New manager: your first five one-to-ones

Here's a training outline. Build it as a draft program in upcoach called "New manager: your first five one-to-ones":
one section per day, with a lesson,
worksheet, task list or check-in for each item, using the text and questions word for word.
Questions marked (1 = ..., 5 = ...) are 1-5 scales.
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Training: New manager: your first five one-to-ones
For: New team leads in their first months
Length: 5 days

Day 1: Open the first one-to-one
- Lesson: The one-to-one is their meeting
  A one-to-one is a regular, private meeting between you and one person on your team. It is their time, not a status update. In this first round your job is to listen and learn how each person works, not to solve problems.
  Keep it to 30 minutes, at the same time each week or every two weeks. Don't cancel; if you must, move it. Open the first one by saying why you're doing it: "I'd like us to meet every week for 30 minutes. This is your time: what's on your mind, what's in your way, and how I can help." Then ask, and listen more than you talk.
- Worksheet: Prep: one-to-one #1
  1. Who are you meeting, and what do you already know about their work?
  2. In one or two sentences, what will you say about why you're starting one-to-ones?
  3. Write the three questions you'll ask. If you're stuck, use these: What's going well for you right now? What's getting in your way? How do you like to get feedback?
  4. What will you not do in this meeting? (For example: fix their problems for them, talk about your own week.)
  5. When is your next one-to-one with them?

Day 2: Ask, then listen
- Lesson: Questions that get past "fine"
  Most first answers are "fine" or "busy". The useful answer comes after one more question: "What makes it busy?" "What would make next week easier?" "Can you give me an example?"
  When they stop talking, wait five seconds before you speak. People often add the important part after a pause. Take short notes in their words, plus anything you agreed to do, and read them before your next meeting with that person.
- Worksheet: Prep: one-to-one #2
  1. Who are you meeting today?
  2. What did you notice in your first one-to-one that you want to do differently today?
  3. Write one follow-up question for each of your opening questions.
  4. What's one thing you could ask about that isn't this week's tasks? (Their goals, how they like to work, what they want to learn.)
  5. What will you write down during the meeting?

Day 3: Agree on what happens next
- Lesson: End with actions, and keep yours
  End every one-to-one with a short recap: what they will do, what you will do, and when you will meet again. Say it out loud so you both hear the same thing.
  Your own actions matter most. If you said you'd find out about the training budget, find out and tell them before your next meeting. A new manager earns trust through small promises kept, more than through anything said in the meeting.
- Worksheet: Prep: one-to-one #3
  1. Who are you meeting today?
  2. What did you agree to do in your first two one-to-ones? Which of those have you done?
  3. Write the words you'll use to close today's meeting with a recap.
  4. Is there something you need to tell this person (a change, a decision, a piece of feedback)? Write how you'll say it.
- Check-in: Day 3 check-in
  1. How confident do you feel running one-to-ones right now? (1 = not at all, 5 = very)
  2. How much of the talking have you done in your one-to-ones so far? (1 = almost none, 5 = almost all)
  3. What's the hardest part so far, in one sentence?

Day 4: Feedback both ways
- Lesson: Ask for feedback before you give it
  Ask first: "What's one thing I could do differently that would help you?" Thank them for the answer, even when it's hard to hear, and don't explain yourself on the spot.
  When you give feedback, make it specific and recent: what you saw, the effect it had, and what you'd like next time. Positive feedback works the same way: "In Tuesday's client call you summarised the options clearly, and the client decided in five minutes."
- Worksheet: Prep: one-to-one #4
  1. Who are you meeting today?
  2. Write the question you'll use to ask for feedback on yourself.
  3. Write one piece of specific positive feedback for this person: what you saw, and the effect it had.
  4. Is there a piece of developmental feedback to give? Write it the same way: what you saw, the effect, and what you'd like next time.
  5. If their feedback on you is hard to hear, what will you say in the moment?

Day 5: Make it a habit
- Lesson: Keep the rhythm
  Your first round is done. What matters now is that one-to-ones keep happening when the week gets busy. Put each one in the calendar as a recurring meeting, keep a running note for each person, and read it before you meet.
  Every few months, ask each person how the meeting itself is working for them: how often, how long, and what you should cover.
- Worksheet: Prep: one-to-one #5
  1. Who are you meeting today?
  2. What's the one topic you most want to cover with them?
  3. What will you ask them about how future one-to-ones should run (how often, how long, what to cover)?
- Worksheet: Day 5 reflection
  1. What did you learn about your team this week that you didn't know before?
  2. Which one-to-one went best, and why?
  3. Which one was hardest, and what would you do differently next time?
  4. List the actions you promised this week, and when you'll finish each one.
  5. How often will you meet each person from now on? Is it in your calendar?
  6. What do you want to work on with your coach next?
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