As the calendar winds down, it’s tempting for leadership teams to coast on momentum or postpone tough conversations until “after the holidays.” Yet, the most successful teams use this time intentionally to assess, recalibrate, and set the tone for the year ahead. The key to a strong start isn’t just making plans—it’s asking the right questions.
Here are seven questions every leadership team should tackle before January 1:
- What worked, and what didn’t? Take an honest look at your results. Celebrate wins, but also identify areas where strategies fell short or initiatives lost traction. Avoid blame; focus on insights.
- Where are we drifting? Even high-performing teams can lose alignment. Are departments or individuals moving in different directions? Identify misalignments before they become entrenched habits.
- What are our top priorities for next year? Clarity is power. Narrow the focus to the few initiatives that will move the needle. Less is more when it comes to strategic attention.
- Who owns what, and is accountability clear? Responsibility without clarity leads to drift. Confirm roles, responsibilities, and decision-making authority across the team.
- What risks should we prepare for? Markets, competition, and internal pressures evolve quickly. Anticipating obstacles—and having contingency plans—prevents surprises from derailing progress.
- What relationships need attention? Strong internal and external relationships are the glue of sustained performance. Consider which connections need nurturing, both within the team and with clients or partners.
- How will we measure success? Metrics matter, but so do behaviors and habits. Decide how you’ll track progress, hold each other accountable, and course-correct when necessary.
Answering these questions isn’t a one-and-done exercise—it’s a conversation starter. It encourages rigorous reflection, exposes gaps, and drives alignment. Teams that commit to this annual reset don’t just plan—they enter the new year with clarity, confidence, and a shared sense of purpose.
Taking the time to reset now ensures the first quarter is driven by deliberate choices, not reactive firefighting. Leadership teams that ask these hard questions—and answer them honestly—start the year not just ready to execute, but ready to win.
