157: Cali Williams Yost - Workplace Flexibility: Addressing Competitive & Talent Realities

Cali Williams Yost, CEO and Founder of Flex+Strategy Group, has pioneered workplace flexibility since 1995. Cali shares her journey from banking to becoming a flexibility strategist. She explains why flexible work is essential for business growth and attracting and retaining top talent. Cali explains the pitfalls of hybrid and flexible model policy-only approaches and the need for full operational system-wide integration. She urges leaders to rethink outdated work constructs and outlines practical steps for embedding flexibility into organizational culture for sustainable success.

TAKEAWAYS

Chapter 1: Origins of a Flexibility Strategist

[01:19] Cali studies English and Economics appealing to her two contrasting interests.

[02:08] Cali's first job at a bank gives her training and allows her to go to New York City!

[02:43] Client relationships are key to success, but rigid systems cause Cali's colleagues to quit.

[03:35] Cali sees flexible work as logical and proposes it, unsuccessfully to bank leadership.

[04:30] A bank client CEO explains he offers flexible working to retain his employees long-term.

[05:14] Urged by his business-driven reasoning, Cali leaves to become a flexibility strategist.

[05:47] Cali gets an MBA to have credibility with business leaders about workplace innovation.

[06:10] Cali joins Families and Work Institute, developing strategies to operationalize flexibility.

[07:35] Workplace flexibility becomes an employee benefit part of policy, not operationalised.

[08:45] Making policies operational, Cali develops 'work-life fit' and publishes her first book.

Chapter 2: Workplace Flexibility Before & During COVID

[10:13] Top down approaches are not effective so Cali dives deep into change management.

[11:15] Cali starts her own firm to take an operational, integrated approach to flexible working.

[12:26] Pre-2020, most companies had flexible work policies but they weren't operationalised.

[13:50] Widespread flexibility was organic and inconsistent with more men working remotely.

[13:55] When COVID hit, companies with operationalised flexibility policies adapted easily.

[14:19] Executives must reassess foundational work constructs and beliefs to adapt effectively.

[17:00] The work challenges presented by leaders and younger employees "clash of contexts".

[18:55] The upcoming demographic cliff makes flexible work necessary to attract and retain talent.

Chapter 3: Leading in the Modern Work Era

[19:26] Finding those ready to lead the change, challenge their context and hold space.

[19:48] Three change phases—assess, align, activate—are critical for embedding flexibility.

[20:10] Leadership alignment is essential; one resistant leader can derail an entire initiative.

[22:45] Employers investing in defining new working parameters unlock many benefits.

[23:59] Leaders need to be aware of what is and isn't working with employees.

[25:31] Critical willingness to hold space for change being messy and looking at work differently.

[27:11] Mandating in-office days without data and strategic input erodes employee confidence.

[27:52] Executives co-creating with employees to achieve aligned operational flexibility.

[29:55] Trust increases when employees participate in experimenting and defining the process.

Chapter 4: Intentional Future of Work Transformation

[32:11] Senior leaders must be intentional about work transformation.

[32:50] The sustainability of 5-day/week RTO policies especially for talent attraction/retention.

[34:07] The significant, essential hurdle of stepping back and rethinking the old work model.

[35:12] Younger employees successfully create an intern integration program when empowered.

[37:45] Talent shortages by 2032 make flexible models essential to business continuity.

[38:33] AI will supplement, not replace, human workers—talent attraction remains vital.

[39:42] Rigid workspace metrics must evolve to support dynamic, flexible workforce needs.

[42:16] Organizational transformation requires change management and relationships with systems thinking.

IMMEDIATE ACTION TIP: Leaders need to assess their talent reality from now through 2030 – aligning the expectations of their workforce and the needs of the business.

RESOURCES

Cali Williams Yost on LinkedIn

flex+strategy group website

QUOTES

Pre-pandemic "Flexibility was happening organically. It was happening inconsistently, and it was not optimized."

"The consistent recognition is - I need to do this differently. So what does that look like?"

"You have to be willing to hold the space because change is messy."

"This [flexibility] isn't a policy. This is a way of operating."

"We're getting ready to hit a historic labour cliff demographic cliff. There aren't gonna be people. The workers who are left? They are going to dictate how they're gonna work. So you should be working right now on being employer of choice."