Sorry to My Old Bosses and Why I'd Be Creating a Predictive Model of My Bosses Moving Forward

This post is inspired after attending Wes Kao’s Executive Communication and Influence course. I highly recommend this to people who are looking for practical frameworks to become sharper communicators.

Looking back on my past work experience, there were definitely times when I got passed over for promotions. It was hard not to blame my bosses for their lack of judgment back then.

But honestly, I probably wasn't the best subordinate either.

I gave my bosses a hard time. I was probably stubborn and tricky to give feedback to. I thought that pointing out their mistakes or gaps was helping the team improve and raising the bar. I thought I knew better and sometimes I did, since I was closer to the actual problems. But I struggled to receive help from them. I tend to withdraw when I don't like a situation. And I thought being open and transparent about my future plans would help them look out for opportunities for me.

I felt like I deserved every promotion that I was got passed over.

Meanwhile, seemingly poorer performing colleagues got promoted instead. Then I learned something important through Wes' course. There's a low probability way to get what I want and a high probability way.

Here's my take on a tell-tale sign you might have a poor understanding of your boss: Your boss can't clearly articulate the steps you need to take to get that promotion. Obviously, they can't tell you they like someone else better. Maybe there's a legitimate reason. But if you're not clear on it, it's likely because they can't give you the actual reason.

Why won't your bosses tell you this? Two reasons. First, most people (yes, even bosses) haven't reached the level of self-awareness where they know their exact preferences. Second, no one wants to come across as self-obsessed. I'm not defending bosses who are abusive here. But understanding this dynamic is important.

Building a predictive model of your boss

The fact is knowing your boss better helps you achieve your goals. Whether that's getting the promotion, securing a transfer, getting more resources, or getting approval for that project you really want to drive and be proud of.

Start by identifying their implicit preferences, ways of working, and how they interact with others. You can craft specific questions, but asking something generic like "what is your working style?" won't get you far. The more granular you can get about specific situations, the better.

Many times, people say and do different things, so you need to observe.

Some managers might grossly overestimate their ability to take constructive feedback or have a specific way they want to hear it without communicating that preference. You want to know that. Take what they say as a 50% of the picture and use your observations to fill in the rest. Actions speak louder than words.

Pay attention to what they find impressive or what they've complimented you on. In my case, my bosses appreciated when I made things happen, provided clarity in communications with clear action items, thought a few steps ahead without prompting and preemptively solved problems. I also needed minimal step-by-step direction and owned workstreams and conversations while increasing our collective knowledge. I reduce their cognitive load by having a point of view.

On the flip side, think about what might have frustrated them. My bosses in the past were probably frustrated when I got stuck doing research and things took longer than expected without being communicated. When I left them out of important communications that created confusion or required extra communication loops, or when I didn't appreciate their teachings or guidance.

Understanding What Your Bosses Care About

Finally, think about what your bosses usually care about at a high level. They probably care about their own performance. This usually means getting things done and solving problems. Securing big deals. Hitting revenue targets. Finding win-win solutions. This depends on you, and having a high-performing, capable team.

They're also managing upwards to their own bosses. The opportunity here is to help them achieve their goals by making them look clearer and more effective to their superiors.

Understanding these dynamics doesn't mean becoming a yes-person or compromising your values. It means being strategic about how you work with your boss to create better outcomes for everyone involved. I wish I knew this sooner.

Reply to this email to let me know how you’ve enjoyed my content so far and it has helped you. This really keeps me going 🙂 

I’ll always be here,

Joping

Joping is Certified Coach based in Singapore. She believes courage helps us embrace our fears and lead the lives we want. This newsletter is the manifestation of her courage.