Who’s the Boss? Part 1 – How Force Multipliers & Executive Assistants Juggle Multiple Stakeholders

This is the first of a three-part series that will explore the complex role of a Force Multiplier (Chief of Staff or Executive Assistant) and how they are called upon to lead and assist various stakeholders across an organization.

As Chief of Staff you are responsible for supporting your Principal and ensuring that their vision is executed, their concerns and questions are asked, and that you represent their viewpoint in various meetings. But in order to be effective in your role, you also have to partner with staff, listening to their concerns and advocating on their behalf when appropriate. Finally, independently of staff and your Principal, you must also represent what is best for the organization (which can be in conflict with both the staff and the Principal, even if they are the Founder).

This doesn’t just apply to Chiefs of Staff. Executive Assistants, too, must constantly be weighing the needs of multiple stakeholders and determining the best course of action on the fly. These are the decisions and judgement calls that the individuals who have the privilege of being next to the corner office have to make on a daily basis. It requires confidence, logic, emotional intelligence, persuasion, leadership, and excellent communication. Quite the tall order for one individual, and yet all necessary skills to be an invaluable business partner and Force Multiplier to an Executive.

So, how do you navigate these various (often competing) agendas? When do you lead, when do you follow, and at the end of the day, who’s your boss?

One of the first steps to navigating these relationships is figuring out which way you will lean when it’s down to the wire and tough decisions have to be made. Your Principal, the staff, and the organization are all important. Equally important? Not quite. But they are probably very close which makes your job as Force Multiplier even more difficult. If you take an honest look at where your responsibilities lie and how you make decisions, one of those stakeholders inevitably trumps another. But we could be talking about a very close 35% / 33% / 32% split here.

For me, the order is Adam (my Principal), the organization, and then the staff. They are incredibly close and make many decisions almost impossible. But when I’m evaluating options from all angles, analyzing the long term effects of a decision, or reviewing who may be affected, ultimately it will swing in the direction of ensure Adam’s vision is protected and executed, followed very closely by what is best for the long-term success of the organization, which is neck in neck with what is best for the individual team members. This does not mean that I agree with Adam all the time. In fact, our relationship is largely based on differences of opinion, arguing ideas from all angles, disagreeing, and then committing to a course of action. I believe it is one of my responsibilities to bring various issues and perspectives to the table and ensure that I am representing what is best for the company, as well as voicing any concerns from staff. Once we have a clear picture from all parties, then we can move ahead.

Have you determined which way you’ll lean? Good. Here are some additional ways to navigate all your “bosses” in business:

  • BE TRANSPARENT WITH YOUR TIPPING POINT – Once you’ve determined the framework for how you will make decisions (Principal vs. company vs. staff vs. fill in the blank), then it’s time to make sure you communicate that with those stakeholders. I get it. It’s not an easy position to be in. You don’t want to alienate staff members from sharing their concerns. And you want to make sure you are sharing organizational challenges with the right people. You also want your Principal to trust you to make decisions without burdening him with all the challenges along the way. What do you say to who and when? I air on the side of transparency in most situations. With all new leadership team members, I make sure I clearly communicate that what they say to me will remain confidential, and that I will bring Adam into the conversation on anything that I deem necessary. I often remind team members of this when they want to “talk privately for a minute”. They can share anything they would like (knowing that Adam may also hear it). That is my tipping point. We use the User’s Manual to help communicate this information. Click here to download a copy.
  • LEAD UP – Many of us have more than one Executive, or an Executive plus a Board, or an entire team asking for tasks to be completed, research to be conducted, or reports run, all with an urgent deadline! Regardless of who you are working with, your Executive, a board member, or another Executive Assistant, lead up. Understand the needs of all stakeholders, find solutions, set deadlines, hold team members accountable, and keep the communication flowing. Leading up is no different than leading any other project, except that you have to navigate many different personalities, each with their own agenda. Figure out what those agendas are, establish expectations, and help them all succeed.
  • ESTABLISH EXPECTATIONS – Establishing clear expectations and deadlines is all part of leading up. When you have more than one “boss” (whether they write the checks or not!) and ten high priority projects that all have the same delivery date, something’s got to give. Communication is key up front, or at the very least, during the project as more and more items get added to your plate. When you are working with other team members, if you are unsure of a deadline, you’ve got to ask. Better yet, give them a deadline. Keep it aggressive but realistic. When you’re given a new project by anyone other than your Executive, ask the requester when they need it completed by. If that works for you, knowing all the other projects you’re working on, great. If it doesn’t, make sure you communicate that and offer an alternative. If your team member says “Whenever,” suggest a time frame for when you can complete the task, and get their buy-in. “Whenever” to your team member might mean two days, while “whenever” means two weeks to you. And don’t forget to refer to the first item in the list. There is nothing wrong with reminding other team members about what you are working on (for example, a hiring search for PR Specialist) and why (to further the company’s mission of providing affordable leadership training to everyone). It’s a great opportunity to remind them of the company’s vision (which is also part of your job) and then help them figure out how their project fits into that, who can help (maybe it’s not you!), and when you can reasonably expect to get to it. Sometimes the best thing to come out of these conversations is realizing that what they wanted to work on isn’t even necessary and can be eliminated from everyone’s plate!
  • LISTEN UP – As much as I, and likely many of my fellow Force Multipliers, like to be in control and in charge, it’s equally as important to know when to take a step back and listen up. A key part of any Force Multiplier role is listening, asking powerful questions to get to the root of an issue, and then listening to what isn’t being said, and then listening some more. Some of the best ideas for the growth of our organization have come from understanding Adam’s goals, talking with several team members, and identifying what the real issue was and than taking action on a solution. These conversations offer a great opportunity to, again, communicate the company’s vision and then work with each party to make it happen. Conversely, keeping an eye and ear on what is happening throughout the company can help mitigate any potential issues with staff.
  • MASTER BEHAVIOR & COMMUNICATION STYLES – What works when talking to your Principal, may not work when talking to a staff member. As a Force Multiplier, it’s important to study your Executive’s behavior, personality, and communication style, as well as use tools such as DiSC Profile, 16 Personalities, or the Enneagram to learn how to best work with your staff and leadership team. It could be as simple as knowing when to send a text vs. when to pick up the phone or as complex as understanding their behavior, motivations, and how they are going to show up (loud and opinionated, passive, or somewhere in between) in meetings. The more you can understand how people are built, how they think, and anticipate how they are going to respond, the better you can be at leading all your “bosses.”

How do you navigate all the relationships in your office? When it comes to making tough decisions, which way do you lean? Which skill (confidence, logic, emotional intelligence, persuasion, leadership, excellent communication) do you lean on when working with your Principal and other “bosses”? Who’s your boss?


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