Five secrets to keeping your best employees

Executive overview

Leadership during times of transition requires connecting authentically with your team, trusting their judgment, investing in their wellbeing, and building a culture that scales. The pandemic revealed that employee retention depends less on perfect policies and more on demonstrating genuine care, autonomy, and opportunity for growth.

Core insight: The path to retention is showing—not just telling—your team they matter.

Be authentically, purposefully vulnerable

Personal, human connection is the antidote to disengagement. Angela Arendts, former SVP of retail at Apple, bypassed corporate hierarchy by recording unscripted weekly videos on her iPhone—three thoughts in three minutes, no editing. When her daughter called mid-recording, she took it. The next day she received 500 emails from employees thanking her for putting family first. Authenticity doesn't require oversharing; it requires strategic vulnerability aligned with your values and the moment.

• Record unvarnished messages your team can trust
• Lead with personal values, not corporate perfection
• Remove barriers between you and the people you lead

Give trust, not micromanagement

Leaders often assume remote or distributed teams can't function without oversight. When Uber's Dara Khosroshahi became CEO of Expedia, he was in every meeting, making every decision. A young product manager told him he was teaching people what to do instead of where to go—and that when he wasn't in the room, nothing happened. The shift to setting direction and trusting execution changed everything. Adam Grant's research showed that leaders who resisted remote work feared the worst without evidence; those who ran the experiment discovered productivity and culture actually improved.

• State the destination clearly; let teams find the route
• Evaluate outcomes, not assumptions
• Treat employees like peers with judgment and agency

Create moments of celebration and pride

Melanie Perkins at Canva runs quarterly "season openers" where the whole company gathers to celebrate milestones and preview future work. When they launched their Spanish product, they threw a La Tomatina tomato festival. During COVID, they shipped physical boxes with hidden clues and treats that teams unboxed together on video calls. These celebrations aren't about gamification—they're about making employees feel included in the tent, not acted upon. The specificity and physicality matter.

• Schedule regular celebrations tied to wins, not arbitrary dates
• Make celebrations feel genuine, not manufactured
• Use tangible elements (boxes, shared experiences) to build connection

Invest visibly in employee wellness

The pandemic taught leaders that work-life balance isn't optional. Claire Babineau Fontenot, CEO of Feeding America, was modeling destructive overwork; her team was working weekends without days off. She was becoming "snarky" and impatient—a warning sign her stress was poisoning leadership. She made time off mandatory on her calendar and announced it publicly, signaling permission for her team to do the same. Ed Bastien at Delta hired a chief health officer and expanded wellness programs to include mental health, financial coaching, and credit-score improvement. Wellness programs work because unhealthy, stressed people can't scale.

• Lead by example on rest and recovery
• Extend wellness beyond perks to financial and mental health support
• Make wellness a business necessity, not a nice-to-have

Empower junior team members as culture bearers

During the 2008 campaign, President Barack Obama's team didn't hire fewer young organizers as they scaled; they hired more, and capped senior salaries to do it. This distributed the culture at entry level where it mattered most. A county organizer in Iowa had decision-making authority and could respond to events quickly. Rachel Carlson at Guild Education found that Black employees using upskilling programs were promoted at 2X the rate of those who weren't—signaling that the company believed in them and they believed in themselves. Investment in junior talent compounds faster than any other retention lever.

• Hire generously at entry level to scale culture horizontally
• Give young team members real decision-making authority
• Fund upskilling and education as recruitment and retention tools