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Checkin Questions for Impactful 1-1s

As a manager, your one-on-one meetings with direct reports represent precious opportunities to connect, coach, and align on priorities. But with busy schedules, it can be tempting to cancel these standing meetings or fail to make the most of the time. Thoughtful check-in questions are key to having productive one-on-one conversations.

Asking the right questions shows you care about your employees' well-being, progress, roadblocks, and goals. It builds trust and surfaces insights you need to empower your team. Make the most of your precious one-on-one time with these check-in question ideas organized into four key areas.

Well-Being Questions

Don't underestimate the importance of questions that show genuine care and concern for your employees as human beings. A few minutes of personal check-in time helps build psychological safety and trust. Here are some warm-up questions to try:

  • How are you doing today?
  • What's top of mind for you right now?
  • How do you feel about your work-life balance lately?
  • What's something fun you have coming up you're looking forward to?
  • How can I help take something off your plate?
  • Is there anything interfering with your ability to get your work done?

Keeping this portion of the check-in conversational shows you see your employees as whole people with lives outside of work. Be sure to actively listen without judgement and offer empathy.

Progress Questions

Once you've established personal rapport, turn the conversation towards discussing projects, progress, and priorities. Sample questions include:

  • What initiatives have you been focused on this week?
  • What progress have you made on [Project X]?
  • Are you on track to meet the timeline for [Project Y]?
  • What's top priority for you right now?
  • What areas are taking up most of your time or energy?
  • What recent wins have you had?

These types of check-in questions help align on status and next steps. Be sure to celebrate accomplishments and progress!

Roadblock Questions

Employees will be more likely to proactively ask for help if you create an environment of psychological safety. Asking about potential roadblocks shows you want to remove barriers to success. Questions to try:

  • Have you encountered any obstacles that are slowing your progress down?
  • What challenges do you anticipate with [Project Z]?
  • Is there anything blocking you from completing your work effectively?
  • Do you have the resources and information you need?
  • Who do you need input or approval from to move forward?
  • How can I help remove barriers for you?

When roadblocks surface, discuss potential solutions, offer resources, and follow up. Helping your team overcome obstacles will allow them to do their best work.

Goals Questions

One-on-one meetings provide the perfect opportunity to discuss professional development and future growth. Here are some questions to understand your employees' goals and aspirations:

  • What skills would you like to develop in the coming months?
  • What are your long term career goals? How can I help you work towards them?
  • What kinds of projects or responsibilities would you like to take on next?
  • How do you want to grow or challenge yourself in your role?
  • What training or education might help you with your professional development?
  • What feedback do you have on your current responsibilities and projects?

Having these development-focused conversations helps ensure your employees continue growing and improving in their roles.

Let Supernormal Help

Supernormal makes it easy to capture key insights from one-on-ones with AI-generated meeting notes. Automated notes free managers from manual note-taking so they can be fully present. Supernormal synthesizes discussion highlights, decisions, and action items so nothing falls through the cracks. Supernormal's notes reinforce the value of regular one-on-one check-ins by capturing takeaways and follow-ups.

Asking thoughtful check-in questions during one-on-one meetings leads to positive outcomes for both managers and employees. Checking in on well-being builds trust and rapport. Discussing progress and roadblocks helps align on priorities and remove obstacles. Setting goals keeps team members engaged, challenged, and developing new skills.

With regular check-ins powered by the right questions, managers gain valuable insights to lead their teams to success. Employees feel valued, supported, and invested in reaching their full potential. Frequent one-on-one conversations supported by AI meeting notes from Supernormal help managers maximize their leadership impact.

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