4 Levels of Leadership Questions

Nanalytics Mind
3 min readJan 7, 2023

If you want to improve your leadership mindset, start reflecting on what types of questions you ask most frequently. Do you most often ask HOW or do you frequently challenge the “WHY”? Different types of questions will lead you to different directions and outcomes. I am writing this specifically for the corporate world, but it may apply to other situations as well. I am using an analogy to the different levels in a building.

Level 1 (ground level — individual contributors): HOW. You are on the ground level. You have no visibility of nor interest in what happens in other places. You focus on getting traffic through the main lobby or answering questions at the front desk. How to complete the tasks? How to get things done on time? How to build good relationships? How to get promoted? When you ask how-to questions, there are assumptions that certain tasks need to get done. You are responsible for completing the work. All the things have already been decided and handed over to you. You just need to figure out how to deliver it. In the corporate world, individual contributors often ask this type of question and wait or even fight for project assignments. They spend a lot of time acquiring specific or technical knowledge and become the go-to person or SME. They hope they will get credit or praise for their deliverables, or get promoted based on the work they complete.

Level 2 (mid-level — frontline managers/middle management): WHO and WHEN. At this level, people still make the assumption that what needs to be done has already been decided and your team is the one to deliver it. You assign the task to your team member who has the skills or capacity to do so. You negotiate with the stakeholders or other partners on who and when to deliver it. You do not challenge the orders but have flexibility on assignments and timelines. At this level, building direct work relationships with and knowledge of the immediate circle is very important. Your goal is to make your stakeholders happy and keep your team engaged.

Level 3 (high rise — middle/upper management): WHAT and WHERE (strategic priority and talent/organization). The direction and purpose of the organization have already been set. You are tasked to figure out what to be done and where to get it done to achieve the organizational objectives. You are proposing and leading new initiatives based on strategy, assigning out projects, or forming new teams to achieve the objectives. People who do this usually get additional resources and get promoted quickly.

Level 4 (rooftop — executive level): WHY and SO WHAT? What to say NO to? At this level, you won’t be able to know how to do it or who’s doing it anymore. You focus on the purpose and impact. You need to tell others why the organization exists and how it impacts society at large. You can not rely on your leadership team to tell you what needs to be done to achieve the purpose. At this level, there’s so much unknown, uncertainty, different opinions, and many potential outcomes. You use your belief, values, risk tolerance, and even gut feeling to make decisions and take responsibility for them.

You also need to decide what not to pursue. It is a lot easier to start a to-do list and add things to it. It is a lot harder to take things off the list and feel good about them. There are so many “should” but we have limited time and resources. Everyone has 24 hours of time a day and an organization has a finite amount of money and people. Until you are willing to give up things, you won’t be able to have more time to devote to the most important things.

Everyone may juggle among the 4 different levels at any point in their career or life; however, you may spend different portions of time at different levels. If you are an entrepreneur, you have to constantly travel between all levels. What you sacrifice is a certainty, in exchange for excitement and a small chance of huge success. If you are working in a big corporation, you may be more fixed on one level without knowing it. Keeping your eyes on the full horizon will help you see the big picture.



Nanalytics Mind

A first-generation female leader, parent, thinker, practitioner, and change agent writing about analytics, leadership, and life philosophy.