This series of “Themed One-on-Ones” was originally created to solve one problem: “not knowing what to talk about”. The backstory is plain: as a leader, I noticed that during one-on-ones people often had nothing to say, or the conversations wandered off course, so I prepared a topic list for each theme — before the conversation, think it through yourself first (prepare your own feelings); then talk through the questions (points to cover); and finally leave an open channel for venting and feedback.

Usage Principles

  • Solve one problem per conversation. Try to keep each theme to 30 to 60 minutes and avoid going too far off track. Each theme below is an independent topic list — pick what you need; you don’t have to cover everything in one sitting.
  • Themed conversations raise many questions, so stay focused. At the start, confirm “which problem are we talking about”; at the end, confirm “who takes the next step, and when”.
  • Anyone can choose the theme. It doesn’t have to be the leader — if a team member has been feeling anxious lately, or wants to talk about product sense, they can simply say “I want to talk about this theme”. Letting the team member set the topic usually leads to more genuine conversation.

Topic Map

The topics are grouped along two dimensions to make them easy to pick: abstract (about cognition and mindset, producing no concrete tasks) and practical (about methods, producing an actionable next step).

Abstract group

  • Anxiety and pressure: from unease, talk your way to an actionable work boundary
  • Slowing business growth: turn the team’s collective anxiety into “set the tone first, then address the critical path”
  • Insecurity, comparison, and long-term capability: turn unease into an actionable direction

Practical group

  • Time management: a conversation about “busy”
  • Growth milestones: turn “I want to grow” into something concrete
  • Ownership and responsibility: turn “taking initiative” into something with clear boundaries
  • Product sense: how engineering and product talk through “is this worth doing”
  • Structured thinking: turn “being organized” into something you can train
  • Capability models and self-assessment: how to know where you stand
  • Goals, planning, and retrospectives: turn “handing in homework” into your own growth
  • How to communicate well: from “not knowing what to talk about” to getting the conversation clear

Universal: start by defining the problem — how to open a one-on-one (applies to the first conversation on any theme).

Three Things That Determine the Quality of a Conversation

  1. Allow declining to answer, pausing, and rescheduling. When there is no sense of safety, information does not become more truthful just because you demand it more forcefully.
  2. Commitments must respect capacity. Sustained overload is not proof of dedication. Time, energy, and existing commitments are all constraints that must be put on the table.
  3. Work conversations can only address working conditions, collaboration, and support. If psychological distress persistently affects your life, sleep, or safety, seek qualified local professional support or emergency help — a one-on-one is not psychological counseling.

Some Open Topics You Can Discuss

Beyond the themes above, here are topics you can bring up at any time:

  • If I have nothing on my plate, what can I do?
  • What is managing up?
  • The relationship between cognition, awareness, and behavior.
  • If you were to redo something, would you do it better? If life could be replayed from now backwards, would you want to relive it? If you knew the future outcome, would you still have the courage to move forward?
  • When faced with something you cannot solve yourself, how should you respond? (For example, when you can’t get others to move on a collaboration.)
  • On “lying flat” and “involution”: mindset and behavior.
  • Share your views on eight topics: freedom, health, happiness, family, love, friends, wealth, and career.

Closing

This series is not meant to be read in one sitting; pick a theme as needed: start by defining the problem, leave a “venting and feedback” channel when you finish, and continue next time. With practice, the journey from “not knowing what to talk about” to “knowing what to talk about” grows shorter and shorter.