Mar 09, 2023 | 6
Minute Read

Confessions of Management: What Leaders Are Really Thinking


Workers often think that their bosses are removed from stresses in their roles, but that couldn’t be further from the truth. No matter how many people someone manages, they still have someone to report to and they still face challenges, obstacles and opportunities in their role. 

We anonymously interviewed leaders in our organization and network to find out how they really feel about their roles, experiences, and triumphs in their roles. People interviewed manage or have managed anywhere from 1 employee to more than twenty, and their time as managers ranges from less than a year to over 10 years.  

There is a wide variety of experiences represented here! Here’s what leaders wish they could say. 


What's something no one told you about managing that you would have wanted to know when starting out? *

“As a manager, you have to look at your people from all different angles and keep in mind what affects them outside work. I suppose no one told me you need a much wider vision of a person than just work stuff!”

“I never set out to be a manager, but it became a necessity to advance my station. People liken management to raising children, but workers aren't children— you aren’t raising them, you are raising them up professionally and developing them to be better at their best. It is similar in that you hope for the best and prepare for the worst, but you aren't dealing with children, you are dealing with adults who have their own issues to attend to.”

“Listening is much more important than talking.”

“To me, [management is] about having good relations with other humans  and treating them the way you wish to be treated. I've been exposed to all kinds of improvement courses, self-help books, seminars, executive groups, etc.  At the end of the day - I think it can all be boiled down and simplified into two things.  

  1. The golden rule: treat others as you wish to be treated! 
  2. Leaders, the good ones, are servants first and foremost.  If a leader never learned anything else, they would still do an excellent job.”

“I would have wanted to know the right amount of empathy to have toward my team. If you give too much, you may get walked all over. If you don’t give not enough, you could be too harsh. I am working on finding my balance.”

What was the worst conflict between your direct reports? Were you able to resolve it?*

“When someone, unintentionally, crossed the line between flexibility and overuse of trust. It is complex because I firmly believe I work with responsible adults, and I am certain this was not intentionally done so it becomes more complex, because you do not want to damage the trust but there is a limit that has to be set. It is all about finding the right time and the right way to do it. Yes, I managed to solve it but I learned that I had to have the patience to find the right moment and I also had to be completely detached emotionally to deal with it properly. This was not against me, as their manager, but an oversight of what they were doing in a moment of crisis.”

“​​I had two working teams in different technologies and they did not see the world the same way. As a result, there was always some sort of conflict about how to create tech, manage it, etc.  There was a lot of mistrust, since they each thought the other foolish or misguided. The situation was only resolved when one department quit!  Throughout this evolution, the rest of the department got pretty tight and well-honed - they all worked well together and accomplished some great things, so it wasn’t all bad.” 

“I haven't had too many yet so far, but I would say a conflict with communication styles has been my worst. Once we understood where everyone was coming from, I felt it was resolved.”

“A lot of conflicts come down to poor or lack of communication. My group can be very tribal, and it's essential that someone new is not only an organizational or functional fit but also a cultural team fit. It's important that a team is aware of its own strengths and weaknesses, as well as what a new team member brings to the table. Communicating all of this to all parties helps ease a new hire into an established team as well as helps them engage.”


What's something you wish you could honestly tell your boss? *

“It is okay to say no—- true partners will always manage productive conversations, and if they can't, then they might not be the right partners.

“I have told all.”

“I wish I could tell my boss how worried I am that I am not good enough to perform at the level required, that the parts of my job I've had to delegate are ones that brought me the most joy, and that sometimes more compensation is truly what can ease stress the best.”

“I don't have a problem being completely honest with my boss. I think that would be problematic if I felt I couldn't.”

“Stop giving me more projects! As a manager, I know you are supposed to be responsible for more and handle more but it's still hard to focus on multiple projects at once while still doing my day-to-day work and managing a team.”

“Let me do what you hired me to do.”


What's something you wish your direct reports would tell you honestly? *

“My short-comings! I want to know the things I am not great at to help me create awareness. They do tell me, but I think they could tell me more.”

“When I create obstacles to them doing their best work and don't know I have done it.”

“If I am asking too much from them. I would hope they would tell me when they are at their limit. In fact, I once was told this and it was really helpful to know so I could do something about it.”

“I often feel that I just don't know where I stand with them. Maybe they nod and agree because they think that's what I want/need, when in reality I am not precious about my work and am just providing a starting place, and hoping it will take them somewhere we need to be. I love feedback but don't actively ask for it as much as I could, or should... I hope everyone under me feels free to challenge me and to be assertive about communicating their viewpoints and experiences.”

“What I can improve upon. I like to think they have no problem telling me things, but I know I'm not perfect and there are lots of things I can be better at, so if I'm not hearing those things…why not?  They do share lots of things with me and I tell them all the time to please come to me with anything. I feel I have a good open rapport,  but again, I'd love to have that type of feedback and I don't get it all the time.”

“If they are committed to our plan.”


What's the funniest situation you've experienced as a manager? *

“Not knowing I was supposed to be managing that person. It was a surprise!”

“I had a hire self-select out (quit) after 2 days because they recognized that they just couldn't make the cultural fit work. The split was amicable, and became funny when then discussing the now departing employee's cold fish handshake with fellow managers: ‘Sure I could have worked with them, as long as I didn't have to shake their hand ever again.’”


What should every manager make sure to do for new hires?*

“Learn to know them! This is a new person you are welcoming in your daily interaction and their performance will depend a lot on how they feel with their direct report.”

“Take time to get to know them as a human being, then work hard to communicate clear, specific expectations.”

“Set clear expectations on how to communicate. I have used our comparison reports to show how we can get off to good start by knowing each other's dos and dont's.”

“Connect with them, not just as a subordinate or in a working capacity, but as a genuine human being. Be curious about them, learn about their interests, hobbies, or family. Keep learning until you find those connection points and then build a relationship from there that is more than transactional (and keep learning after that, too). We've all got our own human stories that we have commonality through, and as managers, we've got to care enough to find them. Be friendly, be accommodating. Don't forget that we're all people, first.”

“Ask them what they want/need/desire as part of their onboarding. Ensure they meet all their key relationships and understand who they are and why the relationship is important.  They hopefully already know why the job exists and what are the key factors of excellent performance and skills, character traits, etc. help excel in the job.”


What’s Your Takeaway? 

There’s a lot of information here; here are some through-lines.


People Are People! Treat Them Well

No matter what level of management someone is at, they all started out somewhere. All of our leaders interviewed here mention the importance of treating their people well and wanting to be treated well in turn. 


Listening Is Your Best Tool 

As one of our leaders said above, listening is much more important than speaking! Not only can you gain insight from what is communicated, you can learn from how it is communicated. Are they hesitating? What is their body language telling you? Do you have the kind of relationships with your team that allow true openness? 

Seek Out Feedback 

When you reach a certain level of leadership, you might stop getting real feedback from your direct reports. This is a huge loss on your part and one of the most pressing reasons for executive leaders to ground themselves. Make sure that you seek out feedback as often as possible from all sources available to you. 

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Jaime Faulkner