Being a boss and being a friend

Recent events in my life greatly dampened my spirit, but I’m not going to let it pull me down. Especially when I realise I’m still so blessed to have many mentors in my life who cared for me even though I had more often than not been trouble to them.

Still, the recent events made me reflect very deeply into people management, motivating staff, team dynamics and other things that comes with trying to be a good boss. I write this here as a public reflection because I think I want my staff to know this, besides benefiting anyone interested to get another perspective on being a boss.

The myth of the tortured artist

Let’s start from the fundamentals. Each person is different when it comes to employment. Some prefer guidance while others prefer autonomy. Even though I came from the later tradition, for me to lead people who want guidance outright turns out to be the simpler option. Through a combination of clear vision, “carrot and stick”, and helping people scope and execute, I rely on this great strength when commanding a larger team of do-ers. As long as everyone’s attitude is right, heart is right (taken for granted in this article as it’s a subject for great debate in itself), usually people will buy into my style of leadership and fight hand-in-hand with full responsibility and pride.

It’s the ones who wants autonomy that turns out to be harder. 6 years ago I saw myself preferring my own bosses to simply set general direction and leave me alone, and I’ll come back with results that surpasses all their expectations. And I thought I was doing great. Until, I had people do that to me. Turns out that people who want these autonomy are also very forceful in their personality, so much so that one has to constantly get hurt, swallow it, and keep putting up with the cordial front that would hopefully rub the ego of the staff the right way, in order to achieve the greater goal of the company.

Most of the time it’s not the idea itself, or even the work. Many young hot blooded man and women have stood up for what they believe, by putting their ideas in to action. These are people who “can think”, is “creative and disruptive”, can “design solutions”, etc. In one previous position I was at, we mistakenly labelled these people tortured artists, and the label stuck. The most common mistake these artists made is the approach taken to engage stakeholders, in this specific case, the boss. Upon reflection, there are many tortured artists who work in silence, prefer to engage only intellectually, and do not require validation from the organization. It’s the ones who confronts everyone, the ones who “engage stakeholders” with a loaded gun on people’s head, that set bosses reeling.

I also realise that, to have a strong team, I don’t always need to have these tortured artist who could forge a new insightful future. As long as everyone’s attitude towards professional work is positive, everyone’s contribution are welcomed because many ideas in this world need a team to make happen. There are exceptions of course (my solo dabbling into music arrangement being a great example), but by and large, companies succeed by having all hands on deck, teams succeed when the boss takes in all the eccentricities of their staff and still presents him or herself professionally, provide a plausible path to victory that’s inclusive of everyone’s dreams, and hustle everyone.

The myth of being your friend

The next point is a bit sadder. I have always tried to connect with people personally. Like, really personally and deeply. One of the push factor I had when I worked in US was that I realise the general work population there don’t connect as deeply with you as people here (in Singapore/Malaysia). Turns out that not only was I wrong (again), I was directly feeding into this almost 三姑六婆 (“nosy aunty”) style of friendship, and it’s finally biting me really hard.

I often lament why I don’t have friends like I had in high school, where there were no secrets between us, no walls, raw and brutal, even though we work together for projects, activities, and everything, and even have protocols (e.g. in band, we call our seniors ‘sir’ and ‘madam’). Maybe it’s true that you don’t get another chance at high school. Everyone was going through identity crisis and searching for themselves then, so there’s nothing to lose for being an honest teenage broncin’ buck.

But in adulthood, things are a bit different. Everyone brings a bit of their past to the table, which includes the good and the not so good. The good is usually what one is hired for, the potential to fit into a particular role of an organization and would hopefully make a difference. The not so good, is usually suppressed at an individual level. You don’t bring up how you were fired in your last job, for example. You don’t tell everyone your private pet peeves, because it has absolutely nothing to do with work, right?

Personalities and past experiences, unfortunately, bleeds into the workplace. And like a raven, I slurped in all these like a savage whenever I am given the opportunity. There’s a bit of secret about how my mind works (that thanks to Mark I manage to quantify): growing up an introvert and an insecure socialite, I build complete logical structures of all knowledge in my mind – everything has its place, its reason – including of every person I meet. I rely on this “program” to interact with people. And thus, the good, the not so good, all gets built into the knowledge tree.

Put that in the context of me being a boss. Now that I have varying degrees of understandings of each of my staff in my mind, I suddenly need to be extremely measured about how I reveal that to others. If I expose my staff’s not so good, even in private, my staff would not be able to defend his front that he brought to this organization. On the other hand, I have a better chance at motivating my staff, if I associate his good with the charter of the team, the goals of the organization, and let the person see how his ego can be rubbed when the organization succeeds.

I finally fully appreciate when people bring up the phrase 没有办法下台 (didn’t let the person off the stage). To be an objective boss means to have my role interface with my staff’s role, not for me the person to interface with him or her the person, by which I mean being friends with my staff. In itself, being friends is such an overloaded and multi-connotation thing – everyone has a different idea of what is it to be a friend (vs acquaintance, vs contact etc.), trying too hard to connect with one’s staff at a personal level can potentially be detrimental not just to the company but to both party’s emotional well being.

So, we can’t be friends. In fact, there might not be such a thing in life as a friend when professional work is concerned. This dark conclusion naturally has its exceptions, and that’s what it should be – an exception. For many years, I was operating where trying to be your high school friend was the norm, doesn’t matter if you were a colleague, a vendor or a customer, because I felt that connecting with people and receiving reciprocity gave my life meaning. Now I have to operate to find where people are willing to be an exception to the opposite rule, where people first play their role in the company, and give each other space to be honest and brutal about life only if there’s sufficient accrued good relationships at work.

* * *

I hope from now on, I won’t take personal relationships for granted. Friendship and autonomy are earned, much like trust is earned. It takes one mistake to break all the trust that was built up over the years; similarly, for a large set of workplace friendship, it can take just one unnecessary “offside” to break through the other person’s facade and lose the friendship that was built up.

Put it in my high school level language: Better be fake and only be real when you’re sure the other person’s heart won’t break. It’s just business.

Comments discussions disagreements agreements welcomed.

p/s for those who fall into my exception list (you guys know who you are) – thank you for taking shit from me and still loving me. I love you all.

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