As we live and work longer, leaders need to redefine how they think about attracting and developing intergenerational talent. Modern Elder Academy’s Chip Conley is at the forefront of this mindset shift, explaining why “wisdom workers” will take the place of “knowledge workers.” A close mentor to Airbnb founder Brian Chesky, Chip stresses that those in mid-career face both more angst and more opportunity than ever. He provides a roadmap for reframing midlife from crisis to calling, and argues that five generations in the workplace requires a new generational compact.

The ability to ask the right questions at the right times of the right people is an essential skill for every entrepreneur. For Michael Seibel, managing director at Y Combinator, action sometimes needs to take a back seat to asking: “Is this working?” Michael learned early on that by stopping to ask the counterintuitive question, he gained the wisdom – and avoided time lost to big mistakes – that ultimately propelled him forward.

Creating a prototype isn’t the same as leading a team of thousands. You need to keep your mission constant, but your tactics fluid as you scale. This is the challenge President Barack Obama faced after winning the 2008 election. In the second part of interview, we dive into how he grappled with the Great Recession, the Affordable Care Act, and the disastrous rollout of healthcare.gov. Through it all, he learned to let first principles guide the way, even as he and his staff adapted to new realities and changing rules.

To win at scale, you need more than great players – you need a team of great coaches. Alex Rodriguez learned this in baseball, and now as an investor at A-Rod Corp., where his mentor is none other than Warren Buffet. Alex and Reid, with Katia Beauchamp of Birchbox and HBS professor Mihir Desai, take questions from the HBS class of ’21.

We’re talking with Baratunde Thurston on how companies can show up as citizens — citizens with the potential for outsize impact.

If you try to avoid risk, you actually risk total failure. Or worse: mediocrity. Take it from Shellye Archambeau. She led the most stunning Silicon Valley turnaround you’ve never heard of. She took the role of CEO for a failing tech company, months from bankruptcy. Through a series of calculated risks, she led it through a complex merger, a head-spinning pivot, and grew it into MetricStream, which now boasts 1200 employees and a valuation in the hundreds of millions. How? Clear goals and big risks — the same principles that have defined her career. With a cameo appearance by champion poker player Liv Boeree.