Listening 6: Deliberate Inquisition

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This is the listening series. Check out all the posts in the series here.

In the last post, we talked about two skills I have worked on to increase my impact in collaborations: deliberate inquisition and deliberate appreciation. This post focuses on deliberate inquisition, and in the next one we’ll talk about deliberate appreciation.

I’ve learned a critical lesson as I have increased in seniority:

rocketships by @lmnsqz_games

If somebody else is doing the work, they should get to decide how to do it.

Of course, I can ask questions that cite my concerns:

  • How high do you think is the risk of X?
  • How do you think we might mitigate Y?
  • What’s the contingency plan if Z breaks?

But I’m not dictating a decision. If someone else is responsible for building and maintaining a thing, shouldn’t that labor come with the opportunity to get the final say?

I have noticed that the inclination to force implementation feedback on others often comes paired with a sense of insecurity about one’s own contributions.

I tend to tell people what to do more vigorously when I feel like I haven’t done enough myself lately. I use dictating others’ work as a defense mechanism. So I conflate “speaking” with “contributing” and try to make up for my own lack of work by micromanaging someone else’s.

Nowadays I fight the inclination to give unsolicited direction, even when I feel like I haven’t been doing enough. I search for the source of my insecurity and work to solve it, while consciously limiting its effect on the way I converse with others. In the words of Zach Beer:

“I have stuff. I react poorly in certain situations. I try not to make my stuff their stuff, as much as is possible.”

I have been on the other side of this at least twice. I had to quit real jobs because I felt like I had responsibility without authority—I was on the hook for the consequences of work I didn’t get to decide how to do. Sometimes I knew about the consequences ahead of time, but people with more institutional power didn’t listen to me and made a decision about my work themselves.

But don’t we give up the chance to make an impact when we stop telling people what to do?

Honestly, not really. In the absence of a steep power gradient—like, as in Power to Fire—the person ultimately responsible for doing it will make the final call anyway. They’ll rationalize away my dissenting opinion and do it their way. So expressing my way is less impactful than helping them introspect on what their way should be. (And no power gradient will prevent the resentment I’d generate by dictating someone to do it a different way than they see fit).

So instead, I’ve learned to ask questions.

In the last post, we looked at an example in a professional situation. This works in personal situations, too.

Here’s a common dilemma that comes up when someone is venting about a tough experience: should I tell them I feel their pain, which is short but might sound empty and hollow, or tell a whole story that shows them I know what they’re going through, at risk of sounding like I’m making it about me?

Well, there’s a third option: ask questions. “Would you like to talk about it?” “I experienced X when I found myself in a similar position. Do you find yourself experiencing that, too?”

Three Levels of Questions

I find it useful to orient my conversational behavior around three levels of questions. The longer I practice, the easier it becomes for me to graduate from level 1 questions to level 2 and 3 questions.

Level 1: Questions that I personally want the answer to.

D20 dice

Example: my conversation partner mentions that he picked up some new dice over the weekend. I’ve been looking to get some new dice myself, so I ask where he bought them. That’s a level 1 question: my interest in the answer relates to myself and my desires.

The example sounds selfish and basic, but it’s a big deal to get to regularly asking level 1 questions. In order to ask level 1 questions, I need to:

  1. Listen to what my conversation partner said
  2. Identify something in what they are saying to which I can personally relate
  3. Care enough about what they said to want further information

Most interlocutors are absolutely not accustomed to doing these three things.

Has a coworker ever complained to you “I offered [Person] exactly what they needed, and it was like they didn’t hear me?” This reveals that [Person] hasn’t adequately practiced doing those three things.

Level 1 questions draw their value from the way that optimizing for them forces us to practice our listening skills—but with a selfish motive, so we feel rewarded for doing it.

When I started practicing my conversation skills, I was not accustomed to this. I spent more conversations than I had realized focusing on myself, bored with the other person, looking for my chance to speak. Once I discovered this, I felt so self-conscious that I googled “How to be genuinely interested in other people.”

This is a real thing that I did, like, in the past year.

I spent about three weeks going through the motions of deliberately listening and asking questions. In that time, I started to feel genuine interest in all of my conversation partners. Yes, all—my gym buddy, my boss, the cashier at Target, the doorman. I didn’t need any other exercises for that interest to show up by itself. Whew :).

Level 2: Questions that my conversation partner wants me to ask.

This dovetails a little with the next post on deliberate appreciation, but we’ll start here/


Example: my conversation partner mentions that she spent a lot of time this weekend working on her side project. I know that, when people bring up this kind of thing, they’re usually proud of it or have something they want to say about it. So I ask what her side project is and why she decided to do it.

But Chelsea, that’s so manipulative!

Nah. Maybe it would feel manipulative if I were trying to get the person to do something that they don’t want to do or shouldn’t want to do, but I’m asking them to do something that they absolutely want to do: brag. Come on, let people brag a little. Someone wanting to brag is a compliment to me as the listener; this person cares what I think and wants me to think they’re cool! Plus, now I get an opportunity to help someone feel appreciated.

In the last post, we talked about this phenomenon:

We’re so focused on these machinations to get recognition, that we forget to give it.

When we don’t create opportunities for people to feel appreciated, they feel left out, or ignored, or inadequate. And they focus on…more machinations to get recognition, instead of giving recognition, which perpetuates the scarcity of the recognition resource.

By inviting someone to share something that makes them feel capable or insightful or kind, I’m supplying some of the recognition that my interlocutor needs to feel fulfilled. People who get recognition have more emotional latitude to stop worrying about getting recognition and focus on giving it to others. This is how we reverse the Tragedy of the Recognition Commons.

And who knows? Maybe I’ll think the thing they’re talking about is cool, too!

Level 3 Questions: Questions that my conversation partner hadn’t considered, that help them reach clarity or validation.

These are the questions that your conversation partner didn’t even realize they wanted or needed you to ask. They are the questions that a good therapist asks. They are the questions that your best friend asks when they understand what you want better than you do. They are not the questions that give you the answer; instead, they are the questions that make you realize that you have had the answer all along.

It is my fondest wish to understand these questions better, so I can describe them more precisely and explain how to reliably ask them. For now, I haven’t found the common thread between them. If I manage to ask one of these, it makes my day.

To improve my sense for these questions, I try to recognize and appreciate when someone is asking a level 3 question of me.

For example,I had a colleague accept a job offer from a company that contracts with ICE, who told me that a massive pay raise had a lot to do with their choice. The admission made me livid, so I was doing some assisted processing with another colleague before I responded. After listening to me be angry for about 20 minutes, my colleague asked me: “For a developer with the opportunity to be hired by [COMPANY], what would you say is the highest leverage action or set of actions for them to take?” His question switched me from anger mode into framework development mode. I’m currently working on a blog series about integrating values into career goals, and I might not be doing it if my friend hadn’t asked me this question.

I also try to detect cues that I have asked a level 3 question of someone else.

I recently had a conversation with a colleague to compare a few job offers she had, including one from a friend of hers. I said: “I understand that you have a rapport with [Potential Manager]. Do you think that they have the capacity to give you what you need as a direct report?” The person sat up, and their eyes widened. From here, the conversation turned toward what they need from a manager, and how to protect a personal relationship with a manager if the manager might not meet those needs.

I guess I have found one common thread between level 3 questions.

Though each question feels unique to the interlocutor and the conversation, they seem to happen most often when the person asking them has set aside their other concerns to be fully present—to give them their full, undivided attention.

And learning to provide one’s full, undivided attention is not easy. I deliberately work on this every single day.

We’ll cover deliberate appreciation in the next post, and the most advanced levels of that skill also benefit from the skill of providing one’s full, undivided attention.

But until we get there, here’s what I recommend:

As you practice asking questions of your colleagues and loved ones in conversations, think about what level you’d assign each question you’re asking. Is it mostly level 1’s? Some level 2’s? Do you ever manage to get a level 3 in there?

Are there conversations where you notice yourself asking zero questions? Why is that? Maybe there’s a good reason, or maybe there’s something useful to improve on there.

If you liked this piece, you might also like:

What software engineering teams can learn from improv comedy (I live in Chicago, which I think makes me legally obligated to write this)

Combatting shitty humor in the workplace (this isn’t the title of the piece because I wrote it when I had less experience and more fucks to give, but the content stands)

Advanced professionalism for the heavily tattooed or otherwise counterculture (again not the title of the piece, see comments on the previous piece)

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