Strategy Requires Grieving

By Minal Bopaiah and Judy Oyedele

When Saying "No" Means Saying Goodbye

In a previous blog post, we wrote about the way tripwires and safety plans can help you respond thoughtfully (instead of reacting impulsively) to threats and dangers in our world. 

These threats and dangers continue to escalate globally under the new U.S. administration, and wise leaders are working on strategies for survival and resistance.

However, one aspect of strategic planning that gets overlooked is the need to say “no” to things. If you or your team don’t know what you’re saying “no” to, what you’re going to stop doing in order to focus on what matters, then your plan is not a strategic plan, it’s a vision board. As Steve Jobs wisely noted, "Focus means saying no to a thousand things to make sure we don't get on the wrong track or try to do too much." 

But here's what they don't tell you in leadership books: every strategic "no" comes with grief attached.

The Emotional Weight of Strategy

Last year, I sat with the executive director of an international nonprofit as she mapped out all her responsibilities on a strategic prioritization matrix. As we filled the paper with more and more sticky notes representing her commitments, her eyes widened with each addition. "I can't fit any more post-it notes on this paper," she sighed, her body physically reacting to the weight of all she was carrying.

"Yes," I told her, "and I think we both know that means you're going to have to let go of some things. Either you decide now to put them down gently, or you try to hold on to all of them and they shatter when they escape your grasp. Which would you prefer?"

The math was clear—their new strategy required a business development push that she personally needed to lead. But this meant letting go of other responsibilities she genuinely enjoyed, like country site visits to meet with member organizations. By day's end, tears welled in her eyes as she confronted the reality: "I can't do all these things."

What became evident in that moment was the emotional toll of strategic decision-making. Despite her training and experience in leadership, nothing had prepared her for how deeply it would hurt to let go of meaningful work she valued in order to pursue what was strategically necessary for the organization.

Her experience isn't unique. As political winds shift and economic realities transform, organizations find themselves forced to make difficult choices. The current administration's policy changes have accelerated this phenomenon across sectors, creating both opportunities and painful contractions. But regardless of your political leanings, one truth remains: effective strategy requires both clear-eyed assessment and emotional intelligence.

Why We Need Rituals for Organizational Loss

Humans have developed rituals for personal grief across all cultures and times. We instinctively understand that meaningful transitions require ceremonial acknowledgment. Yet in our professional lives, we often expect ourselves and our teams to simply "move on" when initiatives end, programs shut down, or colleagues depart.

This oversight isn't just psychologically harmful—it's strategically unsound. Unprocessed grief lingers, creating resistance to change and contaminating future work. When we don't acknowledge what's being lost, we struggle to fully embrace what's next.

Workplace Rituals for Strategic Grief

Here are seven practical rituals that can help organizations process the grief that comes with strategic change:

1. The Completion Circle: Gather team members who worked on the ending project or with departing colleagues. Form a circle and invite each person to share one memory and one lesson they're carrying forward. If you’re meeting remotely, you can create a Digital Memory Wall (using Miro, a Kudo board, Padlet, or even a dedicated Slack channel or Google doc), where team members can post memories, screenshots and reflections about what’s ending. Then schedule a video call to review it together.

2. The Archive Ceremony: Rather than simply filing away documentation from completed projects, create a brief ceremony where key artifacts are placed into a physical or digital "archive," accompanied by brief statements acknowledging their importance. For remote workers, you can send small physical items to team members' homes to arrive on the same day—perhaps a plant symbolizing new growth or a small box to physically "put away" printed mementos of completed work.

3. The Strategic Wake: Just as Irish wakes combine sorrow with celebration, host an event that honors what's ending while simultaneously turning attention to the future. Include both remembrances and forward-looking toasts. You can simulate this remotely with a Synchronized Moment, where everyone on the team lights a candle or pours a drink during a video call.

4. Gratitude Letters: Have team members write letters of appreciation to departing colleagues or expressing gratitude for what a concluded initiative accomplished. These can be shared publicly or privately.

5. The Artifact Exchange: For major transitions, create small tokens (pins, desk items, digital badges) that commemorate what's ending and symbolize carrying its legacy forward.

6. The Shared Playlist: Create a collaborative playlist where each team member adds a song that represents either what's ending or what's beginning. Share stories behind the selections during a virtual or in-person gathering.

7. The Wisdom Jam: Schedule a structured session where team members explicitly identify what should be remembered and carried forward from what's ending. Document these insights formally. 

When Strategy and Grief Align

An international organization I worked with was still processing emotions from a challenging event they had hosted months earlier. Despite conducting an immediate operational debrief, unresolved feelings of disappointment, powerlessness, and anger continued to simmer among the staff. The executive director recognized that these unprocessed emotions were blocking their ability to move forward with strategic changes needed for the next iteration of the event.

Rather than simply pushing ahead with planning, we implemented a Wisdom Jam—a structured process for metabolizing collective grief and extracting learning. Four months after the original event, staff gathered to reflect on a specific question: "What is the wisdom you gained from this experience that will support your future resilience?" Each person had three uninterrupted minutes to share while others listened deeply.

"I was concerned that some voices would dominate while quieter perspectives would be lost," the executive director confided before we began. By establishing a clear process with equal air time for all, we created safety for authentic expression. As people shared, the emotional tone in the room visibly shifted—from hurt, remorse and anxiety to a sense of being supported, powerful, and thankful.

"I was amazed at the difference it made," the ED told me afterward. "Instead of dwelling on what went wrong, people now reference their insights with confidence while focusing their energy on creating a better experience next time."

The timing proved significant too—this wasn't grieving on a predetermined schedule, but rather meeting the group where they were emotionally, allowing them to process when they were ready to extract meaning from the experience.

Handling Resistance to Grief Rituals

Despite their value, organizational grief rituals often encounter resistance. Here's how to address common objections:

"We don't have time for this": Frame the ritual as an investment in future efficiency. Research shows that unprocessed transitions create drag on future work, while proper closure accelerates adaptation. Keep initial rituals brief (15-30 minutes) to demonstrate their value.

"This feels too touchy-feely": Start with more concrete, practical rituals like the Wisdom Capture or Archive Ceremony that focus on knowledge preservation. As comfort grows, more emotionally expressive rituals can be introduced.

"People will just get more upset": Acknowledge that expressing emotions might temporarily increase visible discomfort, but suppressed emotions are what truly damage morale and productivity. And employ a skilled facilitator who can hold space and create a sense of comfort; that’s how you increase trust through the process.

"Our senior leadership won't participate": Begin with rituals among teams directly affected, demonstrating their value through improved morale and adaptation. Share these positive outcomes upward, inviting but not requiring leadership participation.

"This isn't culturally appropriate for us": Invite team input on what feels right for your specific culture. Different teams within the same organization may prefer different approaches, and that's perfectly fine.

Adapting Rituals to Different Organizational Cultures

Organizations, like individuals, have distinct personalities and comfort levels with emotional expression. Here's how to tailor grief rituals to different organizational cultures:

Data-Driven Organizations: Frame rituals as part of "transition management" with measurable benefits. Focus on capturing lessons learned and preventing knowledge loss. Consider using metrics to track team morale and adaptation before and after implementing rituals.

Mission-Driven Nonprofits: Connect rituals to organizational values and impact. Emphasize how honoring ended initiatives preserves their legacy and influence on future work. Incorporate stories of beneficiary impact into the ritual.

Creative Industries: Lean into artistic expression. Invite team members to create visual representations, write poetry, or compose music that captures the transition. Consider creating a permanent installation or digital gallery.

Traditional Hierarchies: Begin with leader-sanctioned rituals that respect existing power structures. Create separate spaces for peer-level processing alongside official organizational acknowledgments.

Startup Environments: Embrace experimentation and iteration with rituals. Try different approaches, gather feedback, and adapt quickly. Connect grieving to the startup value of "failing forward."

Global/Multicultural Teams: Research cultural attitudes toward grief and transitions in team members' backgrounds. Offer multiple ritual options that respect different cultural approaches to loss and change. Be particularly careful to avoid imposing Western emotional norms.

The Courage to Grieve, The Wisdom to Adapt

The path forward for today's leaders isn't about denying reality or pretending changes don't hurt. It's about having the courage to acknowledge loss while maintaining the clarity to adapt.

By integrating rituals that honor what's ending, you create psychological safety that makes strategic pivots more successful. You demonstrate that organizational history matters even as you write new chapters. Most importantly, you model the emotional intelligence that sustainable leadership requires.

Strategy does require saying no. But saying no doesn't have to mean forgetting. And the team at Brevity & Wit can help. With leadership coaching, expert facilitation, and thoughtful grieving practices, your “no”s can become not just endings, but foundations for what comes next.