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How to Manage Your Boss' and Your Team’s Expectations

Congratulations on becoming a freshly-minted manager! Your hard work and great attitude has earned you a well-deserved promotion. But along with the swanky new title and fatter pay cheque comes the inevitable stress of having to manage people – both your new team and your boss.

As a middle manager, you are now a leader who has to juggle several balls. You need to keep in mind the goals for your organization, the Key Performance Indicators (KPIs) your boss has set for you, and train/motivate your team to hit those goals. Suddenly, to be “good at your job” means meeting a much broader spectrum of requirements beyond the technical skills you learned in school! Here’s a look at some common scenarios you may find yourself in, and tips you can try.

#1: Crazy deadline set by the boss

Your boss gives your team an urgent assignment with a two-week deadline. As a first-time manager, you are understandably eager to prove yourself to your boss but this should not be at the expense of your team.

To prevent wasting precious time and effort, get clear instructions about what is needed and the other departments you need to work with. Work smart. Enlist your boss’ assistance to connect you with the relevant people.

If the task is complicated, don’t feel pressured into promising ‘yes’ instantly to the tight deadline. Instead, request to discuss with your team. Communicate clearly and fairly with them. Depending on the urgency, your team may need to put aside current tasks to complete your boss’ task. If existing deadlines don’t allow the team to do so, don’t overpromise your boss and expect your team to pull all-nighters for the next fortnight. Work out a reasonable solution by negotiating with your boss for a longer deadline or seek another solution, such as enlisting an external vendor’s help if budget allows, or focusing on the key aspects of the project first.

Recognise your team’s difficulties but be firm about keeping to reasonable deadlines. Encourage everyone to band together. Walk the talk; work alongside them. While it is tempting, do not complain about your boss to your team, or rant to your boss that your team isn’t committed enough.

“It is tough being stuck in the middle but remember, it is in your boss’ interest to make sure work is done by an efficient, happy team,” says first-time manager Eric Goh, who successfully negotiated a more reasonable deadline for his team while keeping the boss happy with the results. So, work with your boss to make this happen. By being an empathetic and fair leader, your team will appreciate you for it!

#2: Boss expects you to be “more firm and professional” while working with your team

First of all, don’t jump to the conclusion that your boss is being too old school. Some first-time managers have good intentions not to act like a bad boss but sometimes, overcompensate by being too easy-going, which can lead to a lack of structure in the team.

As a first-time manager, take every chance to learn from an experienced one. Think about the following: What is the context of this conversation? Is this a piece of general advice they casually shared, or is it directed at a specific incident or even a complaint? How many times has it been brought up? Obviously, if this has been repeated, it warrants their (and definitely your!) attention.

As a first-time manager, you are not expected to know everything about people management so it is fair, and a good idea, to seek advice. Address the issue as soon as possible so you can improve. Do not wait till it is performance appraisal time, only to realise you’ve been marked down for your leadership skills!

Make an appointment to see your boss and state clearly that you are seeking advice to be an effective manager. Prepare a list of questions. If you are facing specific issues with your staff, compile your concerns.

Start by thanking him for spending time to train you. If this feedback is due to a specific incident, ask your boss to share details of what he has observed. Don’t be defensive; get the facts and reflect on it. If you were indeed not professional enough, apologise and explain how you intend to learn from it.

If it is a misunderstanding or a mismatch of management styles, explain your stance clearly to clarify any doubts but make sure you exit the conversation on a positive note. Again, do not get defensive and God forbid, get into an argument with your boss! Check if there is a recommended management style by the organization and understand the rationale behind it. You should also seek your boss’ advice about his/her personal management style and how it has evolved over the years. Ask for tips on how to solve the issues you are facing, if any.

However, note that every manager has a different management style. What works for your boss may not necessarily work for you, so be discerning. Keep learning from your boss and your mentors to develop your own management style.

#3: Team expects you to take their side, since “you were one of us”

Some of the comrades you earned battle scars with, are now your subordinates. Suddenly, office dynamics may have changed. Instead of being ‘John the kopi kaki’, you are now ‘Boss Man’. Sometimes, teammates may shy away from you; other times, they may be so excited to have their pal at the helm, work standards start to slide!

Nobody wants to be an obnoxious boss but work is work, and boundaries must be set. It is always better to set them before a crisis hits, and you and your team face impending work pressure on top of testy relationships.

When Lynn Chan was first promoted to be her team’s manager, her mentor gave her a great piece of advice: Make time to communicate clearly with your team early on, to earn their trust and support down the road. Lynn interpreted that as being a good listener on the job as their manager, and off the job as their friend.

The first thing on her to-do list was to buy her team a meal to acknowledge and thank them for their support over the years. She highlighted that she hoped their tight bond would continue even as she transitioned into her new role. She outlined her plans for regular work communication: weekly short meetings (to avoid meandering into chit-chat), an Open Door policy and a clear commitment to talk shop only during working hours – not just from her, but from the rest. Lynn also assured them that during their regular lunch dates and occasional after-work activities, there will be no pulling rank.

“It wasn’t easy at first as sometimes, colleagues would complain about our boss during lunch and expect me to take their side, even though my view may differ because I can see the management’s point of view. I learned to hold my tongue so as not to be drawn into a ‘debate’,” recalls Lynn.

She gently reminds them not to talk shop during their breaks, while assuring them that if they still face challenges, they could discuss in detail at a more appropriate time. Lynn also set herself a golden rule: Never tattle-tale to her boss, just because a disgruntled colleague had mouthed off during lunch. “I understand that sometimes, colleagues just want to blow off steam. But if I sense that they face genuine frustration, I will follow up by making a proper appointment to talk in the office,” says Lynn.

Trashing things out in the office setting, instead of during a noisy lunch, lends more weight to the situation. By being firm about such boundaries and avoiding lunch-time gossip while showing her team that she is serious about solving their problems, Lynn has shown herself to be a compassionate but fair leader.

Final tip: It is normal to feel a little out of your league when you become a new manager. Many companies support their first-time managers by sponsoring them for mandatory training courses but this may not be the case for your company. Take the initiative to research management courses (check out for a wide range of courses), seek your boss’ recommendations and propose a programme as part of your professional development plan.

If he supports your request for training, make sure that you follow up swiftly with your HR department to secure the funding, sign up, and complete the training. This shows your company your commitment to become an effective manager, and will equip you with valuable people management skills!

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