I've typically worked on longer and bigger software development engagements, but recently have picked up several small (but profitable) automation jobs via referral. My existing onboarding process is too much for these types of projects.

I’m curious what methodologies or tools (super curious about tooling) people use to help obtain the required context (asynchronously) to scope out a project successfully.

I feel like this is something that I’m good at and, probably, the most important input to delivering great outcomes for my clients. My level of engagement in this beginning phase is my biggest bottleneck, there is so much friction and energy required at the start. For reference on my existing pattern:

I tend to start with 1-1 conversations. This gives me a good starting point of context AND helps earn trust with stakeholders.

Then I move into 1 to many conversations which start to expose nuances as people talk to each other while I observe. This is also typically when I start to tease solutions and build up social excitement for the future state.

Both of these steps are very synchronous and time consuming. They also have valuable social benefits that remove friction when we move into implementation. But that doesn't seem as important in these more short term engagements. Curious what other folks are doing.