Blog 5 Tips To Win Over A Boss

We all have to work with different personalities, and in some cases, it is this diversity that makes our work colourful and exciting. Sometimes we don't always like each other but can often find a level of healthy respect in the workplace. However, when it is a boss that doesn’t seem to like you, it can make the workday feel far less enjoyable.

Maybe it is a reality, perhaps it is a hunch, but the way a boss conveys their dislike for you can vary. Here we look at five different scenarios and how you can win over a boss who doesn’t seem to like you.

The Micromanaging Boss

Micromanagement can feel like you aren't trusted to your job, but in some cases, it is a preferred management strategy of some bosses. It may just be that your boss prefers that management style, but if you are the only member of your team being micromanaged, this may be an indication that your boss doesn’t like you or the way you work.

How to Win Over a Micromanager

Take some time to analyse your recent, attitude, productivity and track record to make sure that you aren't unintentionally (or intentionally) doing anything to solicit the nit-picking. If not, then try and over-communicate the status and progress of tasks, anticipate your manager's needs and try to deliver ahead of time. If you can make your boss feel that they can rely upon you, then they are less likely to be on your case all the time. They may even start to trust you with more challenging work, special projects or promotions knowing you are reliable and on their side.

The Under Appreciative Boss

Positive feedback is not some bosses forte. Sometimes senior leaders are so focused that they forget to provide much needed positive feedback, other times, it just isn't their style, and some may have impossible standards you can never achieve.

First of all, be sure you are delivering as well as your teammates and if not, reflect on what you can change or what additional support you may need to get there. If you are achieving great things and witnessing your colleagues receiving a healthy dose of praise and you are not, then this may be a red flag.

How to Win Over The Under Appreciator

Genuinely ask your boss for some feedback on what success looks like to them for someone in your position and what they deem as high performance. Ask for their advice as to how best you can meet their expectations, what skills you need to develop and how best to improve. Sometimes showing some vulnerability will encourage your boss to be part of the solution which will ultimately lead to the praise you want, deserve and need.

Don't be afraid to share your successes and learning with them along the way, and you may just find you have a trusted advisor who helps push you to new levels of potential.

The Career Limiting Boss

Getting turned down from promotions and new opportunities are part and parcel of any career journey. However, if you are continually being turned down from opportunities without explanation, it may be that your boss Is holding a personal grudge.

How To Win Over the Career Limiting Boss

Let your boss know that the opportunity was important to you and share your disappointment in being overlooked. Instead of asking why you were overlooked on this occasion, ask what you would need to do next time to be considered. Make sure you get specifics and be very clear on what is expected.

Make it respectfully known that you intend to do what is needed to ensure you aren’t overlooked in the future. Ask for your boss's assistance in preparing a development plan - designed to help you achieve your goals. Communicate your progress towards your development plan at regular intervals and thank your boss for their support so that when the time comes, there is no reason for you to be turned down.

If you still face the same obstacles, then seek a mentor in the business who can help guide you on a sideways move away from your boss or perhaps it is time to discuss your concerns with HR.

The Passive-Aggressive Boss

If your meetings with your boss continually get rescheduled, changed or cancelled, then this may be a sign that your boss is avoiding you – which will seem like they don't like you. The same feelings will surface if you are being sidelined on projects and left out of important meetings.

How to Win over the Passive-Aggressive Boss

Passive-aggressive bosses typically don't like or want to deal with conflict. They express their anger towards someone in an indirect manner. They think that by avoiding you or leaving you out of meetings that any conflict will just go away.

It is a natural reaction to get sick of being sidelined and lash out in person or to try and solicit commitment in an email. However, this will likely make your bosses behaviour worse, so they can avoid further conflict.

If they lack the emotional maturity to deal with conflict in a healthy way, it is highly likely they are struggling to be an effective leader. While it may not seem fair, this is one time you may have to take the high road and help them through it – knowing that no matter what you do it is unlikely they will conclude they’re the problem.

Try and find a private, non-threatening time and place, muster up all your compassion and try and approach it delicately. Saying something like “I have been struggling with [issue] and would like to fix this. What can we do to get there?”

The Critical Boss

Constructive criticism can help see you achieve your potential and greater assist the business. However, if you are constantly criticised over minor issues, potentially in front of your peers, it may be that they just don't like you.

Having an overly critical boss can destroy your confidence and self-esteem, and significantly impact on your work output, so be sure to address it sooner rather than later.

How to Win Over a Critical Boss

While you overly critical boss may not like you, often bosses who spend a lot of time criticising others do so because they feel like they are fighting battles on their own. A misstep from a member of their team may create additional challenges for them which is why they seemingly come down hard all the time.

While they may seem like the last person you would want to support, becoming their ally may help ease the criticism overload. Try and learn how you can help your boss succeed. Let them know you are available for challenging projects or to take some work off their hands. If they feel you understand their expectations, they may just share more with you about their world, which may help you deliver better outcomes for them and attract less criticism in the process.


If you can fine-tune your skills to deal with difficult people, bosses or otherwise, it will stand you in good stead throughout your career.

However, if you have tried all of the above and nothing is working, you may want to consider looking for other opportunities. If you love the company and don't want to leave, perhaps there is an internal transfer that may serve you better. If you observe that all the leaders behave the same way, then it could be part of the culture, and a different company may be a better fit for you.

There comes a time when you may have to acknowledge that you have done your best and it’s time to make some job changes not only for you professionally but mentally and emotionally as well.

• Make sure there is evidence that your boss doesn’t like you.

• Reflect on your performance and behaviour and adjust any contributing factors.

• Understand your boss’s expectations, anticipate and act quickly.

• Get them on board with your development plans, guiding and supporting you.

• Try and understand their world better as it may help your overall performance as well as being an ally.

• Recognise your health and wellbeing is essential, so if their behaviour is too much start considering your options.

The Trojan Recruitment Group team are experts in labour-hire, temporary work and recruitment, so if you're looking for new opportunities, feel free to contact a trusted recruitment agency. We can provide personal advice on how to position yourself for your next dream role. With a little professional help, you might find that opportunity is closer than you think.