perspectives and breakthrough thinking.

8. Strategic planning sessions

These questions guide comprehensive strategic conversations that set direction and build alignment for major planning cycles.

• What’s changed in our environment since we last set strategic priorities?
• Which of our current strategies are working, and which need fundamental rethinking?
• What trade-offs are we willing to make to achieve our most important goals?
• How do we want to be positioned in the market three years from now?
• What capabilities do we need to build or acquire to execute our strategy?
• Where do we have competitive advantages that we should leverage more aggressively?
• What scenarios could disrupt our current strategic assumptions?
• How will we measure success for each strategic priority?
• What would cause us to pivot or abandon a strategic initiative?

How often and where to use strategic questions

To avoid survey fatigue while maintaining momentum, inject intentional cadence into your strategic questioning. Different question types call for different rhythms and formats.

Weekly rhythms work best for operational and collaboration questions. Use brief check-ins or one-on-one meetings to address immediate strategic alignment issues. Keep these conversations focused with a maximum of three strategic questions per session.

Monthly cycles support discussions around market awareness and customer impact. Since questions related to these topics require more research and reflection time, they are ideal for business reviews and team meetings where strategic context matters most.

Quarterly planning provides natural opportunities for comprehensive strategic questioning. Use vision, innovation, and planning questions during offsite sessions, strategic retreats, and goal-setting meetings. These conversations will benefit from the extended time and focused attention.

Question formats  depend on both question complexity and team dynamics. Simple alignment questions work well during live meetings where immediate clarification is particularly valuable. Complex strategic questions, on the other hand, may benefit from async formats that allow for more thoughtful reflection. Anonymous surveys work best for sensitive topics like leadership feedback and process criticism.

Avoid questionnaire overload by rotating question categories. Focus, for example, on vision and alignment during goal-setting periods, while emphasizing innovation and opportunity during planning sessions and collaboration and execution during high-intensity work periods.

Turn insights into action with Jotform

Strategic questions are only as powerful as the actions they inspire. To turn insights into results, you need a reliable way to capture, analyze, and respond to team feedback consistently.

That’s where Jotform comes in.

Whether you’re running one-on-ones, preparing for strategic planning sessions, or gathering feedback after a project retrospective, Jotform makes collecting and organizing responses practically effortless. With fully customizable templates, no-code forms, real-time analytics, and AI agents to automatically analyze qualitative feedback patterns, Jotform helps you transform thoughtful questions into clear direction and measurable progress.

Don’t just ask, act.

Build your own strategic feedback system with Jotform today!