Leading With Why
24 May 2014

Up-leveling conversations and breaking down problems

The last two years have been a whirlwind. We grew the Coursera team from the ground up to just over a hundred now, and it was a tremendous learning experience going from a small team to a much larger organization. As we continued to hire, each multiplier increase in growth brought up organizational challenges.

Engineering first organized itself into two teams when we were about twelve engineers, and then three teams, and finally a company wide reorganization into a matrix with both effective cross-functional teams and more specialized functional teams.

How did we decide on this particular organization structure? It came out of a few days of brainstorming and ideation — it clicked when we figured it out; but could there be a better way to do it? More generally, a startup has a hundred moving parts and decisions to make, how do we work through these problems?

Leading with why breaks down a problem or decision by continuously asking why. It forces us to up-level a conversation and discuss our objectives, principles, and values.

Leading with why is one of the tools that I learned along the way that has been incredibly useful that could provide the answer. Instead of tackling a question head on, take a step back and ask why. After getting the first answer, ask why again, and continuously do so. Each why helps to up-level the conversation and uncover what we really care about.

Asking why helps us break down problems. It forces us to up-level a conversation and discuss our objectives, principles, and values. When done right, it provides clarity into our problems and decisions.

Here is an example of leading with why in action. As our team grew, we ran into the question of “how should we organize ourselves”. To lead with why, we first ask:

Why do we want to organize ourselves?

Organizational structure will enable better communications. Communications becomes ineffective as we grow as it becomes harder for individuals to keep track of what other individuals on the same team are working on (communications scales quadratically in a flat structure).

Why do we need effective communications?

In a small startup with many moving pieces, it is important for the team to know what each other is doing.

Why do we need the team to know what each other is doing?

There might be overlaps or dependencies in the work; it is important to understand each other so that there are shared expectations on when dependencies are completed or where work could be synergistic.

Why are there overlaps or dependencies?

As an organization, we undertake projects with big goals. These projects will need to be split up into smaller manageable components that could depend on each other or share common infrastructure.

Why do we have big goals?

We value thinking big.

After up-leveling the original question, we can now work backwards to figure out what is really important:

We value thinking big, and have big goals as an organization. We need to break down our big goals into smaller goals that are more manageable and could be owned by separate teams. The separate teams need to be aware about cross-team dependencies and synergies. Individuals that have high degree of communications should be on the same team. In gist, we want to keep teams loosely coupled, but highly aligned.

Leading with why allows you to move up and down the causal chain. This often gets us to ask questions that probe at our principles and values. When we have clarity in our principles and values, we will be more confident and consistent in our decisions.

When we have clarity in our principles and values, we will be more confident and consistent in our decisions.

This method applies broadly. We recently had discussions around our how we think about expenses, and whether we need a policy or process around it. Leading with why, we converged on valuing trust and responsibility of every teammate, and that resulted in a “spend as if it’s your own” principle.

In practice, we often face questions such as “why are we doing ___”, “should we pursue an opportunity ___?”, “how should we do ___?”. These questions usually lead into discussions about the pros and cons of specific options — while that is useful, it is easy to get miss the forest for the trees.

Leading with why pushes us to go beyond what is right in front of us and gets us to question what is really important. It helps to up-level our conversations to enable us to understand the principles and objectives that help drive decisions.

By having clarity in our decisions, we can work backwards from the causal chain to create compelling stories that effectively motivates change.

Note: Similar ideas found in Start with why (Simon Sinek) and 5 whys (Toyota, Six Sigma).

Jiquan Ngiam
Director of Engineering
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