In my experience, not generally.  Cautious and quantitative managers usually became that way through careful management of every step, fearful almost of not being able to forecast and see the next steps.  So by nature they are nearly impossible to convert.<p>The one way I have seen it and participated in it, is when someone takes it in their own hands and does something bold to prove to the manager that there is traction and profit to be found outside the paint by numbers scheme.  The problem, depending on the manager is that either the bold person is rewarded and the company moves towards some of that greener pasture, or the persons head is cut off and a good project dies right along with all employee morale.<p>More simply to me this is the difference between an entrepreneur and a hired gun&#x2F;manager&#x2F;ceo.  Most entrepreneur&#x27;s are comfortable being uncomfortable, so they will make the &quot;risky&quot; call as people will see it, whereas a hired CEO may not because they are comfortable in measuring and proving to the board how good they are doing by coloring inside the lines.