5 Questions Curious Leaders Ask Before Setting New Year Priorities

Key Takeaways

• Curiosity gives leaders a practical way to pause, question their assumptions, and build priorities that match the reality of their team and their business.
• Honest conversations about pressure, capacity, and expectations strengthen priority setting and reduce the chances of performance-driven decision errors.
• Collaboration becomes stronger when people feel their input will shape priorities rather than simply react to them.
• A deliberate curiosity practice helps leaders catch imagined pressure before it distorts planning and keeps the focus on what is truly required.
• Clear priorities emerge when leaders use grounded leadership questions that challenge stories, reveal gaps, and invite meaningful insight from their teams.

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New Year planning will expose every crack in a leadership mindset. You feel the pressure to show up with a clear plan, a confident answer, and a set of priorities that will not fall apart by March. The calendar flips, expectations rise, and every meeting seems to ask for certainty you know is not fully honest. Curiosity in leadership becomes hard to access when the pressure to perform sits on your shoulders.

Teams feel that pressure as well, even if it never gets named out loud. People want clarity, but they also want to trust that the priorities are grounded in what actually happened this year, not just in a story that sounds good. Strong leadership questions will pull real information to the surface, from misses and wins to capacity and appetite. You will set better priorities when you treat next year as a conversation to open, not a verdict to deliver.

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Curiosity in leadership becomes hard to access when the pressure to perform sits on your shoulders.

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Why New Year Priority Setting Feels Hard For Many Leaders

New Year planning sits at the intersection of hope and fatigue. You are asked to think big while still carrying the weight of projects that did not finish the way you wanted. Boards, investors, or senior leaders expect a confident story about growth, and your team expects stability and support. That tension makes it tempting to pick a direction quickly just to calm the noise.

There is also a quiet belief that strong leaders already know the answer before they walk into the room. That belief will push you away from curiosity in leadership, because asking open leadership questions can feel like admitting you missed something. Many leaders learned to protect their status by acting confident instead of being honest about their assumptions. The cost shows up later in rework, missed signals from the team, and priorities that no longer make sense halfway through the year.

Five Questions Curious Leaders Use To Set Clear Priorities

Curious leaders treat New Year planning as a structured practice of self-curiosity, relational curiosity, and strategic curiosity, not as a one-time performance of confidence. You will build stronger priorities when you ask questions that search for what is true, not for what will justify a plan you already want. The shift starts with pausing long enough to look at your own thinking, your team’s experience, and the system you are leading. Curiosity becomes the filter that stops you from repeating the same patterns under a new theme line.

These leadership questions are not soft or abstract. Each one targets a specific source of distortion that commonly shows up during annual planning, such as storytelling, pressure, and wishful thinking. When you move through them with your team, you surface more honest data and stronger insight. That insight will support a leadership mindset that feels grounded instead of reactive.

1. What assumptions shaped last year, and what proved inaccurate

Curious leaders start with their own stories. You walked into this year with beliefs about the market, your customers, your budget, and your team’s capacity. Some of those beliefs held up, and some did not, but they still influenced your choices. Treating those beliefs as neutral “facts” will weaken your planning for next year.

This question forces you to separate evidence from narrative. You will notice places where you overestimated demand, underestimated risk, or treated a guess as a guarantee. You might also see where caution held you back from moves that were available earlier. The goal is not self-criticism, but clear recognition of the mental shortcuts that shaped your year.

A curious leadership mindset treats inaccurate assumptions as valuable data, not as personal failure. You can look at what led you to trust those assumptions, who helped you challenge them, and where silence in the room allowed them to stand untested. That reflection will guide how you structure conversations for the year ahead. It will also remind you that every plan rests on assumptions, so you must stay curious long after the kick-off meeting ends.

2. What matters most to the people who rely on you

Your priorities do not live on a slide; they live in the daily experience of the people who depend on your choices. That group includes your direct team, cross-functional partners, customers, and sometimes investors. Each group carries different hopes, frustrations, and non-negotiables. Curiosity in leadership means you do not guess those needs from a distance.

This question pushes you to gather direct input before locking in your New Year priorities. You will listen for patterns in how people describe trust, support, and clarity. You will also hear honest feedback on where your leadership mindset helped or hurt their ability to do meaningful work. Those insights become practical constraints and design cues for next year’s focus.

A curious leader views these conversations as relational, not transactional. You are not running a quick survey just to tick a box; you are signalling that their experience will shape what gets attention. That signal builds psychological safety and encourages more honesty over time. It also helps you avoid priorities that look strong on paper but create quiet resentment because they ignore lived pressures.

3. What pressures are influencing decisions, and which are imagined

Pressure sits in every New Year planning meeting. Some of it is real, such as revenue targets, runway, or known external risks. Some of it is imagined, such as assumptions about what your board expects or what peers will think of your goals. Without curiosity, imagined pressure will quietly take control of your leadership questions.

This question asks you to name your pressures out loud. You list them, then sort them into “confirmed” and “assumed.” You check which pressures you can validate through direct conversations or clear data. You will usually find that several heavy feelings are based on stories, not on facts.

Curiosity in leadership helps you challenge each pressure instead of letting it shape your choices from the shadows. You will ask who benefits if you keep believing that story, and who pays the price. You will also ask what priority you would pick if that pressure dropped away. That process does not make real constraints disappear, but it does stop imagined ones from stealing your focus.

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Curiosity acts like a compass in this stage.

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4. What opportunities appear when you pause before choosing direction

Most leaders are rewarded for speed. Quick answers, sharp plans, and rapid action often get more recognition than steady, reflective work. That pattern quietly trains you to jump to solution mode as soon as someone asks about next year. The cost is that you skip over signals that only become visible when you slow down.

This question invites a pause, not for the sake of delay, but to widen your field of view. You will revisit conversations from the year, especially moments of friction and unexpected success. You will ask what those moments might be pointing to if you treated them as clues. Often, the most important opportunities sit just outside your first idea.

Curiosity acts like a compass in this stage. Instead of chasing every possibility, you ask which opportunities align best with your values, your team’s strengths, and your long-term intent. You pay attention to energy, not just to spreadsheets. That combination will lead you to priorities that feel both ambitious and honest about your current capacity.

5. What would be possible with stronger collaboration across your team

Many New Year plans quietly assume that leaders will carry the thinking and the team will carry the execution. That split feels efficient, but it disconnects the people closest to the work from the design of the work. Curiosity in leadership challenges that habit and invites more voices into planning. This question focuses your attention on what could shift if collaboration became a non-negotiable part of your process.

You start by asking where collaboration has already worked well this year, then study what made it effective. You look at cross-functional projects, crisis responses, or experiments that brought people from different roles into the same room. You listen for what allowed those efforts to move quickly without collapsing into chaos. Those stories will show you what your system looks like at its collaborative best.

Next, you ask where isolation or turf protection slowed you down. You will likely find projects that belonged to one team on paper but actually needed shared ownership. Stronger collaboration here does not mean more meetings; it means shared context, shared language, and shared accountability. Curiosity leads you to invite your team into priority setting early, so they help shape what they will later bring to life.

A leadership mindset that treats collaboration as a strategic advantage will produce more resilient priorities. People feel ownership because they helped build the plan, not just receive it. They also understand the “why” behind trade-offs, which reduces friction when things get hard. That foundation will support you during the inevitable surprises of the year ahead.

The more regularly you ask these five leadership questions, the less New Year planning will feel like a once-a-year high-stakes performance. Priority setting becomes an ongoing practice of curiosity, reflection, and dialogue. You and your team build a shared understanding of what matters most, where you misread reality, and what you want to do differently. That rhythm will keep your priorities honest long after the calendar resets.

How Curiosity Helps Leaders Build Priorities That Actually Hold Up

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Curiosity is not a personality trait that only belongs to certain leaders. It is a repeatable discipline that strengthens every step of planning, from reflection to execution. When curiosity sits at the centre of your leadership mindset, you will ask cleaner questions, tolerate uncertainty longer, and build plans that fit the system you actually lead. The result is not a perfect year, but a more honest one.

Curious leaders are less likely to cling to old stories just because they feel comfortable. They treat every conversation as a chance to learn instead of a stage to perform on. They also build teams that feel safe sharing dissenting views, which sharply improves the quality of annual planning. Curiosity in leadership does not slow you down; it protects you from rushing in the wrong direction.

• Focus on learning, not defending: Curiosity keeps you focused on what you can learn from outcomes instead of what you need to protect about your reputation. This shift reduces defensiveness and makes it easier to adjust priorities when evidence changes.
• Ask specific, grounded leadership questions: Curiosity turns vague prompts into clear questions about metrics, behaviour, and process. You will get better input from your team when your questions point to concrete moments rather than abstract themes.
• Build space for reflection in the calendar: Curiosity needs time. You strengthen your planning when you schedule regular check-ins that review priorities against reality, so you do not wait until next year to discover misalignment.
• Make it safe to say “I do not know”: Curiosity in leadership normalizes uncertainty. When leaders admit they do not have all the answers, teams feel invited into the problem-solving process and are more likely to share ideas earlier.
• Test priorities with small experiments: Curiosity turns big bets into informed experiments. You can design small, time-boxed tests that gather data before you commit more resources, which keeps priorities flexible and grounded.
• Use curiosity as a filter for new requests: Curiosity gives you language to question incoming requests from stakeholders. You will ask how each new idea supports agreed priorities and what will have to move if you say yes.

Curiosity holds your priorities accountable to reality instead of to ego. When you keep asking what is true, what has shifted, and what you might be missing, your plan becomes a living tool instead of a static document. Teams respond well to this because they can see that their input and experience will matter across the year. That sense of shared responsibility will support stronger follow-through on the goals you set.

How Curious As Hell Supports Leaders Planning Their Year Ahead

Leaders who are serious about curiosity often know what they want to do differently but lack a simple, grounded way to start. Curious as Hell offers a practical lens for self-curiosity, relational curiosity, and strategic curiosity that fits into the rhythm of leadership, not outside it. The questions and stories collected through hundreds of conversations with founders, executives, and operators give you language that feels real, not theoretical. You get tools that help you hold pressure honestly while still showing up with confidence for your team.

Curious as Hell supports your New Year planning by giving you repeatable practices, not just ideas. You can use its questions to structure off-sites, one-on-ones, and leadership team sessions so your priorities reflect lived experience as well as ambition. The focus on curiosity in leadership helps you reframe tough conversations, name unspoken tensions, and turn resistance into useful information. Leaders who apply this work build stronger trust, clearer priorities, and a leadership mindset that holds steady under pressure.

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