1:1 Question Bank

How is your mental battery and energy level this week on a scale of 1 to 5?

Context: Quick quantitative pulse check that normalizes talking about energy.

What was the highlight of your past week, inside or outside of work?

Context: Encourages positive reflection and shares personal context.

What is one thing about your day-to-day work environment that you would change if you had a magic wand?

Context: Uncovers low-hanging ergonomic or environmental friction.

Did you get to do any deep, uninterrupted work this week, or did it feel fragmented?

Context: Evaluates calendar fragmentation and maker time.

What is one small thing I could do differently or start doing to support you better?

Context: Lowers the bar for constructive criticism with "one small thing".

Where do you feel I am providing too much guidance, and where would you like more context or direction?

Context: Calibrates the micro-management vs under-management spectrum.

Is there any decision made recently where you felt out of the loop or disagreed with the direction?

Context: Unearths silent disagreement before it turns into disengagement.

How clear are our team’s top three priorities for this quarter in your mind?

Context: Tests strategic clarity without putting the employee on the defensive.

Am I giving you feedback early enough, or does it ever feel like a surprise?

Context: Ensures feedback latency is near zero.

Who on the team or in adjacent squads has been especially helpful to you recently?

Context: Surfaces invisible glue work and positive peer recognition.

How comfortable does it feel to voice an unpopular opinion or admit a mistake in our team discussions?

Context: Direct measure of psychological safety within the squad.

Is there any simmering tension, friction, or misalignment in the team that we need to address?

Context: Catches interpersonal friction before it escalates.

Do code reviews and technical debates in our team feel constructive and collaborative, or stressful?

Context: Validates health of the day-to-day engineering culture.

What is taking up too much of your time right now that feels unnecessarily painful or bureaucratic?

Context: Identifies systemic overhead and process waste.

Which recurring meeting on your calendar feels least valuable or could be handled asynchronously?

Context: Protects focus time and prunes stale meetings.

Is there any dependency on another team that is stalling your progress or causing uncertainty?

Context: Signals where the manager needs to step in to negotiate cross-team boundaries.

If we could improve one part of our local development, CI, or deployment workflow, what would make the biggest impact?

Context: Pins down developer experience bottlenecks.

Looking at our upcoming roadmap, which problem space or project are you most excited to tackle?

Context: Aligns project staffing with genuine personal motivation.

What is a skill or technology you don’t currently use in your day-to-day work that you would love to master?

Context: Informs stretch opportunities and learning budgets.

When you imagine your role 1–2 years from now, are you leaning more toward technical leadership, domain depth, or people management?

Context: Helps navigate the dual career ladder (Staff+ IC vs EM track).

What is one recent piece of work where you felt you performed at your absolute best?

Context: Identifies high-water marks and energizing work.

How sustainable does your current pace of work feel over the next 2–3 months?

Context: Assesses marathon pace vs unsustainable sprint burnout.

Are you able to completely shut down your laptop and work notifications in the evenings and weekends?

Context: Guards boundaries and unplugs culture.

If you had to drop one task or project this week to breathe easier, which one would it be?

Context: Instantly surfaces lowest-value/highest-stress work.

Do you feel pressure to respond to messages outside working hours, even if it’s unspoken?

Context: Surfaces accidental peer or leadership pressure.