Leadership
How to Deal with a Demanding Boss
The trap of unspoken rules and risks of managing upwards in the corporate workplace
Work relationships can be very complex. Unspoken rules prevail in the workplace. Many employees suffer from naivety and bad career advice.
I want to cut to the chase because social media, professional platforms like LinkedIn, popular publications, so-called self-help books, and even expensive seminars by reputable coaches are full of wrong advice for aspiring professionals. Managing up is a critical skill for success.
Let’s take the advice of being assertive and escalating unfair situations to your second-line or third-line managers as an example. This advice is risky.
Assertiveness is a good thing at work and in life. However, when it conflicts with unspoken rules in the workplace, it can be detrimental to one’s career development and progress.
When unfair behavior is observed in the workplace, going above your boss is recommended by some career advisors as a bold and assertive move. It sounds great and feels palatable, but it is a deadly move most of the time.
Apart from exceptional situations, complaining about your boss to their manager can hardly produce any good results. From my involvement and interactions, escalations to a higher level always created a lose-lose-lose outcome.
It creates an unfavorable position for your managers because they get threatened and their primal resources put into a dangerous situation.
Their bosses are awkward because their essential resources are deemed to be performing poorly.
As an assertive employee, you become the worse loser because you gained an enemy and a person who gets suspicious of your motives.
Your boss becomes an enemy because they are forced to defend themselves. Their secrets are revealed. Your boss’s boss got more unnecessary information about you, possibly all allegations from your performance and motives.
And you made your position worse than it was before.
This vital situation in the workplace causes many dramatic problems. Let’s take Heather’s experience. Heather was a professional designer with the utmost client focus. She noticed an unfair situation created by her boss.
After being a hundred percent sure her boss made an unfair case to her team, she decided to complain to her second-line manager and escalated to the HR (Human Resources) department.
Heather was so sure that her manager would be penalized. She was naive and had a blind spot, like many other innocent employees in the workplace. Guess who lost the case! Yes, as you correctly guessed, the biggest loser, in this case, was Heather.
You may think Heather did the best thing ethically, but she ironically committed a political workplace and corporate crime. Ethics and politics frequently clash in the corporate world.
Through my resources, I investigated this situation as it was a topic close to my heart. I found out that Heather’s boss was only implementing an unspoken business rule mandated by three levels of executives.
Heather was also breaching the organization’s unspoken and undocumented rule by complaining and escalating the situation to the second-line manager.
Naturally, the second-line manager listened to her and even praised her for taking noble action. But breaching the unspoken rules created a negative HR file for Heather.
After a while, things got harder and harder for Heather. She was in the spotlight, and even minor mistakes she made were exaggerated and recorded in the HR file.
Business people cannot survive and thrive without taking risks and making mistakes. But when your mistakes are examined under the spotlight, it can put you into the position of a lousy performer, as happened to Heather.
Despite her noble intentions, diligence, and hard work, Heather’s motivation, creativity, and performance diminished after a while.
Needless to say, she had to give up her fantastic design position just because of a single mistake of escalating her manager to higher levels for a tricky situation.
Another deadly sin in the workplace is talking behind your boss. I call it a deadly sin because modern places have no such concept of true confidentiality.
Spoken words, confidential emails, and private Slack chats in the workplace are never safe. They never stay discrete. Confidentiality in modern workplaces is an illusion.
And worst of all, your confidential words can sometimes be manipulated and even sound intoxicated. You make a comment about your boss to your team members, perhaps with good intentions. But your boss may receive your comment in a totally edited and manipulated format, such as reflecting your bad intention.
Talking behind your boss will most likely sabotage your career.
How do I know that escalating to your boss and talking behind them can be so detrimental?
I know because I made these deadly mistakes and sabotaged opportunities that, I invested in skill-building, preparation, and hard work. I also witnessed many colleagues who experienced similar situations and outcomes. In addition, I read hundreds of case studies and study results from eminent academics and executive advisors.
Rhetoric on fair speech and freedom of information are false premises. They serve as sugar-coated poison.
Understanding the unspoken rules and staying in the reality zone can be a better approach to dealing with a bad boss. We need to approach any career advice with well-thought caveats.
Throughout the four decades of my career in the corporate world, I have hardly come across a manager genuinely dedicated to customer success above and beyond their personal gains.
Yes, they always showed interest in client success, but their real motive was to get the next higher-level potential management role or an executive position in the organization.
Understanding the goals and capabilities of your manager is the most important insight into your plans.
If you ever need to communicate with your second-line manager, the approach could be to organize a feedback session agreed upon by your manager and second-line manager.
Rather than complaining about the situation, asking them open-ended questions during the meeting can give you more than what you need to know.
I’ve tried it many times, and it worked for me. I also noticed that it worked for many technology executives I coached at the start of their careers.
Unless you gain 360-degree feedback, you never know what your manager is trying to do. You never know whether your manager is after another lucrative job or they truly care about the client. Probably, your career aspirations are not even on their agenda.
The point in this post may sound like a pessimistic view, but it reflects reality.
Thank you for reading my hard-learned lessons from the corporate world. I wish you a happy and healthy life.
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