Your first 1-on-1 meetings as a new manager are the most important meetings of your career. They are your single best opportunity to build trust, calm fears, and gather the critical information you need to succeed. But most new managers get them wrong. They talk too much, and they ask the wrong questions.
Your first 1-on-1 meetings as a new manager are the most important meetings of your career. They are your single best opportunity to build trust, calm fears, and gather the critical information you need to succeed. But most new managers get them wrong. They talk too much, and they ask the wrong questions.
The goal of these first meetings is not to provide solutions; it is to listen. Your job is to understand the world from your new team’s perspective. To do that, you need to ask powerful, open-ended questions. Here are the three “secret weapon” questions every first-time manager should ask.
Question 1: “What’s working that you’d hate for me to change?”
This is the single best opening question you can ask. It immediately shows respect for the existing team and their work. It calms the universal fear that a new boss is going to come in and break everything that’s already working. It’s a powerful act of humility that says, “I’m here to learn from you.”
Why it’s a secret weapon: The answer to this question instantly reveals what your team values most. It could be a specific process, the team’s collaborative culture, or the flexible work schedule. Whatever it is, you now know what you must protect to maintain morale and stability.
Question 2: “What’s the biggest ‘pebble in your shoe’—the small, annoying thing that gets in your way every week?”
This is your hunt for easy, quick wins. You are not asking for a grand strategic plan. You are asking for a small, persistent annoyance. It could be a clunky piece of software, a confusing weekly report, or a meeting that should be an email.
Why it’s a secret weapon: Solving one of these small “pebbles in the shoe” in your first 30 days builds more trust and credibility than any big, strategic announcement. It proves, beyond a shadow of a doubt, that you were listening, that you care about your team’s daily experience, and that you are there to help, not just to command.
Question 3: “If you were in my shoes for the next 90 days, what would be your number one priority?”
This is a brilliant way to ask for advice without looking weak. You are not saying, “I don’t know what to do.” You are saying, “You have a valuable perspective, and I want to hear it.” It empowers your team member, shows that you value their strategic mind, and gives you unfiltered insight into what they believe are the team’s most pressing challenges and opportunities.
Why it’s a secret weapon: The answers to this question will form the foundation of your own 90-day plan. Your team will literally give you the roadmap to your own success. It’s the ultimate way to build alignment and get buy-in from Day 1.
These three questions are just the beginning of your journey. They are the cornerstone of the “Survive & Observe” phase of your first month as a manager. For a complete roadmap covering all three months, from building trust to leading with a strategic vision, be sure to read our main pillar post: The Ultimate Survival Guide for New Managers: Your Definitive 90-Day Action Plan.
To turn these insights into a structured, day-by-day action plan, you need a framework. The First-Time Manager’s 90-Day Journal is the actionable companion designed to help you apply these lessons and build the confidence you need to thrive.
FAQ: First 1-on-1s
How long should my first 1-on-1 meeting be?
Schedule at least 45-60 minutes for each initial 1-on-1. This sends a powerful signal that you are not rushing and that you genuinely want to listen. You may not need the full time, but having it booked shows respect for the conversation.
Should I take notes during the meeting?
Yes, but ask for permission first. A simple, “Do you mind if I take a few notes? I want to make sure I remember everything you’re sharing,” is perfect. It shows you are taking their input seriously. Use a pen and paper, not your laptop, to avoid creating a physical barrier between you.