Entrepreneurs: Keep Asking

For the last few years I’ve done a lot of consultation work with more startups than I even care to keep track of. More recently, I’ve been working in business development and product management roles and helping company founders and CEOs move their business to the next level via technology and good strategy. As you probably know, most startups fail. Companies go under for many reasons, but one thing I’ve seen consistently in those that do fail is this: they stop questioning what they’re doing.

Now, the traditional American business advice you’ll hear from many says, “Have a go get ’em attitude! Never look back! Pick a path and don’t stray from it! Confidence is the number one thing!” That’s all bullshit. If you want to succeed, especially in the fast-moving tech business, you have to constantly question what you’re doing and where you fit in your market. You have to ask the right questions, so you can find the right answers that will lead your company forward. If you’re not questioning what you’re doing, you’re not thinking about what you’re doing.

Years ago, I read a Forbes article targeted to company leaders called, The 10 Questions You Should Never Stop Asking. One of the key questions the author points out is:

Why does anyone need what we’re selling? All too often we fall into the trap that people want something because we like it. This is the road to perdition.

Far too often, company leaders fall into that trap and fail to create true value in what they’re offering. You have to be your toughest critic, and ask the tough, objective questions that expose weakness and lead to real solutions.


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