Struggling With Boss – Transform Your Most Important Work Relationship

Struggling with boss? You might feel unappreciated. Or don’t have their respect. The only feedback you get is critical. You don’t know what they want. Or you hardly speak to them. Maybe your most important work relationship has started to go downhill, and you are not sure what to do.
Struggling with Boss? Transform Your Most Important Work Relationship
- Be perceived by your boss as good at your job.
- Overcommunicate in the right way.
- Find ways to reduce your boss’s pain.
Early in my career, I had my worst boss ever. I didn’t like him and very much felt undervalued, ignored and unappreciated. I made a huge mistake – the worst mistake in boss relationships – I just got on with my job and largely ignored the situation.
I didn’t know what to do and didn’t really understand the impact of a poor boss relationship on me. Not proactively working to improve my relationship with my boss really came back to bite me. I had to get another job.
Don’t make the mistakes I did when struggling with manager relationships. When you don’t really have a relationship with your boss or things are not good with your boss or they are starting to go downhill, the most important thing you can do is take action. The worst thing is doing nothing.
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You can absolutely transform your most important work relationship. It does take a bit of courage to take the first steps.
I was fairly shy in my early 20’s. I wasn’t super confident nor was I a great communicator. After my worst boss ever, I was determined to always have a good relationship with any boss. I didn’t need them to like me – just view me as a valuable person to have on their team.
One of the bosses I had to work with at this time was known to be difficult. For the first month, she literally ignored my phone calls and emails. I didn’t let that put me off. I kept trying to find her pain points and help remove them. Eventually she started phoning me back and responding to my emails.
After six months, she was raving about me. She had become one of my most vocal supporters. You can have the same success. Take action and keep at it until you win them over. You can get respect even from painful, difficult and toxic bosses. If you don’t change what you do, you won’t get a different outcome. Commit to yourself to take action.

The first thing you must work on when struggling with your boss is to be perceived as good at your job
The key word here is PERCIEVED. I know a ton of people who are really good at their jobs BUT their boss doesn’t really value them. Creating the right perception is not about working extra hard. Perception is about HOW you work and HOW you communicate what you achieve to your boss.
If your boss doesn’t know what you are doing, how can they value it. If you don’t explain the value of your work in terms of what matters to your boss, chances are they won’t value it as much as they should. A common mistake in boss relationships.
A key action to being perceived as good at your job by your manager is ensuring you don’t create problems for your manager. For example ensure:
- You don’t miss deadlines. If you can’t avoid being late, warn your boss as early as possible.
- Avoid submitting work with mistakes – always make the time to check your work
- Help your team members out – so your boss doesn’t have to step in to help them
- Take responsibility and ownership for your work – so your boss doesn’t need to chase you or check up on you all the time
- Cultivate a positive team-orientated attitude. A “can do” attitude is so much easier to work with as a boss compared to a “I can’t because…” attitude.
The easier you make it for your boss to manage you, the more they will perceive you as being good at your job. Cultivating this perception is hugely helpful to improve your relationship with your boss, no matter where it is right now.

The second action you must take with any boss is to overcommunicate in the right way
Your boss can only appreciate what they know about and understand. When a relationship with a boss starts heading downhill it is really easy to withdraw and communicate less. This is a very natural reaction. You must fight this reaction and do the opposite. Relationships are about communication. The worse your communication, the worse your relationship becomes in general terms.
I coach a lot of senior managers and leaders to improve their relationships with bosses, with other board members, and with their own team members.
An Example
A high performing senior manager’s relationship with his boss had hit rock bottom. The manager was looking for other jobs and was very unhappy. I asked him how many times he spoke to his boss. They spoke about once every other week. Sometimes less often. These meetings were difficult, energy draining and demoralising. The manager felt his boss only criticised him, which pushed him to want to communicate less.
The manager agreed a plan with me which involved speaking face to face with his boss at least twice a week. An increase in communication of at least 4 times. He also worked on his style of communication to make it more open and informative so there were no surprises for his boss.
In the next coaching session – about 4 weeks later – the manager had a huge smile on his face, looked a lot happier, more relaxed and came across as a lot more positive. The relationship with his manager had improved dramatically in a short space of time, despite being poor for over a year.

How to Overcommunicate
Work at overcommunicating with your boss. They should know what you are doing and the key projects or activities you are working on and why. If you are not speaking to your boss at least twice a week, increase the effort you put in to get face to face time.
If they don’t want to book meetings in, pop round to their deck to chat. If they are busy, go see them before 9am or after 5pm. If they work in a different office, book in video calls. If they are hard to get hold of send them email summaries every other day.
When you are communicating, don’t run down a long list of everything you are doing. Pick out the most important tasks, activities and projects and report on progress towards goals or completion. Update by exception. Update on what has changed since your last email or chat. Be respectful of their time.
Above all, focus on communicating what matters to your boss most of all.
find ways to reduce your boss’s pain – the most important action to really transform your relationship with your boss
One of the best ways I know to get your boss’s attention and appreciation is to reduce the pain they feel. Bosses will value your efforts a lot more when you take away painful problems so they don’t have to deal with them. Or you deliver results or outcomes your boss really wants.
In practice, this is a lot easier to do than many people think AND removing small pains are noticed, especially when you can remove several of them.
To have success in removing your boss’s pain points, you have to know what these pains are. Find out what your boss needs. What are they working on? What are they talking about and asking about? If you are not sure, just ask your boss directly.
Where To Look
Other options are looking at team objectives or speaking to team members to find out what problems they are experiencing AND which have an impact on your boss. Think about what you can do to help.
Can you create a solution, so your boss doesn’t have to? Are you able to get team members together and organise the implementation of a solution? Can you help improve communication across the team, so your boss doesn’t have to do as much? Are you able to secure resources that team members need to hit team targets, so your boss doesn’t have to? What information and insights from other areas in the business would your boss find useful? Gossip and feelings in the team can be as valuable as what projects are happening elsewhere.
Think through what problems you can take on and solve so your boss doesn’t have to do the work instead. This is a great place to start if you are not getting on with your boss.
Removing pain is an amazing way to help any boss, and they will love you for it. An incredibly valuable and effective way to transform your most important relationship at work.
in summary
If you are struggling with boss relationships, have problems with your boss or you don’t know where to start to build a trusting and valued relationship with your boss, start by looking at what you do and how it is valuable to helping your boss achieve their goals. Or how you can help them avoid pitfalls or pain.
Communicate what you do – the tasks, activities and projects you are working on – in terms of how you are helping your boss achieve their goals or avoid pain or problems. Think of providing updates and align your language and how you position your updates to what matters to your boss.
Lastly, make the time to find out about and think through current pain points for your boss. What can you do to remove this pain or the problem BEFORE you boss has to deal with it. Don’t forget to communicate what you have done to your boss.
Additional Development Options
If you are struggling to improve your relationship with bosses, peers or team members then take a look at our resources on building better relationships with your boss.
If you have senior managers and leaders in your business, that are struggling with relationships (bosses, peers, team members), please email support@enhance.training to discuss the coaching options to transform their relationships.
Learning how to manage bosses and get on their good side was a huge factor in my 13 promotions during my career. When you support your boss, they are a lot more likely to support you.
I didn’t need to like my boss nor have them like me. I did need to be able to work with them productively and effectively. As soon as you are useful to your boss, they appreciate you a lot more. Communication and relationship building is as important as the work you do!
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