A Tough but Critical Balance in Supervising Others

Published July 24, 2020


Leading OthersSupervising People

I had just begun a coaching assignment with the CEO of a global company and was really excited to find out more about this leader. She had been heralded in many circles and had an impressive background, and the curious psychologist in me wanted to know more about how she worked and how she had accomplished all she had.  

So, I began by interviewing her direct reports, and I quickly encountered the first surprise of the project. Consider this: 

I sat down with her marketing VP, Ryan, and began by saying, “So, tell me about Leah.” 

“Don’t get me started,” he said. “I have worked around the world in this industry for 30 years and have met them all. And without a doubt, she is the best boss I have ever had. Hands down.”  

“Wow,” I said. “That’s really saying something. I have read your history, and you have worked for some really good ones… real icons.” 

“I know,” he replied. “But no one comes close to her.” 

“So, tell me why. What is it about her that makes you feel that way? What does she do that is so much better in the way that she supervises you?”  

“Easy,” he said. “It is the freedom she grants. She tells me the target, what she wants the outcome to be, and is really clear about the results she wants. And then (as he leaned forward for emphasis) …. she gets out of my way and lets me do it. I love itI am free to do what I do best, and I love getting results for her.”   

So, chalk one up for trusting your people, empowering them, giving leadership clarity, resourcing them well, and letting them be the smart people you hired them to be. It was not rocket science, but in some ways, often rare. Leah had the quality of making him feel free to perform, letting him have the autonomy that high performers need to have. She trusted him. 

Then came the surprise…. 

I went into my next interview, and it was with Jason, the COO. A no nonsense guy, I expected him to praise his new boss since in similar fashionBut I was shocked. When I asked him to tell me about Leah, he said…  

“There is no other way to say it. Without a doubt, the worst boss I ever had. She is absolutely horrible. The board is asleep at the switch…she should be fired.” 

I was speechless. He was not a nutcase. In fact, he also had a stellar record. But he was giving me the direct opposite description that I had gotten from Ryan. I had to ask, “So tell me why?” 

“Because she gives me no direction and leaves me out to drift at sea. She tells me what she wants, and it is like I never get anything close to direction from her along the way. She totally abdicates her leadership and leaves me out to dry,” he lamented, and with some pretty discernable scorn. “She just does not help me to do my job.”  

Wow. Wow. Wow.  

Same CEO…. same boss….one person scores her to be a 10 and one is chanting “fire her today.” What is the difference?  

How are we to understand this dynamic and what can you learn from it? 

The Issue 

It is the most basic human conflict that exists…and for good reason: God designed it.   

It is the conflict between having a relationship with accountability that supports and resources us—while at the same time having a relationship that gives us freedom and autonomy to perform using our own talents and gifts.  

Connection vs. freedom. Some leaders get it wrong in one direction, being too connected and hands on, thereby crushing the very autonomy that is needed for their best performance. But other leaders get it wrong in the other direction…. they give so much autonomy that the person they are supervising feels like they don’t even have a leader or boss or supervisor at all. And then there is Leah, who gets described in both directions.  

So, what’s a leader to do? Knowing the answer to that question is almost like one of the holy grails of leadership.  

The answer is: it depends 

  • Who are you supervising?  
  • What do they need?  
  • What feels helpful vs. controlling to them 
  • What feels like you are nowhere to be found to them 

It is a tough dance. Here are a few tips to get this right: 

  1. Start with awareness of theconnection vs. freedom dynamic. 

God has designed the human race to have an ongoing dynamic tension of:   

  • Being deeply connected to the people you supervise, by knowing them, resourcing them and supporting them, coaching them and helping them along the wawhile at the same time 
  • Giving them freedom and autonomy to use their gifts and abilities to do it their own way to achieve mutually desired outcomes.  

It is a “both/and.” 

One of my favorite verses is in Genesis where God told Adam to name the animals. As supervisor, God defined the outcome, the results that he wanted. And he let Adam use his gifts and brain to figure it out. 

God formed every beast of the field and every bird of the sky, and  

brought them to the man to see what he would call them; and whatever  

the man called a living creature, that was its name. (Gen. 2:19) 

What incredible freedom, and can we say delegation?  

love that phrase: “to see what he would call them.” God was relishing in the freedom that He gave Adam do his job in his own wayGod set the outcome He wanted and set Adam free to deliver that outcome 

  1. Identify the preferences of those you are supervising.  

Do you have a Ryan? Or a Jason? What feels like freedom and empowerment to them vs. detachment and abdication or abandonment?  

Remember: What feels like empowerment to one person is abandonment to another. What feels like coaching to one is micromanagement to another. So, find out who this person is. Sit down and have an ongoing conversation.  

Ask, “What do you need from me to succeed? Let’s get on the same page as to what success is, what the outcomes we want are to be, and then let’s talk about how much or how little input you need from me along the way. I want to help you get there, so tell me how much contact, coaching, structure, feedback, and the like you want and when and how you want it.” 

Setting mutually agreed upon expectations on how to best serve the person you are supervising is one of the best steps you can take to make it all work well.  

  1. Realize this is an ongoing conversation. 

Always be asking and re-asking, “Are you getting from me what you need to get the results we agreed upon? What can I do differently? More input? More freedom to make more decisions and execute? Give you more control over resources?”  

You will not always agree, but you will making sure that you are not having very different expectations as were Ryan, Jason and Leah. You will be on the same page, and able to adjust.   

  1. Finally, not every match is made in Heaven. 

Ultimately, Jason and Leah were not a good fit. He needed more “handholding” than she wanted to provide. She wanted someone who could take direction and deliver. They were not fit for each other, so they parted ways. That’s ok at times.  

There is no black and white answer. I have seen other situations where the “Leah” involved had to adapt to giving more connection and when she did, the “Jason” thrived.   

Leaders have to be open to adjusting and learning from each other. That is what good teams and relationships do. We make each other better. Iron sharpens iron.  

In sum, one of the greatest leadership dynamics you can be aware of in supervising is the knowing the dynamic tension between connection vs. freedom with your supervisee.  

When you get that right, you will be leading like God designed us to thrive. Give people the resources they need that match their talents, empower them and walk alongside them to coach and correct when needed, but, let them do their thing to get the mission accomplished that you have both signed up for.  

And remember, not everyone is alike! 



About the Author
Henry Cloud

Dr. Henry Cloud

Clinical Psychologist & Acclaimed Leadership Expert

Leadership University

Dr. Henry Cloud is an acclaimed leadership expert, clinical psychologist and New York Times best-selling author. His 45 books have sold nearly 15 million copies worldwide. He has an extensive executive coaching background and experience as a leadership consultant, devoting the majority of his time working with CEOs, leadership teams and executives to improve performance, leadership skills and culture. Dr. Cloud founded and built a healthcare company starting in 1987, which operated inpatient, and outpatient treatment centers in forty markets in the Western U.S. There, he served as Clinical Director and principal for ten years. In the context of hands-on clinical experience, he developed and researched many of the treatment principles and methods that he communicates to audiences today. After selling the company, he devoted his time to consulting and coaching, spreading principles of hope and life-change through speaking, writing and media. Throughout the same years and until the present, he has devoted much of his career to leadership performance and development, blending the disciplines of leadership and human functioning to helping CEO’s, teams, organizations and family entities. His book, Integrity, was dubbed by the New York Times as “the best book in the bunch.” In 2011, Necessary Endings was called “the most important book you read all year.” His book Boundaries For Leaders was named by CEO Reads in the top five leadership books of its year. His newest book, The Power of the Other, debuted at #5 on the Wall Street Journal bestseller list. Dr. Cloud’s work has been featured and reviewed by the New York Times, Wall Street Journal, Boston Globe, Publisher’s Weekly, Los Angeles Times, and many other publications. Success magazine named Dr. Cloud in the top 25 most influential leaders in personal growth and development, alongside Oprah, Brene Brown, Seth Godin and others.

Years at GLS 1996, 2005, 2011, 2013, 2016, 2021