Why a Leadership Offsite Could Make or Break Your Reorganisation

Research consistently shows that 60–80% of reorganisations fail to fully achieve their intended objectives (McKinsey, Bain, and others).

The problems that derail them are rarely the new org chart itself. They occur in the leadership system around it. Essentially, these are human, relational, and execution problems. 

The solution? A well-designed leadership offsite where you can get the issues out onto the table and work out strategies to move through it.

This sounds obvious, but it's surprisingly easy for offsites to become disconnected from the real work. You get a speaker talking about leadership. A team-building activity. A few breakout discussions. Maybe a values exercise. A leader presents results. Everyone has a nice day. Then Monday arrives, and nothing changes.

As someone who has been facilitating offsites during a reorganisation over the last 10 years, I want to share with you what works.

5 Leadership Challenges That Can Derail a Reorganisation

Here are the five common problems a reorg creates, ranked by how frequently and severely they appear across the research, together with workshop design for offsites:

1. False Alignment Among Leaders

Senior leaders often believe they agree on the “why,” the “what,” and the “how” of the reorganisation when they actually do not. This is one of the most common and destructive issues (sometimes called the “false alignment trap”).

The executive team may agree to the restructure in principle but hold different views about:

• The future operating model.
• Which functions should have authority.
• What “efficiency” means.
• How much centralisation is appropriate.
• Which people or capabilities are critical.
• What trade-offs are acceptable.
• How quickly the change should occur.

This creates what might be called leadership drag. They nod in meetings, then interpret the new structure differently, protect turf, or quietly undermine decisions. Without genuine alignment at the top, middle managers and teams receive mixed signals and the reorg stalls.

McKinsey research identifies leadership undermining the change as one of the most harmful issues in less successful reorganisations. 

Offsite implication: In my Thriving, Trusted Teams workshops, the real work is trust-building and deep conversations. Workshops are structured so people feel safe for leaders to surface real differences in priorities, test assumptions, and reach genuine commitment rather than polite agreement.

This happens over the course of the offsite. I always push for my workshop to be one of the first items on the offsite agenda. The reason is that I know it does the important work of opening people up, so by the second day of the offsite you can really create agreement on the difficult choices, non-negotiables and leadership behaviours required.

2. Underestimating Culture, Resistance and the Human Impact

Reorganisations are treated as structural events when they are primarily identity events. People experience loss of status, relationships, clarity, and control. This triggers resistance, anxiety, withdrawal, and change fatigue.

During a restructure, employees may be asking:

• Will my role still exist?
• Who will I report to?
• Will my skills be valued?
• What happens to my team?
• Will there be opportunities in the new structure?
• Is this a safe place to build my career?

Even employees whose roles are secure can become distracted or demoralised. Key people may leave because they do not see a future, do not trust the process or feel excluded from decisions.

This is not only a cultural concern. Loss of critical talent, reduced productivity and weakened customer service can undermine the intended benefits of the restructure. McKinsey specifically identifies transitional risks including business interruption, talent loss and customer-care lapses.

Leaders frequently dismiss culture as “soft” and focus on boxes and lines. The result: productivity drops, top talent leaves, and old behaviours reassert themselves.

Offsite implication: Building psychological safety and trust allows leaders to acknowledge the emotional reality, model the new behaviours, and equip themselves to lead others through the transition rather than just announce it.

Ask leaders:

“Where are we most likely to underestimate the human impact?

Map the likely experience of different groups:

• People whose roles may change.
• People who may lose their role.
• People who remain but inherit more work.
• High performers who may be recruited elsewhere.
• Managers expected to communicate decisions.
• Customers who may experience disruption.

3. Prolonged Uncertainty and Poor Communication

Research on organisational redesign consistently points to communication and the quality of the change narrative as critical factors. McKinsey identifies the need for a compelling redesign narrative, while its reorganisation research highlights employee distraction and demoralisation major implementation challenges.

One of the most damaging mistakes is the “wait and see” approach such as keeping details secret until everything is finalised. The information vacuum fills with rumour, which is almost always worse than the reality.

Often, organisations don't explain clearly why they are changing. 

Leaders may have a financial, strategic or operational rationale, but employees hear a vague message such as:

• “We need to become more agile.”
• “We are streamlining.”
• “We are removing duplication.”
• “We are preparing for growth.”

When the rationale is unclear, people create their own explanations. The restructure becomes associated with cost-cutting, political manoeuvring or job insecurity. Even when the stated intention is growth.

Even when communication happens, it is often one-way, high-level, or focused only on the new structure rather than how day-to-day work will change. Middle managers are left without the clarity or support they need to translate the change for their teams.

Offsite implication: Use the offsite to align on a clear, consistent narrative and decide how leaders will communicate (and keep communicating) so uncertainty is actively managed rather than left to fester. 

Help the leadership team create a shared answer to:

“What business problem is this reorganisation solving, and what will be better when we are through it?”

By the end of the offsite, you want leaders to be able to consistently answer the question: “Why now?”

4. New Structure, Old Ways of Working

A restructure often creates more ambiguity before it creates clarity.

People are unsure:

• Who owns a decision.
• Who has authority to approve it.
• Which responsibilities belong to the centre or the business unit.
• How functions should work together.
• What to escalate.
• What they can decide without permission.

The result is duplication, delay, excessive meetings and decisions being pushed upwards.

The org chart changes but processes, decision rights, accountabilities, hand-offs, and governance do not. People report to new managers yet continue working in the old ways. Roles remain unclear. Ownership of outcomes is fuzzy.

This is why many reorgs deliver little lasting improvement. The “skeleton” changes but the “nervous system” (how work actually flows) does not.

This problem is especially common when leaders focus on reporting lines rather than the operating model. McKinsey recommends defining decision rights, responsibilities and escalation paths, and warns against overlapping authority.

Offsite implication: Accountability focus and forward-planning work are important here. Force clarity on who owns what, how decisions will be made, and what new behaviours and processes are required. Turn insight into named commitments.

Ask:

“What are the five to ten decisions that must become clearer or faster after the restructure?”

5. Failure to Sustain the Change After the Announcement

Typically, the business loses execution capacity during the transition. The organisation is expected to perform business as usual while redesigning itself.

At the same time, leaders and managers are pulled into:

• Design meetings.
• Consultation processes.
• Role evaluations.
• Reporting-line discussions.
• New process development.
• Communication activity.
• Technology and systems changes.

Leaders invest heavily in designing and announcing the new structure, then under-invest in embedding it. There is little reinforcement, limited coaching of middle managers, weak follow-through on new ways of working, and no clear rhythm for checking progress.

Within months, people quietly revert. In some cases, roles that were eliminated reappear under different names within 18–24 months.

Offsite implication: Create a transition plan that protects essential performance while the new model is being built. End with concrete 30/60/90-day commitments, clear ownership, and a simple tracking rhythm so the energy of the offsite converts into sustained behaviour change rather than a one-off event.

Ask:

“What must not be allowed to deteriorate while we reorganise?”

Reorgs Need More Than a New Org Chart

A successful reorg requires more than changing reporting lines. Leaders need to align on the case for change, understand the human impact, communicate consistently, clarify decision rights and create the conditions for new ways of working to stick.

That’s where a leadership offsite can make a real difference. It creates the space for leaders to tackle the difficult issues, make clear decisions and commit to how they will lead the transition.

If you’re about to announce the reorg: Focus on leadership alignment, the shared case for change and consistent communication.

If the reorg has been announced but hasn’t started: Focus on stakeholder impacts, decision rights and a clear 90-day transition plan.

If the reorg is already underway and isn’t working: Go back to the five problems above, identify what’s getting in the way and tackle it directly.

A reorg is a leadership transition, that's all about people. If you think its just a structural change, you'll get resistance. If you’re planning a reorg or already in the middle of one, book a chat with me about running a workshop at your offsite or designing the full agenda.