The Greek word for philosopher (philosophos) connotes a distinction from sophos. It signifies the lover of wisdom (knowledge) as distinguished from him who considers himself wise in the possession of knowledge. This meaning of the word still endures: the essence of philosophy is not the possession of the truth but the search for truth. … Philosophy means to be on the way. Its questions are more essential than its answers, and every answer becomes a new question. — Karl Jaspsers

Most of my job is answering questions. Advising companies on behavior change science pretty much means being paid to answer questions from product managers, designers, CTOs, and sales teams. Being a CEO pretty much means getting money in exchange for answering questions from investors. And managing employees pretty much just means answering their questions. I guess with all this practice I’ve gotten “not-shitty” at it because this morning, someone I work with asked me:

During interviews and Q&As you seem to have this ability to articulate a concise answer without having to plan it — can I ask any tips or bits of advice at all on how you do that?

So I thought I’d answer that (yet another question) in a Medium post rather than just leave it confined to an email.

Needs first, truth second.

Asking a question is a scary thing. I personally find asking questions far more nerve-wracking than answering them because questions make us so vulnerable. They immediately create a power imbalance between the asker and the asked, and everyone hates looking like a jackass.

When people ask me a question (especially in public) I do my best—and am at my best—when I remember the hot rush of blood to my face every time I’ve raised my own hand in a Q&A session, or sent an email to someone I admired. And remembering that, I strive to answer questions by first connecting with the asker and communicating:

“I like you; I think you’re capable of understanding more; and I can tell that you care about this…”

Anyone who knows my work will recognize that as supporting Basic Psychological Needs. And it’s only after I do that that the real job is easier:

“…now let me share with you how I see the world.”

The “Triple-A” Rule

Between my liberal arts middle and high schools and my undergraduate degree in philosophy, I spent ages 13–22 steeped and drilled in Critical Thinking. Which is a fancy, capitalized way of saying “arguing.” Every day for those 9 years, I argued with peers, teachers, and writers to suss out what was true, beautiful, and good. I’m not saying that it was the “best” education, it’s just the one I had. And it’s where I learned a lesson that’s important to me:

A person’s truth is not in their words; it’s in their assumptions.

If you want to connect with someone and give a meaningful answer to their question, you can’t just address what their words said. You have to address their assumptions about how the world works. This is what the Socratic Method and Zen Kōans do so well. And while I’m not that a good teacher, I aspire to the clarity that these methods bring by always trying to listen past what people are saying to the assumptions that they are making.

• When a client asks me “do leaderboards work?”, the most important thing I need to address is this client’s assumption that Behavior Change Techniques effect everyone in the same way across all contexts. No one asks, “does penicillin work?” because most people know enough about medication to know that the better question to ask is “in what contexts and on what patients is penicillin effective?”
• When someone asks me in a Q&A session, “should I get a PhD?” the assumption I feel most compelled to address is that they are “missing something” now. I can’t properly answer that question without addressing that feeling of “missing something” or “needing something else” in order to be effective.
• And when a kid I was baby-sitting once looked up at my wall and asked, “what does that painting mean?” what was interesting to me was that a 3 year-old already assumes that all paintings have one, objectively true hidden meaning. Simply telling him what I think the painting “means” might actually reinforce that assumption!

So remember the “Triple-A Rule”:

Always Address Assumptions.

4 Kinds of Requests

One of the coolest things a philosophy degree taught me is that there are no new questions. As a fellow philosopher Donald Schön said even better: “Old questions are not answered — they only go out of fashion.” When someone works up the courage to ask me something, especially in a public Q&A session, I have found that the questions can be classified into 4 basic requests:

1. Tell me I’m smart.
2. Tell me everything is going to be OK.
3. Tell me everything is fucked.
4. Tell me there’s more.

There’s probably other types of questions, but this is useful heuristic for zeroing-in on what people want to hear when they ask stuff. And I know that if I don’t at least address those requests, then I won’t have meaningfully answered their question. And as usual, I tend to think of things in terms of Basic Psychological Needs.

• If someone’s question contains a reference to work they have done prior to asking it (“I read a book that said…”; “In my experience I’ve found…”; “I was talking to [person more famous than you]”; etc.) then it’s a pretty safe guess on my part that they could use some competence support. So I’ll give it to them. “I can tell you’ve put a lot of thought into this problem…”
• If someone is asking about the future (“what are your thoughts on the potential impact of [technology]”; “how should we address [pending problem]”; [any other question about A.I.,M.L., or politics]), then I assume they are seeking autonomy support in the face of uncertainty. They probably want to hear that they have control over something. So even if I have a nuanced answer that will not assuage their feelings of uncertainty, I can at least address that uncertainty and remind them of things over which they do have control. “I don’t know what will happen. But here’s what I do know…”
• And if someone wants to know about other people, books, or institutions, (“what are your favorite [books, movies, tools, resources]”) then I know they are seeking relatedness support. Most of the reasons we take the risk to be vulnerable and ask questions is the hope that we can discover that we are not alone. That there are others out there who think like us and that is a cause bigger than ourselves to which we can contribute. So I never miss this opportunity to remind them of the community out there of other people who give a damn, too.

Words are hard.

Finally, if there’s one thing that it took getting out of liberal arts to learn (1,200 supervised hours of counseling-skills training later), it’s that people rarely say what they mean because saying what you mean is really damn hard.

Articulating thoughts with words is a skill.

When people ask what I think are stupid, weird, or muddled questions—off the cuff and under pressure no less—I try to remember how goddamn hard it is to make words into sentences. Since I write, I turn new thoughts into words every day. And it’s easy to forget that most people don’t get that much practice. I’ve been insanely privileged to have to the time and support to practice that skill, but it’s skill that is 100% useless in a vacuum. Words communicate. As the person with the most practice, if there is a failure of communication, then it’s on me. I’m the asshole who was supposed to know how to answer this person’s question. Emerson said “language is a city to the building of which every human being brought a stone.” If someone is asking me a question, they’ve brought their stone. And no matter what shape that stone takes, it’s on me to craft my own stone into an answer that fits theirs. Otherwise, we’re not building anything and any truth, beauty, and goodness we’re striving for will be on hold until this person feels heard.