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Fresh conversations on leadership, hiring, workplace culture, and the future of work.

The Executive's HR Playbook

Systematizing Hiring, Retention, Performance & Engagement

Built for CEOs and Executive Leadership Teams

How many executive teams struggle with misaligned hires, disengaged employees, or leaders who avoid tough conversations?

These are not HR issues. They are profitability issues.

Most leadership teams have built disciplined systems for sales, operations, and finance. But when it comes to people, many executives are still managing through instinct, urgency, or personality.

The result is high turnover, inconsistent accountability, and cultures that feel fragile.

In The Executive’s HR Playbook, Kendra Prospero shows CEOs and executive teams how to treat people operations like every other core system in the business.

This session delivers practical frameworks for systematizing hiring, strengthening retention, driving performance, and building cultures where accountability scales.

Participants leave with an organizational health assessment, implementation tools, and a clear 12 to 18 month roadmap for building a team that delivers measurable results.

Key Takeaways:

  • A system for hiring smarter that filters for character, accountability, and culture fit
  • Retention strategies that help high performers stay and thrive
  • Performance management frameworks that empower managers
  • Practical tools for strengthening culture and accountability across the organization

01

Empower your employees for higher job performance using a simple tool.

02

Take away a self-assessment roadmap to attract and retain game-changing talent.

03

Empower your management team so it’s not all on you to make it work.

Get Off the Recruiting Treadmill

Every growing company is looking for talent, yet filling open roles often feels overwhelming and frustrating. Hiring can be time consuming, expensive, and discouraging for busy leaders. It can take months to fill a position, and even then leaders are often unsure if the person they hired is truly the right fit.

Finding great talent is more of a science than an art, but many organizations still rely on inconsistent processes and intuition when hiring. When companies struggle with turnover or a revolving door of employees, the hiring challenge becomes even more difficult.

In this practical and inspiring talk, Kendra Prospero draws on her experience as a CEO, founder, and recruiter who has personally recruited for hundreds of positions. She shares the systems and strategies she used to build a company with a consistent pipeline of strong candidates, low turnover, and a culture where employees thrive.

Key Takeaways:

  • Understand the seven steps of a strong hiring process that consistently attracts high quality candidates.
  •  Build a reliable pipeline of talent so open positions do not stall business growth.
  • Use powerful interview questions and evaluation tools to identify candidates who truly fit the role and culture.
  • Focus on the single most important factor that drives a strong, accountable culture.

How to Build a Business Case for HR Initiatives

Using Data and Metrics to Drive Leadership Buy-In

Most founders and entrepreneurs start their companies to build great products, make an impact, and grow a successful business, not to spend their time solving people problems.

Yet nearly every business challenge eventually becomes a people challenge.

Human Resources has the potential to solve many of these issues, but HR initiatives are often overlooked or underfunded because leaders struggle to connect them to measurable business outcomes.

In this session, Kendra Prospero shows leaders how to translate people challenges into clear financial impact. By using data, benchmarks, and practical frameworks, leaders learn how to build a compelling business case for HR initiatives that resonate with executive teams and drive real investment.

Drawing from her experience as a founder and CEO, Kendra shares the strategies she used to build a profitable company with low turnover, strong culture, and a highly engaged team.

This session provides leaders with practical tools to demonstrate how strong HR systems improve performance, reduce turnover, and protect profitability.

Key Takeaways:

  • Understand the seven steps of a strong hiring process that consistently attracts high quality candidates.
  •  Build a reliable pipeline of talent so open positions do not stall business growth.
  • Use powerful interview questions and evaluation tools to identify candidates who truly fit the role and culture.
  • Focus on the single most important factor that drives a strong, accountable culture.

Building a Bench of Talent

Strengthening Succession Planning and Developing Future Leaders

Succession planning often fails not because organizations lack talent, but because leaders struggle to intentionally develop the people around them.

Many leadership teams know they should be preparing future leaders, yet they rarely step back to examine how their own behaviors, expectations, and leadership habits influence the growth of others.

In this session, Kendra Prospero helps leaders rethink succession planning by starting with the leader. Participants learn how to identify critical roles within the organization, evaluate internal talent, and create development pathways that prepare the next generation of leadership.

Leaders will leave with practical tools for mentoring, coaching, and developing middle managers so leadership growth becomes a natural outcome of a strong culture.

Key Takeaways:

• How leadership behaviors and mindset influence the development of future leaders

• Tools for identifying critical roles and building intentional succession plans

• Practical methods for assessing team strengths and development opportunities

• Strategies for creating structured learning and development plans

• Mentoring, coaching, and delegation techniques that help middle managers grow into leadership roles

Building a Culture of Belonging

Practical Steps for Creating Stronger, More Inclusive Teams

Most leaders recognize the value of building a diverse and inclusive workplace, but many struggle with where to begin.

Hiring, developing, and retaining a more diverse team can feel overwhelming, and many organizations attempt initiatives that create little lasting impact.

In this practical and inspiring session, Kendra Prospero helps leaders move beyond theory and focus on the everyday leadership behaviors that create cultures where people feel valued, supported, and motivated to contribute.

Drawing on her experience as a founder and CEO, Kendra shares the strategies she used to build a company with strong representation across her team, low turnover, and a culture employees are proud to be part of.

Leaders leave with practical tools for strengthening culture, expanding their talent pool, and building organizations where people thrive.

Key Takeaways:

• The six foundational elements organizations need to begin building a culture of belonging

• A new framework for understanding diversity across multiple dimensions

• Practical steps leaders can take to expand and strengthen their talent pipeline

• Leadership behaviors that create environments where people feel valued and motivated to contribute

Frequently Asked Questions

Is The Executive’s HR Playbook a keynote or a workshop?

The Executive’s HR Playbook can be delivered as a keynote presentation or as a half day executive workshop depending on the needs of the organization. Many CEO peer groups and leadership teams choose the workshop format to allow deeper discussion and implementation.

Is this program designed for CEOs or HR leaders?

This program is designed primarily for CEOs and executive leadership teams. It focuses on building systems for hiring, retention, accountability, and performance that improve business outcomes.

Can this program be delivered for CEO peer groups like Vistage?

Yes. Kendra Prospero regularly delivers this program for CEO peer groups, executive leadership teams, and organizations looking to strengthen their people systems and leadership accountability.

Bring Kendra Prospero to Your Next Event

Kendra Prospero delivers practical, high impact programs for CEOs, executive leadership teams, and peer advisory groups. Her talks focus on building stronger hiring systems, improving accountability, and helping leaders create cultures where high performers thrive.

Each program can be delivered as a keynote presentation or an interactive executive workshop.

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