Leadership Team Growth and Resilience Workshop

A CEO I’m working with shared a moment of crisis they’d gone through recently.

Their company was on the brink of bankruptcy, and the pressure to make decisions weighed heavily on everyone, including the leadership team.

In that situation, they had two choices:

1. Take the easy route by letting the business limp along in the hopes that things would get better.
2. Or make the tough decision to cut costs, restructure, and risk losing some of the team.

It wasn’t an easy choice, but the longer they delayed it, the worse things got.

After a lot of internal struggle, they decided to take the bold step.

What followed was a difficult yet transformative process.

The company restructured, people were laid off, and they had to face the emotional fallout.

But because the CEO chose to lead through the crisis, communicate openly with their team, and stick to the hard decisions, they eventually emerged stronger.

The company didn't just survive; it began to thrive.

The team became more cohesive, more focused, and more aligned with the company’s long-term vision.

This story highlights an important lesson: leadership in tough times is never easy.

This workshop is based on the insights from the book "The Hard Thing About Hard Things" by Ben Horowitz.

It's in those moments when the weight of the world feels like it's on your shoulders that you’re faced with the real test.

Do you shy away from the tough decisions, or do you lean into the discomfort and lead your team through it?

The CEO could have taken the easy way out, but they chose to face the hard things.

And that decision set them on a path to long-term success.

That’s exactly what we will be exploring in this workshop for leadership teams.

We will look at real-world challenges, like the one this CEO faced, and work together to build the tools that will help you lead your team with resilience, make the tough calls when needed, and come out stronger on the other side.

It's about embracing adversity, not avoiding it, and recognising that through those tough moments, you build the strength and clarity needed to succeed.

In this workshop, your participants will learn how to:

• Make tough, but necessary, decisions that move their team forward.
• Lead with resilience and clarity, even when things get tough.
• Build a culture that can thrive under pressure.
• Create a team dynamic that empowers everyone to succeed, even in adversity.
• Commit to actionable strategies for growing as a leader and as a team.

If you are ready to face the challenges head-on, learn from the tough moments, and lead teams to long-term success, this workshop is for you.

Let’s get into it…

Navigating the Hard Things: Leadership Growth and Resilience

Duration: 2.5 hours

Audience: Leadership Team

Workshop Objectives

• Reflect on personal leadership challenges and how to embrace adversity.
• Understand the importance of making tough, not easy, decisions.
• Learn how to lead effectively during crises and tough times.
• Recognise the role of leadership in building a resilient team culture.
• Develop practical actions for fostering resilience within their teams.
• Commit to specific leadership improvements for both individual and team growth.

Materials Needed

• Flipcharts or whiteboards
• Markers
• Post-it notes
• Printed handouts with key insights from the book
• A timer
• Slides and Projector

Workshop Plan

Welcome and Introduction (10 min)

• Briefly introduce the workshop purpose: to help the team grow individually as leaders and improve their collective effectiveness by applying the lessons from The Hard Thing About Hard Things.
• Outline the key themes:
  • Embracing struggle and resilience
  • Navigating tough decisions
  • Leadership during crises
  • Building a strong company culture

Individual Reflection: Embrace the Struggle (20 min)

Objective: Get leaders to reflect on their personal leadership challenges and how they deal with adversity.

Activity:

1. Ask each leader to reflect on a recent "hard thing" they faced (could be personal or professional).
2. Have them write this down, including:
   1. The situation
   2. The decisions they made
   3. The outcomes

Discussion Prompt: How did you embrace or resist the struggle? What did you learn? After reflection, invite each participant to share their experience with the group.

Facilitator Tip: Encourage openness and vulnerability. Emphasise that everyone faces challenges, and growth happens when we embrace these moments.

Group Discussion: Leadership During Crisis (30 min)

Objective: Examine what makes leadership effective during tough times.

Activity:

1. Break the team into pairs. Each pair discusses a crisis situation they've faced (or are currently facing) in the company.
2. Ask the pairs to focus on:
   1. How did they lead the team through this?
   2. What worked and what didn’t?
   3. What would they do differently now?
3. Bring the team back together for a larger group discussion.
4. Collect insights on leadership behaviours during crises and identify common themes.

Facilitator Tip: Highlight the importance of clear, decisive leadership during tough times, as discussed in the book.

Building Resilient Teams (30 min)

Objective: Strengthen the leadership team’s collective ability to navigate adversity and build a resilient team culture.

Activity:

1. Split the team into small groups. Each group discusses the following:
   1. What does a resilient team look like to you?
   2. What key elements of company culture support resilience?
   3. How can they, as leaders, foster resilience in their teams?
2. After the group discussions, have each group share their insights with the larger team. Use a flipchart or whiteboard to capture ideas.
3. Ask the leadership team to identify three key actions they will take to build a stronger, more resilient culture.

Facilitator Tip: Focus on the importance of transparency, trust, and shared purpose in building a resilient team culture.

Closing Reflection: Leadership Responsibility (15 min)

Objective: Help leaders recognise their responsibility for both individual and team growth.

Activity:

1. Ask each leader to reflect on the workshop and write down one commitment they will make to improve their leadership and the team’s performance.
2. Have them share their commitment with the group.
3. Close by reinforcing that leadership is a continuous journey of growth, especially when dealing with challenges.

Facilitation Tips

• Managing discussions: Encourage honesty, but ensure respect is maintained. This can be a vulnerable space, so gently guide the conversation if it veers off track.
• Engaging participants: Use questions to provoke thought and facilitate discussions. Encourage every leader to participate.
• Handling challenges: If any difficult emotions or disagreements arise during the discussion, acknowledge them calmly. Use them as an opportunity to model constructive conflict resolution.
• Time management: Keep the activities on track, especially when the group is diving deep into their reflections. Use a timer to stay focused.

Outcome and Takeaways

• Leaders leave with a better understanding of how to navigate adversity and lead through crises.
• Actionable insights on making tough decisions and building a resilient team culture.
• A renewed commitment to growth and leadership responsibility.

Conclusion

In leadership, it's not the easy decisions that define you. It's the tough ones.

It's the moments of crisis, the hard calls, and the uncertainty that separate those who simply manage from those who lead.

True leadership requires resilience, the ability to embrace struggle, and the confidence to face challenges head-on.

This workshop isn’t about offering easy answers or quick fixes.

It’s about preparing a leadership team to handle the tough moments with clarity and strength.

They’ll leave equipped not just to face challenges, but to turn them into opportunities for growth.

The tough moments will come. How they are handled shapes success.

See you next week.