When leaders view technology as merely a source of answers and solutions, they miss opportunities to innovate in bigger, bolder ways.

In a recent conversation, John Donahoe, the former CEO of eBay who currently runs ServiceNow, told me about the most important phase in a company’s digital transformation: the part where you start asking better questions. Instead of seeing new technologies as a means to develop more efficient answers to known problems, managers should view them as opportunities — even requirements — to revisit the problems themselves. They should go back to first principles, Donahoe says, and ask, “Have we identified and framed the core issue in the right way? Instead of solving for X, should we be solving for Y?”

Marc Benioff of Salesforce is thinking along similar lines. At the company’s new headquarters in San Francisco, the top floor has been designated an “Ohana” floor. The word, Hawaiian for “family,” is a nod to the island culture that Benioff values so much for its spirit of collaborative work and play. One of the biggest uses of this and the company’s other Ohana spaces is to host clients for Ignite sessions, where they think at a strategic level about what enterprise software should help them achieve. It’s a space where people are prompted to ask big questions that could change how their companies compete.

Given the businesses they are in, Donahoe and Benioff have front-row seats to thousands of companies’ efforts to digitize their operations. As they’ve observed, many management teams begin that journey by asking how they can make back-office functions like help desks and HR information centers more efficient and less expensive through automation. That’s the low-hanging fruit; the business case can be made based on near-term productivity improvement alone. Things get much more interesting, both executives believe, after those systems are in place. New information starts flowing, and more intriguing questions materialize. As managers begin to see patterns in users’ activity, they often find surprises lurking there. They’re inspired to ask, for example: Is there a basis here for us to build a predictive model? If we’re worried about retention risk, could seeing patterns in employee HR queries help guide better employee engagement strategies?

That’s how breakthroughs happen in many digital realms. Modest questions about how today’s problems could be better solved lead to applications of technology with easily foreseeable gains.