As a people leader, this might be the most valuable five minutes you spend reading anything this year. These five questions can set you up for a smoother, more successful year ahead.
As a former organizational leader turned leadership coach & consultant, I’ve seen one truth play out again and again:
the quality of your engagement with your team shapes both their commitment and your organization’s results.
Before You Begin: Two Non-Negotiables
Step 1: Make the Time
If you don’t already have individual check-ins scheduled — not just with direct reports, but with indirects where feasible — make it happen before year-end.
Thirty minutes of focused conversation can prevent months of frustration later.
Step 2: Do the ‘Defining Success’ Gut Check
Here’s the test: Could both you and each of your team members clearly describe what success looks like in their role, and how it connects to our broader priorities?
If the answer isn’t an immediate “yes,” that’s your starting point. It’s the foundation for everything that follows. Alignment here prevents confusion and underperformance later.
Make the Shift: From Checklist to Connection
Most year-end check-ins or reviews are run like status updates: a list of metrics, feedback, and “growth opportunities.”
However, when done right, they can build trust, reveal blind spots, and energize your team for the year ahead.
The key is shifting from a one-way review to a two-way conversation rooted in reflection, learning, and dual clarity. Are you ready for a discussion vs. a lecture?
If you’re thinking about how to embed this mindset permanently, explore our Leadership Competencies series for more tools and frameworks.
The 5 Questions
- “What accomplishments are you most proud of this year, and where do you feel you’ve made the biggest impact?”
Opens with positivity and helps you see what they value. - “What part of your work energizes you most, and how well do you feel your strengths are being used?”
Reveals motivation and [mis]alignment between role and strengths. - “What challenges stretched you the most this year, and what did you learn from them?”
Encourages self-assessment and a growth mindset. Good prompt for aligning future goals. - “Is it clear to you what success in your role looks like, and how it connects to our broader priorities?”
Assesses alignment, and provides invaluable systemic insight. - “What do you need more (or less) of from leadership to be successful and grow in the coming year?”
Invites upward feedback and helps identify blind spots (leadership, team dynamics, etc.). Good prompt for aligning goals.
Why It Matters
These conversations shape more than individual performance, they define your team’s culture.
- You’ll leave with insights that drive engagement, retention, and realignment heading into the new year.
- How you listen, respond, and follow through tells your team what leadership really means at your organization.
- Every moment of reflection and alignment builds the trust that drives results long after the meeting ends.
You still have time. Block a day, or a few afternoons. Thirty minutes per person can change a year of reactivity into one of momentum.
And if you want help creating the kind of trust and candor that make these conversations game-changing, that’s what we do at Emerging Trails; We help leaders evolve through better conversations.
Pro tip: Do this again midyear. It’s the simplest way to stay ahead of attrition.
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