Pinar R.O.
Do you think you can ask this question to the people you work with? Are you sure? Be honest—do you think you could ask your entire team, “What’s it like to work with me?” Can you imagine opening that door to real feedback, even anonymously?
Now, ask yourself this: Are you sure you’re ready to handle the responses? If your answer is yes, it means you’re strong enough, confident enough, and competent enough to lead with purpose and authenticity. That’s a powerful position to be in.
But if your answer is no—or even “I’m not sure”—then you’re in the right place. Keep reading because this isn’t about criticism. It’s about growth. Leadership isn’t about being perfect; it’s about being willing to reflect, learn, and adjust.
Why This Question Matters in Leadership
Asking, “What’s it like working with me?” isn’t just a leadership exercise—it’s a moment of truth. It’s about understanding your impact on those around you and facing the reality of how you lead. Leadership isn’t defined solely by the goals you achieve but by the environment you create and the legacy you leave.
Leadership is about influence. According to Dr. Brené Brown, a research professor at the University of Houston, leadership requires vulnerability, courage, and the ability to build trust (Brown, 2018). By asking team members to describe their experience working with you, you demonstrate vulnerability and openness, which fosters trust and psychological safety.A study published in the Harvard Business Review also found that leaders actively seeking feedback from their teams are perceived as more effective and approachable (HBR, 2016). This feedback loop allows leaders to grow, adapt, and create environments where employees thrive.
When you open yourself up to this question, you:
- Build Trust: Showing vulnerability signals to your team that their opinions matter.
- Foster Growth: Honest feedback reveals areas for improvement and reinforces strengths.
- Enhance Workplace Culture: Understanding your impact helps you create a more inclusive and empowering environment.
Pro Tip: Take a quiet moment to think about how you lead and how you’d like to be remembered by your team.
Facing the Mirror: How Feedback Fuels Growth
When we ask others for their honest perspectives, we open ourselves to the possibility of uncovering blind spots. According to Dr. Amy Edmondson, a professor at Harvard Business School, creating psychological safety is key to fostering trust in the workplace (Edmondson, 2019). This means inviting feedback and making it clear that honesty is valued, not punished.
Steps to Gather Constructive Feedback:
- Create a Safe Space: Use anonymous surveys or third-party facilitators to encourage honesty.
- Ask Targeted Questions: Focus on areas like communication, decision-making, and team dynamics.
- Act on Feedback: Show your team that their input leads to actionable change.
- Improving workplace culture: Feedback helps you identify areas to adjust, creating a more inclusive and collaborative work environment.
Receiving feedback requires humility. It’s not about defending ourselves but about understanding how we can do better.
Asking the question, “What was it like working with me?” is also akin to holding a mirror to yourself. It requires courage to face the truth—whether it’s positive, critical, or somewhere in between. This process involves:
- Acknowledging blind spots: Even the most self-aware leaders can have areas where they’re unaware of how their actions affect others.
- Building empathy: Understanding how your leadership style impacts your team fosters deeper connections.
Pro Tip: Shift your mindset. See feedback not as criticism but as a gift—a way to grow and build stronger connections.
Why It’s Hard to Ask the Question
Let’s be honest: asking, “What’s it like working with me?” can feel intimidating. A study in the Journal of Organizational Behavior found that many leaders avoid seeking feedback due to fear of criticism or loss of authority (Ashford & DeRue, 2010).
However, avoiding feedback limits growth. Great leaders like Brené Brown remind us that vulnerability is not weakness—it’s courage. By seeking feedback, you’re telling your team, “Your experience matters, and I want to improve.”
The Importance of Anonymous Feedback & Turning Feedback into Action
Dr. Amy Edmondson, a professor at Harvard Business School, emphasizes the role of psychological safety in workplaces (Edmondson, 2019). Employees are more likely to provide honest feedback when they feel safe from judgment or repercussions. Offering an anonymous feedback option ensures team members can share their perspectives candidly.
Feedback is only valuable if it leads to change. Here’s how to use it effectively:
- Identify Patterns: Look for recurring themes in the responses.
- Prioritize Changes: Focus on the areas with the most impact, whether it’s clearer communication or fostering more inclusivity.
- Celebrate Strengths: Don’t just focus on what needs improvement. Recognize what you’re doing well and build on it.
Pro Tip: Schedule follow-ups to discuss progress with your team. This shows commitment and keeps you accountable.
Leadership in a Professional Role-Playing World
In the workplace, we all play roles. We present ourselves as professionals, colleagues, and leaders while navigating expectations and dynamics. It’s easy to focus on others—judging their actions, critiquing their behaviors—but leadership asks us to go deeper.
Before calling someone “difficult” or “toxic,” consider your role in the dynamic. Have you contributed to miscommunication? Have you been clear about expectations? Looking in the mirror is as much about accountability as it is about empathy.
Pro Tip: When faced with workplace challenges, ask yourself, “How am I contributing to this situation?”
Practical Tips for Building a Leadership Legacy
Leadership isn’t just about achieving targets; it’s about the memories and experiences your team carries forward. A study by Gallup found that employees are more engaged and productive when they feel valued by their leaders (Gallup, 2020). This underscores the importance of fostering positive relationships and creating a culture of mutual respect.
Asking for feedback directly impacts your legacy as a leader. Will your team remember you as empowering, supportive, and inspiring? Or will they recall feelings of being undervalued or micromanaged? Your willingness to ask questions, listen, and act on the feedback determines the kind of legacy you leave behind.
- Model Vulnerability: Share your own growth journey with your team. This sets a tone of openness.
- Celebrate Contributions: Regularly acknowledge the efforts and achievements of your team members.
- Practice Empathy: Take time to understand the perspectives and challenges of those you lead.
- Create Safe Spaces: Encourage honest communication without fear of judgment or retaliation.
- Own Your Mistakes: When you misstep, acknowledge it and demonstrate how you’re working to improve.
Pro Tip: Develop a leadership mantra that reflects your values, such as, “I lead with integrity and empathy.”
The Stories We Leave Behind
At its heart, leadership is about legacy. It’s not measured solely by goals achieved or profits earned but by the experiences you create for others. Will your team remember you as inspiring and empowering? Or will they recall feeling undervalued and unsupported?
By asking, “What was it like working with me?” you take a bold step toward shaping your legacy with intention.
Pro Tip: Regularly reflect on the stories you’re creating as a leader. Are they stories of growth, connection, and impact?
Why Leaders Resist Feedback
Despite its benefits, many leaders hesitate to seek feedback. According to a study in the Journal of Organizational Behavior, fear of criticism and a reluctance to appear vulnerable are common barriers (Ashford & DeRue, 2010). Overcoming these fears requires a mindset shift. Instead of viewing feedback as a threat, see it as an opportunity for growth and connection.
A Personal Note from the Author
Leadership isn’t about perfection—it never has been. It’s about growth, connection, and the willingness to look in the mirror and ask ourselves the tough questions. I’ve learned this firsthand through my own experiences and challenges as a leader. The moments that transformed me the most weren’t the ones where I thought I had all the answers—they were the moments when I had the courage to ask, “What am I missing?” and “How can I do better?”
It’s not easy. Let’s be honest: looking in the mirror and asking, “What’s it like working with me?” takes guts. It means opening yourself up to feedback that might sting. It means confronting your blind spots and acknowledging that your best intentions might not always align with the impact you’re having on others. But here’s the thing: those moments of vulnerability are where the magic happens. That’s where real leadership begins.
For me, asking those questions has been both humbling and empowering. It’s taught me that leadership isn’t about being perfect or having it all figured out. It’s about showing up, listening, and striving to be better every day. It’s about saying to your team, “Your experiences matter to me. You matter to me. And I’m committed to growing not just for myself but for all of us.”
If you’re feeling hesitant or unsure, let me say this: it’s okay to feel scared. It’s okay to worry about what the answers might reveal. But what’s not okay is letting fear hold you back. Growth only happens when we’re willing to step into the discomfort and learn from it.
As leaders, we have a profound impact on the people around us. It’s not just about the goals we achieve or the projects we complete—it’s about the stories people carry with them after working with us. Did we make them feel valued? Did we inspire them? Did we leave them better than we found them?
So, as you think about your own leadership journey, I encourage you to ask yourself:
- “Who do I want to be?”
- “What do I want my team to say about me when I’m not in the room?”
- “How can I use my position to uplift and empower others?”
It’s not always easy, but it’s always worth it. The legacy you leave as a leader isn’t built on perfection; it’s built on intention, empathy, and a willingness to grow.
And let me leave you with this: Leadership is a journey. You don’t have to have all the answers today, but you do have to be willing to ask the questions. Be kind to yourself in the process. Celebrate the small wins, learn from the setbacks, and remember that every step forward is a step in the right direction.
The next time you stand in front of the mirror, ask yourself: “Am I leading with purpose and heart? Am I the leader I aspire to be?”
You’ve got this. Growth isn’t easy, but it’s the most rewarding journey you’ll ever take. And trust me, your team, your colleagues, and your future self will thank you for it.
Books to Read for Leadership and Self-Reflection
Brené Brown – Dare to Lead: Brave Work. Tough Conversations. Whole Hearts.
A must-read on vulnerability, courage, and building trust in leadership.
Amy Edmondson – The Fearless Organization: Creating Psychological Safety in the Workplace for Learning, Innovation, and Growth.
Learn how to foster an environment where employees feel safe to take risks and innovate.
Daniel Goleman – Emotional Intelligence: Why It Can Matter More Than IQ.
Understand how emotional intelligence impacts leadership and relationships.
Simon Sinek – Leaders Eat Last: Why Some Teams Pull Together and Others Don’t.
A practical guide to creating trust and collaboration within your team.
Marshall Goldsmith – What Got You Here Won’t Get You There: How Successful People Become Even More Successful.
An insightful book on how to recognize and change habits that hinder leadership growth.
Liz Wiseman – Multipliers: How the Best Leaders Make Everyone Smarter.
Learn how great leaders amplify the intelligence and capability of their teams.
Sheryl Sandberg – Lean In: Women, Work, and the Will to Lead.
An empowering read for women navigating leadership roles and workplace dynamics.
John C. Maxwell – The 21 Irrefutable Laws of Leadership: Follow Them and People Will Follow You.
A classic for understanding foundational principles of effective leadership.
Kim Scott – Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity.
Offers practical advice on balancing feedback with empathy.
Carol Dweck – Mindset: The New Psychology of Success.
Explores how a growth mindset can transform your approach to leadership and challenges.
References
Brown, B. (2018). Dare to Lead: Brave Work. Tough Conversations. Whole Hearts. Random House.
Edmondson, A. (2019). The Fearless Organization: Creating Psychological Safety in the Workplace for Learning, Innovation, and Growth. Wiley.
Ashford, S. J., & DeRue, D. S. (2010). Who Will Lead and Who Will Follow? A Social Process of Leadership Identity Construction in Organizations. Journal of Organizational Behavior.
Gallup. (2020). State of the Global Workplace. Gallup Press.
Goleman, D. (1995). Emotional Intelligence: Why It Can Matter More Than IQ. Bantam Books
