CEO Chronicles 3: Managing the boss

Welcome to the third chapter of CEO Chronicles – the serial guide to navigating your liferaft in corporate rapids.

In the previous article, Horrible Bosses, we discussed five “don’ts” – traps that we should avoid when dealing with bad bosses. In this one, we will discuss a few “dos” as well as different kinds of bosses and the strategies that we can use when dealing with each kind.

Before we start, let’s try and classify bad bosses. While I am sure there are many, many classifications, I prefer to segment them into four categories for the sake of simplicity, each of which is a possible permutation of the below statements –

  • Bosses who don’t know the effects of their behavior
  • Bosses who do
  • Bosses who can change
  • Bosses who cannot

Our strategies and actions can be split into two parts –

  • One, things we should do regardless of the type of boss
  • Two, things we should do depending on the kind of boss we are dealing with.

Let’s start with examining what we can do regardless of the type of boss.

Understanding a situation is the best way to manage it. Analyse your boss. What drives him? What scares him? What past experiences seared him? What makes him feel good? Why does he react the way he does? If you can, get hold of his psychometric assessment results – they can reveal a lot about his personality and the buttons that work.

As a rule, when we like someone, we take every opportunity to engage with them, and when we don’t, we find reasons to avoid them. In a professional situation, this is counter-productive. The less you engage, the more you add to the disconnect. Put aside your emotions and talk to him. Find non-office locales if you can, they help in more open and honest discussions.

It’s also very important to document as much as you can. More than 80% of conflict in the workplace (and in life) is due to misunderstanding. Verbal communication is great, but often the participants take away very different understandings. To ensure that we are on the same page with the boss, we need to minute meetings and discussions. It is also a great practice to share a weekly review of what was planned and what was achieved. And to give updates on projects proactively, rather than wait to be asked.

Fourth and last, complement your boss. This may sound contrary, but you will gain much from proactively working around your boss’ shortfalls. (If your boss is indecisive, lay out options and recommendations; if he is disorganised, manage his calendar; if he is unprepared for meetings, give him cheat sheets). You will quickly become indispensable, not only to your boss, but to the others who have to deal with him. Very soon, you will become the ‘go-to’ person.

Teach. Manipulate. Guide. Run!

Next, let’s look at what can or should we do if we are faced with bosses who don’t know the effects of their behaviour and can change (ROOKIES):

Teach. Bosses are human. Often, they don’t know the impact of their behaviours on their team. Whether they ask or not, they need us to talk to them and gently point out how they can be so much more effective it they change certain aspects of what they do or say. You will be surprised at how much impact you can have, and how much gratitude you will earn!

Bosses who don’t know the effects of their behaviour and cannot change (IGNORAMUSES):

Manipulate. Yes, I know this word has negative connotations. But, when we are faced with a person who is unlikely to change, we need to suggest and influence and manoeuvre him into a more amenable course of behaviour. This is like dealing with unruly hair – we will gel and rebond and trim and smooth till it behaves in a manner of our choosing. Successful manipulation can make you the “boss-whisperer”, which can be quite rewarding indeed!

Bosses who know the effects of their behaviour and can change (APPRENTICES):

Guide. I have found that bosses who know what they are doing wrong are halfway to redemption. They want to breakout of the vicious spiral they are in, and just need someone to counsel them and be a sounding board. They will first need to build trust in you and be confident that you will never exploit their weaknesses. Once this happens, you will become their right hand person, and enjoy the benefits that accrue from this position.

Bosses who know the effects of their behaviour and cannot change (LOST CAUSES):

Run! I have never dealt with such a boss, but have heard horror stories. I wish I could give you better advice, but all I know is that if I were in such a situation, I would see no light at the end of the tunnel. I would start tapping my networks, looking for options and find an exit route as soon as I can, either into another part of the company or in another company altogether.

So, now you have both the Don’ts and the Dos. However, as we all know, principles and theories sound and look good. But do they actually work? To answer this, in the next article, we will delve into a real-life case of a young lady who learnt how to manage her (difficult) boss and turbocharge her career in the process.

Venkatraman Sheshashayee

Venkatraman Sheshashayee (Shesh) is Managing Director of Radical Advice, a business transformation advisory based in Singapore. He has over 34 years of experience in manufacturing, shipping and offshore oil & gas. Shesh’s previous roles include CEO of Miclyn Express Offshore, CEO & ED of Jaya Holdings Limited and Managing Director of Greatship Global. In his new avatar, Shesh helps SMEs, start-ups and aspiring professionals achieve their potential.
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