Lessons from an Avenger: knowing your principal

A deep understanding of the principal’s personality, preferences, and peeves forms the foundation of the relationship between a chief of staff and their principal. It is more than knowing the sum of the experiences from the principal’s CV and the names of their immediate family members. A chief of staff must invest in the relationship and be a student of the boss in order to best support her. What does she need? How and when are the best ways to communicate with her? What irritates her? To whom can she delegate tasks? Which tasks cannot be delegated and must be completed before the end of the week? An effective chief of staff must realise and employ these factors consistently. Leadership speaker and author Shane Hipps says that problems exist when conversations are wrong or missing. He recommends that when communication is bad, chiefs of staff become ‘a student of words’, guard their emotions, and help the boss communicate. [3] It is a chief of staff’s responsibility to schedule the missing conversations, but it is (mostly) the chief of staff’s responsibility to ensure good communication. I put the ‘mostly’ in parentheses because everyone is responsible for their own actions–the principal may be a poor communicator, or angry, or frustrated (and she will have the consequences of those attributes) but it still falls to the chief of staff to make the information flow work. The best way to learn the boss’s preferences is to ask. The second-best way is to observe, and then match those observations with the boss’s words. Whenever I get, or am assigned to a new principal, I schedule an hour-long one-on-one session with them. On my calendar, I name it ‘Understanding [Boss’s Name]’. On her calendar, I name it ‘Stuff Mike Needs to Know to Succeed as Chief of Staff’. Both names are accurate but reflective of perspective. This foundational knowledge of how the principal prefers to communicate allows the chief of staff to anticipate needs and adapt strategies accordingly. Effective communication is essential to a chief of staff for maintaining the relationship with the principal but also for ensuring a cohesive, efficient team. Mantis, with her empathetic abilities, bridges emotional gaps with her ‘principal’ by perceiving and addressing unspoken needs and tensions. A chief of staff builds their relationship with their principal on three core components: understanding the leader, ensuring effective communication, and handling difficult situations with care.

The second important part of the relationship with a principal is the chief of staff herself. A relationship between a chief of staff and principal rests on many factors, but only one you can control – you. The primary rule for supporting a principal is not to become your own obstacle. I elaborate: don’t let your friction points and default stress responses obstruct your relationship with the principal or others on the team. When the boss has a bad day, don’t let that add to the challenge by making it your bad day. Similarly, when you are not your best, work to ensure that your emotions are not contagious. Tact is essential for navigating the interpersonal dynamics that often arise as a chief of staff. Just as Mantis uses her empathy to gauge her teammates’ emotions and respond to sensitive situations appropriately, a chief of staff must employ diplomacy to manage conflicts and difficult conversations. When working alongside a principal, tact helps mitigate hurt feelings, misperceptions, and other barriers to understanding and action. A technique that I have found helpful in contentious situations with a principal is to ask, “may I offer a different perspective?” The savvy bosses will recognize something they need–but perhaps don’t necessarily want–to hear. The trick with the others is to let the issue go and to not get tied in emotional knots. Flexibility is particularly crucial for a chief of staff, especially when facing shifting priorities and challenges. It is best to have no strong opinions when disagreeing with your principal. Or at least, temper your perspective with a flexible mindset. Mantis is consistently adaptive through her journey with various teams but remains grounded in her core values. Similarly, a chief of staff must maintain a strong sense of self, balancing personal beliefs with the demands of the role, while remaining flexible enough to adjust to the principal’s needs. Your part of the relationship exists on a foundation of self-awareness and adaptability. A chief of staff must recognise her own strengths, limitations, and values and provide effective support. This self-knowledge allows chiefs of staff to manage their responses, diffuse stress, and align their actions with the principal’s needs, fostering a harmonious and productive partnership. As a good teammate, chiefs of staff ensure their actions consistently support the principal’s goals without letting personal dramas or stray emotions interfere. Speaking of teammates, there exist other relationships that affect the chief of staff’s relationship with the boss: everybody else who regularly interacts with the boss.

An essential part of a chief of staff’s role is understanding not only the principal’s needs and goals, but also the dynamics, strengths, and challenges within the broader team. This knowledge equips the chief of staff to foster an environment in which the principal and team can thrive together. The chief of staff of an organisation is uniquely qualified to observe and influence broader team dynamics. Mantis’s ability to empathise and understand each of her teammates exemplifies this role; she acts as a bridge between strong, diverse personalities. She uses her insight to support her leader by enhancing team cohesion. Similarly, a chief of staff who knows each team member well can help the principal delegate tasks strategically, align projects with individual strengths, and maintain team morale. By cultivating these relationships, the chief of staff, indirectly perhaps, but significantly, supports the principal by creating a stable, cohesive environment for effective leadership. If the principal shows up in somebody’s office and asks, ‘What’s going on?’ the staff may have fears of an instantaneous surprise performance evaluation and shape their answers to hedge against a favorable outcome. Yet a chief of staff can show up in the same office and ask, ‘I understand you are working on project XYZ. Can you help me understand what your challenges are a little better?’ and get a completely different response. It is this freedom of movement within and between all levels of an organisation where a chief of staff can really enhance the principal’s efficiency. While the principal’s arrival commands attention, a chief of staff can move across different organisational levels with less formality, allowing for candid interactions. This unique freedom enables observation of the team in their own spaces, building trust and gathering unfiltered insights. As Mantis interacts naturally with her teammates, understanding their needs and temperaments, a chief of staff gathers knowledge that helps bridge gaps between the principal and the team. This behind-the-scenes insight is invaluable when the chief of staff must provide the principal with a genuine sense of the team’s morale, strengths, and areas that may need attention. A chief of staff’s understanding of team members’ individual talents and working styles allows them to facilitate smoother delegation and accountability. Just as Mantis intuitively grasps how each teammate contributes, a chief of staff leverages team insights to advise the principal on task allocation, ensuring the right people are assigned to the right responsibilities. By fostering a culture of accountability and aligning tasks with each team member’s strengths, the chief of staff contributes to overall productivity and morale. This support enables the principal to lead with confidence, knowing that the team is aligned, and each member is well-positioned to succeed. Effective chiefs of staff find value in working quietly behind the scenes, contributing to the team’s success without seeking personal recognition. Mantis’s influence is most powerful when she works unobtrusively to understand and mediate team dynamics. Likewise, a chief of staff who values their role as a ‘backstage’ supporter can influence outcomes positively without overshadowing the principal. By reinforcing team cohesion and providing steady support, they indirectly strengthen the principal’s ability to lead without distractions, allowing the team to stay focused on shared goals. The anecdote at the beginning is not fictional. It is from an earlier version of me. Years before I was qualified to be a chief of staff, I was an Aide-de-camp. When this story happened, I was a week into the new job, in a foreign country, and my boss had orders from the President of the United States to stand up an organisation and work to alleviate a growing humanitarian crisis. I was fairly stressed. My ‘principal’ gently and with humour communicated to me that people were important to him. It made the next 18 months we worked together go much more smoothly. I learned to present information to him in the context he desired–what does it mean to the people affected by the decision he’s about to make? I learned not to let my frustrations get in the way of communicating with the boss or with his team. I learned to help his other teammates understand the preeminence human factors had in his decision making. It turned out to be a good deployment, with a good team, and a great boss. I wished I had Mantis’s superpowers of empathy and mind-reading. I didn’t get them. I had to learn the hard way about emotional intelligence, strategic thinking, and adaptability. But all of that helped me later as a chief of staff. Starting with a gentle conversation in a hallway, I learned to be a student of my boss, understand my limitations and abilities, and help the team interact better with the principal. All in all, good preparation to become a chief of staff.