Bosses come in all shapes, sizes, ages, and psychological packages. The worst kind of boss to have is an insecure one. Insecure bosses undermine their team’s mission. They cannot see beyond their little agendas and schemes in how to get ahead. Their main focus is to promote their own agendas and not that of the customer, their company, or even their department. For those under them who are secure, intelligent, and perceptive, such working arrangement can be demoralizing, stultifying, and de-energizing. Such bosses must be made irrelevant. Secure bosses, on the other hand, inspire others to achieve things that they would not otherwise achieve. Such bosses bring out the best in their direct reports and those around them. But, when you are stuck with an insecure boss your whole life seems to take a left turn, heading south. Dealing with such bosses in most organizations is not easy. So, what is one to do to deal with such a quisling?
The following prescription may be useful:
- The conventional wisdom is to challenge the boss and to make them feel even more insecure. This does not work because then they can find ways to make you irrelevant or even make you lose your job. Remember, insecure people are manipulative magicians. They can even set you up for a fall and that can hurt your resume.
- Others retreat when they come to realize that their boss is a feckless aberration in the scheme of their organization’s hierarchy. They quietly resign to their fate and stay out of sight and off the radar screen. This is a mistake.
- One strategy that can work with an insecure boss is to meet with them privately and to ask what their agenda is. This must be done tactfully. If you already have had an adversarial or confrontational relationship with them it is time to recognize that this must stop.
- In this “agenda discussion” see if you can slowly open up the dialog to bring in the broader aspects of the job: the department, the company, the customer and the relationships your company has with them, and so on. Generally starting a discussion from the customer’s vantage point can work well. You just need to connect the dots between the customer expectations and your team’s behaviors that accommodate those expectations.
- Because insecure people are suspicious by nature, do not drag others from your department in these discussions. Any negative remarks about someone, especially, their favorites can scuttle your mission. Stay objective, focused, and non-judgmental. Even if they ask about someone else, if you do not have a positive thing to say about them, pass on the opportunity.
- You may need to have a series of dialogs in this vein just to bring the boss to think that you are there to make them look good. Once that trust begins to develop you may want to start setting things up so that your ideas on how to repair customer relationships or to improve department’s performance slowly become your boss’s ideas.
- Collaborating with your boss start implementing the ideas to improve things and to give your boss credit in departmental meeting or even in larger venues. Insecure people like nothing more than to be acknowledged for things that happen despite them.
- Once the boss start feeling secure in your relationships with you, you have taken charge of that relationship. The boss will continue to get credit and feel increasingly more secure in their ability to do things that are happening in spite of their insecurities. As you turn up the gain on your initiative the chain of command will come to see the change and the progress in areas that had tanked in the past. If the chain of command is otherwise smart, higher ups will know who is really pulling the strings.
- Once the higher-ups come to know what is going on, you need to decide whether you want to gradually expose your ideas to these managers, thus making your boss gradually irrelevant.
- If your chain of command is not smart enough to see this, you must update your resume (make sure the updates include this achievement) and get out.
It is estimated that more than 50% of the managers reflect some deficiency that is based on their inability to lead. Working for such feckless managers prevents your own growth, especially during your early career and as you are looking for opportunities to expand your reach.
Good luck!

