If you’re an outsider who is trying to solve a big institutional problem or create a big shift in behavior, you first need to deeply understand the status quo. Despite how things might look from the outside, behaviors that seem totally illogical actually have pretty good reasons behind them. Before trying to change anything, you first have to figure out why things are the way they are.
If you’re running a startup, or you’re working on a new project, this becomes a lot harder. You’re either commercializing a new technology, porting a business model from one context to another, expanding into a new vertical/customer base, or some combination of all three. This means what you think you know, you probably don’t really know for sure.
Does my product really have value in [new market]? Does [target customer] really want to pay for this or is the problem not big enough? One way of figuring this out is to just get out there and try. Conventional Silicon Valley wisdom encourages us to talk to customers aggressively, because chances are high that we’ll learn pretty quickly. This works particularly well for consumer-facing businesses. But for projects that target big or complex institutions (enterprise sales, government lobbying, M&A, private equity, etc), the number of possible target customers is low. You don’t have that many shots, and asking the wrong question in a meeting will kill your credibility fast.
I’ve learned to first ask dumb questions early, and to ask them of other outsiders. This means not going straight to an executive or their staff. It means waiting on those meetings and getting as close to the truth as possible by learning from people with experience. In the world of government relations, it means talking to NGOs and multilateral institutions with a local presence, chatting with researchers at in-country think tanks, and grabbing dinner at embassies with diplomats.
The goal is to find people who are deeply familiar with the problem you are trying to solve. Who else has tried to solve it? Surely you aren’t the first one. Who else is working with the organization you’re targeting, and what are their insights? What do they say about the incentives, competing priorities, and challenges within that organization? In the case of health, there are so many non-profit experts with both in-country and broad global experience who are happy to offer amazing perspective into the challenges of last mile and rural healthcare, and the ways of working with government institutions that manage these areas.
I’ve also learned to ask the same questions often, and to ask them of many different people. If you’re asking the right questions, they probably won’t have a single answer, and 10 people might give you 15 different opinions. But being a good listener, probing a lot, having an open mind, and having a genuine interest in the problem you’re trying to solve can all go a long way in getting close to the truth.