The Dichotomy of Leadership for Executive Assistants, Executive Business Partners, and Chiefs of Staff

I’ve always believed that Executive Assistants are leaders, but it’s more important than ever for Force Multipliers to lean into leading up. As AI and technology moves faster and faster every day, operating as a leadership partner in their organization is a must.

Leadership is never easy, especially for those of us in Force Multiplier roles who have had to battle against stereotypes, ignorance, and a general under-appreciation of what individuals in this role actually do. But that has never stopped me. And it isn’t going to stop you from taking charge of your career, becoming an invaluable business partner, and leading through influence.

Let’s take a look at some core leadership principles through the lens of Willink’s work, including Extreme Ownership: How US Navy Seals Lead and Win and The Dichotomy of Leadership: Balancing the Challenges of Extreme Ownership to Lead and Win. Leadership isn’t easy, but it is simple. See below for the dichotomy of leadership and how we can apply it to Force Multiplier (Executive Assistant, Executive Business Partner, Chief of Staff) roles.

1. A leader must lead but also be ready to follow.

Force Multipliers were built for this. At any given moment, we may be called upon to support the team, back-up our leader, provide information for a final decision, lead a committee, or even be asked to step into a meeting on behalf of our Executive. Force Multipliers must be able to flex and adapt to leading, leading up, and knowing when to step back and give others an opportunity to step in.

2. A leader must be aggressive but not overbearing.

This is especially true when EAs or Chiefs of Staff are either leading up to their Principal or working through the team to get something done. Principals will generally appreciate a little aggressiveness and assertiveness from their Force Multiplier. Someone who is going to challenge their thinking and look out for their best interests, even if that requires a little tough love. But there is a fine line between leading up and becoming overbearing. Share your intel, but don’t lecture your Executive. Offer your insights and opinion, but allow space for their final decision.

This goes for teams as well. As Force Multipliers, we also must lead through influence, often aggressively. However, beware of stepping over the line to becoming overbearing, when your follow-up turns from supportive accountability to badgering or when your influence turns to hierarchical “I work for the CEO” type behavior. Sure, that might be easier, but true leadership isn’t easy.

3. A leader must be calm but not robotic.

We are human and we work with other humans. As such, we all have emotions, egos, and energy that must be acknowledged and managed. Force Multiplier are well-accustomed to staying calm and cool under pressure. That’s nothing new. As we continue to level-up our leadership, just make sure that calm exterior is coupled with compassion and candor. Staying clear and neutral will ultimately ensure you make better decisions for yourself, your team, and your Executive, but don’t forget to be vulnerable and authentic too.

4. A leader must be confident but never cocky.

There is a marked difference between confidence and arrogance. Confidence is about your belief in your own abilities to figure out a solution to any challenge or opportunity that comes your way. Cockiness or arrogance is about over-stating your abilities or relying too heavily on past accomplishments, while engaging in comparison and believing you and your abilities are better than those around you. Your Executive and your co-workers will know the difference.

5. A leader must be brave but not foolhardy.

This is a great time to revisit The 40/70 Rule, developed by former Secretary of State Colin Powell. The 40/70 Rule says to strive to not make a decision with less than 40% of the information needed, but then ultimately make the decision when you have, at most, 70% of the information. If you don’t have enough information for yourself or your Executive, you may be making a foolhardy decision. However, waiting too long can be foolhardy, too! You must gather as much information as time and impact of the situation allows, assess, and then be brave and make the decision to lead the team or your Executive forward.

6. A leader must have a competitive spirit but also be a gracious loser.

There is nothing wrong with a little competition, especially if you are competing against yourself. Strive to be the best Executive Business Partner, learn everything you can, be engaged with helping your team and company achieve their goals and be top in your market. And when you make a mistake or miss the mark, own it, congratulate those who may have achieved more, and then find out everything you can about what you can do differently next time. Don’t let one failure take away your competitive spirit. Let it fuel you to learn and emerge victorious next time!

In addition, when you are sharing feedback or your perspective with your Executive, enter into the conversation with an open mind and the willingness to be wrong. If you’re right, then any push-back from your Executive will have only strengthened your idea or the final decision. If you are wrong, then you have just learned some valuable information, including how your Executive makes decisions and how they think. That is a victory, too.

7. A leader must be attentive to details but not obsessed with them.

This is a great lesson for Force Multipliers. Details matter. And so does the ability to zoom out, understand the full context of the task or project, and see the whole puzzle before diving in. Again, details matter, but usually not in spite of the end result. Being able to simultaneously see the big picture and how all the details will come together (without obsessing about them) is a critical skill for EAs, Chiefs of Staffs, and Executive Business Partners. If you are not clear on the big picture, ask. It will actually make the details come together even better than before.

8. A leader must be strong but likewise have endurance, not only physically but mentally.

Sure, Force Multipliers are some of the strongest (i.e. hardest working and most resilient) team members. That is important, no doubt. But so is the ability to endure and persevere in a sustainable way that prevents burnout. Establishing clear boundaries is a very personal thing and will change depending on the season you’re in in your life. It’s not just about working harder than everyone else, but working smarter too—in a way that supports your mental and physical health. Get clear on what you want and need in order to show up as your best self day after day. And then communicate that to your Principal. You’ll be able to create a much more fulfilling and sustainable career path that way.

9. A leader must be humble but not passive; quiet but not silent. 

I think great leaders are humble and curious, and exude a quiet, clear confidence. But that should never be confused with passivity or indifference. Confident leaders are not the loudest or even the smartest ones in the room, but the ones who help facilitate impactful conversations and ask powerful questions to get to the best solution for the company. And in order to ask great questions, you must be humble enough to acknowledge that you don’t know everything and be willing to get curious and ask great questions. This is where Force Multipliers shine. By learning to master the art of asking powerful questions, you can humbly and confidently participate in the conversation and potentially change the trajectory of a decision or your company in a truly meaningful way.

10. A leader must be close with subordinates but not too close.

This is a delicate dance that Executive Assistants and Chiefs of Staff are all too familiar with.  Force Multipliers are in a strange position where they need to form strong relationships inside and outside the organization, and yet, they must also be careful about how much, and with whom, they share information. If you say too much, you may be breaching confidentiality with your Executive and could lose trust. If you say too little, you may not be able to build rapport with team members and it becomes a struggle to get anything done. This can breed loneliness and a feeling of isolation. Make peace with this part of the job and consciously work to combat loneliness and build connections in a different way.

11. A leader must exercise Extreme Ownership. Simultaneously, that leader must employ Decentralized Command.

Extreme ownership means that “all responsibility for success and failure rests with the leader.” As a Force Multiplier we must be conscious of how extreme ownership effects the leaders we work with and how we have the opportunity and responsibility to support our leaders with their responsibility. It’s a heavy load to carry and that’s why a strategic partnership between a leader and Force Multiplier can be so powerful.

And yet, while the responsibility lies with the leader (and by extension their Force Multiplier), that doesn’t mean they should micromanage or that they are responsible for every outcome. Great leaders must rely on decentralized command and trust their team members to execute. Meanwhile, leaders must ensure their communication and decisions are clear to the team. Force Multipliers can work hand in hand with their leaders to make this happen. Extreme ownership (together) and decentralized command will win the day.

12. A leader has nothing to prove but everything to prove.

In theory an individual in a leadership position (yes, that means you too, Force Multipliers!) is seen as the one in charge and therefore has “nothing to prove.” Okay, fine. That’s a decent place to start. But we know that it doesn’t work that way—like at all. Especially if you’re an Executive Assistant, Chief of Staff, or Executive Business Partner. Our authority, requests, and decisions are often questioned. Internal and external stakeholders attempt to go around us. And we’re often dismissed for a variety of reasons. So, even if we’ve worked for the Founder & CEO of a company for 10 years, we still have everything to prove. That’s okay. We can do that. Leadership is influence and this is a skill that can be learned and honed. You never really “achieve” or “arrive” at being a leader. Great leaders are always learning and evolving.

Leadership is hard. There are so many nuances, dichotomies, theories, and tactics that go into being a successful leader. Force Multipliers who want to level up their leadership must embrace these dichotomies and practice leading up, down, and sideways with their Principal and teams. Practice makes progress. And progress, not perfection, is what we’re after.

Want to dive deeper? Grab your copy of The Founder & The Force Multiplier: How Entrepreneurs & Executive Assistants Achieve More Together!

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