6 min and 31 sec to read, 1628 words
Imagine a world in which your resume was the kinds of questions you are better at asking than most other people? If your skills were translated to the kinds of questions where you excel and really make a difference in a team? And if we then also decided to recruit on the basis of which new questions we need to ask in our different teams — how would that work?
It seems clear that a team where everyone asks the same questions is likely to be less effective than a team where the members ask different questions, if for no other reason than the fact that the latter team will cover more information than the former. Different questions build a richer model of the world, and, to some degree this will help make better decisions. At some point the richness of the model may make it impossible to use as a model, but we are usually not even close to that in most corporate settings. The problem there, I think, is usually that we have models that are so simple – or even unarticulated – as to make decision making weak.

So, imagine then that you want to put together a team of questioners – what would you be looking for? Here are a few ideas.
- Fact-based questioners. People who ask after the facts, after data and relentless seek observations and empirical evidence. Their key question is “What is going on here?”
- Process-questioners. These are folks who ask what questions we are not asking, what would change our minds, and similar things about the process.
- Political questioners. Here we find the folks who understand organizational politics, figure out how needs to be in the loop, manage stakeholders in different ways.
- Allocation questioners. To keep us honest when it comes to how we allocate attention, time and resources.
- Holistic questioners. Folks who ask how what we do fits together with the larger picture, and with the wider mission of the organization.
- Learning questioners. The idea here is that someone should always ask what we have learned during the process — this is a little like process questioners, but focused on how we compound our knowledge into actionable wisdom.
These are just a few different ideas, you can surely come up with your own team set up here too — the team, then, can be viewed as running of a series of questions that they evolve, curate and build on in order to sketch out a provisional answer. You can also think about this as different roles if you want to, and try to build an ideal set of roles to fill:
1. The Historian
- Role: The historian brings context and depth to questions by linking them to historical events, trends, and figures. They ask questions like, “How has this issue evolved over time?” or “What can we learn from similar situations in the past?” – and their key questions are based in historical analogy.
- Skills: Deep knowledge of history, ability to draw parallels across time periods, contextual analysis.
2. The Philosopher
- Role: The philosopher challenges assumptions and delves into the fundamental nature of concepts and ideas. They ask questions like, “What are the underlying principles at play?” or “Is this line of reasoning logically sound?” – their key questions are conceptual.
- Skills: Critical thinking, ethical reasoning, expertise in philosophical traditions.
3. The Scientist
- Role: The scientist approaches questions with a methodical and evidence-based mindset. They ask questions like, “What empirical evidence supports this claim?” or “How can we test this hypothesis?” – their key questions are experimental.
- Skills: Research methodology, data analysis, empirical reasoning.
4. The Detective
- Role: The detective is skilled at uncovering hidden details and exploring the depths of a situation. They ask questions like, “What details are missing?” or “Is there an alternative explanation?” – their key questions are abductive, looking for different explanations.
- Skills: Investigative techniques, attention to detail, pattern recognition.
5. The Journalist
- Role: The journalist focuses on uncovering the truth and communicating it effectively. They ask questions like, “Who benefits from this information?” or “How can this be clearly explained to the public?” – their key questions are communicative.
- Skills: Communication, investigative reporting, ethical journalism.
6. The Analyst
- Role: The analyst dissects information to understand its components and implications. They ask questions like, “What are the key drivers of this situation?” or “What are the potential outcomes?” – their key questions are model building.
- Skills: Data analysis, logical reasoning, strategic thinking.
7. The Ethnographer
- Role: The ethnographer brings a cultural perspective, asking questions about the social and cultural contexts. They ask questions like, “How does this issue affect different communities?” or “What cultural factors are influencing this?” – their key questions are based in a focus on human elements.
- Skills: Cultural analysis, qualitative research, empathy.
8. The Technologist
- Role: The technologist explores the impact of technology on the issue at hand. They ask questions like, “How does technology shape this problem?” or “What are the ethical implications of this technology?” – their key questions are actor-network theory questions.
- Skills: Understanding of technology, digital ethics, systems thinking.
9. The Legal Expert
- Role: The legal expert examines the legal frameworks and implications of a situation. They ask questions like, “What laws are relevant to this issue?” or “What are the potential legal consequences?” – their key questions tend to be institutional.
- Skills: Legal analysis, regulatory knowledge, rights advocacy.
10. The Sociologist
- Role: The sociologist looks at how social structures and relationships influence the issue. They ask questions like, “What are the societal implications?” or “How do social norms affect this situation?” – their key questions are normative.
- Skills: Social theory, structural analysis, community engagement.
11. The Creative Thinker
- Role: The creative thinker challenges conventional wisdom and explores out-of-the-box ideas. They ask questions like, “What if we approached this differently?” or “How can we innovate here?” – their key questions are contrarian.
- Skills: Lateral thinking, innovation, ideation.
12. The Strategist
- Role: The strategist focuses on long-term goals and plans. They ask questions like, “What is the big picture?” or “How does this align with our broader objectives?” – their key questions are asked against a different time horizon.
- Skills: Strategic planning, foresight, risk assessment.
Now, you may say that this is a complicated and labored way of thinking about teams, and I would – perhaps surprisingly – agree with you. But the main point here is not to say that this way of composing teams is ideal, but rather to draw your attention to the fact that this is how we compose teams today, but with answering skills. Skills are, usually, cast in terms of the kinds of questions you can answer, rather than the kinds of questions that you are very skilled at asking. And that is as silly as just focusing on the questions — so maybe the overall insight here is that we need a balance, and we need to make sure that we understand how people ask questions too.
I have made it a practice in interviews to leave some space for the interviewee to ask questions. Most of my hiring decisions, I think, come from the kinds of questions people ask me in this part of the interview – since the questions are so much more revealing than the kinds of answers you get in a job interview. We all prep for job interview questions and know that we should have answers to questions like “why do you want to work here?” – even if that is a particularly bad question in itself. You can use it to understand if people have indeed prepped, because this question will then be answered like someone reciting the answer to a test question — with main points prepared and launched at you. But opening it up for questions is different — where someone has prepared real questions the interview suddenly becomes a dialogue, and you can explore how people think in a very different way.
The perhaps most problematic reply you can get is that the interviewee has no questions at all. Sometimes this is out of respect for your time, and you may need to stress that you have time — but sometimes it is because the person interviewing genuinely does not have any questions, and that is surprising to me. You want to work at this company, and you have no questions about it?

Some of the most effective people I know are defined by their questions. They use questions to prioritize their work, they ask more questions in a 1.1 than lecture, and they think through the kinds of question map you are likely to face in a complex project: when you answer one question, there will be others, and look to address those dependencies effectively. They have stock questions like “what does a good outcome look like here?” and “what happens if we do nothing?” — and often use these to make sense of complexity, overload and noise problems.
So maybe we would do well to explore what kinds of questions a new team member will bring to the table?
And if we use this idea for some self-reflection – which questions are you better at asking than many other people? Are there questions you often ask in a group that would otherwise not be asked? What are your top ten questions for work? Your most undervalued questions? The questions you dislike the most? Adding a small component to your resume that is titled “My questions” would surely signal at least the curiosity that we all look for in a candidate?
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