The CHRO Insider's Workbook: Tested strategies for organizational success

This workbook supplements SeekOut’s CHRO Council Workshop Series, five webinars led by former CHROs to pack your toolbelt with strategies that enable workforce agility and business longevity. You’ll find key webinar takeaways, tips, and worksheets that help lay the groundwork to drive change and develop your role as a CHRO.

You'll deep dive into common challenges that CHROs and talent teams face today:

• Strategic workforce planning

• Building a holistic talent roadmap

• Finding clarity in the DEI landscape

• Skills intelligence and talent mobility

• Inspiring change across your organization

In HR, you stand at the intersection of your organization’s most pressing challenges and its greatest opportunities. Whether you’re catching up with an evolving DEI landscape, reimagining talent mobility, or building community in the workplace, your actions greatly impact the health of your organization. But the reality is, it can sometimes feel like you’re doing it all on your own.

SeekOut’s CHRO Council

Our CHRO Council advisors are seasoned leaders who now advise organizations through the complexities of creating holistic talent strategies that break down organizational silos. While their solutions are not a one-size-fits-all approach, they are invaluable in helping clear the fog to find a path forward. Their firsthand experiences and lessons learned have helped organizations transform their talent strategies and achieve meaningful results.

A note on the journey ahead

The content of this workbook is foundational and not meant as a quick fix. Each worksheet tackles distinct yet interconnected challenges whose strategies may require months to get off the ground and often take years to fully realize. True organizational transformation takes time, patience, and unwavering commitment. As you work through these exercises, remember that you’re building a foundation for lasting change. While the results may not be immediate, the framework you develop here will guide your organization toward sustainable, long-term success.

Strategic workforce planning: How to get the right people involved

Your expert advisor: Dermot O’Brien

Dermot is the former CHRO and Chief Transformation Officer at ADP. He has nearly 20 years of experience reporting to CEOs and led global teams for over 30 years.

Think of strategic workforce planning as a blend of art and science where organizations match the right talent to the right business priorities. HR’s responsibility is working with stakeholders to extract meaning behind business objectives and translate that into an actionable plan.

“When the business is clear on detailing what they’re trying to achieve, HR can play its role as experts to deliver on the needs of the business,” says Dermot. “It’s simple, but we tend to complicate things with too many processes and not getting the information we need ahead of time.”

Why do organizations struggle with strategic workforce planning?

• HR teams are separated from the business. 72% of HR teams lack full integration with business planning processes. 1

• Talent acquisition isn’t valued as a strategic partner. 92% of TA teams aren’t involved in workforce planning and mobility initiatives. 2

• Most hiring is ad hoc. 66% of HR teams are stuck in basic headcount planning. 3

Dermot’s tips for breaking through these challenges

• Bridge the silos. When HR, finance, and business leaders plan together from the start, everyone wins. No department can do this alone.

• Involve talent acquisition early. Your talent team knows what’s really happening in the market. Use their insights early to shape smarter decisions.

• Think HR architected, business led. Stop reacting, start planning. Your workforce strategy should drive business growth, not just fill empty seats.

Building a holistic talent roadmap: How to break down silos

Your expert advisor: Annie Rihn

Annie is the former VP of Talent at Discord and Zillow. She has over 20 years of talent experience. Having spent time in various recruiting roles, she is a champion of cross-collaborative relationships at work.

A holistic talent strategy places skills at the center of all talent decisions, where capabilities are seamlessly identified, developed, and mobilized across the business. Organizations can better adapt to changing market conditions, increase retention, and plan critical skills ahead of demand. When talent initiatives work in concert, organizations maximize ROI and create a sustainable talent ecosystem.

“People leaders often do things in a vacuum, but getting the right people in the conversation early is the critical starting point to creating a holistic strategy,” says Annie. “If you aren’t unified, you end up with a lot of external hiring, expensive redundancies, and missed opportunities.”

Why do you need a holistic talent strategy?

• It mitigates talent shortages. Organizations are 107% more likely to place talent effectively. 4

• Keep your best talent longer. Organizations are 98% more likely to retain high performers and have a reputation as a great place to grow and develop. 5

• It’s critical in achieving business returns. Companies that centralize talent in their business strategy realize higher total shareholder returns than their competitors. 6

Annie’s tips to building your holistic talent roadmap

• Pick one problem. Start with a single business challenge that matters to all talent teams. Success comes from focused momentum, not trying to fix everything at once.

• Connect your data. Get your talent teams together to identify their “wish we had known” moments. These gaps show exactly where to start breaking down silos.

• Identify your tools. Integrate the data with the right tools to foster effective cross-collaboration.

What’s up with DEI? How to find clarity in a changing landscape

Your expert advisor: Betty Thompson

Betty is the Chair of SHRM’s Board of Directors and the former CHRO at Booz Allen. With decades of experience in HR, executive leadership, and board positions, she has directed human capital strategy and human resource functions for large

Over the last several years, organizations have attempted to address diversity and inclusion but made less progress than expected despite significant resources and good intentions. The fundamental barrier to success lies in repeating ineffective approaches rather than addressing the core organizational culture.

“It’s time for a reset,” says Betty, noting that organizations should prioritize nurturing an inclusive culture to start making real progress. “Inclusion is the harder part because you have to change the behaviors that compound over time and contribute to what I call ‘invisible barriers,’ such as recognizing who isn’t speaking in meetings.”

To support behavioral changes, organizations should shift to skills-based hiring, which focuses on what candidates can do rather than where they come from. Betty encourages teams to adopt AI-driven analytics to forecast talent needs while ensuring DEI objectives are met through more data-informed decision-making processes.

Reality check: The DEI landscape today

• 97% of organizations say they’ve made changes that are improving DEI outcomes... 7

• But only 37% of workers strongly agree on progress. 8

• 70% of enterprises will need to shift to adaptive AI strategies to advance DEI goals by 2029. 9

Betty’s tips for revitalizing your DEI initiatives

• Inclusion comes first. Hiring diverse talent only goes so far if your culture, behaviors, and daily decisions don’t support their success.

• Track micro-decisions. Real inclusion happens in everyday moments, such as who gets high-visibility projects and who gets mentored.

• Use AI as a flashlight, not a filter. AI should help you discover hidden talent and create new pathways, not reinforce old obstacles.

The business case for talent mobility: How skills intelligence strengthens retention and agility

Your expert advisor: Jeff Diana

Jeff is the former CHRO at Calendly, Atlassian, and SuccessFactors. He is a seasoned HR executive known for his leadership in scaling global businesses. He is currently a consultant for high-growth companies.

Internal mobility turns your existing workforce into your competitive advantage, moving people and their skills where needed while creating career growth opportunities that support employee retention. Historically, HR hasn’t had access to the right information to make agility possible. This is no longer an excuse given the sophistication of AI tools available today that can leverage the talent intelligence we need to make smart decisions.

“The quality of having people in the most impactful jobs with the most impactful skill sets has never been more critical in the history of business,” says Jeff. “Your business will not perform if you don’t do this well.”

Why is talent agility gaining momentum?

• Career paths fail to meet modern workforce needs. 86% of HR leaders believe career paths at their organization are unclear for many employees. 10

• Talent intelligence has become more important than ever. 84% of CHROs said talent intelligence was a top priority for 2024. 11

• A perfect storm of opportunity and urgency. 79% of CHROs say they’re hiring fewer new employees compared to 12 months ago, yet 67% of employees would switch jobs for learning opportunities. 12

Jeff’s tips for achieving successful business outcomes with talent agility

• Find strategic alignment to business priorities. Dig into your company business strategy and why each goal was determined. Learn about your competitors and the workforce at large.

• Integrate your talent tech stack. You’ll get a complete view of both your team’s skills and the job market, so you can make smarter, faster decisions to fill gaps.

• Foster a culture of mobility. You’ll maximize the capabilities of your people by deploying the right skills to the right work at the right time. And it starts by setting clear career paths that employees can follow.

The most exciting chapter for HR: How to inspire change across organizations

Your expert advisor: David Landman, Ph.D.

David is the former talent leader at Goldman Sachs and has over 20 years of experience as an HR executive. He dedicates his time helping companies, innovators, and investors redefine what it means to thrive at work.

Transformative change happens through authentic networking—how you understand your audience and show up to these conversations. These opportunities happen within your organization and across your professional connections. Networking with purpose in both circles builds a deep connection through trust and community that leads to long-lasting business success.

“The power of having connection and community within your company opens the aperture to understand different experiences and perspectives of the people you serve,” says David. “Externally, community is where challenges and lessons learned are exchanged so you can gather intelligence to support your role as an HR leader when driving change forward.”

David emphasizes a critical mindset shift for today’s fast-evolving HR tech landscape: successful HR leaders acting as shepherds, not dictators. HR leaders should go beyond technical expertise to listen and learn so they can guide their organizations through digital transformation and create solutions that work for everyone.

What top CHRO must do in 2025

• Lead with empathy. In a recent survey of 3,000 HR professionals, one-third felt empathy was lacking at the top of their organizations. 13

• Lead the charge to find solutions. 74% of HR leaders report relying on IT to some extent for identifying new digital technologies for their most critical digital initiative. 14

• Lean on your community to learn what tech is right for your business goals. Eight out of 10 HR software buyers experience regret. 15

David’s tips for networking your way to transformative change

• Practice active listening. Lead with curiosity by asking questions and seeking to understand others’ experiences and emotions before proposing solutions.

• Check your ego. Be willing to compromise and adapt. Prioritize getting 70% of your great ideas implemented over holding onto 100% of a perfect, unshared concept.

• Make real connections. To connect authentically, introduce yourself as a human first, not just a title. Focus on what gives you joy and purpose, and use that to create meaningful, vulnerable connections with your stakeholders and peers/colleagues.

SeekOut’s Talent Intelligence Platform helps thousands of organizations of all sizes and industries hire, grow and retain great talent. Founded in 2017 by a team of enterprise software veterans, SeekOut is backed by leading investors at Tiger Global Management, Madrona Venture Group, Mayfield and Founders Circle Capital. SeekOut has two primary product offerings—Recruit, for identifying new talent, and Grow, for maximizing a company’s existing internal talent. Leading companies, including Peraton, Experian and Northrup Grumman, rely on SeekOut to unify their talent acquisition, talent management, and talent analytics in a single people-first platform.

This workbook is a great way to start 2025 with a renewed focus on your talent goals! To get your Worksheets download the E-Book!