To go beyond a problem's surface, you can try the following approach:

1. Write down the problem or question you're facing
2. Try to understand the underlying need
3. Brainstorm approaches to address that need (at least two)
4. Write down what you think about each approach
5. If the problem is difficult or complex, introduce more structure: define criteria, then evaluate each approach against those criteria

Example: How should we do estimates: fibonacci, t-shirt sizing?

Many teams discuss on the level of this question, but we first need to ask something else: What underlying need are we actually trying to address here? It could be something like:

• Predictability for the business?
• Engineers aligning on scope and approach?
• A requirement to follow a given process?
• Something else we're not seeing yet?

These discussions often feel like stepping into the unknown, which can be uncomfortable. Some people tend to rush through.

So let's say it's predictability, and we choose not to explore that need further. How can we make the work more predictable? Some approaches:

1. Point estimates: might still be too micro-level to be truly predictable?
2. Fixed project time (e.g., 6-week cycles like Shape Up): requires the ability to adjust scope accordingly
3. Continuous evaluation: requires incremental delivery and ongoing alignment with the business
4. No change, keep doing what we're doing: maybe suitable if there's too much other stuff going on right now?
5. Something else?

Capturing this thinking and decision-making process in writing or in a diagram can be helpful as well.

When you make a decision after this kind of exploration, you'll likely have a clearer understanding of both the problem you're trying to solve and the solution space. As a result, the choice you make is likely to be stronger.