What Level of Question are You Playing at? 5 Levels of Value

One of the compliments I receive most often in my work is something along the lines of:

“You ask such great questions.”

This probably comes after I ask someone some questions that I’m curious about. You get better at asking questions when you begin seeing them as a tool to have better and more valuable conversations. Questions set the frame of the discussion, and so leading someone is often about questions rather than making statements. Questions can be used for a variety of different purposes. Today I wanted to outline 5-levels of value oriented by particular questions that people ask of me and ask themselves. 

If you want to create/expand value, ask questions higher up the ladder.

The Value Ladder: 5-Levels of Questions for Leaders

1. “What do I do?”

When you are working in a new role you’ve never been in before, you get tripped up on the question “What do I do next?” When you don’t know what to do, you don’t act. And so you wait or search for someone or something that can tell you what to do. Most often, this is a way of procrastination. You can’t act until you clearly see a specific, short-term step and action you can take. What do I do is the lowest leverage and least valuable question to ask of yourself or others. But it is often the place we start.

2. “How do I do it?”

Many people take similar actions, but not all get the same results. Why? When you don’t understand the “why” behind how something works, you lack proper form. Form is “how” you do something. “How” is a question about form. 

How helps get you to feel/experience the action rather than intellectually understanding it. How is for practitioners seeking to learn how to apply something they’ve learned. How is for doers… in an organization, team, community, or political structure. “How” is, relatively low value. Often, to succeed with how, you sell something at lower price points and therefore must have a large audience.

This is why “how” is the most prevalent form of content on Youtube, for example. “How” is also the easiest question to waste your time on. “How” is a great game of telephone. You read someone else’s “how” and translate it poorly to your own situation and then get frustrated by not getting the right results.

3. “Who?”

When you wake up to the limits of your own “doing” you begin to see the benefit of collaboration, hiring, delegation and managing and leading a team.

Who is the first leadership question outside of self-leadership. Who is the shift from Founder-Doer to CEO-Manager, from actor to recruiter. Who marks the beginning of systems-level questions. Before you get to “who” you focus on your input into the system.

When CEO’s come to me with struggles for their personal productivity, I often take them out of “how” questions and into “who” questions. I’m less interested in them and more in the teams and systems that support them.

4. “Where should we go?”

Systems need direction. “Where?” charts the course. “Where” is about the future, whereas the previous questions are more about the present. Where questions are about owning the responsibility of taking people into the unkown. If organizations don’t know where they are going, then everyone is working out of sync and unison. Where is one of the greatest possible filter questions because it completely changes the course of a company or team. 

Change the where, change everything. A where question for Kodak Cameras was: “Double down on Film, or Enter the Digital Camera Space?” A question for NASA is: “Moon or Mars next?” As you can see, asking “Where” is risky. This is why “Where” is the CEO's question. With “Where?” there are consequences, or regret. Aligns a system to a destination, puts resources on the line, and creates definitive direction.

The trick of understanding organizations, communities, and political parties is that they crave direction. They ask, “Where are we going…together?”

5. “What does it mean?”

The final level of value is in meaning questions. When you’re so distracted by the doing of things, you try to ignore lives deeper questions around meaning or meaninglessness.

The good news is that we are meaning-making machines. Meaning making is about how we interpret the events around us, and how we contextualize every other question listed above. The highest levels are about context.

In meaning questions, you are playing with the container, not the contained. You start playing with the rules, the stadium, the field, not the game or players on the field. You start working on the museum rather than the art sitting i