In any conversation, whoever is asking the questions is leading the conversation.

Many people treat questions as an admission of ignorance. They avoid asking questions in meetings because they want to look competent and self-sufficient. But conversational direction follows the person asking the prompts.

This can be used at parties and at work. Sometimes you can switch conversation topics by broadening the scope (“will it scale?”, “does this policy work in other countries?”), sometimes you can dive deeper by asking follow up questions (“what is the better way of managing ex-East German factories post unification?”, “what problem does this architecture solve?”)

You can use it while receiving feedback: “What would a stronger technical specification have looked like for that project?” or “If you were presenting that rollout to the VP, what would you have highlighted differently?”

This remind me of my Personal Agency post. You don’t have to always flow with the conversation and leave thinking how boring or stupid it was. But don’t be pushy, you know yourself how easy it is to detect someone being pushy/manipulative.

Asking questions is also a good way of asking for thing without looking needy. People detect neediness immediately too, and calm curiosity puts people at ease.

For example, the good way to connect with seniors is to make low-friction requests. You do not need to corner an executive or ask someone to “be your mentor” like a formal proposal. Ask “I saw how your team handled database sharding during the last migration. My team is running into a similar constraint, could I get twenty minutes of your time to see how you evaluated those trade-offs?”

You do not lead by having all the answers. You lead by asking the questions that force the room to clarify what actually matters.

Wrote after listening to Soft Skills Engineering - Episode 189: Building relationships and handling negative feedback with special guest Jeff Leiken