MHQ: Most Helpful Question

I’ve advised hundreds of early stage entrepreneurs and often I find that they come to the conversation hungry for help, but unsure of what to ask for.

After a lot of trial and error, I’ve found that the most valuable question I can ask is “What are you most uncertain about?”

This gives me the opening to learn more about how they view the critical assumptions in their business and what to prioritize. Maybe they are panicked by uncertainty in an area that we dig into and find doesn’t matter, or the opposite, after taking about it I understand why this would be keeping them up at night. From there, I can engage with them around how to mitigate the most important areas of uncertainty - suggesting testing methods, making connections to experts, sharing case studies, etc.

I used to ask entrepreneurs what their biggest challenge is as a starting point to engage.

This is still a great question that I use all the time, especially when catching up with friends who are more experienced entrepreneurs and I want to find a way to help out. However, I find that when I ask that of someone at a very early stage in their first venture, I often hear some variation of “It’s all so overwhelming and there’s not enough time in the day to do it all”. So true, being an entrepreneur is HARD, but that’s such a general comment that it’s hard to really engage with.

I like that my MHQ about uncertainty helps with cutting straight to more specific business issues.