Managing Managers: The Leadership Leap Few Talk About (Leadership Series 7/7)

Moving from managing individual contributors to managing managers is one of the steepest transitions in leadership. Suddenly, you’re not only accountable for the work - you’re accountable for the people accountable for the work. It’s leverage at its highest form. And while it can be deeply rewarding, it’s also one of the most misunderstood and mishandled steps in a leader’s career.

Too many leaders assume that managing managers means more power or less hands-on work. In reality, it requires a mindset shift: from controlling outcomes yourself to creating the conditions where managers - and their teams -can thrive.

What Makes Managing Managers Different

When you manage individuals, your focus is clear: coach, guide, and evaluate their performance. When you manage managers, the game changes in three important ways:

1. You lose the illusion of control. You will not know every detail of what’s happening, and you shouldn’t. Your job shifts from direct oversight to trusting processes and relationships.

2. Your leverage multiplies. The ripple effect of your decisions continues to grow. How you guide managers shapes how they, in turn, guide dozens - sometimes hundreds - of others.

3. Relationships matter more than goals. Goals, metrics, and OKRs only work when the manager - employee relationship is strong. As Amy Gallo writes in Harvard Business Review, managers of managers must “pay attention not just to business outcomes, but to the quality of relationships their managers build.” Put simply: weak relationships undermine performance far faster than unclear goals ever will.

The Common Pitfalls 

·       Acting like a “super-manager.” Hovering over your managers and redoing their work.

·       Avoiding the role. Retreating into functional expertise because “managing managers” feels abstract.

·       Ignoring management as a skill. Hiring managers based only on technical success, not on their ability to build trust, hold accountability, and develop people.

·       Letting power concentrate. Allowing one manager to hold sole authority over promotions, hiring, or firing can erode fairness and trust.

What Great Managers of Managers Do:

Managing managers isn’t about having all the answers. It’s about shaping the ecosystem in which managers and teams can thrive. The best leaders consistently do five things:

1. Make Management Part of the Job. Be explicit: building strong relationships, holding one-on-ones, and coaching are not optional. They’re core responsibilities.

2. Set Clear, Transparent Goals. Tools like OKRs are powerful, but only if they’re built with managers, not for them. Research from Stanford professor Nick Bloom shows that goal-setting systems succeed when employees help create them — not when they’re imposed from the top. Co-creating goals builds ownership, alignment, and the commitment needed to deliver on them.

3. Build Systems, Not Bottlenecks. Ensure no manager has unilateral control over hiring, promotions, or pay. Systems should empower fairness and transparency.

4. Coach for Leverage. Help managers not just with their business goals but with their management practices. Ask: How are you building trust? How are you holding people accountable?

5. Model Feedback and Openness. Don’t just solicit feedback privately — show publicly how you respond to criticism. It sets the tone for how managers handle feedback with their teams.

A Mindset Shift for Leaders

Managing managers is less about control and more about influence. Less about doing and more about designing. Less about your personal expertise and more about creating conditions where others can do their best work.

It’s a paradox: you are responsible without always being in control. That can feel uncomfortable - but it’s also where leadership becomes its most powerful.

The quality of a company’s culture often rests on the quality of its middle managers. As a leader of managers, your job is to love them, support them, and set them up to succeed. Because when managers flourish, their teams flourish. And when their teams flourish, the business thrives.

Reflection Question: If you’re managing managers today, where do you spend more time - diving into details or developing the people leading those details? How might a shift in focus change your impact? Comment and share below, we would love to hear from you.

Quote of the Day: “Management is, above all, a practice where art, science, and craft meet.” – Henry Mintzberg

As a leadership development and executive coach, I work with leaders to sharpen their leadership skills and navigate tricky situations, contact me.

How do you manage managers?

From Insight To Action: Effective Method To Develop Self-Awareness (Self-Awareness Series 3/3)

In the first article in this series, we explored the concept of self-awareness and the gap between how self-aware we believe we are and how aware we actually are. In the second article, we examined the biases and barriers that make it difficult to develop self-awareness. The natural question that follows is: How do we actually build self-awareness?

Insight alone is not enough. Self-awareness develops through reflection, feedback, and intentional experimentation.

Let’s explore practical strategies to translate insight into growth and unlock your full potential.

1. Reflect on Yourself. Self-awareness begins with intentional reflection. Leaders who develop strong self-awareness regularly examine their motivations, behaviors, and performance.

1A. Inventory of strengths, non-strengths, values, and opportunities.  Identify both strengths and limitations. We sometimes do this work when preparing for an interview and find that it is helpful to get super clear, so making the space to answer these questions is important. You can take many assessments such as Myers-Briggs, The Big Five, or CliftonStrengths, to gain deeper insights on personality, behavior, and natural talents.

1B. Create reflection time.  Many leaders say they are too busy to reflect. Responding to emails and solving immediate problems often feels more productive.  Yet reflection is one of the practices that separates good leaders from great ones.  Setting aside time to reflect helps leaders examine questions such as: What is going well and why? What could be going better?  How did I respond to recent challenges or setbacks? What lessons can I extract from those experiences?  Reflection helps convert experience into learning. 

1C. Ask better questions.   Self-awareness grows when we challenge our own assumptions.  Questions such as these can expand perspective: What if I am wrong?  What might I be missing?  What are other viewpoints I should consider?  Team coaching expert David Clutterbuck suggests asking questions that increase awareness of our thinking and emotions:  How do I feel about the way that I think?  How do I feel about the way that I feel?  How do I think about the way that I feel?  How do I think about the way that I think? Questions like these encourage deeper reflection.

1D. Test Your Assumptions.  A useful question for building self-awareness is: How do you know if something is true? For example, a leader might wonder, " How do I know I am approachable?  Start by identifying behaviors that support the claim. I leave my office door open for others to enter when they need something; I ask if they have any questions during a meeting; I prompt them to respond to my email with any follow-ups; I participate in activities with my team, such as attending their meetings and connection gatherings.

Next, seek others' perspectives on your approach and how you can improve. E.g., “I am working on being an approachable leader, how approachable do you think I am, what do I do now that supports my approachability, and what can I do to be even more approachable?” Comparing your intentions with others’ experiences often reveals valuable insight.

You can also measure progress over time. If you are working on a skill such as listening, define what success looks like and identify a few indicators. After several months, evaluate your progress using both your own reflection and feedback from others. Self-awareness improves when we move beyond assumptions and begin testing our beliefs against reality.

1E. Compare yourself to your future self.  Write a letter to yourself outlining what you want to improve.  Open it in a few months to compare your progress. Marshall Goldsmith suggests thinking about what gifts your current self has given to your future self.  

1F. Learn from Others. Whatever skill you are trying to improve, read about it, and observe others who excel. Identify effective behaviors and compare them to your own. Learn from those you admire and avoid the mistakes of those you don't.

2. Work with a coach.  Many leaders accelerate their self-awareness by working with a coach. Coaches help clients see beyond assumptions and narratives to understand their present reality more clearly and shape their future more effectively. They often use questions, reflection, metaphors, stories, and synthesis to help clients see patterns they may not notice themselves.  They also ask questions, such as " Why do you do what you do? Why do they believe what you believe, and how is it serving you now? 

2A. Perception management.  Coaches help clients think about their current and ideal perceptions, and their impact. They assist in building their brand to manage these perceptions effectively.

2B. Use of self-reflection assessments.   Coaches provide frameworks and assessments for clients to evaluate their skills. For example, using key leadership traits from "The Leadership Challenge" to understand their strengths and areas for improvement.

2C. Use of Coaching Tools. 

·      Johari Window - A psychological tool created in 1955 by Joseph Harrington to help people improve self-awareness and understand relationship dynamics through 4 quadrants: open area, blind area, hidden area, and unknown area.

·      Gaps Grid.  Developed by David Peterson, Former Head of Executive Coaching at Google, it’s a 2x2 matrix that enhances insight and motivation by mapping goals and values, success factors, abilities, and perceptions. 

3. Seek Perspective From Others. Self-awareness is difficult to develop alone. Others often see patterns we cannot see ourselves. Leaders can gather perspectives in several ways.

3A. Collect Informal data by asking for specific feedback.  Start by asking for input from trusted individuals in your professional circle—your manager, peers, mentors, or team members.  The key is to ask specific questions.  For example:  Instead of asking “Do you have any feedback for me?”  Try asking:  "What is one thing I could do to improve my listening in meetings?"  Specific questions produce more useful answers.

3B. Anchor your feedback.   Guide observers by informing them about the skills you are working on and asking for feedback on your progress. This helps them provide more focused and relevant feedback.  Examples include - “I started working on a new set of skills that I want you to watch for or A month ago, I was working on listening skills, what has been improved?” It is helpful for you to guide the observation because they are still in the throes of what they are doing, and they might not be seeing the wins.  It’s kind of like when relatives you see once a year as a kid will point out how much you have grown and how different you are, and you don’t see it at all because day-to-day, not much is different.

4. Use Formal Feedback. More structured approaches can provide deeper insights.

4A. Run an automated 360.  Collect feedback from the people you work closely with at all levels, directs, peers, managers, customers, partners, and other stakeholders.  You get to do a self-assessment based on leadership competencies and then they also get to weigh in, and you can evaluate the anonymous data and look for patterns.  When I do this with clients, they are always surprised, either by how many great comments they have received, how others have overrated themselves in some areas, and how they did not realize they were falling short of the mark.  It is an eye-opening experience.

4B. Stakeholder interviews.  Similar to a 360, but instead of being automated, a coach will run the process.  They will conduct interviews with the stakeholders, ask questions, and then compile a report. 

4C. Create brief surveys.  Liz Wiseman recommends asking about some accidental diminishing behaviors, which means that despite your best intentions, you may be having an adverse impact on others.

·      What am I inadvertently doing that might be having a diminishing impact on others?

·      How might my intentions be interpreted differently by others? 

·      What messages might my actions actually be conveying?

·      What can I do differently?

Developing self-awareness is a continuous journey that significantly enhances personal and professional growth. By engaging in self-assessment, seeking feedback, and working with a coach, you can gain deeper insights into your strengths and areas for improvement. Over time, these practices help leaders make better decisions, build stronger relationships, and lead with greater impact.

Quotes of the day: "We learn who we are in practice, not in theory." - Herminia Ibarra

Quote of the day:  As you start to walk out of the way, the way appears – Rumi

Reflection Question: What practice do you engage in to raise your awareness?  Comment and share your experiences below; we’d love to hear.

As a leadership development and executive coach, I work with leaders to raise their awareness to increase their performance, contact me to explore this topic further.

What practices raise your awareness?

The Journey Within: Overcoming Challenges and Enhancing Self-Awareness for Better Outcomes (Self-Awareness Series 2/3)

In the previous article, we explored the concept of self-awareness and its core dimensions. But understanding the idea of self-awareness and actually developing it are very different things.

The reality is that self-awareness is difficult to cultivate. Psychological biases, social dynamics, and our own defenses often prevent us from seeing ourselves clearly.

In this article, we’ll explore some of the biggest challenges that make self-awareness difficult—and why developing it is still one of the most valuable investments a leader can make.

Challenges of Self-Awareness

1. Ignorance and discomfort.  Plato’s Allegory of the Cave illustrates how difficult self-awareness can be: ignorance limits awareness, while knowledge liberates. In the allegory, prisoners are chained inside a cave where they see only shadows projected on a wall. Because that is all they have ever seen, they assume the shadows represent reality. When one prisoner is freed and sees the outside world, the experience is overwhelming. Gradually, he realizes the shadows were merely reflections of a deeper reality. But when he returns to share this insight with the other prisoners, he is met with disbelief and hostility. This story captures an important truth about self-awareness: seeing ourselves more clearly can be uncomfortable. Sometimes, the most difficult part of self-awareness is confronting truths about ourselves we would rather not see. It’s why, for many, ignorance feels easier than awareness.

2. Our Backgrounds Shape Our Perspective.  Our experiences shape how we interpret the world.  Generational differences, upbringing, economic circumstances, education, culture, and career experiences all influence how we think about risk, opportunity, and success.  For example, someone who grew up in poverty may think very differently about risk and stability than someone who grew up with financial security.  President John F. Kennedy once acknowledged that he could never fully understand the impact of the Great Depression because he grew up wealthy.  Each of us experiences only a small slice of the world, and that slice shapes our assumptions.  Self-awareness requires recognizing that our perspective, while valid, is also limited.

3. Dunning-Kruger Effect.  This cognitive bias is one of the most well-known barriers to self-awareness.  Psychologists David Dunning and Justin Kruger discovered that people with lower ability in a domain often overestimate their competence. Because they lack expertise, they also cannot accurately evaluate their own performance.  For example, someone new to software may believe they have mastered it after a brief introduction—while more experienced users recognize how much deeper the skill actually goes.  The overestimation can lead to mistakes and oversights.  As people gain expertise, their confidence often becomes more calibrated and realistic. 

4. Ego.  An inaccurate self-view can hinder leadership growth. For instance, a leader I was working with had a Direct Report submit a self-assessment on his performance review, and wrote “n/a” for what to improve.  When pressed, my client suggested to the Direct the topic of delegation to achieve results through others, rather than doing it all himself.  The Direct dismissed the feedback because he is so talented at getting his work done.  His progress is hampered because he cannot scale by doing all the work himself; he has to get results through his team.  To increase his awareness, the leader then provided a competency framework and clear expectations to get to the next level and help align his self-perception with reality.

5. Defensiveness.  When receiving feedback, we might disagree, believing we’re better than assessed.  For example, someone might think they’re a great listener despite feedback suggesting otherwise. In this case, asking for specific data points and providing evidence from peers, directs, and other stakeholders through anonymous 360 feedback is helpful. Seeing the negative impact can motivate change.  Another form of defensiveness is dismissal.  Some might say, "This is just how I am," or "I've been successful with these behaviors so far, why change?" Marshall Goldsmith says, "What got you here won’t get you there," highlighting that success often comes despite derailing tendencies, not because of them. Past successes do not guarantee future effectiveness.

6.  Lack of feedback.  Many people lack self-awareness because they seldom receive feedback, especially negative.  People avoid giving bad news or lack the skills to deliver it constructively.  This issue is more pronounced for senior leaders, who receive less accurate self-assessments as they climb higher, mainly due to a shortage of honest feedback and being limited to what they might be able to share with others.  One study showed a leader frequently interrupting others was unaware of it, illustrating the loneliness at the top, where they are often surrounded by yes-people.

Benefits of Self-Awareness 

Despite these challenges, developing self-awareness provides powerful advantages.

1. Reduces Stress & Regulates Emotions.  Self-awareness helps us understand and manage our emotional responses. Research in cognitive psychology shows that when individuals reflect on their values and interpret stress as a challenge rather than a threat, they experience lower stress levels and greater resilience. Reflecting on our core values, goals, and principles helps us regulate stress and respond more deliberately. By recognizing our emotional triggers, we can choose thoughtful responses rather than reacting impulsively.

2. Greater performance and Focus.  Research suggests that high performers tend to be more self-aware.  Visionary leaders know what they want to achieve and how their actions affect others.  Self-awareness allows us to focus on the right opportunities and keep emotions from holding us back.

3. Stronger leadership.  Tasha Eurich’s book "Insight" found that internal self-awareness is critical for successful leaders.  They know their strengths, weaknesses, needs, goals, and how they come across.  This is in contrast to clueless leaders who tend to be ineffective.  Great leaders continuously ask questions to diagnose their needs and goals and wonder what blind spots they may have.  Maslow said, “What is necessary to change a person is to change his awareness of himself.”

4. Enhances Authenticity.  Nancy McKinstry, CEO of Wolters Kluwer said, “You can’t be authentic if you are not self-aware.  How can you be transparent and open, talk about your goals, or share how you influence change without self-awareness?”  It enables transparency, openness, and the ability to influence change. 

5. Increases humility.   Self-aware individuals know what they are good at and what they are not.  Even confident individuals can acknowledge their ignorance in certain areas, fostering curiosity and humility.  Steve Jobs, for example, was aware of his limitations and welcomed disagreements.   He held strong convictions but was willing to change his mind when presented with better information.   Ed Catmull shared a story about Jobs, who wanted Apple to make the iPad before the iPhone.  However, his team convinced him otherwise, and he agreed.  He insisted that Apple provide the app despite his team’s disagreement.   When the iPhone launched, Jobs quickly realized his team was right and changed his mind, demonstrating his ability to adapt and embrace humility.   

Developing self-awareness is crucial for overcoming personal and professional challenges. It allows us to break free from ignorance, understand our unique backgrounds, manage cognitive biases, and receive constructive feedback. By fostering self-awareness, we can reduce stress, improve performance, enhance leadership, and cultivate authenticity and humility.  Embrace these practices to unlock your full potential and achieve greater success

Quote of the day: “If we think of this existence of the individual as a larger or smaller room, it appears evident that most people learn to know only a corner of their room, a place by the window, a strip of floor on which they walk up and down.”  – Rainer Maria Rilke

Question: What do you see as the biggest challenges of self-awareness?  When is ignorance bliss, or is it not?  Comment and share your experiences below; we’d love to hear.

The next blog in this series 3/3 will focus on ways to develop your self-awareness.

As a leadership development and executive coach, I work with leaders to raise their awareness to increase their performance, contact me to explore this topic further

What benefits have you experienced?