THE MANAGER LEVEL UP: Three Essential Nuggets to Help Manage Your Boss

Managing Up

In 2009 I left my executive level position in the private sector to work fulltime as the Chief Implementation Officer in the Office of the Prime Minister (PM) in Antigua and Barbuda. I made the move at the request of then second-term Prime Minister, Honourable Winston Baldwin Spencer. The move was both exciting and somewhat frightening.

Prime Minister Baldwin Spencer

Ironically, the very features that made the job offer exciting were the same ones that made it intimidating. You see, the PM essentially told me to write my own job description. On the positive side, there were so many possibilities to chart a path that was exciting, and which would enable me to contribute to nation building. On the other hand, clearly the stakes would be high and wouldn’t necessarily come with a safety net given the fickle nature of the electorate.

One thing that was certain is that in addition to effectively managing any projects that would be assigned to my portfolio, I would need to be equally successful at managing my relationship with my boss.

When you’re that close to the seat of power, managing up takes on a heightened sense of urgency and importance. At the same time, the room for error is miniscule since your performance – and by extension your boss’ performance – plays out on a very public and a very unforgiving stage.

During my tenure as Chief Implementation Officer, I learnt many valuable and lasting lessons. Some lessons emerged from my successes. However, there were even more valuable ones that I extracted from my mistakes. I can sum them up in three nuggets of wisdom, which if applied diligently, will enable you to successfully manage up.

1.    Establish Mutual Expectations

You don’t need to be a rocket scientist to figure out that it’s important to ascertain what your boss expects you to accomplish. However, what’s less obvious is that it’s equally important for you to identify and communicate your expectations.

By the way, please don’t make the mistake of thinking that the things that you need are restricted to a budget and a particular number of employees.  You also need to articulate Intangible requirements such as communication, access, delegated authority to go along with assigned responsibilities etc. You take a terrible risk when you assume that it’s obvious.

Additionally, take advantage of the honeymoon period to negotiate how you will navigate conflict in the relationship. Speaking truth to power can be quite difficult. I’ve found that it’s much easier to secure permission to do so when the waters are smooth and not in the midst of a storm. 

If you’re already well advanced in the relationship with your current boss, don’t despair. You can still initiate this conversation. Just ensure that you do so when there is little or no active tension and couch it in the context of your commitment to best support their success.

2.    Know and Understand Your Boss

Invest the necessary time and effort in getting to know and understand your boss, their work preferences, their strengths and weaknesses etc.

With a country to run in the midst of a global financial crisis, my boss was insanely busy.  So, for me to add value rather than be a drain on his time and mental energy, I had to ensure that I understood his communication preferences, how he liked to receive information and what was his decision-making process. That understanding enabled me to increase both the effectiveness and efficiency of my interactions with him. That, in turn, meant that I knew that my requests for face-to-face time with him would be given priority attention.

In fact, the ladies in the secretariat frequently commented that the PM always seemed to have time to squeeze me in. The reality is that I made it my business to ensure that I added value in each interaction – either by tailoring it to advance his agenda or to alert him to upcoming pitfalls or obstacles and advise on steps to mitigate same.

Another essential component of adding value to your boss is being able to discern and respectfully articulate the difference between what they WANT and what they NEED. More often than not, the boss’ focus is on a desired outcome. They may even share ideas on how that outcome is to be achieved. However, based on your knowledge and expertise, you may be aware that what they are proposing, or contemplating is less than ideal. In such instances, it is important to be able to draw on your in-depth knowledge and understanding of your boss to know how to talk them down from the precipice and guide them along a safer path to the targeted destination.

3.   Live Up to Your Commitments

Your boss doesn’t have the time or inclination to be cleaning up after you.  Neither do they want your performance – or lack thereof – to attract negative attention. Therefore, when they are relying on you to get something done, do it!

My first indoctrination with this principle came from eleven years of Catholic School.  It was one of the many lessons that I learnt in childhood that have served me well throughout life. The words that were drummed into me by the nuns and lay teachers at the Christ the King High School would later be reinforced when I read The Four Agreements by Don Miguel Ruiz[1]. The first agreement simply states: “Be impeccable with your word.”

On the rare occasions when, due to extenuating circumstances, you are unable to live up to a commitment ensure that you give your boss a heads up. And don’t just show up with the bad news; be ready with a mitigation plan to help salvage the situation. While your plan might not necessarily be adopted, it will show that you were committed enough to apply your mind to solving the problem, rather than just dumping it on them.

[1] In this New York Times Bestseller, the author reveals the source of self-limiting beliefs that rob us of joy and create needless suffering

Closing Thoughts

Managing the relationship with your boss is one of the most common complaints that I hear in both my coaching and consulting practices. In many of those conversations what strikes me is the extent to which persons believe that their bosses lack empathy – that they don’t understand or appreciate just how challenging the job is.

There are indeed bosses who focus exclusively on results and frankly don’t care about the blood, sweat and tears that might go into producing those results. However, it is far more likely that your boss is preoccupied with satisfying their boss. And no matter how far up the chain of command they are, they do indeed have to answer to someone. Even when my boss was the Prime Minister of the country, as he frequently asserted, he was the Chief Servant and answered to the citizenry.

So, a good rule of thumb if you find yourself in a challenging relationship with your boss is to apply the law of the harvest and sow the seeds that will yield the fruit that you want to reap.

Please like, share and comment below.  For a deeper dive into the topic, pick up a copy of my book Managers’ First Aid Kit


Ambassador Joan H. Underwood is a senior management consultant and policy advisor with extensive experience in both the public and private sectors.

Professional designations held by Ambassador Underwood include that of a Senior Professional in Human Resources (SPHR) from the US-based HR Certification Institute, the Society for Human Resource Management Senior Certified Professional (SHRM-SCP), Accredited Director (Acc.Dir.) and credentialed Master Trainer as designated by the Association for Talent Development (ATD).

She also holds the designation of an Erickson Professional Coach (EPC) and is a member of the International Coaching Federation (ICF).

Joan’s most recent professional accomplishments include certification by the Human Capital Institute (HCI) in Strategic Workforce Planning and Change Practitioner as certified by Prosci© Canada and the Change Management Learning Centre.

If you are looking for the resources required to help you take your management performance to the next level in 2021, click HERE to obtain a FREE SAMPLE from the book which is being described in editorial reviews as a “must have for new, aspiring and even experienced managers” – Managers’ First Aid Kit.

Follow her on FB, IG or LinkedIn for other valuable tips and special promotions.


Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.