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18 Strategic Questions To Ask Your Team

Last Updated: Thu Apr 04 2024

Only 2% of leaders are confident they'll nail their strategic goals. That's right, just 2%. It's like having a map but not knowing how to use it.

And, 80% of these leaders are champs at making plans, but when it comes to getting things done? Only 44% hit the mark.

This is where strategic questioning comes in. It's not just about asking questions; it's about asking strategic questions to your team.

Let’s dive in and take a look at 18 such questions.

6 Strategic Questions for Team Engagement

67% of strategies tank because of poor execution. Add to that, 4.5% of strategy potential gets lost in translation.

Not great, right?

Scottish-American industrialist and philanthropist Andrew Carnegie said something around this: “Teamwork is the fuel that allows common people to attain uncommon results.”

Let's break it down with six strategic questions that'll turn your team into engagement superstars.

  • What’s our main goal and why? This one's a classic. It aligns everyone's sights on the big picture, fostering unity and purpose.

  • How does your role drive us towards our goal? Personalize it. Let each team member see how they're a crucial piece of the puzzle.

  • What barriers are holding us back? It's like opening a can of worms, but in a good way. Identifying hurdles is step one to leaping over them.

  • How can we be more effective in our roles? This isn't about finger-pointing. It’s about growth, finding ways to be better, together.

  • Where do you see opportunities for innovation? Everyone's got ideas. This question turns those light bulb moments into game-changers.

  • How can our team better support each other? Teamwork makes the dream work, right? This question strengthens those all-important bonds.

Each question is a key turning the lock of engagement. They're not just queries; they're conversation starters, icebreakers, and idea generators.

They tap into the collective brainpower of your team, transforming strategy into action.

5 Strategic Questions for Understanding Goals

Clarifying goals is crucial. About 61% of executives feel like they're in deep water when it comes to strategic challenges.

English-American author and inspirational speaker Simon Sinek hit the nail on the head: "No one knows everything. But together, we know a whole lot.

So, let's dive into five strategic questions that'll bring your team's collective smarts to the forefront.

  • What does success look like for our project? Vision is key. This question paints a clear picture of the end goal.

  • How do our individual roles contribute to this success? Like pieces of a puzzle, everyone needs to see where they fit.

  • What are our immediate and long-term priorities? It's like zooming in and out on a camera, ensuring clarity at every level.

  • How will we measure our progress? If you can't measure it, you can't manage it. This question sets tangible milestones.

  • What are potential roadblocks and how can we navigate them? Forewarned is forearmed. Identifying challenges early on is half the battle won.

Each question is a tool, sharpening the focus and honing the strategy.

It's about tapping into that shared knowledge pool, ensuring everyone's on the same page.

These questions transform confusion into clarity, turning the tide from feeling unprepared to being unstoppable.

4 Questions for Unearthing Team Challenges

Unearthing team challenges is like a treasure hunt – you need the right map.

With 74% of organizations struggling to support an agile culture, it's clear there are hidden challenges.

Let's explore four key questions to uncover these obstacles.

  • What are the most significant barriers we face in adopting an agile approach? It's about identifying the elephants in the room. This question lays bare the biggest hurdles.

  • How does our current workflow hinder our agility? This digs into the nitty-gritty of processes and practices that may be slowing the team down.

  • What resources or support do we need to overcome these barriers? It's not just about spotting problems. It's about finding solutions.

  • How can we foster a more supportive culture for agile practices? This addresses the critical aspect of culture in implementing agile methodologies.

Each question acts as a spotlight, illuminating challenges that might be lurking in the shadows.

These queries will drive the team towards a more agile and responsive way of working.

It's about turning the tide from resistance to resilience, ensuring your team isn't just surviving but thriving in an agile environment.

3 Questions to Encourage Solutions and Innovation

Sparking innovation and solutions in your team can be a game-changer.

With the right questions, you can unlock a 237% boost in performance, as seen in organizations with a robust agile culture.

Here are three strategic questions to fuel this transformation.

  • What innovative solutions can we introduce to improve our agility? This question encourages thinking outside the box, inspiring creative solutions for enhanced agility.

  • How can we leverage diverse perspectives to drive innovation? Emphasizing inclusivity, this query taps into the varied experiences within the team for fresh ideas.

  • What steps can we take to make our process more adaptable to change? It’s about being proactive, seeking ways to evolve and stay ahead of the curve.

Correct questions are your toolkit for nurturing a culture of innovation.

These inquiries are the seeds of change. Each answer brings a new perspective, pushing the boundaries of what's possible.

It's about creating an environment where innovation is the norm.

Crafting the Right Environment for Strategic Questioning

Crafting the right environment for strategic questioning is key. It's like setting the stage for a great performance.

Naturalist and geologist Charles Darwin said, “It is the long history of humankind (and animal kind, too) that those who learned to collaborate and improvise most effectively have prevailed.

  • Timing is everything: Choose moments when the team is most receptive, not during high-stress periods.

  • Setting also matters: Opt for a neutral, comfortable space that encourages open dialogue.

  • Follow-up is crucial: It shows you value their input and are committed to action. This approach not only fosters openness but also aligns well with the increasing adoption of agile methods across various sectors.

The right environment is the breeding ground for innovation and success.

Strategic Questions for Leadership Development

Strategic questioning is a goldmine for personal growth in leadership.

By engaging in this practice, leaders learn directly from their team's feedback. This is a two-way street: leaders grow, and a culture of continuous improvement blooms.

Create an environment where feedback is heard and acted upon. This dual benefit enriches both the leader and the team, creating a dynamic of mutual growth and ongoing development.

Think of it as sharpening your leadership skills while elevating your team's performance.


Wrapping this up, strategic questioning is the secret sauce for a stronger, more unified team. It's about turning every conversation into an opportunity for growth and connection.

For leaders, it's a call to action: weave these questions into your daily interactions. Watch as they transform your team dynamics, fostering an environment where everyone thrives.

Remember, the right questions don't just elicit answers; they spark innovation, build trust, and drive performance.

So go ahead, ask away and lead your team to new heights.