Three signs of a cool boss

This is a good list. I would add that a common theme with the first two is this: They make it safe for you to speak honestly. I often see employees who clearly don't feel safe talking to their boss about future plans (because maybe the boss will push them out earlier, stop giving them good assignments, or whatever) and I definitely see a lot of employees who won't talk candidly with their boss about things that make them unhappy at work. A good boss wants to know these things and won't hold them against you — and will make it clear to you that that's the case.

One of the most important things I look for in a boss (and unfortunately haven't always found) is someone who is willing to go to bat for you and have your back. I'm all for handling your own problems, but sometimes office politics, policy or protocol tie your hands and you need someone who is willing to step up for you.

It makes it a lot easier to take risks and try new ideas if you know someone will back you up out on your limb.

Great list Ryan. I have been lucky enough to have good managers, but I suspect the reason why more do not exists.

My managers were great and I would do extra work for them. On net, I bet it was good for the bottom line. But it got them in trouble.

Official company policy suggested managers keep distance from their subordinates, especially in social situations. I think the company was worried about whether managers would work us less if they were friends with us: would a manager be reluctant to assign weekend work, if he knew I had an important personal social event that weekend?

Maybe, maybe not.

I disagree with company policy because I'd rather get work from someone I got along with. But I don't know if that works in the aggregate.

[...] Healy offers a similar perspective in his 3rd sign of a cool boss – Be friends at work, but not outside of [...]

I think this list drives home the point that the best managers are people persons. Being a manager is mostly about the people skills, with technical skills taking a back seat. This is one of the reasons it is so difficult to make the jump from being an individual contributor to be ing a manager (and why I don't want to be a manager).

Scott – I think you're totally right. Being a manager is all about people skills. The problem is that managers are responsible for a huge amount of work as well, so even if you have people skills, finding the time to focus on people is difficult.

It really is too bad managers don't have the time to do what their titles imply; manage. But I guess that wouldn't be very efficient. Or would it?

-Ryan

You could easily interchange "boss" with "parent" and use the same skills to deal with your children. Part of the problems with parents these days is the stress required to deal with everything that comes your way as well as the need to meet your goal, hopes and dreams. The same could apply to a boss.

A department could been seen on the same level as a family unit. You have different personalities that require different approaches to deal with encouraging, rewarding and, to a certain extent, disciplining/correcting your subordinates.

Remeber that managers are in the middle between their bosses and their subordinates. On the subject of standing up for and protecting your staff when necessary, it is equally as important to deal appropriately with negative or destructive behaviors at work. A good manager knows how to distinguish between the two and knows what type of response is required depending upon the subordinate and the situation.

It's definitely a journey of survival. All or us need to work in order to survive, whether we start our own business or work for someone else. You've got to know what you want to do, go after it and be happy in your journey of life. You may need to make adjustments along the way and you should be willing to accept and admit that every choice leads to some type of conclusion, whether it be a wrong decision calling for a change in direction or whether you've hit the right path to sail into the sunset.

Good list but I disagree with the boss as friend part. Perhaps this is a generational thing but like a good parent, the boss can be friendly but it can be tricky to become a subordinate's friend. First of all, you don't want to be friends with all your employees but you can treat them all with respect and be "friendly." If I were in my 20's or 30's, I may think differently but I think a more structured relationship is best.

I think it is more appropriate to interchange "boss" with "coach". The problem with the parent reference (see Alan's comment below) is that your connection with your children is much different than with a subordinate with respect to the emotional attachments. That is where a good coach distances themselves a bit by being constructive, critical and motivational. Can a good coach/manager be a friend as well? I think it is better to have a friendly relationship with all the players/subordinates, but being too close is a problem as favoritism can be perceived and can affect the motivation and performance of the team.

Cool bosses are like cool parents – they fail at their job. Bosses and parents should be role models and leaders that earn respect/trust, give clear direction and boundaries, and act in a consistant and fair manner. You should strive to become a solid leader that instills values and expects the best from his subordinates. If your goal is to be "Cool", you will fall short as a manager and won't help co-workers reach their full potential. If you look to be a real leader, people may not want to "shoot the shit" with you, but you will be a more positive influential presence in their career.

Ryan, as is shown in most of your articles, you lack too much experience to be a credible writer on these subjects. But keep plugging!

Ryan – Thank your your insight. However, I have to 100% disagree with you on this. The command and control style you mention is dead, it just doesn't work. I might respect someone who demonstrates they are a hard worker every day and puts their nose to the grindstone to get the job done, but without a relationship you will not gain loyalty from your employees.

It is completely possible to be a "cool" boss or parent, and earn respect. It's a fine line to walk, but it's the only way to really connect with your employees. If there is no connection, there is no positive influence on their career, and quite frankly you will come across as selfish.

Finally, to act consistent and fair with everyone is just plain wrong. Everyone does not work the same way, we all have different strengths and weaknesses. A good manager will adapt to each employee appropriately.

I don't claim to have a boat load of experience, just my humble opinion. But that's the beauty of the blogosphere!

-Ryan

Call me old school, but I completely agree with the comments Ryan posted on 12/06 @ 5:56p. I have my own set of friends away from work and don't feel that work and play should mix. A manager is someone that can direct and lead a team; to become over friendly with subordinates leads to diaster, when difficult decisions need to be made. As in Ryan's example, a cool parent cannot properly discpline a child nor can a cool manager handle difficult decsions if they are too close to employees.

I agree. I think the point about them investing in your career is an important one. When a boss can look at the reality our current workforce and grasp that you may not be with them forever and really invest in your career – not just your current job – that instills a loyalty that is hard to build any other way.

And it's important to get along with and have an appropriate level of friendship with everyone you work with – from your co-workers to your boss to those you manage yourself. Trust is a component of a relationship, and you can be a role model, leader and friend. This is a difficult balance, but it's possible. You will really fail as a leader if you don't have any real relationship or trust with those you are supposed to be leading.

Everyone here has differing opinions about what makes a good manager. So a good manager needs to have enough people skills to manage everyone according to their expectations.

I think what has really changed is not the move from command-and-control to a more personal style, but that a manager needs to use many styles with different people. Good managers recognize that they need to be more flexible to bring out the best in each employee. Some employees want to be 'friends', others just want to be told what to do.

If you can tailor your management style to the correct person and correct situation, then you are a good manager.

A great, easy and spot-on post.

A boss is there to ensure things happen and get things done and the best way to do that is through their staff! Sounds so simple doesn't it. What about customers, budgets, office politics, monthly reports, complaints, meetings…and on and on…the list is endless.

However, if you have fantastic relationships with your staff then many of all those other things can be delegated to them to help them grow, etc.

I would like to expand a little on 'They take an interest in your career'. In fact, the best bosses take an interest in your entire life dreams. Recently I was lucky enough to interview Matthew Kelly regarding his latest book – The Dream Manager. I believe this book is a 'must read for anyone who desires to help others achieve their dreams' Whether you are a manager, leader, mentor or coach this book will help transform the way you relate to others. Individuals have dreams. The book teaches you to understand the dreams of individuals and then help to fulfil them. The book is a fictional story and I found it very easy to relate my life and experience to the story.

As the boss, you are there to remove any obstacles or problems to enable the staff to get on with their job easily and simply. Great bosses also ask their staff 'what is stopping you from providing a great service'. It is amazing the responses you get. I have had such responses as:

'The lights in the office need to be brighter'
'Can we have a scanner?'
'The coffee shop shuts at 3pm but our break doesn't start until 3, can we start our break earlier'

Some simple changes can make a big difference.

Andrew

The whole "being friends with your boss" is a thin line to tread on. I believe it really depends on the personality of the boss. Some bosses can be just creepy and odd when they try and be your friend (see Scott, Michael). Personally I've had at least one boss who freaked us employees out with his obviously forced efforts at trying to be "one of us". Have you ever been forced to go out to Hooters with your boss? Or, worse yet, been roped into going to a strip club?" Not a pleasant experience.

Ryan –

I guess we will have to agree to disagree. But to defend my points, I was not inferring a "command and control" style in parenting or leadership roles at all. But I am against "the buddy system." You have to understand your ultimate objective as a manager – inspire others to perform at their optimal level while increasing the companies bottom line. This is the goal of "good" leaders, not "cool" leaders. When people are inspired, they gain a greater deal of satisfaction and personal growth. It's good for you, the company, and the employee. It would be disengenous to put your desire for friendship with employees before the ultimate objective. You are inferring that to inspire others, you need to be friends. This simply isn't true. I agree with others who have posted when they make the distinction between being "friendly" and being friends. I have been around long enough to see more than a few manager's judgement affected by making the mistake of getting too close to his/her subordinate. It can also give a perception of favoratism, etc.

I'll give you an example. For my birthday, one of my subordinates wanted to take me out to lunch. She scheduled a meeting on my calendar (that the whole office has access too) stating, "Birthday Lunch – I'm Buying!!" I had a very light discussion with her that I didn't think it was appropriate for us to schedule this lunch because: a) she had done excellent work all year and I didn't want anyone to question why she received a good review, and b) I don't ever want her to feel like I "owe" her anything because we have a personal relationship outside of work.

I don't really understand your comment about "adapting to different strengths and weaknesses." Consistency and fairness are crucial keys to managing any organization (and as a parent). People need and want to know where the boundries are and what the consequences of those boundries will be. You can't talk out of both sides of your mouth regarding company policies and you can't play favorites with staff. For example, you can't tell one employee that they can tele-commute because they have kids at home, but tell others at the same employees job status they can't tele-commute because their personal reason for staying home doesn't really matter. That would be neither consistent nor fair. That's not even "cool."

I will say, that you seem to be speaking specifically from a subordinate/child perspective rather than a boss/parent perspective. If company policies were create for the SOLE purpose of pleasing the front-line worker, companies would be in big trouble. When you become a manager, you lose some of the ability to "hang" with group. Just like when you become a parent, you lose the right (to some extent) to "hang" with you kids. You have a job to do, and the ultimate objective is not to be "cool." It sucks, but sometimes that's just part of being a boss/parent. That's what we do when we grow up.

Actually what I find odd, Manager Ryan (not Ryan Healy) is that you seem so blinded by your experience that you can't imagine there are situations other than the terribly boring and truly awful sounding corporate environment that you exist in. Contrary to popular belief the world does not consist solely of hierarchical office space-like corporations anymore. Claiming the Ryan lacks perspective and experience seems a bit like calling the kettle black.

Brad – Like Ryan, you are reading between lines that I am not drawing. I have said nothing of hierarchies, corporate america, "command and control", or anything else that has been extrapolated from my comments. The problem that I have with Ryan's article is the whole way he is framing things. Do I think you should communicate and ask for feedback from your employees? Yes. Do I think you should take an interest in your employees career? Of course. Do I think you should be friendly and geniunely interested in their life inside and outside of work? Absolutely.

My problem is the whole way Ryan framed this peice. The mere title, "Cool Boss" is just not the way I would frame a discussion on how to become an effective manager. Then to back it up with statements like the need to be friends and "shoot the shit" with employees really strays from the most important aspects of being a good manager. His analysis of good management is shallow at best.

ALSO NOTE that his favorite manager at IBM, while seeming to get the popularity points in this article, wasn't able inspire Ryan to be anything more than a "B-employee" (check Ryan's other posts). And his manager was so "cool" that he didn't notice Ryan began to start a side-business out of his cubicle during regular work hours. Let's face it, Ryan needed a "cool" manager, because he really wasn't a very good employee. And he needed the brown noser points because of his "B" level work. If he had had a real manager/leader that wasn't trying to win a popularity contest, Ryan may have either been out of a job or would have started performing at a higher level. That's the managers job.

BTW. I work for a very flat organization that is as people-oriented as it gets. It's because of my constent interaction with my employees that I know the importance of keeping an appropriate distance from sub-ordinates. It has nothing to do with the size of an organization or how flat the structure is — it's just good management in most situations. Ryan asked for feedback, so I gave it.

I said Ryan lacks experience, because he does. It's just a fact. However, I have a lot of respect for him because he throws his ideas out and asks for comments. Good for you Ryan. By the time you are 30, you will be leaps and bounds ahead of any of your peers, simply because you have the courage to venture out and take a little abuse. And I think it is great that you are trying to instill new ideas, but you would be wise to listen to others who have gone on before you. Don't let you youthful exhubrence get the best of you.

I'm going to back up Ryan (the manager, not Ryan H.) on this one. I actually really liked Ryan H's post, but I took it as a list of things that make a boss cool from the employee's perspective, not a definitive list of what makes a good manager. If we're talking about the definition of a good manager, well, ultimately it's someone who gets things done — everything else is a subset of that. Yes, you should be nice to your employees, help them develop, etc. — but that's because good morale, engaged employees, and skill development means a more productive team, which means better results. (I'm speaking from a strictly utilitarian perspective here, obviously; of course there are other reasons for doing that stuff, like being a nice person.) Ultimately, you've got to look at everything through the lens of what is going to get you results.

As others have already said, you had me until #3 ("They are your friend, at work"). I agree that a good manager is friendly with his or her team, and that it's important to find some common ground for those non-business-related moments, but that doesn't make a "friend." Being friends, even if it's only during work hours, can create strong tensions when tough business decisions need to be made, especially when it comes to things like promotions, performance reviews, salary increases, bonus distribution, etc. There's a reason for the phrase, "business is business." Sometimes it just is, and other emotions can really get in the way.

My current manager ran into this situation when she chose to promote me over someone who was her longtime friend. I was better qualified; that's all there was to it. Her friend left the company within two months. I'm sure there would have been hard feelings either way, but his deep sense of betrayal and embarassment didn't help.

Friendships, like dating–especially between employee and employer–are best kept outside of the workplace. That's not to say that it never works out, but when it doesn't work out, entire careers can be shattered.

@ "Manager" Ryan (sorry about that; I really hope that name doesn't stick) and Ask a Manager: I think you're both hitting the nail on the head. We can keep talking circles around this issue as much as we like, but the perspective you're bringing to this discussion comes from realism and experience, and I hope people are listening.

Very well said. Sean said what I was trying to say (through babble) in a clear and concise manner.

Ryan:

I think your perspective on this is uniquely Gen Y. And that's cool. I'm one of the people who believe your generation will revolutionize the American workforce. However, as an Xer, I think it's nice to have a boss I can be pseudo-friends with at work, but I don't really care if I am or not. My two top priorities are 1) have a boss I can learn from (from good experiences, not the bad ones) and 2) a boss who is confident enough in himself/herself that they can allow me to succeed (I've worked with a lot of Boomer women who want to be the only girl in the board room). I'd take a boring-as-hell boss – who's idea of fun is a rerun of Murder She Wrote – who I can succeed with, rather than the great conversationalist who is terrified that my success will tarnish his.

However, I think the point here is moot. Ten years from now, the corporate structure will be so flat that being the "boss" probably won't mean anything. Sometimes I'll be the boss, sometimes you will. It'll just depend on the project. (Oh, and I know when you're in you 20s, 10 years seems like a lot – but not so much when you're in your 30s).

My two cents. Keep up the good work. You guys rock.

Great discussion. Asking for your input is also key. I'm not saying they have to get the entire team involved in every decision, but it's good to know they value your opinion on a project, idea, etc. And, through that process, good bosses communicate enough information for you to know what's going on and for you to be successful, without overloading you with unnecessary details.

I agree with Suzanne that Ryan's take on this topic is very Gen-Y. It seems that our generation is obstinate about not just finding a job that pays well, but one that they like, too. And behind every great job is a great boss. A boss can make our break one's opinion of the workplace. Having a boss express interest in your ENTIRE career, as you put it, suggests that he or she encourages you to assert all of your potential, which breaks one free from one feeling limited by their job.
And always, supportive bosses encourage employees to respect the company where the work. Thus, they desire to feel like a part of the company, and in turn, they do. Thus they take their work seriously and personally.
Great discussion. I can definitely relate!

Wonderful discussion here. Allow me to throw in my two cents. I'm 26 years old and manage a marketing department of seven other people. Three of which are older than me, the other four are younger. We are all very friendly with each other. I've even gone out to a happy hour with some of them. However, I know that I must keep it professional at work and be fair and consistent with all my people. In my opinion, the best way to get results from people is to inspire trust and confidence. The best way, I feel, to do that is to be friendly with your subordinates. Being friendly allows you to build rapport. I tell my people that I'll jump over the moon for them so long as we share the same work goals and that they feel just as invested in the success of the organization as I am as their manager. The key is being fair and consistent with discipline, criticism, and praise.

I've read a lot about this topic since I struggle with it myself as a young manager. I think both Ryan the author and Ryan the manager are correct. This issue is one of those that depends on the individual situation, manager, employees, corporate culture, etc.

The best advice I've read on the topic comes from Jack Welch.
http://www.businessweek.com/perm/content/06_47/b4010119.htm?chan=careers_the+welch+way_the+welch+way

Keep the thread going!

Absolutely right about not crossing the lines into friendship outside of work. It just becomes too personal then. There's nothing wrong with the occasional happy hour or business lunch, but there's something wrong with weekend barbecues.

I don't care so much if I can drop in to my boss' office and shoot the breeze with him. What I look for is:

* He tells me clearly what he wants and when he wants it, prioritizes tasks or allows me to prioritize them myself and gives me feedback on that.

* He insulates me from political crap from above.

* If I do something wrong, he lets me know quickly and helps me to avoid making the same mistakes in future. He does not withold feedback, then use it as ammo in a performance review.

* He is approachable.

* He is present, and not constantly away on trips or in meetings, or if he is, then he is that much a better communicator that it doesn't affect his communication with me.

Most importantly:

* TRUST. I will not work for anyone if I feel I must get everything in writing, save it on a USB thumb drive so that it doesn't magically disappear and in general, constantly cover my back just in case he's running around telling everyone I'm the reason his mismanaged project is overdue, reneges on promises, or invents new deadlines or requirements on a whim.

Any boss who consistently breaks more than one of these, or, the last one on its own, with me gets my notice.

I was just sent a link to this website from a friend who is the Vice President of a very well known company. I am 33 years old so I am not a generation Y. I have just a couple of questions for this generation. One is why do you feel you are special? Why should I try to retain you?

In this market and with my company, I have plenty of people who want to work and who do not expect special treatment. It has been my experience and the same with my HR and V.P. Friends, that this generation comes in late and plans to leave early , will be brazen enough to ask to relocate for a boyfriend or girlfriend and then ask for a raise. You also have to "nag" to get them to finish projects in a professional manner.

Now after reading a few of the articles I am not sure I want to hire this generation. I know you can't discriminate due to age but you can because of attitude. It seems that generation Y is a bunch of kids who think the world owes them something. No one owes you anything. When I hire you I expect you to come in on time, complete your tasks, and leave at the correct time. At the very least I expect 40 hours a week! Now for this I give you four weeks vacation a year, health insurance and a starting salary of 45,000 . I don't believe that is an unfair trade. I also won't give you a raise just because you ask for one. I give raises because you have done the work and deserve one.

I guess I am trying to help and explain that this is not the job market to get over confident about and expect your bosses to behave as your indulgent older parents did. I know that there has to be a few good eggs in this brat basket and I will be sure to hire those; if I don't have an older more qualified candidate. I am just glad that I have enough qualified candidates from other generations that I won't have to deal with this one. What should be scary for your generation is that I am not alone in feeling this way and right now we (employers, HR and hiring resource manager) have other options and your generation has unemployment.

Good point on the feedback, Ryan. Feedback is really important to Gen Y, and feedback (at least the positive kind) doesn't come naturally to older-generation managers. The manager who can bridge that gap, and then genuinely welcome two-way feedback on top of that, is definitely a winner.

On the "friends with your boss" thing, it can be a fine line – especially for women. There's another risk of being labeled a kiss-up by co-workers. You need to get along with your colleagues just as much as supervisors. Anyway, it's a tricky balancing act, but not an impossible one.

I had the coolest boss when I was an Office Manager with a local home health agency in New Orleans. He was my friend, but it was understood that "business was business". He was friendly and we would joke around some, but there was always that slight separation that distinguished boss from employee, and I respected that.

When I received my promotion to Office Manager and had my own team, I duplicated his style. I had some very close friends whom I now had to manage, and I made sure that they knew that between the walls, business came first. I had to lay a couple of them off when we had to cut back, and it was hard. But having that established professional relationship there made it easier.

Those are 3 very important things that a lot of managers don't work on and don't care about. And that's not cool.