The 5 Questions Every Tech Leader Should Ask Their Team This January

January is reset season. While resolutions dominate our personal lives, it’s also the ideal time to recalibrate professionally. For tech leaders, this means engaging your team in meaningful conversations—not about bandwidth or backlog, but about vision, roadblocks, and potential. The right questions now can prevent drift later.
Here are five questions worth asking in your first one-on-ones or team huddles this year:
1. What’s one thing that slowed us down last year—and how do we fix it?
Encourage your team to reflect. This isn’t about blame; it’s about friction. Whether it was manual testing, unclear handoffs, or surprise scope creep, identifying root issues early sets the tone for improvement.
2. Where do you see opportunities to use AI or automation?
With generative AI moving fast, your team likely has ideas—if not prototypes. Ask, listen, and log the patterns. It shows you’re open to innovation and can unearth grassroots experiments worth scaling.
3. What’s one skill you want to develop in 2026—and how can we support that?
Employee growth is leadership gold. Give people permission to speak openly about where they want to go—and then point them toward courses, mentorships, or stretch projects to get there.
4. Where do we risk getting stuck in “the way we’ve always done it”?
Legacy thinking isn’t always tied to legacy systems. This question reveals hidden inertia. Look for dated processes, tooling habits, or meeting formats that need rethinking.
5. What would make our team more connected—even while working remotely?
Hybrid work isn’t going away, but silos can be. This question opens the door for small culture upgrades—more in-person meetups, Slack rituals, cross-team shoutouts, or monthly BBQs (like we do at Intertech).
Final Thought:
Great leaders start the year with curiosity. These five questions won’t just inform your strategy—they’ll demonstrate that your leadership is grounded in listening, alignment, and continuous improvement.



