from interrogation to exploration
using the Left/Right Column to balance advocacy & inquiry
Over the last three posts, we have learned to surface the private thoughts that are in our heads (the Left/Right Column) during conversations, to learn how we are getting to actions from observed data with the help of the Ladder of Inference, and to iterate on actual discussions with the Four-R loop.
Today, we focus on three varieties:
Genuine questions – curiosity in its purest form.
Leading questions – curiosity wearing a judge's robe.
Advocacy and Inquiry – even genuine questions, when asked, can be treated like cross-examination and can feel like a storm of questions.
To work with these three varieties, we need the left/right column tool to help us expose our thoughts associated with what we said. Why? If we were to ask someone, "Did you send that email?", can we determine what kind of question it is?
Are we curious about it?
We know it was not sent, so we put pressure on that person.
We gently remind that person to send an email.
Hard to tell? Let's explore how we can identify and address any issues, if necessary, to facilitate better collaboration. But first, let's define what genuine questions are and what advocacy and inquiry are.
What counts as a genuine question?
A genuine question is one that:
You want to know the answer to, you are interested in hearing it
The answer can surprise you
You are willing to change your opinion/view based on the answer
Getting back to the email example, if we ask the question with the thought, "I'm curious if the email was sent", it passes a definition of genuine questions.
All other options are not genuine; they expect an answer / or confirmation of what we know. It's what is called a leading question. Like in court: Was that you who drove a silver Honda Civic into a cherry tree on the night of 23rd of January 2025 at 11:45 pm?
We will discuss leading questions further below.
Advocacy & inquiry: showing your map and asking for theirs
Think of advocacy as laying your map on the table - data, hunches, worries, even the knot in your stomach you'd rather hide. Inquiry is the move where you lean in and ask, "What does your map look like?"
When the two alternate, a conversation breathes. Pure advocacy becomes a lecture; pure inquiry feels like an interrogation lamp. A well-timed sentence of advocacy helps the other person see why you are asking (an inquiry that follows your advocacy).
Example:
The last two sprints, we lost a day due to late migration issues, and I'm nervous about repeating that. How are we planning to test the script this time?
First half: advocacy. Second half: inquiry. Together: collaboration.
Spotting a leading question before it escapes your mouth
If any answer other than the one you expect would irritate you, the question is leading.
Common giveaways are the nervous tag-word at the end ("…right?"), the negative yes/no ("You haven't pushed to prod yet, have you?"), or a hidden judgment ("Don't you agree this API is over-engineered?").
Rewrite your question by stating the concern plainly, then posing an open question:
"I'm worried this API feels heavy for mobile bandwidth. What constraints did you weigh when you designed it?"
Two examples
Conversation context: The senior (S) is discussing migration with the junior (J). The release is happening Friday afternoon, and today is Monday.
We will also use the left/right column tool to surface hidden thoughts and feelings. This time I will simplify this by showing a dialogue using bullet points, and then on the right of what was said in brackets, the thoughts of S.
The leading version
S: You’ve run the migration locally, right? (S's thoughts: Ugh, the migration script is still missing. He should already know this matters. Let me corner him.)
J: Not yet; I wanted to write it and execute it on Thursday morning. (S's thoughts: If he says no, I can prove my point.)
S: Don’t you think it’s risky to leave it so late? (S's thoughts: Great, here we go.)
Outcome: junior braces, senior gathers evidence, nobody learns.
The balanced rewrite
S: In the last two sprints, we discovered migration issues late and lost a day each time. I’m nervous about repeating that. How are you planning to test the script this time? (S's thoughts: I’ve been burned by late migrations before. I should say that aloud, then find out his plan.)
J: I was going to pair with Alex on Thursday, but you're right, I will move it to tomorrow for safety reasons. (S's thoughts: Nice, there is a plan! And we have also mitigated a risk)
S: That sounds great. Alex is the best guy to pair with, and thank you for moving this session a bit earlier. (S's thoughts: Nice.)
Outcome: once the senior puts his worry on the table, the junior can respond with facts instead of defensiveness, and collaboration replaces coercion.
A quick pre-flight check
Right before you hit Enter in Slack or let the words leave your mouth, breathe once and ask:
Could the reply genuinely update my view?
Have I revealed the data or feeling that drives my question?
Am I about to ask a third straight question without offering any of my thinking?
If you answered yes to the first two questions and no to the third one, then iterate, or do not ask :)
Try it this week
Pick one tense exchange from the last few days and write it in Left/Right form. Circle every question. Score each as 1 (genuine) or 0 (leading). Rewrite the 0s by adding a slice of advocacy and turning them into open inquiries. Then, read the new version aloud or role-play it with a teammate. Feel the difference when curiosity is real.
Post your before-and-after (anonymised) in the comments. Your experiment might be the nudge another reader needs to move from interrogation to exploration.
Happy debugging of code and questions