Dan  Springer founded Responsys in 2004 and after a successful exit, he took  four years off to be a stay at home dad. In 2017, Dan Springer joined  DocuSign as their CEO. In this episode of Cloud Giants, Byron Deeter talks to Dan about transitioning back to work, how to be a good leader, setting boundaries, and how Dan increased DocuSign's value by $14 billion during his time as CEO.

Takeaways include:

• As a leader, be aware of your gender bias: “People make this construct around being a stay-at-home dad and describe how strange it is,” Dan said. “Usually people say, ‘You were at the top of your game. All these people must be calling you for these great deals.’ My feminist friends say if I were a woman, people wouldn’t be asking that question. They’d get, ‘Well, you should have been staying home with your kids anyway.’ We should be aware we have these biases. I probably had a little bit of that bias myself at the time, but I’ve been educated. As we like to say, feedback is a gift. Thank you for all the women and men who are great feminists that have given me that perspective that I missed.”


• Why ambiguity kills productivity for leadership teams: “As a founder, be unbelievably clear on what skills you’re bringing in and how the company is going to change over time. Are you bringing in a COO who over time is going to maybe grow into the CEO? Well, then how much time? When will you know that person is ready? What will your new role be? Get clarity on all those questions because most issues arise when people are too polite and ambiguous.”


• If you failed the first time, set the boundary the second time: “As a person who is admittedly weak on setting boundaries, this is a big lesson for me still,” said Dan. “If someone shows up at my office or someone sends me an email asking me for something, I say yes. I’ve learned to set the boundary on the second time. I say, ‘Hey, happy to help. In the future, I need you to do it this other way.’ For example, we have all hands meetings every quarter where I speak to the entire company and I also do town hall meetings in all our offices. I try to drive people into those lanes where I’ve already allocated the time. So that means if I’m visiting customers, this isn’t the time for you to ask me about another issue. I’m with a customer.”


• Leadership is about understanding the trade offs: “One of the biggest things that executive leadership can provide is the ability to bifurcate the discussion into which things are really competing with each other and which things are independent,” said Dan. “If you get down to each of those discussions, you’re able to find better solutions because of the way you’ve framed the question.”