Managing Up | A summary based on the lessons in Wrangling Squirrels

The relationship between a boss and his subordinate is often fragile. Of course, we want to keep our jobs. But it’s not always easy with the pressures of meeting targets and expectations, plus the feeling of having your boss’ eyes always on you, as if waiting for you to mess up. We know our bosses hold the strings on which our jobs hang, so we want to be careful as if we’re walking on landmines when working with them. We always want to put our best foot forward and constantly prove our place in the organization. On the other end of it, however, your boss is actually concerned about your performance, constantly checking if you are working to the best of your potential. They are also concerned with themselves and with workplace morale as they are responsible for turnover and productivity.

In project management, your relationship with your boss can seriously make or break you. Your project is more dependent on your boss than it is on you because your boss holds the key to all the factors that will come into play for the success of your project. If you’re unable to manage your relationship with your boss well, you might place your project in serious jeopardy. However, establishing a harmonious connection with your boss where you both can work in your individual ways and have a sense of understanding and respect for your differences will give you the superpower to succeed in your project.

A lack of support from upper management is often identified as the number one reason why projects fail. Consequently, upper management support is one of the biggest determinants of the success of any project. The kind of support needed from top management varies across industries, but the existence of management support practices can be determined through the following:

1. The upper management had a hand in starting your project. This means the upper management saw the need for the project and initiated it.

2. Your boss, or a member of the upper management team is involved in the planning phase and makes time to be present in project-related meetings and gatherings, such as the project kick-off conference and other major events.

3. Your boss and the upper management team has a comprehensive understanding of the project goals, objectives, and direction.

4. Your boss or a member of the upper management team participates in succession planning exercises for the project.

In technical terms, you need your manager’s support for the following items:

1. To clearly define strategic objectives. Your manager is in the position and has the power to help you set clearly defined strategies to achieve your project goals.

2. Project funding. This is among the most critical aspects of your project. You will need as much support you can to ensure that your project is sufficiently funded, and it’s your boss who can control the funding mechanisms, managing the budget, costs, and overall financial impact.

3. Project resources. Your manager is your partner in making this happen; she has the power to influence functional teams, get you a good pool of candidates, and help you get the right people on board.

4. Decision-making. In making critical decisions, you want your boss to be on your side, right? Upper management teams may not always see things from your perspective; they might have different opinions and lean towards choices that differ from preferences. When you have a good relationship with your manager, you can have your opinions voiced through him and have an indirect influence on the decision-making process within the upper management.

5. Damage control. In unfortunate circumstances where your project runs into trouble, an unsupportive manager is less likely to assist in resolving your issue. When things go wrong, you’d want your boss to be there to back you up.

Understand your boss As a project manager, you know how crucial it is to have a strong understanding of your project. But in managing up, you must understand your boss as well. This means getting to know their working context, personal mission, values, goals, objectives, pressures and challenges, their strengths and weakness, their work- and communication styles, their metrics and measures of success.

The same way that your project team members have different personalities that you must understand to work well with them, you must not forget that your manager also has her personal and unique characteristics. Here are some questions you might want to consider to better understand your boss:

How does she communicate with her subordinates?
What is her preferred work style?
Is she on build-up mode or cost-cutting crunch-time?
Does she face conflict head-on or does she allow it to resolve itself in time?
Is she the confrontational type or does she have an avoiding personality type?
Does she like to conduct regular meetings and expect time-to-time updates or does she prefer a onetime report on your progress?
Does she micromanage or is she hands-off with you and your team?
Does your boss want to see data first before discussing or does she want to talk before seeing the data for herself?

Communicate with your boss

To begin your upward influence, you must learn to communicate with your boss. To start with, find out from your boss what success means to her and what her measures of success are. You need to make sure that you have a clear understanding of this to check that you are meeting your boss’s expectations. Not all managers will systematically provide you with the information that you need. In this case, you’ll have to pull it out of them.

If you haven’t ever done so, prepare a list of items you want to discuss with your manager and set an official meeting to have a sit-down with her. This conference will be just the first of many, but it will be critical because this is your opportunity to go over expectations and have a constructive dialogue about the best ways to work together and manage your team.