Bosses, Managers, and Leaders
A lot of people who start off as first-time managers do not know how to manage. Over my long career, I have had many different bosses, and during the later years, I’ve also had my own experiences with leading people. If you read the previous three sentences you will notice that I have used three different terms - Boss, Manager, and Leader - to describe the person you report to. In this post, I’ll argue that they all mean very different things and why it’s important.
Over the years, I have tried to identify the difference between these to tease out which one of these I was as well as to evaluate potential managers during interviews.
Most advice that you will see for a first-time manager relates to processes that are important. The problem is that such processes create a “one size fits all” template for the manager to follow. This results in them thinking that they are doing a great job if they follow these processes. Some examples are how long should your 1:1s be, how often should you have them, how you should delegate responsibility, and how you should keep your direct reports accountable. I think these are all great questions but not the right questions to start with. Why? Because no human being is the same and has the same career paths, accountability levels, as well as personalities. If you’ve been using frameworks to manage people without context it is likely that the person who is reporting to you is dissatisfied! Before jumping into frameworks the first thing you should do when you have a new direct report is to understand their background, career progression, what drives them, and how you can help them “get to the next level” whatever that means for them. This is similar to how a doctor would ask you for your health history, medications, and family medical history in order to figure out the recommended course of action for your health.
As an example, one of my direct reports at a previous company needed a bit more hand-holding and that person wanted to meet more often and oftentimes ad hoc because that made that specific person more comfortable. My 1:1s used to last an hour because I used it for updates as well as coaching even setting up more time to ensure that they got the right level of coaching and feedback. Another report wanted the 1:1s to be as short as possible and 1:1s with that direct report were shorter. Had I just used the standard 45-minute 1:1 both of them would have been dissatisfied. I only knew this because I had spent the time to understand them before prescribing how long the 1:1s should be.
I recall when I became a manager for the first time 15 years ago, I was asked to attend “manager” training which covered a variety of generic frameworks for how to uh well, manage people in order to become a “good” manager. I’ve since attended several such training sessions. Reading that, you all probably think I must be a crappy manager. LOL. Well, the secret is that most of us are pretty bad when we start off managing our very direct reports’. The ones that get better only do so because they clearly realize that people are not all the same and that sometimes you are not the right fit for that specific direct report and that direct report is not a fit for you. This is perfectly normal and in fact a good thing!
In addition to personality, I also think that irrespective of how long someone has managed people, you will find managers on a continuum: Bosses, Managers, and Leaders.
Below I’ll describe how you might be able to identify where you stand on the continuum and how to transition from one phase into another.
Bosses
A majority of first-time managers start off as bosses and believe that their main goal with their employees is to command either because they don’t know what to do or because they had bad managers themselves. How do you find out if your direct reports’ think that you are at this stage of the continuum? One of the ways is you can ask your direct reports to be honest with you. It's highly unlikely that at this phase of the continuum they will be honest with you since they don’t trust you. Another option might be a skip-level meeting with the person you report to, or actually caring and listening in an exit interview. Lots of employees who leave are running away from something versus running toward something and can provide valuable feedback!
An even easier way would be to consider your interaction with your direct. Do you just “throw something across the fence” and “expect it to get done”? Do you support and stand behind the work that you expect to get done? Do you spend a lot of your time explaining the why before the what? Do you update your reports when something changes? If you answered NO to most or all of these questions then you will not quite make the cut in the long run. In the tech world especially do not expect longevity of your employees or real respect (ie what your directs say about you when you are not in the room)
I know the story of an engineering manager who started managing a team of five senior people when he probably should not have been allowed to take care of a toy car. This person got promoted, likely due to his tenure as well as the fact that if he leaves because he was not given the promotion replacing him would be hard. The choice the company faced was to push him up the ladder or he leaves and joins another company at the position that you did not give him. In this specific case, every senior employee who reported to this engineering manager quit within a year. The only people who were willing to report to this person were junior employees with no experience with good and bad managers.
Many years ago, my own experiences mirrored the same thing. Two stories that come to mind. The first was, my manager at the time, came over to my desk at about 7 PM, looked at me, and smiled contentedly that I was working to get him his bonus and then he turns around and asks me why his other report, who sat next to me .. and I quote from memory vividly after 2 decades “had left so early” and “didn't he want to grow in his career”. I smiled and nodded my head thinking that had the manager invested the time he would have known that the person who left early had to take care of a sick parent (and in fact, that is why he left the United States and moved back home!)
The second story that comes to mind is when we were hiring, there was a somewhat older (perhaps in his 30s) and I really thought the guy was great but my manager did not want to hire him because he was afraid that he’d be at risk of losing his own job. Yep, he told me this.
So there are bad managers because they don’t know how, they don’t want to learn, and they think that it's about them and they think that just throwing things across the fence and staying out of the trenches is the best way to be a good “boss”. There is a reason the term “bossing around” exists!
If you believe that this is where you are, the best way to move up the continuum is to consider your interaction and involvement with your directors. Questions to ask at this stage
Do I throw things across the fence with little to no context and expect them to get it done?
Do I problem-solve along with my direct reports?
Do I check in with them, if needed, and ask how things are moving along?
Do I explain the why in addition to the what?
Managers
The second level on the continuum is managers who are better than bosses because they have more empathy for their direct reports and set up clear goals, and expectations. They work hard to remove roadblocks from their direct reports’ way. They realize and understand that people are different, need different levels of interaction, and learn to identify and course-correct. What these leaders don’t think about and plan for is the future direction of the employee. You are sometimes going to have a really smart employee that is struggling because you cannot give them the kind of work they want to do. Other times you are going to have an employee that is performing badly and in just the wrong job. Oftentimes managers will not offer guidance, preferring to let the problem “work itself out” by indirectly “pushing the employee” out of the door.
You’re already doing most things right if you are at this stage of the continuum. However, you are managing in isolation. You are not considering the core motivations, stage of career, or what is next for this direct report here or at another company which are very important. How can you identify if you are at this stage?
Does your direct report have regular career conversations and what it takes to get to the next level?
Do you provide guidance to your direct reports on their overall career or just in isolation?
Do you help your direct report map their various roles and help them figure out what the next ideal step might be?
Do they trust you enough to have honest and open career conversations?
Do they trust you enough to hang out with you outside of work and get a beer or a coffee or a walk?
Leaders
The third and final level along the continuum is a leader. You might have heard the term “servant leadership”. A leader does everything a manager does but in addition knows what drives an employee and what their best skills are and supports their career ambitions or in some cases the desire to not be that ambitious. To such a leader, a direct report leaving is not anathema but a natural progression that is to the benefit of both the leader and the direct report. One of my old bosses always knew of my ambition to switch to Product and not only did he support and encourage me, but he also went out of his way to reach out to people who could help me become a Product Manager and he did not only wait for me to approach him for help. He was proactive, cared, asked how he could help, and kept his word!
Over the years I have found that the best leaders provide extremely clear direction (this does not mean a map but a clear unwavering destination), are brutally honest with their employees, and push their employees to do better at the edge of their comfort level, know when something is not working out (it should not be a surprise to the employee when you have this conversation since the employee would have known about this all along)
This post is not to say that every person that has direct reports for the first time goes through the continuum. Some are naturally great and empathetic having had the experience of being leaders while in school or learning from their experiences. The key point here is that you can learn how to move up the continuum if you are willing to invest in your direct reports’ and learn how better you can make them successful. The best leaders always put the company’s needs alongside direct reports' needs and figure out the best way forward. The best leaders listen, pattern match, and can be honest with their direct reports when there is a misalignment between the company’s needs and the direct reports’ needs. They are honest, empathetic, and caring.
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Acknowledgments
Thank you so much to Leo Ariel , Henk Bruinsma, and Chris Wong for feedback on early drafts and for making this more understandable and relatable. You beautiful people!
