The usual difficulties with a one-on-one are two: not knowing what to talk about, or discovering halfway through that the two of you are answering different questions. It is enough to start from a concrete phenomenon that can clearly state “what problem we are solving.”

At the opening, write the problem out first: what phenomenon we want to change; whom it affects; what decision we need to make this time. Keep facts, guesses, and conclusions separate, so the other person doesn’t have to push back on your tone first and can instead directly add the evidence they have seen.

Preparing Your Own Feelings

Before getting into the topic, each person first answers these few questions on their own. Their purpose is to let both sides come in with concrete observations rather than with emotions or conclusions.

  • Which recent thing made you feel you “should talk with the other person”? In which specific collaboration did it happen?
  • If you could describe this thing in only one sentence, what would it be?
  • What checkable phenomenon have you observed? (Not “it doesn’t feel great,” but “in the last two handoffs, the key decisions weren’t recorded.”)
  • What impact are you worried it will have? Is this a fact, a guess, or your emotion?
  • What output do you hope to get from this conversation — a decision, an explanation, or a next step?
  • Which things have you already thought through clearly, and which are you still guessing about?

Points to Discuss

The questions below can be started from the first one and talked through in order; when you reach a point you can’t stop talking about, keep going around it.

  • Specifically, which problem are we dealing with? Can you give a recent example?
  • What phenomenon have you observed that makes you think there’s a problem here?
  • Whom does it affect? What does it affect — time, experience, quality, risk, or the choice of the next step?
  • What cause do you currently suspect? How can this suspicion be verified?
  • Which parts are facts, which are your judgments, and which are only assumptions?
  • There is really one thing we need to decide in this conversation: what is it?
  • Which things are explicitly out of scope for this discussion? Mark them out clearly first to avoid drifting.
  • If we leave it unhandled for now, what will happen? How severe will it be, and how soon will it surface?
  • What evidence is needed to confirm this problem? Who has it?
  • What is the smallest next step we can take? Who will do it, by when, and what will they deliver?

When closing, confirm three things: what problem we agree on, what we explicitly will not handle this time, and who will bring back what information or action by when. If after talking you find that the real problem is different from what you first thought, rewriting the problem is more valuable than forcing the conclusion through — the output of communication is not necessarily consensus; it can also be a clearly stated disagreement and a smaller validation.

Venting and Feedback

A one-on-one is not one-way questioning. Either side can proactively stop and say: I’m not interested in this topic / I’m not ready yet / are we solving the same problem right now. Allow refusing to answer, pausing, and rescheduling.