Being Proactive and Walking the Fine Line

As executive assistants we are expected to be helpful, accommodating, and abiding, while also being forward-thinking, 10 steps ahead, and sensitive to others' needs, emotions, and whims.  For a long time, I struggled with the fine line of being supportive, yet proactive, while making sure things would be executed in the best way possible - that someone’s method, choice, decision, or line of thinking was effortlessly congruent with the business goal and task at hand for my boss or the company's benefit.  Because being proactive can sometimes be perceived at face value/initially as disagreeing, not trusting someone's judgment, pointing out something could be better, overstepping boundaries, or being a naysayer, it can be a sensitive subject no matter how delicately you communicate.  Your best intentions to save the company money, a headache, and stress can be interpreted in so many ways by different people.  Perhaps a  new perspective, idea, or suggestion would help, though at times, it could very well be what was assigned and how to carry it out had been vetted by the entire senior executive team and this was, oddly enough, the best way to handle something.  With life and work, the greatest question always seems to be, where do you draw the line?  

Since I was groomed in the same way in so many CEO offices, how to delicately ask a question with a curious, humble tone was not so much the issue as which “battle” I should pick to ask for further details, clarification, and if improvements were needed.  Most times it’s best to jump in and do the work and ask questions once you hit a roadblock.  At other times, you realize your boss hasn’t thought much of an idea through out of being too busy or unfamiliar with admin processes, little details, the inner workings, and it’s your job to shed some light or make sure all the pieces of a project fit together smoothly.  It is rare that instances like this come up for me since I’ve been doing EA work for so long and learned a lot.  Yet every now and then, a similar situation arises, and because I’ve been in the role long enough that as my responsibilities have grown I am now facing the issue on the OTHER side of the situation - where I am giving the instructions and overseeing the work I’ve delegated out to other assistants, coordinators, interns, vendors, etc.  

First, let me give you a little background on how I was groomed.  Whenever someone (my boss or another supervisor) told me to do something, I did it.  I also did it EXACTLY the way they told me to.  I didn’t ask WHY it had to be that way, I just did it.  If I wasn’t given all the information up front, and turned in work slightly off, they realized they forgot to tell me something, or changed their mind, or just asked me to fix the item because how was I to know any different.  I had very wise, patient, and excellent bosses.  In this sort of working relationship, as most are, the boss is responsible for all the work that is done, even if they did not do it themselves because they are the leaders.  They oversee, they delegate, they provide vision, and direction.  They are the leaders because they know how to manage people.  It would be my job to carry out the work.  In some instances, I would ask gently, was this component considered, was that also taken care of, and I would ask in a way that made it clear, I did not wish to step on anyone’s toes, but wanted to make sure for the greater good of the team, something was not overlooked or somehow the ball not was dropped along the way.  A system of checks and balances when properly executed with a ton of two way communication is better than one individual working in a vacuum.

People make mistakes all the time, whether they are leaders, amazingly smart, or are regular people.  No one is perfect.  The balance comes from trusting your boss and your boss trusting you.  The management of a project also comes from knowing your boss’ role/responsibility and your own.  It’s about understanding what your boss controls and what you are in charge of.  And any gray areas should be discussed before anything is done or changed.  Nothing should happen without your boss/everyone’s knowledge because they oversee you.  Your behavior reflects on them and how you or your team does reflects on their leadership ability as well.  (Do people in their dept get promoted, have good morale, stay at the company for many years, speak highly of the boss, etc?)  So it is a very symbiotic and important working relationship.  

So, this is how to be proactive and walk the fine line.  This is how a mutually-beneficial, harmonious relationship at work should look.

1)  Your boss trusts you to follow directions and carry out tasks.

You were hired after passing a bunch of tests, interviews, and a screening process.  You are trusted to have basic logic, problem solving, reading/comprehension, writing, critical thinking,  analytical skills, and how to read and follow directions.  You are given a task and you do it.  

2)  You should trust your boss that he has his, yours, and everyone’s best interests in mind.

Your boss was hired for being bright, a good leader, smart, driven, and a visionary.  Almost everything he has asked you to do, whether for his professional or business life, has been mulled over, brainstormed, and discussed out loud with his boss, team, the dept, board members, shareholders, and/or his spouse, family, or friends.  The main goal for them is to communicate what they need done.  

3) If you think your boss/colleagues overlooked something, then ask gently and leave room open for yourself to be wrong.  Don’t make assumptions and decisions, especially when that work can’t be undone or reversed.  

When assigned a task, no matter how complicated or simple, other people or resources are involved and affected.  It could be time, money, energy, effort, emotional investment, manpower, being sensitive to morale, office politics, public scrutiny, or just taking the time to consider or think about something.  Everyone is busy, short on time, dealing with their personal lives, and they have their own preferences or quirks.  Most likely, your boss does not have the time to explain every little detail to you on why something was decided, perhaps it is confidential or private.  What to you may be a glaringly obvious solution has most likely been vetted or negated for one of the above reasons - too costly, impractical, not emotionally intelligent, etc.  However, it is true, it could have been so simple no one thought of it or just forgot because they were too close to the situation.

4) Unless something is illegal or grossly immoral, even if you don’t agree with something or dislike it, do it anyway - it’s your job.

If something doesn’t make a lot of business sense, is not logical, or lame, it’s irrelevant.  You have to do it anyway or they will find someone who will; your annual review, working relationships, and work reputation will suffer.  It’s easy to get frustrated and wonder why things have to be done a certain way or why things are decided that make absolutely no sense to you.  Whether it’s explained to you or not, standard operating procedure, routine, admin process, and certain checklists or steps are in place for a reason.  Granted, they are probably not perfect, but it’s what works in the current environment, for better or for worse.  When an executive is trying to lead, manage, and oversee 5 people or 6000 people, there are only so many priorities that can exist.  And there is only so much one person can do to try to have everyone on the same page.  One can only control their own actions, thoughts, and behaviors.  Everyone has free will.  So once you delegate, as the CEO or as the EA, you have zero control of how something turns out unless you trust someone and have a solid working relationship.  So do the job you were hired to do and try to help foster change once you’ve proven yourself and know with absolute certainty your boss trusts you because you not only understand your current role, but the next level of your job, and/or the big picture of how all his depts and the company interacts.

5)  Collaborate, have a partnership, and be patient.

Aside from doing what you’re told and trusting your boss and colleagues, the best working relationship is one of dialogue, discussion, and allowing people to wonder and ask questions without being penalized.  This also means admitting you are wrong when you are, praising others when they do well, and being open to all ideas and thoughts no matter how insane or dumb.  In brainstorming and thinking out loud as a group, without fear or judgment, good things can happen.  There are a lot of gray areas at work.  Most of them you have to let slide as there isn’t enough time in the world.  You can only solve so many problems at once, so be patient with yourself and those around you as much as possible.  I realize this is very, very hard even for the kindest of people because life is difficult, unfair, trying, and sometimes you just have a bad day.  Luckily, things ebb and flow. Things change, nothing stays the same.  Resilience and practice can only make you stronger, so I will leave you with great words by Nelson Mandela as reminder to be patient.

“Resentment is like drinking poison and then hoping it will kill your enemies.”

***New “rule” - when you ask me a question for anonymous advice and I answer it, could you write an anonymous comment so I know you read the post?  You can just write “Thx!” or something!  :) 

As always, I usually tweet any new posts I have. And anyone can email me questions and I respond only via this blog, not to your personal address. It usually takes me 5-6 days to answer.

I also write over at Jobstr.com under Hollywood Executive Assistant.

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