I was also told that a brand-new CEO shouldn’t be trying to make huge acquisitions. I was “crazy,” as one of our investment bankers put it, because the numbers would never work out and this was an impossible “sale” to the street.

The banker had a point. It’s true that on paper the deal didn’t make obvious sense. But I felt certain that this level of ingenuity was worth more than any of us understood or could calculate at the time. It’s perhaps not the most responsible advice in a book like this to say that leaders should just go out there and trust their gut, because it might be interpreted as endorsing impulsivity over thoughtfulness, gambling rather than careful study. As with everything, the key is awareness, taking it all in and weighing every factor—your own motivations, what the people you trust are saying, what careful study and analysis tell you, and then what analysis can’t tell you. You carefully consider all of these factors, understanding that no two circumstances are alike, and then, if you’re in charge, it still ultimately comes down to instinct. Is this right or isn’t it? Nothing is a sure thing, but you need at the very least to be willing to take big risks. You can’t have big wins without them.

Strong management of board and shareholder expectations and perceptions is critical. Indeed, often the core problem is the perception of performance, which makes powerful and highly persuasive communication with the board, shareholders, and analysts a CEO’s priority. One director told us, “Even when you think you’re communicating too much, you’re probably not communicating enough.

Nigel Travis, who led Dunkin’ to strong revenue growth in nine years at the helm, observed in his book The Challenge Culture that companies “can quickly go from success to trouble . . . because the culture does not allow for challenging the status quo.” He shared with us that finding ways to break the spell of satisfaction with success was a main focus of his leadership. That was in part because of what he’d witnessed as a senior executive at Blockbuster.

Advice on combating the status quo bias by methodically rethinking business assessments and gaining perspective from outside the firm is not new. But the problem is that far too few leaders develop a rigorous and continuous discipline of doing so. And if CEOs don’t impose that discipline on themselves, nobody else will.

The imperative to challenge yourself becomes more difficult to achieve the longer you have been doing the job successfully. Nigel Travis said, “Being a CEO for longer is tougher because you have to find ways to keep improving.” Some CEOs recalled feeling less engaged in this stage, with boredom creeping in. “When you get into years six to ten, the intellectual stimulus is less,” one shared. “You come in with lots of ideas,” another commented, “and then run out of them.” Someone else said, “Years six to ten is a period of time when the luster is off the rose and what was new and exciting is no longer new and exciting.

Travis found a number of additional ways to regularly tap into the perspective of those outside the firm. He would appear at Q&A sessions with MBA students, which gave him access to the views and attitudes of younger people. In addition, twice a year he attended CEO Summits held by Yale School of Management professor Jeffrey Sonnenfeld. These are vigorous debate events in which leaders across industries and from around the globe, as well as government figures, research analysts, and journalists, are challenged to engage in wide-ranging discussions of topics, from global political issues, such as competition with China, to leadership style. Attendees are often put on the hot seat, for example, to defend a statement they made in the press. Travis recalled that one summit he was pitted against an investor who had very publicly shorted Dunkin’ stock and whom Travis had strongly rebuked in a press interview. As he wryly commented about the encounter, the sessions ensure that “you can't fall asleep.”

The single most helpful source of outside perspective Travis found was gained by joining the boards of other companies. “If you asked me about the one thing I’ve done in my career that really helped my development as a CEO,” he told us, “it was sitting on another board. Every time I got to a board meeting, I write down more about the company I’m running than I do about that company.” Acknowledging that many CEOs say they don’t have time to serve on another board, he stresses that not only does it help to see how other companies operate but also the other company has “got a plethora of experiments going on that you can utilize for your company.