Some people really like having rules to follow. Others can handle a bit of ambiguity -- they’re willing to experiment, but it’s outside their comfort zone. Only a select few are truly comfortable embracing the unknown. Yet that third group is vital when you’re launching a start-up, or staffing a new initiative. You want the people who willingly throw themselves into the fire.
Established businesses often tackle known problems that require management, coordination, execution, and optimization. In contrast, entrepreneurial problems are unknown problems that require radical search, experimentation, and flexibility. Rather than a stable organization executing to maximize, a startup is a temporary organization designed to search for a repeatable business model.
When you hit internal moments of doubt you need the team members who say, "Guys, we can do this! We’re up against the ropes but we’re not down. Let’s dig in." You need team members who do that when you're NOT there. You need...mafia.
If you have a trade-off between somebody who is more talented but a "bad seed" versus somebody who is very talented (but perhaps less so) who is a motivator -- I’d hire the latter any day of the week.
So how do you hire the "young Turks" that can handle ambiguity?