Why do startups fail?
They run out of money, of course. That's an oversimplification and actually it's more the result than the root cause.
A lot of times, it comes down to failing to produce results, and enough of them. What I've realized recently, though, is that smaller, faster results are key--and it doesn't always matter whether those results are good or bad.
I know a few startups that are struggling with their execution and it strikes me that they don't have any enough small victories. Their goals are all or nothing, like big product releases. For months, they're building the next thing, and there's little for the CEO to accomplish in the meantime.
Similarly, they get stuck in trying to negotiate with a huge customer for months on and end it ties up their resources.
Even in the beginning, some founders can't move forward until they raise their seed round. All you ever hear from them is whether they raised their seed round or not--and the company just seems dead in the water.
There are no small victories.
Having small victories isn't a function of winning and losing--it's about the design of your goals and your approach to them.
Language is incredibly important here. It starts with your team's disposition around new goals.
When your team decides that enterprise users should be able sign themselves up, that's a big project. That involves automating a ton of things that aren't automated yet and untold headaches for your tech team.
What's the reaction when the CEO says "I've gotten feedback from customers that they want to just try the product out themselves, and the setup and support team is already overloaded...what would it take to allow people to set themselves up?"
If the first reaction from an already overloaded tech team is a face palm and an "ugh", that's a problem that goes deep. That means the people involved are only thinking of the end goal and nothing in between--and not positioning themselves to allow for small wins. [...]