We need to re-structure the executive team by the end of the quarter?
Those words mark the beginning of what might be your most visible leadership challenge this year—transitioning a senior executive out of your organization.
For HR leaders and CHROs, executive separations create sleepless nights. The impact is immediate and far-reaching: How will the executive team dynamics shift? Will key client relationships suffer? How deeply will this impact your carefully cultivated employer brand?
Executive outplacement decisions aren’t just about the individual departing—they’re about everyone watching how you handle this critical moment of truth.
"I Thought I Knew Everything About Outplacement—Until I Needed It Myself"
What happens when the person who once designed outplacement programs suddenly becomes the recipient? The blind spots revealed are profound.
Karen Hague lived this exact scenario. As a seasoned Head of HR, she had orchestrated numerous executive transitions. Then suddenly, she found herself on the other side of the table. Everything she thought she knew was challenged.
“I’ve sat in the job seeker seat twice and I’ve sat in the client seat several times as well,” Karen shared in a recent interview on the Courage to Advance podcast. This unique vantage point revealed blind spots she hadn’t recognized when implementing outplacement as an HR leader.
“As a participant, I thought I knew exactly what I needed to do, and I didn’t,” Karen admits. “I knew how to do it from a hiring manager or certainly an HR perspective, but I didn’t know how to do that from a job seeker perspective.”
This revelation highlights an important insightfor HR leaders: even with extensive experience managing outplacement programs, the emotional and practical realities of career transition remain largely invisible until experienced personally
"This Is a Cost We Can't Afford Right Now"—The CFO's Challenge You Must Overcome
Your CFO reviews the executive outplacement proposal with a concerned expression. ‘In this cost-cutting environment, is this investment for departing executives truly justified?’
It’s the objection every HR leader dreads during restructuring, and it stems from a fundamental misunderstanding. While executive outplacement appears as a line-item expense, its absence creates hidden costs that far exceed the investment. Here’s what your CFO needs to understand:
- Enhanced Employer Brand: How you handle visible executive departures directly impacts your organization’s reputation. These alumni become powerful brand ambassadors—or detractors—based on their transition experience.
- Culture Preservation: “It’s important for the people who are left behind to know that you did everything that you could in that moment,” Karen notes. “It doesn’t make it any less tough, but it does make it a little bit more manageable.” The remaining workforce observes how departing executives are treated, drawing conclusions about the organization’s values.
- Mitigated Business Disruption: Properly supported executives’ transition more smoothly, minimizing knowledge drain and productivity loss during restructuring.
- Strengthened Alumni Engagement: Executives who experience compassionate outplacement often maintain positive relationships with the organization, becoming valuable referral sources and potential boomerang hires.
- Unlocked Talent Pipelines: A strong executive outplacement program demonstrates your commitment to supporting leaders throughout their career journey, enhancing your ability to attract top executive talent.
As Karen explains, “When we think of managers, what they do and what they say has a big, oversized impact on their team than one of the individuals on their team.”
The 9:00 AM Calendar Invite Everyone Dreads: Moving Beyond the Dreaded "Separation Conversation"
You’ve seen that look of realization when an executive receives a mysterious meeting invite from both HR and their manager. The anxiety hits. What happens in the 24 hours before that meeting—and the moments that follow—will determine whether this transition becomes a damaging wound or the foundation for something new and purposeful.
Effective executive outplacement isn’t about that single difficult conversation. It’s about creating a thoughtful, strategic framework that begins long before the separation meeting:
1. Preparation Is Everything
“Get ahead of it,” Karen advises. Rather than improvising during a reduction in force, develop a comprehensive outplacement strategy that defines:
- Communication protocols that prioritize transparency and respect
- Support resources tailored to executive-level transitions
- Clear timelines and transition processes
- Specific messaging for the remaining team members
2. Meet Executives Where They Are
Executive transitions require a tailored, high-touch approach. Karen emphasizes that when supporting executives in transition, “it’s eight different approaches for what that person needs in that moment.”
Effective support requires:
- Recognition of the unique emotional journey each executive faces
- Personalized coaching from certified experts who understand executive transition
- A balance between emotional support and strategic career guidance
- Flexibility in outplacement service delivery
3. Balance Business Necessity with Human Dignity
While reduction decisions may be driven by financial imperatives, the implementation should be guided by strategic compassion. As Karen notes, “There can be empathy and transparency and honesty in the process.”
This balance requires:
- Clear communication of business rationale
- Acknowledgment of the executive’s contributions
- Appropriate time for processing the information
- Comprehensive support during the transition
"I'm Not Just Losing My Job—I'm Losing Who I Am"
Twenty years shaping this company. This division exist from vision. Without that role, I am not sure who I am anymore.”
This refrain echoes in every executive transition. For senior leaders, the separation isn’t just from a position—it’s from a core identity, a purpose, a community, and often, a future they had carefully mapped out.
The executive who has always been the one supporting others through transitions suddenly finds themselves vulnerable, uncertain, and forced to rebuild not just a career, but a sense of self. Effective outplacement addresses this profound identity disruption through three critical phases:
Phase 1: Stabilize and Process the Transition
The initial shock of job loss can be particularly acute for executives whose identities are strongly connected to their positions. This critical first phase focuses on:
- Creating space to process emotions and rebuild confidence
- Developing a transition narrative that preserves dignity and authenticity
- Assessing immediate needs and priorities
- Establishing a structured approach to the career transition journey
Phase 2: Re-envision Strengths and Possibilities
Karen describes how outplacement became an opportunity for her to reassess her professional values and strengths: “When I show up as my authentic, transparent, vulnerable self, I’m at my best. And it took me a while to realize what was my best, but I can’t fake it. It gave me the opportunity to look at that and say, that’s okay, because this is really where I want to focus my time and energy anyway.”
This phase helps executives:
- Reflect on their authentic strengths and preferences
- Identify values that must be present in their next role
- Consider how this transition might enable better alignment
- Evaluate career options with fresh perspective
Phase 3: Launch into Next Chapters
“The first time I told that story, it kind of got caught in my throat,” Karen recalls explaining her departure. “Am I going to be this transparent and authentic? I tell you what, it gave me the biggest boost of confidence.”
This final phase prepares executives to:
- Craft and confidently deliver their transition narrative
- Strategically activate their network for maximum impact
- Navigate executive search processes effectively
- Negotiate and onboard successfully into their next role
Karen discovered that her network was more valuable than she had realized: “I didn’t always realize it as a network, and I didn’t realize how powerful my network was until I went to it for some help.”
"We're Letting Go of 30 People—Why Should This One Executive Get Special Treatment?"
This pointed question from skeptical stakeholders can catch even seasoned HR leaders off guard. It forces you to articulate why executive transitions require distinct handling—and why the investment delivers outsized returns.
The answer lies not in preferential treatment, but in strategic risk management. An executive’s departure creates unique vulnerabilities that require specialized care. Here’s how to reframe this conversation from expense justification to strategic investment:
- Elevate the Value Proposition: Position executive outplacement not as an obligation but as a strategic investment in human capital that protects employer brand, culture, and relationships.
- Highlight Impact on Remaining Leaders: “The care and feeding of your organization, of people who remain, that you want to be great, productive, happy citizens in your company is really important,” Karen notes.
- Emphasize Long-Term ROI: The true cost of mishandling executive transitions extends far beyond the immediate event, potentially damaging vital relationships and reputation for years. Kim adds,“It matters to the brand impact; it matters to the engagement. It matters to the involuntary turnover that could come after or to the voluntary turnover that could come afterwards with people not feeling like things were handled well.”
- Frame as Talent Lifecycle Management: Effective outplacement demonstrates your organization’s commitment to treating talent respectfully throughout the entire employee journey
From Crisis to Clarity: Your Roadmap When Executive Outplacement Can't Wait
You’ve just learned about an imminent executive restructuring that needs to happen within weeks. There’s no time for lengthy vendor evaluations or program development—you need a proven approach now.
Whether you’re a CHRO faced with an unexpected executive departure or preparing for a planned restructuring, this three-step roadmap provides immediate clarity:
- Connect: Reach out to specialized outplacement providers to explore how their executive-focused solutions can support your organization’s unique needs. The right partner will understand the sensitivities surrounding executive transitions.
- Customize: Partner with your outplacement provider to tailor the program to your organization’s culture, values, and objectives. Ensure alignment with your existing HR processes and employer brand strategy.
- Implement: Launch the executive outplacement program with support from dedicated success teams who provide ongoing guidance and regular reporting to ensure measurable results.
"The Best Leaders I Ever Worked for Were the Ones Who Fired Me"
This surprising statement comes from executives who experienced thoughtful, strategic transitions. It represents the transformational potential when difficult endings become catalysts for powerful new beginnings.
As Karen’s journey from HR leader to job seeker reveals, outplacement isn’t just a separation service—it’s an opportunity for profound reinvention and growth. When handled with strategic vision and genuine care, these transitions can create lasting positive impressions that transcend the pain of separation.
“I think almost always people move on to something bigger and better with that support,” Karen reflects. By reimagining executive outplacement as a strategic transformation opportunity, HR leaders can:
- Protect vital relationships and organizational reputation
- Transform difficult transitions into opportunities for growth
- Create lasting value even in challenging organizational moments
- Build a reputation as employer brand champions who invest in leader success
The most forward-thinking organizations understand that how they handle executive transitions speaks volumes about their values and culture. By investing in high-touch, transformative outplacement experiences, you don’t just ease transitions—you build a powerful legacy of care and strategic vision that strengthens your organization for years to come.
This article was inspired by insights from Karen Hague’s conversation with Kim Bohr on the Courage to Advance podcast. To hear the full discussion about executive career transitions, listen to “From HR Leader to Job Seeker: Mastering Career Transition with Authenticity and Strategic Networking” on the Courage to Advance podcast.
