Career Tips #4: Manage Upward – How To Deal With Boss?


(This post is part of Career Tips blog series)

What? Manage upward? You might be shocked to see this post title. Isn’t it managers are here to manage us? That’s true, but the reverse is also true, we have to manage our managers. With good managers, our career is likely to be on highway, with poor managers, unfortunately our career might suffer from that.

“Talents don’t leave companies, they leave managers.” Not all managers are equipped with knowledge and wisdom of managing team. More than often they are made managers because they are promoted based on work achievements, and that do not guarantee they have the right people skills to lead others.

No I don’t mean that we manage our manager’s responsibilities, daily tasks, meetings and etc. I mean, we manage the relationship with managers and their expectations. Unhappiness is caused by unmet expectation, this is so important at work.

There can be many different scenarios which our relationships with managers could go wrong:

1) being assigned with too many tasks

2) being tasked with undesired responsibilities

3) feeling helpless at work because of lack of management support, conflicts with colleagues or office politics

4) having different opinions at work

Well, it is the time we need to manage up.

1. Do not fight with boss

Remember we could never win a fight with boss. They are authorized to manage staff, that includes firing unwanted employees. Do not argue with boss in front of others. For disagreement, discuss in private. Instead of challenging our managers, discuss how to best resolve issues and problems from a macro perspective. Instead of coming in strong and say things like “I don’t agree, you should not do this”, come with better suggestions and solutions. “How about we do it this way…?” “Doing it this way might have some issues such as XXX. What if we try…” Do it in a suggestive manner, instead of a commanding statement.

2. Have open and honest one-to-one discussions

This is incredibly important! Firstly, use this session to understand our boss’s priorities and challenges, so that we know how we can best support them. Secondly, discuss our own issues with boss to help them to understand our challenges and aspirations. Want a promotion? Tell them. Too much work? Let them know. Come forward with not just problems but also constructive suggestions.

Sometimes one-to-one does not need to occur in official settings, change from meeting room to coffee table might help to open up discussion too.

3. Ask for feedback

It can be done during one-to-one or at any other time, ask for feedback from managers about work. Understand their expectation (deadline, desired outcome, work quality etc), check in with them regularly to see if you are still on track.

4. Prioritize work together

Having too much work? Check with managers to understand if this is because of temporary shortage of manpower or for other reasons. Nobody can work 15 hours a day every day, if it hits your limits, it’s your responsibility to discuss with managers. Instead of telling boss directly that “I cannot do all these”, ask for suggestions. “Task A has to be done by Monday, Task B is pending with team X and has to be done by Wednesday, Task C just came in but it is urgent and needs to be done today, can we move the due date of A to Friday? Which task would you like me to focus on first?”

5. Always keep managers informed

Don’t let them hanging and chasing you for updates. Update them regularly for progress and issues, send a simple regular updates (daily / weekly based on criticality of the tasks) to management. Do not hide issues from reporting to management. Instead, update them that certain issues happened and how they are being rectified.

Subject Status (Green / Amber / Red) Deadline Updates

6. Do not be overly emotional or take things personally

Always look at big pictures, think from different perspectives (boss, or other stakeholders). Whenever conflicts arise, look at facts and statistics, present solutions that are best for the situations. Do not be emotional when opinions and suggestions not taken, continue to support managers or colleagues to achieve desired outcome.

Bonus Tip:

Whatever cannot be resolved in a meeting room, usually can be resolved during informal settings, by that I mean lunch / coffee. Take your boss out for lunch!

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