Leadership Effectiveness Retrospective Template (Free)

Our Achievements

What were our most significant accomplishments as a leadership team?

Our ability to navigate the company through the economic downturn while maintaining employee morale and minimizing layoffs.

The successful launch of our new product line, which was a result of our collaborative decision-making and effective cross-functional coordination.

Our proactive approach to addressing diversity and inclusion issues within the organization, leading to a more inclusive and equitable workplace culture.

Areas for Improvement

What aspects of our leadership could we improve?

Our decision-making processes could be more inclusive and consider diverse perspectives from across the organization.

We could improve our communication strategies to ensure alignment and clarity across all levels of the organization.

There were instances where we could have responded more proactively to emerging trends or market shifts.

Strategic Alignment

Did our actions and decisions match the organization's vision and goals?

Our decision to invest in sustainable practices aligned perfectly with our commitment to environmental responsibility and long-term sustainability.

The acquisition we pursued last year may have been a short-term win, but it diverted resources from our core competencies and long-term goals.

Our focus on cost-cutting measures helped us weather the economic downturn, but it may have compromised our ability to innovate and stay competitive in the long run.

Stakeholder Feedback

How well did we incorporate feedback from key stakeholders into our decisions?

We could have done a better job of soliciting feedback from front-line employees before implementing the new performance management system.

Our customer advisory board gave us useful input that helped shape our product roadmap and prioritize features that truly mattered to our users.

While we engaged with shareholders regularly, we may have placed too much emphasis on short-term financial metrics at the expense of long-term sustainability.

Team Dynamics

How well did we work together and use each other's strengths?

Our diverse backgrounds and experiences brought different perspectives to the table, so we considered issues from multiple angles before making decisions.

At times, we struggled to find a balance between healthy debate and reaching a consensus, which led to delays or suboptimal outcomes.

The open and respectful communication within our team created an environment where everyone felt comfortable voicing their opinions and challenging assumptions.

What is the Leadership Effectiveness Retrospective?

Leadership teams rarely review their own performance the way they ask delivery teams to. The Leadership Effectiveness Retrospective gives a leadership group a structured session to do that, from the wins it can point to through to the way it makes decisions together. The board has five columns. Our Achievements is for the initiatives and decisions that went well. Areas for Improvement names what the team could do better, with specific examples. Strategic Alignment checks whether recent decisions matched the organization's goals or pulled away from them. Stakeholder Feedback asks how well the team listened to employees, customers, partners and shareholders before deciding. Team Dynamics looks inward, at trust, debate and how disagreements get resolved. Senior people often hold back in front of peers, so anonymous input matters more here than in most retros, and an outside facilitator can help. End with a small number of commitments the leadership team will report back on.

Leadership Effectiveness retrospective format

Our Achievements What were our most significant accomplishments as a leadership team?: Ask the leaders to reflect on what they achieved together. Guide the discussion toward specific examples, such as a successful initiative, a good decision or a hard stretch the team got through, and ask what made each one work.
Areas for Improvement What aspects of our leadership could we improve?: Here the team names where it can improve. Keep the discussion safe and specific: what was the challenge, what caused it and what might fix it? Leaders who ask their teams to reflect should be willing to do the same.
Strategic Alignment Did our actions and decisions match the organization's vision and goals?: Ask whether the team's actions and decisions matched the organization's vision and goals. Look for cases where they supported the strategy and cases where they pulled away from it, then talk about why the gap opened and how to keep the team focused.
Stakeholder Feedback How well did we incorporate feedback from key stakeholders into our decisions?: This column looks at how well the team gathers and acts on feedback from employees, customers, partners and shareholders. Ask where the team listened well, where it missed something, and how it weighs competing interests when it decides.
Team Dynamics How well did we work together and use each other's strengths?: Turn the lens inward. Discuss team norms, communication and how decisions get made. Explore where the team worked well together and where conflict or misalignment got in the way, and look for ways to build trust and better debate.

When to use this retrospective

When the leadership team wants to step back and look honestly at how it's performing together.
After a major project, initiative or organizational change, to review how the leadership team handled it.
On a regular rhythm, such as quarterly or once a year, so problems in the team surface early.
When new members join the leadership team, to agree on expectations and how you'll work together.
During a restructure or other transition, to check the leadership team is still aligned.

Ideas and tips for your retrospective meeting

Make it safe to be candid. Agree up front that the session is about how the team works, not a performance review of any one person.
Make sure every voice is heard, regardless of seniority or tenure on the leadership team.
Push for specific examples and solutions instead of dwelling on past mistakes or assigning blame.
Consider an external facilitator or coach, so the most senior person isn't also running the session.
Follow up on the actions at your next leadership meeting, and share progress with the wider organization where it makes sense.
Celebrate what went well, then spend most of the time on what to change.

Frequently asked questions

What is a leadership effectiveness retrospective?

It's a structured session where a leadership group reviews its achievements, areas for improvement, strategic alignment, stakeholder feedback and team dynamics. The goal is to agree on a few changes to how the team leads.

When should a team run this retrospective?

Run it quarterly or twice a year, or after a major initiative or organizational change. Holding it before a planning cycle means the lessons feed into the next set of priorities.

Who should facilitate a leadership retrospective?

Ideally someone outside the leadership team, such as an agile coach or an HR partner. A neutral facilitator makes it easier for the most senior person to take part as an equal.

Should input be anonymous?

Usually, yes. Leaders often hold back criticism of peers or of the most senior person when their name is attached, and anonymous ideas in TeamRetro get those points onto the board.

How long does it take?

Plan for about 90 minutes for five columns. If time is short, cover Our Achievements and Areas for Improvement first and save the rest for a second session.