Take Care of Yourself!

I am ending the series on the Executive Assistant and Respect with some comments on self-care.  If you have read the previous posts, you have watched me paint a picture of the ideal executive assistant – one who is skilled, wise, reliable, poised, and extremely hard working. You may have asked yourself, “How does this person manage to be all things to all people, still attend to her own personal needs and stay mentally and physically healthy?” 

My fictional “ideal” executive assistant is Blake, in “Madame Secretary,” a Netflix series chronicling the adventures of a woman US Secretary of State.  Blake, her assistant, is the perfect example of the EA who is always one step ahead of his boss, anticipating her every need. He is integrated into her personal life, getting involved in the exploits of her husband and children (occasionally to provide levity in otherwise grim situations, and sometimes to perform the kind of salutary miracle that only a super-assistant can pull off.) 

Blake is “always on,” “always ready.”  His character is humanized by his quirkiness; perpetually dressed in a suit and tie no matter the occasion, while others appear in pajamas or evening wear depending on the setting.  He has a dry sense of humor, making “on-target” remarks and facial expressions when the camera jumps to him amid national and international crises. He even sings and plays the piano!   He can get any world leader on the phone in a matter of seconds, has his boss’ coat held at the ready before she even knows she needs to exit, and hands just the right report to the Secretary as she steps out of the elevator each morning.  He is, of course, a caricature – one that is the paragon of behind-the-scenes effectiveness. The Secretary trusts him completely.  Their partnership, at least for me, is one of the most ingenious and interesting subplots of the series.  But, at least so far, the story has not delved into Blake’s personal life.  The other supporting characters have all shown their vulnerability from time to time, but Blake remains aloof and cool – the unflappable super-EA.

Not so the EA’s I have known in real life. Not so myself when I worked in this role.  Behind the scenes and sometimes barely hidden in the workday, we exhibit signs of exhaustion, mental and physical overload, discouragement, frustration, anger, and the full gamut of other human emotions. Acting in a role where one is “always on,” but perpetually “off-stage;” a role where the EA is expected to respond with a cheerful “Come in!” when a knock is heard at the door, ultimately takes its toll.

The most effective executive assistants are particularly susceptible to the self-destructive habits of overwork, the inability to say no, perfectionism, and ignoring their own personal needs. Like other professionals with these traits, they may “burn out” under prolonged stressful conditions.

In my case, the stress created by the expectations (my own and that of others) that I would be ever-efficient, continually responsive, and unfailingly reliable, built up in my body over more than 10 years until I was in almost constant pain. I decided to retire earlier than I had expected to seek relief for these physical symptoms. After retirement, I realized that stress was causing my pain, and I began the long effort to undo the damage. 

The advice I am about to offer applies to everyone but is tailored to EAs specifically. I am embarrassed, truth be told, to make suggestions that I was not able to implement myself when in the furnace of a stressful work atmosphere. Knowing what I know now, however, compels me to make these recommendations, embarrassment or no. 

First, create work boundaries and do your very best to maintain them.  Don’t allow them to become porous with too many exceptions. Know your limits and remember that extending them may have detrimental consequences for you and those close to you. Though it may be hard to recognize or admit, you will probably breach your own boundaries more often than others will.

Second, know yourself well – look deeply into your own motivations. Know yourself as profoundly as your well-honed insight will permit, but eschew judgementalism. Reflect on your personal work-life motivations with the kindness, generosity, and self-respect that you deserve and that you would not hesitate to offer to others. Are your attitudes toward your work partially responsible for the stress and burdens you are experiencing? Must everything be done perfectly?  Are you proud that you work harder than others? Do you like being the last person to turn out the lights and close the office door? Are you taking yourself and your role too seriously? 

Take responsibility for your own well-being. No one else will “fix” the unhealthy situations in which you find yourself, nor rescue you from them. Identify what you need to feel mentally and physically healthy, and courageously claim it.  Be prepared that others may misunderstand or condemn your “self-protectiveness.”

While making these essential changes for your sake, be kind and respectful to those who cheer and those who boo, alike. Loosen the tether of expecting approval or disapproval from others. Be completely upfront with your boss about the physical and emotional toll that workplace stress is taking on you.  Ask if he or she will brainstorm with you how to change the work situation for the better – for both of you. If your boss does not understand your needs or support your decision to make changes in work patterns, it may be that you are not well-matched as a team. You may need to sacrifice an otherwise valuable work relationship for the sake of your health.

Cultivate a physical activity that can supplement the mental gymnastics that you are called to perform during the workday.   Find a creative outlet that can act as a counterbalance to the routine work tasks that are essential but can be both tedious and spirit-numbing. 

Find a trusted colleague or mentor who can help you to navigate the challenging and sometimes toxic work situations that you may encounter. Counter the loneliness of the “secret-keeper” EA, with supportive relationships outside the office.  I was exceedingly fortunate during my working years to be able to confide in my life-partner about situations that troubled me, knowing I could rely on her complete discretion.

Beyond all this advice, I suggest a practice that has been a healing agent in my own life – meditation. I began to practice meditation shortly after retiring, as a way to ease chronic pain.

Its use in such a situation is based on the Mindfulness Based Stress Reduction (MBSR) program. “Developed at the University of Massachusetts Medical Center in the 1970s by Professor Jon Kabat-Zinn, MBSR uses a combination of mindfulness meditation, body awareness, yoga and exploration of patterns of behaviour, thinking, feeling and action. Mindfulness can be understood as the non-judgemental acceptance and “open-hearted” investigation of present experience, including body sensations, internal mental states, thoughts, emotions, impulses and memories, in order to reduce suffering or distress and to increase well-being.” (Kabat-Zinn, 2003).

Meditation may involve sitting still in a comfortable position for periods of 20 minutes (or more) while focusing the attention on one’s breathing.  The practice quiets the body and the mind, promoting relaxation, a sense of peace and rest. Meditation is not, however, a quick panacea. Commitment, discipline, and patience are necessary to change old habits and reap new benefits. For me the continuing  effort is certainly worth it.

Regular meditation fosters the habit of mindfulness – paying attention to what is really happening in the present moment with acceptance, curiosity, and compassion. Mindfulness sets us free from the inclination to create storylines in which we are victims, heroes or saints.  It wakes us up to the gift of life in the here and now.  We can turn away from stewing in regrets about the past or worries about the future, to live as fully and gratefully as possible in the present moment. I find it to be one of the best forms of self-care in the midst of demanding situations.

Everything is constantly changing, including our thoughts and feelings about our work and all the other parts of our lives. Mindfulness creates an openness to the flow of things – an awareness of the bigger picture. It can also foster insight – a catalyst for change. The practices of meditation and mindfulness calm the body and the mind and awaken curiosity, creativity, hopefulness, and courage. 

A friend of mine has written a book about the impact of the practices of meditation and mindfulness in the workplace:  Mindfulness, a better me, a better you, a better world by Annabel Beerel.  I recommend it highly for leaders, executives, managers, and staff.  The book describes mindfulness, teaches meditation, and illustrates the benefits of both.  Annabel presents scientific data demonstrating the positive effect that mindfulness has on the brain and its advantages for the individual and, therefore, for the organization in which he or she works. She suggests introducing it as a workplace change-agent and believes that it is most effective when it is fostered and practiced by all levels of the workforce. 

Meditation and mindfulness have helped me, in retirement, to deal with experiences  similar to those I faced during my career as an EA:  feeling overwhelmed by the number of tasks on my plate,  trying to juggle and prioritize responsibilities to meet the expectations of those around me,  over committing, rushing, attempting to multitask, catastrophizing, and failing to comprehend the bigger picture.  Meditation and mindfulness have given me the courage and energy to change ineffective habits and harmful patterns of thinking. They have increased my self-understanding and self-compassion and my understanding of and compassion for others.   

My concern throughout this series of articles on the Executive Assistant and Respect has been for the health and well-being of EAs who serve valiantly and brilliantly, often behind the scenes, to promote the success of their principals and their organizations.  So, from the viewpoint of a retired EA: “Whatever nourishes your creativity, authenticity, self-respect, and compassion will make you a better EA, your boss a better executive and manager, and your workplace a better microcosm of the world.  Take care of yourself!”

The Failed Partnership

Disclaimer: Not every executive assistant (EA) is a woman and not every executive is a man, but for the purpose clarity in this post (and in keeping with my practice in the rest of the blog) I will use “she” for EA, and “he” for executive in most instances. Please don’t let my use of these pronouns cloud the point I’m trying to make.

A partnership is defined as an association of two or more people as partners. Synonyms for partnership include, cooperation, collaboration, coalition, and alliance.

Few circumstances are more disappointing in an executive assistant’s career than to enter into a relationship that she believes will be a working partnership, only to discover that the executive does not understand what partnership means and is incapable of building or sustaining it. Of course, the same disappointment may occur for the executive.

A professional partnership with one’s boss is not expected to be an equal one.  The executive is the employer and the EA the employee.  A natural imbalance of power is built into the relationship.  However, if the two are to create an effective two-person “collaboration” or team, a degree of partnership – a characterized by mutual respect, trust, reliability and even friendly intimacy – is essential.

Starting Right

The creation of an effective partnership begins with the interview process.  It is hard to learn much about the suitability of a prospective partner in a series of relatively short interviews in which each party is putting the best foot forward. (Or at least one party is!)

In a world in which there is a perceived “glut” of laborers, the power differential in an interview is skewed in favor of the boss.  He schedules the meeting and conducts it on his turf. He has the power to hire or not and decides the offered salary. The dynamics of the process are often crafted to create as much stress as possible for the interviewee.  The candidate meets with a confusing series of individuals and groups, one after the other, with little transition time in between, answering the same questions multiple times. A job interview is often characterized as a marathon.  

It may seem as if the potential boss/ hiring team hold all the cards.  But the prospective EA holds cards as well.  And it’s best for both parties if they each put as many of them as possible on the table during the hiring process. 

EAs, try as best you can to discover the executive’s work style. If you are interviewing with others on his team, ask about this directly.  Indeed, ask the executive himself. (It will give him a chance to self-reveal in a way that may be key to your decision about the suitability of the match.)  Is the executive able to delegate?  How does he do so? Is he open to suggestions from his team, does he seek them?  Is he a visionary who hopes for an EA who will embrace and help him implement a vision? Does he like to be involved in and consulted about the details of all projects or is he more of a big-picture – only if you hit a roadblock – kind of manager.  Is he capable of articulating a work style and a vision?

Look around. Is his office messy or neat?  Does he ask you questions during the interview, or does he talk only about himself, his needs and those of the organization?  Is he passionate about the goals of the organization and his own role in it? Does he seem interested in your career development?  Is he willing to go to bat for a fair salary?  How hard does he work?  What is his work-life balance and what are his expectations of his EA in this regard?   If he is likely to value a true partnership with his executive assistant, he will not be “put off” by such questions.  He will know how important they are in establishing a partnership.

Of course, each party comes out of an interview process with only a limited amount of information, and the reliability of first impressions will be dependent upon how open and honest both parties have been.

I interviewed for a job four times during my career. During all but one of these interviews, the hiring manager monopolized the conversation, describing the position, the organization, and his or her needs.  He/she seemed to have given my resume a cursory glance and to be uninterested in learning more about me or in asking probing questions to determine what I might have to offer. 

In the best interview, the interviewer (who was not the executive herself) asked very complex hypothetical questions about how I might handle certain situations that were likely to arise while assisting the executive with whom I would work.   By the end of the interview, I had a good idea of what I might be getting myself into, and what the relationship between my new boss and me might be. And the interviewer had a fuller picture of how I was likely to react in various real-life situations and whether my reactions would suit the executive with whom I would be working.

More and more, the real hiring decisions for executives are now made at the lower levels of management – human resource (HR) departments and office managers – with the executive simply giving a final blessing to a candidate that has been recommended by his staff.  Depending upon the skill of the HR hiring officer (and the salary and personnel constraints under which HR is operating), the personal compatibility of the executive and EA may or may not be given its due weight. Indeed, if you find yourself offered an EA position with an executive whom you have hardly met, the chances are very slim that he is looking for a true partner.

Several times during my EA career, my bosses inherited me from their predecessors. I knew the circumstances of the office, the personalities of their colleagues, the job description of my boss, and the goals of the organization better than he or she. Therefore, I was in a stronger position to demonstrate how my own skills and talents could add value to their work lives and to position myself for a working partnership.

All of this is to say, that the seeds of a true partnership are sown during the interview process. The EA who wants to partner with her boss should not be shy about demonstrating a “partnership” attitude or about speaking openly of her hopes to develop such a relationship for the good of the office and the organization.  If this attitude and the open expression of her hopes are rebuffed or ignored by the hiring executive, the chances are good her efforts to build a productive partnership later on will be frustrated.

Let me not be “pie-in-the-sky” about the interview process.  In the present employment climate, in the majority of workplaces, employees are expected to do more and more for less and less salary, with longer hours and shrinking benefits. Any job, with any boss may seem more attractive than unemployment.  You may need to “settle.”

Developing the partnership

If an EA has been hired by an executive who has demonstrated clear signs that he wants to work together as partners, both will start building such a relationship immediately. Their “check-in” time together (daily if possible, except when the boss is traveling) will be held sacrosanct. It will be well organized; information will be exchanged in a streamlined and efficient manner.  It is primarily the EA’s responsibility to schedule, plan and conduct these check-ins.  Each will listen deeply to the other, learning essential details about every agenda topic, but also studying the other’s reactions, way of thinking, values, concerns, and priorities. The EA knows her executive will make decisions without seeking her input in many instances, but still, she will feel comfortable offering her views and expects them to be valued by her boss.

Red flags should go up for the EA if the executive routinely cancels their meetings, isn’t willing to listen when she has a viewpoint to offer or seems uninterested in her concerns.  The executive will feel comfortable sharing confidential information with his assistant.  He will realize that situations will be handled more professionally and effectively if his EA has the full picture.

The executive must understand that the EA needs uninterrupted time to accomplish tasks and projects that require extended periods of focused thought and he will ensure such time is available. The executive will also understand that an assignment that he thinks is relatively simple and quick to accomplish might take much longer than he imagines. He will, however, trust that all the invisible (to him) steps will be taken, hoops jumped through, or emails exchanged.  He may be happy in his ignorance, but he is solid in his trust.

Failed Partnerships – Some scenarios


Cindy walks into her boss Jay’s office soon after he has taken on his new responsibilities with the company that she has served for six years.  She and Jay have both read a series of emails from others in the company complaining about a problematic employee who reports directly to him.  Suspecting that Jay may not have a complete picture of the situation and wanting to help him deal with it effectively, she says, “May I offer some information and a suggestion….?” Jay cuts her off, responding. “No.”  Cindy is dismayed but hides her reaction and leaves the office to process what has just happened. 

Her interactions with Jay up to that point have been positive.  She will, of course, give him the benefit of the doubt, but will, in the future, carefully choose those moments when she offers an opinion or a suggestion.  Over the next few months, her observations of and interactions with Jay confirm her initial impression.  He is not open to her ideas, does not value her input and prefers to use her as a clerical secretary.  He is insecure enough to believe he must have all the answers and make all the decisions unaided by her experience.  Others in the company are whispering about similar interactions with Jay.


Deborah hired Naomi with great fanfare and goodwill.  She liked Naomi’s professional manner, her energy and self-assurance and her extensive experience. She felt an immediate rapport with Naomi.  In the first months of their work together, Naomi proved competent, reliable, and a good problem solver.  She usually came to Deborah to report how she had headed off a problematic issue, rather than to dump the problem in Deborah’s lap. 

For her part, Naomi felt trust growing between her and Deborah.  She felt respected and valued.  But about nine months into their partnership, Deborah made a business decision that shocked and disappointed Naomi.  She thought long and hard about all Deborah’s possible motives, trying to understand what had brought her to this decision. Finally, Naomi decided to talk with Deborah directly about her discomfort and to offer her perspective on the injustice the decision had created. She hoped that their conversation would not only help her to understand Deborah’s point of view, but also that Deborah might change her mind.

Deborah listened to Naomi’s views and offered reasons for her decision, but Naomi did not believe those reasons were justified or valid.  She left the meeting feeling that Deborah was blind to the injustice she had caused.  Naomi struggled with her convictions, sought counsel from trusted friends and ultimately decided she must resign from her post.  Her values were incompatible with Deborah’s on this matter.  She believed that their promising partnership could not sustain this incompatibility.  It had foundered on opposing values. Deborah was sorry to lose Naomi but understood the strength of her EA’s feelings and respected Naomi’s commitment to her values.  They parted saddened but understanding each other’s perspectives.


Richard respected those who worked for him.  He said openly and frequently that he could not do his job without the skilled, loyal, dependable staff who supported him and the organization so effectively.  He took an interest in their career development, offered them opportunities for continuing education, and understood their needs for flexible schedules and a healthy work/life balance.  He was proud of them when they moved on from his department to higher levels of the organization and to more challenging work.  He was exceptionally gratified by the professional growth of his EA, Alex.  He had hired him as a temp fresh out of college, seen his potential and promoted him to be his executive assistant.  He trusted Alex completely, and Alex didn’t disappoint.  They worked together happily and productively for eight years. 

Though he didn’t carry the title, in many ways, Alex functioned as Richard’s chief of staff making the whole department run more smoothly.  They understood each other perfectly, Richard thought.  Alex could anticipate his unspoken needs and fulfill them.  Others commented on their close partnership.

In their ninth year together, Alex started arriving late to work in the mornings.  Richard ignored this, thinking that Alex would explain himself at some point and that the reason must be good.  Alex worked as hard as always but began making odd errors, forgetting important but routine responsibilities. Richard tried to talk with him about the possible causes of these mistakes, but Alex said he was tired and that things would get better when he began sleeping better.  One day Alex did not show up at work leaving Richard stranded with an important meeting to chair.  The meeting room had not been reserved, the catered lunch did not arrive, materials were not printed and distributed. 

This was the last straw.  Richard called Alex at home, exploding about his frustration and embarrassment.  Alex apologized vaguely but showed up at work late again the next morning and seemed not to remember their heated call the day before.  Richard called HR and asked the senior human resources officer to meet with him and Alex.  The HR officer was skilled in handling such situations and created safe space for Alex and Richard to talk about what was happening to their partnership.  Alex admitted to experimenting with drugs, during a time of personal loss (his father’s death).  The HR department recommended a treatment program, leave was arranged, and he was assured that his job would be waiting for him when he returned. 

During Alex’s leave, Richard struggled with his fear that his and Alex’s trust had eroded.  He felt he had failed Alex by not noticing the depth of his mourning for his father, and that Alex had failed him by not reaching out earlier to tell him what was happening.  Alex struggled with embarrassment and shame and wondered how he could face Richard and work with him again.  At the end of his sick leave, Alex resigned from his EA position.  He and Richard said a sad farewell and eventually lost touch with each other. Alex flourished in his next job. Richard found a new EA and built a solid partnership with her. Both acknowledged that they had learned from their failed partnership.

Trust is the bedrock of any relationship.  And trust is the rock on which a partnership can founder.  Choose your partner carefully – eyes wide open.  Trust your intuitions early on.  Don’t overlook signs of the relationship’s instability. Invest your best energy, your best self, in developing a loyal, trusting, relationship. Be clear about your values and your boundaries. Seek to understand those of your partner. Communicate and keep communicating. Accept that things change, and people change – you and your partner are no exception. Value your partnership; don’t take it for granted.  Do your best to strengthen it if it becomes fragile. If it fails, let go and move on but learn from the experience. Don’t allow yourself to become jaded; do be careful. Invest wisely in the next partnership.  Respect yourself.  Respect your partner.

Why is a working partnership between the EA and the executive so important? If both feel secure and draw out the best in each other in the workplace, the benefit for the organization will be invaluable.

The EA may sometimes feel misunderstood and undervalued.  She works behind the scenes deriving her satisfaction from the success of others.  She doesn’t seek the limelight; she may be embarrassed when placed in it. She doesn’t consider herself a leader but nor does she feel like a follower.  She knows the value of her contributions and thrives on using her skills and wisdom in the service of her boss’ accomplishments. She doesn’t seek praise, but she appreciates the thankful smile, or the knowing glance, or the simple “Excellent!” now and then.  The failure to achieve a partnership with her “principal” (as EA’s call their executives) can be a considerable disappointment in her life and career.  When respected and valued, when allowed to use all her skills and talents, experience and wisdom, she will flourish and so will the career of her boss and the mission of the organization.

When Respect Is Not Offered

Blog article by Moriah Freeman

Now I touch on the situations in an Executive Assistant’s (EA’s) life that disappoint and cause heartache. 

Occasionally, at Harvard, EAs who supported deans across the university would gather for a “retreat day” or an “off-site;” a day together, away from their offices to encourage each other, share experiences and lessons learned, and hear from an expert in some area of higher education.  These days were few but treasured. Few because getting away from our desks was such an enormous undertaking.  Yes, we could arrange our own work lives to make time available, but we didn’t live and work on our own schedules, instead, on those of our boss and his or her team. Treasured because they assuaged the isolation that we sometimes felt, wondering if anyone else really understood our concerns, problems and, yes, even our victories.

At one of these retreats, I happened to be part of a small group whose members included the EA of the dean of one of Harvard’s most prestigious graduate schools. Her boss had recently been appointed the president of another renowned higher education institution and had invited the EA to join her in the move.  The assistant felt honored. Her life circumstances made it possible for her to accept, and so she did.  She talked about the partnership she and the former dean had developed over the years; conversations they had at the beginning or end of many days, reflecting together on the issues that had emerged and how to resolve them.  Her boss, she said, was always open to her perspective on any situation, bounced ideas off her and valued her judgment and input.  The EA looked forward to the same kind of relationship as they faced this new challenge together. 

We, her colleagues, rejoiced with her.  Congratulations flowed like wine, and it was a very happy small group discussion.  But I came away feeling deflated, and I wonder how many others did as well.  I suspect few of us had this kind of mutual partnership with our bosses or felt so valued.  I have lost track of this EA over the years, so I don’t know how things went as she and the new president settled into their roles. Perhaps in a different setting, the partnership was harder to sustain.  I hope not.

Many EAs have poured out their energies, insight, and hearts to support executives who do not value the treasure with which they have been graced.  The executives are glad that the office runs smoothly, that projects are completed, and their needs are anticipated and met.  But they never give a thought to what goes on behind the scenes during the work day, late at night or on weekends to accomplish these feats.  One of the most disheartening experiences for an EA is to know, in her heart, that her boss doesn’t have a clue what she is doing to perform the miracle the executive requires. 

A gift from his travels, a remembered birthday or special occasion, faithful “thank-you’s” don’t touch that place in the heart of a dedicated, hardworking, insightful, and wise EA who longs to partner with her executive.  What would be her true reward? To be consulted about projects, to have her advice and insight sought, to be treated as a valued problem-solver and an integral part of the executive team.  In other words, to be a partner in the endeavor at hand, not a servant, however relied upon and appreciated that servant might be. 

My advice to all bosses would be to look up and around you; to look deeply into the potential of your Executive Assistant; to comprehend the opportunity to foster a close and mutually beneficial relationship that will serve your goal, your EA’s, and the good of your organization. Nurture, support and grow your partner.  Invest in him or her as she/he invests in you.  Consider your EA an invaluable resource and treat him or her as such.  You will never regret it.

Reliability and Loyalty

I have saved the least glamorous traits of a good EA for near the end of this series.  I should, perhaps, have mentioned them first as they are the bedrock of her relationship with her executive. Occasional brilliance is welcome, but reliability is essential.  Disloyalty is flagrant, but loyalty is a quiet and hidden jewel.

When I retired from Harvard, my school threw me a retirement party.  I was “blown away,” as they say, by the number and diversity of those who attended.  I was honored by the presence of the five deans I had served in the last 15 years of my career there, and by the words, they spoke about my service.  I was touched and happy that the guests included other assistants and program managers, custodial staff, and colleagues and leaders from across the university. 

When my former bosses spoke about the kind of service I had offered them, the word “reliable” came up time and again. What memories did that word conjure in their minds as they spoke?  I imagine they remembered that I was in the office before they were on many mornings and sometimes still there when they left at night.  They could count on me doing my very best to make it to work on snowy winter days when the university remained open, and, if I couldn’t get there, to work and be available from home.  They knew if I was sick, that I would try to rise above it and come to work anyway if there were crucial tasks or events that needed attention. If I was so sick I couldn’t “rise above it,” they relied on me to arrange for coverage from among the team of assistants with whom I worked closely.  They knew no balls would be dropped and they would never be left high and dry, never embarrassed, never unprepared. Deadlines would be met, projects would be on track, deliverables delivered. 

Of course, I was not perfect, sometimes, at particularly busy times, something would slip through the cracks.  But I had learned, over the years, to minimize these omissions by setting up systems to check and double check myself.  And when something did slip through this fine sieve of backup techniques, I had learned not to “freak out” but remain calm and fix the problem quickly.

They all knew I had their backs, which brings me to loyalty.  In a real, EA/Executive partnership, the boss is not paying only for all the qualities I’ve discussed in previous posts – prescience, discretion, humor, equanimity, political savvy, diplomacy, and humility – but also is investing in a strong bond of allegiance or loyalty.  The executive may not have realized that loyalty is a two-way street, but he/she certainly wants it coming in his/her direction. 

I made it a practice, no, a policy never to discuss an executive with his successor.   During my  my last executive assistant role, Executives came and went, and while I passed on to each new one the lessons her predecessors and I had learned, I never spoke about the personality, strengths and weaknesses, victories or screw-ups of the ones who had come before. We only talked in the most general terms of insights gained or disappointments that turned into learning experiences.  Because I didn’t break confidences from one executive to another, I assume they concluded I would be loyal to them each in turn. I was.

Sometimes I watched the reputation for reliability of my young EA colleagues falter on the mistake of many sick days taken in short periods; on lateness, ball dropping, confidence breaking and careless mistakes.  And sometimes I watched them soar as they grew in expertise, maturity, wisdom, reliability, and loyalty.  And I celebrated with pride in my heart the careers they were launching, the growing responsibilities they would assume and the excellent references they would receive as they moved forward.

You, my colleagues, are a dedicated, brilliant and versatile lot.  May you know your worth in your hearts, and may your worth be recognized by those you serve.

[NOTE: The next articles on “Partnership/The Failed Partnership,” “The Boss who doesn’t Value and Respect,” and “Taking Care of One’s Self,” will finish this series on Respect and the Executive Assistant.  I plan to follow it with some posts on the topic of Homelessness. Thank you for reading With All Due Respect.]



“Fail, fail again, fail better.”

  • Pema Chödrön, Buddhist Monastic

When Pema Chödrön’s granddaughter was accepted to Naropa University, the nun promised she would speak at the young woman’s commencement ceremony. Her address was entitled, “Fail, Fail Again, Fail Better.” It was based on a quote from Samuel Beckett, the Irish author, “Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”

Do Pema Chödrön and Samuel Beckett glorify failure?  What do they mean, fail once, fail again and fail better?  Isn’t once enough?  Isn’t failing again, especially at the same task or enterprise, a demonstration of incompetence, stupidity or the inability to learn from one’s mistakes.  And how can you pair the words “fail” and “better”? Isn’t that pairing an oxymoron?

I could not continue this series of articles on respect and the Executive Assistant (EA) without mentioning that all EA’s, even the best of us, are human and that failure, on occasion, is inevitable for everyone. Some failures lead to catastrophic events in our lives: dismissal from a job, the end of a marriage, the loss of esteem from those we love most.  Such enormous failures may leave us broken, consumed by guilt and wondering if there is a way to go on, to go forward.  Other failures are less consequential, merely embarrassing, and leave us wondering about our own competence and worth.

The mature, balanced and equanimous EA, like everyone else with these qualities, is not devastated by her mistakes and failures – small or large. She knows that they are events in the flow of her work life, and not a descriptor of her as a person.  Every failure is an opportunity to learn.  When the EA finds herself in her personal vortex of negligence, oversight, and carelessness, she will first ask herself: “How can I get through this?” And second, “What can I learn from it?”  She might also say, “How can I make sure I don’t fail again?” but this is an unrealistic hope. Failure is part of the fabric of life; hence, “Fail, fail again, fail better.”

A few excerpts from Pema Chödrön’s commencement address at Naropa may shed light on the concept of “failing better.” 

“…James Joyce wrote about how mistakes can be ‘the portals of discovery.’ In other words, mistakes are the portal to creativity, to learning something new, to having a fresh look on things…[But first, you must]  allow yourself to feel what you feel when things don’t go the way you want them to… ‘Fail better’ means you begin to have the ability to hold the rawness of vulnerability in your heart, and see it as your connection with other human beings and as a part of your humanness… Failing better means that failure becomes a rich and fertile ground instead of just another slap in the face.”

How does the Executive Assistant feel when her carefully constructed and meticulously detailed travel itinerary, the hundredth she has created, is missing a crucial piece of information, causing her boss to call, in a panic, from Los Angeles on his way to Japan saying he has no seat assignment?  How does she feel and what does she do when her executive calls, irate, from downtown saying that the meeting on the calendar for 2 p.m. was over before she arrived?  What will she say?  What kinds of checks and balances will she initiate for the future?  Will her self-confidence take a nose dive?  How does she recover and move forward?  What if a confidence entrusted to her has been exposed due to a momentary lapse of caution?  Or a report is published containing errors that embarrass her manager?  What if she commits a cultural faux pas while welcoming high-profile international guests causing offense to the visitors? 

I could go on and on with examples of common mistakes and failures.  Virtually every EA I know can find herself somewhere in the above list of omissions or missteps. The brave ones call on deep reserves of humility and fine-tuned grace to recover quickly and correct the situation.  They own up to the mistake, take responsibility for it, apologize and describe how they plan to avoid it in the future.  They do not spend time wallowing in guilt, shame, and blame, knowing these emotions don’t help themselves or the others involved.  They respect their larger, fuller personas and they offer the same understanding and respect to others when they fail.

I want to emphasize the invaluable practice of self-respect.  Saying that you respect yourself while sitting quietly and reflecting on what about you is respectable is all well and good.   Practicing self-respect under challenging conditions, when your actions are unsuccessful or less than optimal, is another matter entirely.  Refusing to listen to the inner voices of blame, or to get stuck with the self-accusation that you are a failure takes strength and practice.   You are bigger than the current fiasco.  Your identity is broader, fuller, more comprehensive than the bungled incident at hand.  So, do not waste energy pasting a “failure” label on your forehead; focus on what can be done now and then reflect on what might be done in similar situations in the future. Failing better takes practice, and you will learn to see it as a “portal to creativity.”

The principle of “non-identification,” is a hard one to grasp and practice. Refuse to allow the small persona of the momentary failure to train-wreck your larger persona – who you really are at the core and in the bigger perspective of your life.  To practice successfully you must be honest with yourself and eschew self-judgment. Breathe deeply, calm the embarrassment and self-recriminations, find a quiet place and time to get in touch with the roots of your distress and shame, stay in this inner space and be kind to yourself.  Allow yourself to accept your own humanness and essential goodness.  Celebrate it!  And then, go forth and…

Fail, fail again, fail better!

The Executive Assistant: Political Savvy and Diplomacy

I’ve touched on both political awareness and diplomacy in several previous posts in this series, but in this one, I’d like to write about them more directly.  What am I talking about when I commend them as qualities of a competent and respected Executive Assistant (EA)?

An article entitled “Political Savvy in the Office: What it really means,” from the website Success Labs gives an apt description of the kind of savvy an EA should seek to develop.

“At its core, political savvy is simply a deep understanding of what other people need, born of empathy, listening, and honest communication.”

“Political savvy” can get a bad reputation — too often it can conjure up images of backstabbing co-workers and up-and-comers who stop at nothing to get to the top…. Political savvy reflects [the] ability to understand the [work] environment. People sometimes shy away from developing political savvy. They may not want to be seen as a “plotter” or “fake,”… But in any workplace, nothing is black and white — there’s always ambiguity, unwritten rules and different personalities to deal with. You need political savvy to deal with those personalities and rules…”

It’s fashionable now, in politics as well as business, to look for “outsiders” to fill various roles and bring new perspectives to the table.  While there may be merit in such an approach, and “fresh ideas” are valuable in any organization, I’m usually attracted to the more experienced insiders, provided they are not jaded and manipulative, and they demonstrate political savvy. They are the ones who know all the players and their habits and tricks; the ones who know who will help them to advance a cause, who to avoid, and with whom to seek closer relationships.

Diplomacy is stitched into the cloth of political savvy. The art of dealing with people sensitively and effectively, diplomacy’s synonyms describe the kind of person everyone wants as a colleague: one who acts with tactfulness, discretion, subtlety, finesse, delicacy, savoir-faire, politeness, thoughtfulness, care, judiciousness, and prudence.

So, with these understandings of political savvy and diplomacy, let me turn to an example of them in the work of an EA. Suppose the assistant is given a delicate task to complete, one that requires perfect timing, confidentiality, teamwork and an optimal outcome in a complicated situation.  Let’s say she is asked to place an important and controversial report, already vetted by the CEO, in the hands of the organization’s communications officer. The head of the company is holding her boss, the author of the report, responsible for a public release that will paint the organization in the best possible light. Her boss is in Asia; they’ve had extensive phone conversations about publishing the report, but he believes a face-to-face delivery to the director of communications is optimal.  His EA must stand in for him. 

The first thing the EA must know is how the communications office works and how much confidentiality can be expected from it before publication. Can rumors or leaks be expected?  How can she and the communications director head them off?  A trusting relationship with the director must already be established, and a clear understanding of how she or he operates in such situations will be essential. How should the report be delivered and with what caveats? Does the EA command enough respect in the communications office to be accepted as a stand-in representing her boss’ concerns with authority, subtlety, and tact? Are there any pitfalls that she has encountered before that must be avoided? The timing of the release is key, and she must negotiate it with an understanding of the constraints and concerns of the director.  She must be ready to respond to questions out of a nuanced grasp of her boss’ values, views, and goals. She must function as an ambassador and a diplomat. She will shepherd this matter to its successful conclusion acting as a liaison between the CEO, her boss, and the communications office. Who should she avoid, who should she engage? Who should she stand up to, and when should she acquiesce?

Admittedly, in this situation, the number of players appears to be limited, and they are well known to each other.  However, other industry news outlets and the public media will also be involved. Other EAs will read their bosses’ emails or merely overhear phone conversations. The intricacy of the task emerges, and the delicacy required is apparent. 

So, let’s step back. Who would you rather have in the center of this complex hub?  An outsider, new to the organization, or a seasoned, politically savvy and diplomatic Executive Assistant. You do not want her to be manipulative or self-serving, insensitive or indiscrete, and certainly not uninformed and bumbling.

The EA, who maintains a low profile, operates in the background, keeps her eyes and ears open, and synthesizes all the information, cues and motives swirling around her can steer a straight (or, if necessary, convoluted) path to the goal.

There are many EAs like this in organizations across the country. Shall we elect one as “Speaker of the United States House of Representatives?”

Disrespect and Humility

When I told some of my former colleagues, the EAs I worked with during my career at Harvard, that I intended to write in my blog about Executive Assistants and respect, a couple of them told me stories.

Each said that they have a very respectful partnership with their executives, but that gaining the respect of others in the organization, particularly those who report directly to their executive, is frequently difficult, at times frustrating and, in some cases, a failure.

I’ve thought about this phenomenon and admit that I don’t fully understand it since I haven’t been in the shoes of those who do not respect their bosses’ assistants.  Trying to put myself in the shoes of such direct-reports, I imagine that they see the EAs as barriers between them and their bosses. The EA is the hindrance that prevents direct access when they want unfettered entry to the executive’s space, time and hearing.  They bristle at a “go-between” passing messages. She might get it wrong. They are sure that she can’t possibly understand the urgency or full context of their need. They want her out of the way so they can get their need met instantaneously.  Or, they haven’t gotten what they needed in the past, and they suspect it is the EA’s fault. Certainly, their boss would not deny their request. If it is known that the assistant reads her boss’ email, they may feel deprived of the privacy and intimacy they imagine would exist if she were not always listening in.

Do you notice that my tone in the above paragraph belies my own lack of understanding of the direct-reports’ perspective? I’m having difficulty getting into their shoes. That, by the way, is the cause of disrespect in many if not all situations – the unwillingness or inability to see what is going on from the other person’s point of view.

The truth is, in many cases, the executive has asked her EA to be a doorkeeper in general, and in particular, for certain individuals.  This responsibility puts the EA in an awkward position because the boss wants her to do so without the slightest hint that she, the executive, is behind the practice.  The EA must take the flack and the disrespect with equanimity.

Other situations where the EA is frequently disrespected include relationships with EAs of executives further up in the hierarchy.  Make no mistake, there is a pecking order.  “My boss is more important than your boss, so I don’t have to be polite to you, I can demand whatever I need,” may be the attitude of EAs at the top level. Perhaps they don’t express such blatant contempt, but, rather, a subtle lack of respect.  Wise assistants at any level will work hard to build respectful relationships with her peers and those up and down the line.  They know it’s the best way to accomplish what they should all want to achieve – smooth and efficient interactions in the interest of their bosses’ success.  More crudely expressed it’s, “You scratch my back, and I’ll scratch yours,” with a modicum of grace and humor added to the mix.

What about the individuals in the organization who exhibit poor interpersonal skills (including lack of respect) with everyone? In those instances, the EA may become the tutor and mentor, encouraging a more respectful, softer touch in the interest of the other’s career, and for the benefit of the organization.  Since the assistant is on the front lines, she may be the brunt of much rudeness and learn not to take it personally. She will try to turn the situation around so she can advise on the best way to accomplish a task without ruffling feathers. But she is not a doormat.  She will not allow rude behavior to become the norm for interactions with other staff.   She is called upon to model and describe the acceptable and effective behavior that will help others to accomplish their goals.

EAs often experience a sort of generalized disrespect because some of them don’t have college or higher degrees. They are viewed as “a dime a dozen” and easily replaceable.  Or, they are considered unambitious because they have not focused on upward mobility.  They love their work and are happy to make a career of being an Executive Assistant.  Those who want to play that role impeccably are avid about professional development and continuous learning, but they do not want to go back to school to get a Ph.D.  They are always honing their technical and interpersonal skills and are enthusiastic about taking on new challenges. The EA’s best tools for countering the “dime a dozen” mentality are self-knowledge, self-acceptance, and self-respect – realistic humility.

I don’t mean to paint all EAs as exemplary and all those who do not respect them as unfair and self-interested.  Of course, there are situations in which esteem is not earned or deserved. In those instances, the respectful course of action would be to speak directly to the EA concerned about the problems experienced.  If he or she is humble and open to constructive criticism the relationship and situation may easily be mended.  If improvement does not occur then discussing the issues with the assistant’s boss is both appropriate and respectful.

Good EA’s are the oil that lubricates the whole organization, and the best ones both know it and are known for it!







Stress, Equanimity and a Sense of Humor

Why would an Executive Assistant’s job be stressful?  Isn’t it just a matter of typing most of the day and doing routine tasks like making appointments and booking flights and hotels?  Don’t EA’s have it easy compared to the executive – less pressure, fewer decisions to make?  They just do as they are told, right?

Wrong!  Imagine this. Your boss’ calendar is already full of vitally important meetings when you receive a call from the CEO’s office that an urgent two-hour meeting will be scheduled for sometime the following day. You must clear that day on your principal’s calendar and hold it open until further notice. She is at an off-site (the latest lingo for a planning day away from the office with her team) and unplugged from all technology, so you can’t consult with her to determine who to reschedule when and who to cancel.  So, as an experienced, knowledgeable, intuitive EA you set to work rearranging everything.  This change will affect perhaps an entire month of meetings.  Each person (or their EA) must be emailed or called, and the contacts must be made in priority order.  You will have to wait for responses before contacting the next individual or group.

All the plans for your own workday must be put on hold while you tackle this unexpected rescheduling project.  You will call into play your knowledge of your boss’s preferences and priorities.  You must also be sensitive to the needs and feelings of those you are canceling or rescheduling.  You must have developed an excellent working relationship with their EAs.  You are required to accomplish this project quickly and efficiently while being constantly interrupted by others.  You are trusted to keep your cool; have confidence in yourself and your relationship with your boss; smooth ruffled feathers; and diplomatically explain the reason for this change.  You may even have to cancel travel plans at the last minute and keep track of the financial implications of doing so. And, in the midst of this, you must remain calm and cheerful, juggling multiple balls with faultless skill and perfect equanimity.

By the end of the day, you have made significant progress, but you are stressed and exhausted.  You realize that, unknowingly, you have been holding your breath all day. Just before the workday ends, you receive a call from the CEO’s office that plans have changed and the crucial meeting will be delayed until the following week.  Do you cry? Do you scream? Do you throw your mouse at the wall?  No.  You sigh, shake your head and pack up to leave the office.  This is no surprise, this has happened multiple times before.  You’ll deal with it tomorrow.  Perhaps you’ll stay on an hour or two to catch up on the work you had planned for the day just passed:  pay some bills, reimburse some travel expenses, proofread a report, get a head start on arranging an upcoming trip.  Perhaps you’ll walk down the hall to chat with a fellow EA about the day, and you’ll laugh together to release some of the tension. After all, the day was relatively typical.  It could have been worse.

I’m tempted to leave it at this and to draw some conclusions now about respect and the qualities of equanimity and humor exhibited by a top-notch EA, but I feel compelled to tell an even more stressful story –  the responsibility of being in-between.

An angry employee calls to say he needs to see your boss immediately.  Your principal has widely disseminated an “open door” policy.  She wants to welcome and listen to others in the organization.  But you know the situation with this employee, and you know your boss has already discussed the employee’s concerns with him several times.  There are plans in the works to address these issues, but they are not fully developed.  Today your boss has blocked off a couple of hours to work on a critical report and has said she doesn’t want to be interrupted.  All of this is running through your mind as the employee demands an immediate meeting and says he’ll be arriving in five minutes, despite your protests.

You calculate that your boss will welcome an interruption from you in this case and you quietly enter her office telling her the employee will arrive any minute, and she should stay closeted in the room until further notice; you will handle the situation.  She gives you a grateful look, there is complete understanding between you. You close the door and return to your desk.

A few moments later the employee arrives, red-faced and shouting.  You speak softly and offer a relaxed demeanor, trying to mirror the kind of behavior you would like him to exhibit.  You explain that your boss is not available at the moment, but you are aware she is working on the problems the employee is worried about. She will be in touch as soon as plans have been developed. You ask the employee to sit down and explain his concerns further while you take notes.  You want him to know he is being heard and taken seriously.  As he talks he calms down, and you gently communicate that you are in the middle of a project but that as soon as you can, you will inform your boss about the conversation that has just occurred.  You stand up, the listening session is over, and he departs.  You prepare a brief email to your boss, low priority, to communicate any new information or nuances you have just gained.  She will read it when she has finished the report, or she’ll check with you on the way out to her next meeting.  She has complete confidence that you have handled the situation appropriately and may say thank you or may just accept your talents as an intermediary with silent gratefulness.

You sigh, take some deep breaths – another uncomfortable situation diffused – and go back to your project.  But later you notice how tired you are, how tight your shoulders.  A slight headache hovers around your temples.  Perhaps tonight you will go to the gym, listen to your favorite soothing music during your commute, or enjoy a delicious dinner cooked by your understanding spouse.

I have watched many talented EA’s keep their composure during extremely stressful incidents.  They relate delicate situations that they have handled quietly, to prevent them escalating, or to save their boss time, effort and stress.  They understand that their role is sometimes to smooth troubled waters and always to remain flexible, changing projects on a dime in response to the needs of their boss and others.  They feel the stress these situations create, but, for the most part, they don’t show it.  They welcome interruptions with a smile and stay late to finish tasks that have been pushed aside during business hours.  They do their best to maintain a sense of humor about themselves and those they serve.  Sometimes these efforts at equanimity fray slightly and take a physical toll, but they try to maintain a life balance that keeps them healthy and productive.

None of this differs from the lives of countless workers at all levels in all jobs and professions.  I write about it because I admire the EAs with whom I have shared such stresses. I respect their backstage brilliance, strength, and dedication. We may commiserate in private, but in public, we strive to be models of calm professionalism. If you have such an Executive Assistant, she/he is worth her/his weight in gold.






The Executive Assistant:  Discretion/Confidentiality           

One of the most commonly required qualities listed in Executive Assistant (EA) position descriptions is “the ability to handle highly sensitive material and information with discretion and confidentiality.”

This seems like a no-brainer to anyone who has worked in a business environment.  Secrets abound and are indiscreetly shared daily, doing damage to morale, team dynamics, and sometimes to the bottom line. The ability to keep a secret for your boss or from your boss is an invaluable capacity for an EA.

Because she is party to many high-level management confidences, the executive assistant’s position in the organization may be a lonely one.  Her peers may choose not to share work problems with her, out of concern that she will pass the information on to her boss.  And she can share very little about her work, her opinions and dilemmas with her associates without compromising the confidentiality expected by her boss. Loneliness, in this instance, is the price paid for professionalism.

If her executive trusts her, she may have access to his voicemail, email accounts, credit cards, social security number, bank accounts and other highly sensitive information of both a business and personal nature. She will also see and hear things, as people come and go from his office, that reveal very delicate situations and decisions.  She is expected not to share this information and sometimes not even to acknowledge awareness of it.  In a sense, she is like the butler standing by at a family dinner.  She hears all the family secrets and sees them at their best and worst but must keep these insights to herself.  The difference for the EA, hopefully, is that the head of the “family” respects her role and knows that the more information she has, the better she can assist him/her.

The executive, if she respects her EA, will encourage her to contribute the insights she has gained from watching and listening to sensitive situations.  Those insights may bring another valuable perspective to the decision-making process and may help the executive more fully understand the complexities and nuances of workplace issues. The executive will also ensure that her EA fully understands the reasons for her decisions and that they openly discuss differences of opinion.  This builds trust and encourages loyalty.

The EA must develop keen intuition about when to share with her boss sensitive information that she has learned from other employees.  Her first loyalty is to her principal, to the fostering of her effectiveness as a manager and leader.  She will know when sharing information is essential and when it is gratuitous. She will be careful not to promise confidences and then to break them.

As I write, I am aware that I am describing two persons with integrity.  The work and the relationship can go badly wrong when one of the parties (executive or assistant) acts in an unprincipled fashion. Mutual respect and understanding are crucial. Any wonder that an executive worth his salt would put the phrase, “the ability to handle highly sensitive material and information with discretion and confidentiality” in his assistant’s job description?

Executive Assistants and Respect: Anticipation or Prescience

Nothing gave me more satisfaction as an executive assistant than anticipating what my boss would need before she asked for it.  On several occasions I walked into her office holding a file of information I predicted she would need. Just as she said: “I need…” I placed the file on her desk. Her exclamation, “Excellent!” made my heart jump for joy. Those moments of harmony and sense of partnership were valuable to both of us.  They cemented the feeling that we were in this together.

There is no magic in this anticipation or foresight. The EA’s prescience is not that of a soothsayer.  Rather, it is a skill honed by deep study of the person she is serving and the circumstances at hand.  Experience and the desire to make the executive’s work life as effective as possible contribute to prescience. But there is another element of foresight: intuition – the “gut feeling” sharpened by the cultivation of awareness and concentration.

Travel itinerary preparation is a perfect example of the value of foresight.  While making travel arrangements and preparing an itinerary may seem like a straightforward and simple task, it is an exercise in paying attention to the minutest details of the traveler’s preferences and expectations.  For what airlines does he have frequent flier memberships? How will departure and arrival times affect his personal life and work?  How does he prefer to travel to the airport and how soon does he want to leave the office to ensure he has plenty of time for security and boarding?  Is he a last-minute person or a plenty-of-time person?  Where does she prefer to sit on the airplane and why?  What kind of hotel does she prefer?  Have all the registrations been made for the conference she is attending?  Are there meetings to be scheduled in the city or country she is visiting?  What kinds of advance materials does she need and are they included in the travel briefing folder? How do time differentials affect any conference calls scheduled during the trip?  How quickly does she recover from jet lag?

It can take months to years to learn the traveler’s preferences and needs, and the above is only a small sample of the kind of detail the EA internalizes to lay a clean, polished, and complete itinerary before her boss at the exact moment he or she needs it before departure. Once internalized, of course, this kind of detailed anticipation becomes second nature, even rote, perhaps, for the executive assistant.

Highly developed intuitive anticipation, however, is a different matter.  It comes into play, for example, when a staff member, or perhaps an executive’s peer walks into the office with a problem.  If the EA knows her executive well, she will intuit if this is a problem he will want to deal with immediately, even welcoming an interruption.  Or is the issue something that, for various good reasons, he will want to delay.  Will the assistant handle the situation respectfully and sensitively? Can she anticipate her boss’s reactions and motivations?  Is her intuition a refined and reliable tool transferable to various circumstances?

Anticipation is fifty percent preparation and fifty percent intuitiveness.  Honed by learning from one’s mistakes, it requires constant awareness and concentration. It is one of the executive assistant’s most valuable skills.