5 Actions of Insecure Managers & How to Work with an Insecure Boss

Working with an insecure boss can be very bad news for your development, your happiness at work and your career progress IF you don’t know how to handle the situation. It is easy to find yourself on the end of put downs, criticism, and undermining when you don’t know how to work with an insecure boss. Even worse – when you are doing a really good job, you are much more likely to run into trouble with an insecure manager.
5 Actions Of Insecure Managers & How To Work With An Insecure Boss
- 5 Classic Signs Or Actions Of Insecure Managers
- And 5 Key Actions To Take To Gain The Support And Trust Of An Insecure Boss
A very competent senior manager I have been coaching recently has an insecure boss. I will call him Dave. The relationship between Dave and his boss had hit rock bottom. They were barely talking. Dave’s boss kept criticising and shooting down Dave’s plans and ideas. The boss kept Dave away from the other leaders in the organisation. Dave felt undervalued, attacked and very unhappy.
Dave made a number of very specific changes to his approach to his insecure boss. In a short space of time their relationship has become a lot more positive. Dave’s boss is starting to compliment and praise. Plus Dave now is being supported rather than attacked. Dave is getting permission to implement more of his ideas and plans. Dave is a lot happier and planning to stay rather than leave.
The point of the story is that most people’s natural reactions to being treated poorly by an insecure manager are to respond in kind, to interact less, to think poorly of their boss … all of which makes everything WORSE for them and their boss.
Watch on YouTube
Listen on Podcast
To improve the relationship and reduce the tension and issues between you and an insecure boss, a specific counterintuitive approach is what is needed.
The stronger and better your relationship with your boss, the more benefit you personally get in terms of support, autonomy, access to better development opportunities, increased pay and bonuses and earlier promotion. Not to mention, you will feel less stress, be a lot happier and have much higher psychological safety and job security.
Take proactive action today to improve your situation with an insecure boss. You are going to the biggest winner.
5 classic signs or actions of insecure managers
Knowing the signs, you can quickly spot an insecure boss and take action that will improve rather than damage your relationship with your boss.
Firstly, insecure managers will try to exert a lot more control over you and your work compared to a confident boss. You might be micromanaged, asked to do everything the way your boss wants, need to get permission or approval for almost everything … in short NOT encouraged to think or act independently of your boss.
Secondly, insecure bosses are usually overly concerned about what others think of them. They often do what is best for their popularity rather than what is best for the team or business.
Thirdly, insecure bosses talk themselves up, often at the expense of others. This might mean taking credit for others work or believing the success of the team is only down to them.
Fourth, insecure bosses are often quite critical of others and don’t praise often. Putting others down makes them feel better and lowers the perceived risk of others outshining them.
Fifth, insecure managers often prevent team members access to or interaction with their own peers, more senior staff or even co-workers in other parts of the business. Controlling the relationships and flow of information makes them feel more valuable.
This is not an exhaustive list yet covers the most likely signs that you have an insecure boss.
If your boss starts taking any of these actions with you, don’t take is a personal attack and respond negatively. A negative approach is not in your best interests. Instead take 5 key actions to reduce the threat your boss perceives.
The best 5 actions for how to work with an insecure boss to gain trust and greater autonomy
The 5 actions are
- Play to your bosses needs
- Be an ally not a rival
- Give them a sense of control
- Make your boss feel and look good
- Build and manage your own reputation
Each in a little more detail with practical examples and tips so you can put them into action quickly.
1 – Play to Your Boss’s Needs
When you have an insecure manager, play to your boss’s needs. Understand what makes them feel insecure. What actions or language trigger their defences, or negative reactions? What actions or language create positive responses? Experiment as every manager is different. Sensible practices include:
Avoid challenging them directly, or criticising ideas or plans directly. Instead of saying “I don’t agree …” or “I don’t think that will work…” use indirect questions. “I am a little unsure. Can you explain the benefits of taking this approach over say XYZ?” or “I am confused. I thought a similar approach was tried 4 months ago, which resulted in major cost overruns. What makes this plan more likely to come in under budget?”
Position your disagreement or challenge as an indirect question that gives them the chance to educate you.
2 – Be an Ally Not A Rival
The second action to work with an insecure boss is to be an ally not a rival. Do not try to compete with your boss or prove that you are good at what you do. Focus on creating a partnership, where you both succeed together. Two approaches to try:
- Link your ideas and suggestions to their ideas. “I really liked your idea to ABC, so I explored it further and as a result came up with XYZ. Are you happy for me to implement this solution?”
- Link your ideas and suggestions directly into how it helps them look good. “I analysed all the sales data as you suggested, and discovered that if we do XYZ, we should be able to reach your target of £1.2m in sales for this month – 5 days earlier. Would you like to speak to the team about this or are you happy for me to?”
Create a partnership approach with your boss.
3 – Give Them a Sense Of Control
To win over an insecure boss is to give them a sense of control. The more you involve your boss and give them a sense of control, the more relaxed they will become and the more trust you will get. 5 practical actions you could take:
- Over-communicate what you are working on and how progress is going
- Make them feel included by giving them plenty of opportunity to give input and feedback
- Seek their opinion and their approval for your plans and actions regularly.
- Tell them who you are working with and talking too outside of the team
- Schedule at least a weekly one-on-one meeting with them so you spend time working with them and discussing your work, ideas and solutions
Work to ensure you are giving them a sense of control. You will gain a lot more freedom as a result.
4 – Make Your Boss Feel Good
When for working with an insecure boss, your boss feel and look good. The better you make your boss feel, the more they will trust you and the more autonomy you will get. Give them positive feedback about what went well without sucking up. Re-affirm their good ideas, decisions and actions and be very careful talking about the poor ones.
Communicate to colleagues outside of the team what your boss is doing well and their achievements in a matter of fact way. Help your boss hit goals and targets – particularly the very visible ones. In short do everything practical and sensible to make your boss feel and look good.
5 – Actively Build Your Own Reputation
When working with an insecure boss is to actively build and manage your own reputation. Insecure managers rarely shout other people’s praises or communicate what their team members are doing well. Make the time to build relationships outside of your team, with your boss’s peers and with leadership team members.
When speaking to these groups, give them updates on what you are delivering and how the team is progressing. Drop into the conversation your achievements and results. Offer and provide them help when opportunities arise so they can see you in action. In short, proactively look after your own reputation.
Working very successfully with an insecure boss is knowing what to do and using these approaches in a considered way. You absolutely have the skills to start doing each of these actions successfully. The more you practice, the better and more natural each of these actions will become.
in summary
Learning how to work very successfully with an insecure manager will make your life at work a lot happier, a lot more rewarding and a lot more professionally successful. A lot of managers have some level of insecurity. Managers are just as human as everyone else AND are under more pressure and scrutiny.
As a quick recap the 5 actions to win the trust and confidence of an insecure boss are:
- Play to your bosses needs
- Be an ally not a rival
- Give them a sense of control
- Make your boss feel and look good
- Build and manage your own reputation
Don’t forget to take a look at our resources section to learn how to manage any boss more successfully and how to market the great work you do more effectively in any organisation.
If you have any questions on “5 Actions of Insecure Managers & How to Work with an Insecure Boss”, please email me at support@enhance.training and I will get back to you.
Insecure bosses are tricky to work for to start with. Once you are have proved that you are not a threat to them, working life becomes a lot easier, more enjoyable and more professionally rewarding.
Your own worse enemy is your reactions to being treated poorly or as if you didn’t have all your skills and experience that you have worked hard to gain. Do work hard to manage these reactions carefully and turn your frustration into positive actions that will help your situation.
Above all, over communicate with an insecure boss, support them and build a partnership where you both succeed.
Jess Coles


