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Communicating with your Executive – Ask an Admin

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Welcome back to Ask an Admin, the best place to get peer to peer advice for administrative assistants and executive assistants!

This question comes from A Very Frustrated Admin, and the question is:

I am at a loss and am completely frustrated. In the past, I’ve been extremely fortunate to work with executives who have been great at communicating. I’ve always been able to build a good partnership with the many different executives I’ve supported, all with different personalities and quirks, and even communication styles. But I recently had to relocate for health reasons, and take a new job in a new company. My new executive is a very nice person, but his communication is non-existent. I’ve tried speaking to him a few times now about it, but he seems to think I’m worried about my communication with him and not the other way around. And that’s not the problem. For Example, during the two weeks of Christmas and New Years, our office was closed Dec. 24th, 25th, & 26th, open the 27th and 28th. Then open the following week on the 31st, closed the 1st, and open the rest of the week starting the 2nd. 

He worked the 27th and told me he decided to take the 28th off. No problem, I re-scheduled the meetings on the 28th to the following week. Then all day on the 27th, and the morning of the 28th he emailed me to schedule several meetings for the following week. Which I did. An hour before I was supposed to leave on Friday the 28th, our COO mentions that our CEO won’t be in on Monday, the 31st. (I support the CEO). I was never told by my executive he wasn’t coming in on the 31st, and I scheduled two very important calls for that day based on his previous emails to get the meetings scheduled right away. I texted him, to verify if he was going to come in or not, and never got a response. I texted him again on Saturday, still no response. Monday morning, 30 minutes before that first meeting, he finally texts to tell me he won’t be in and to please reschedule the two calls. I was scheduled to be off that day but was able to call into the office and get another admin to help make the changes.

This is not the only time something like this happened. It’s a regular issue. I’ve told him many times, I need him to respond to my texts or emails. I need him to sign papers I put on his desk. And it takes days to get anything done. And then I’m the one that looks incompetent!

Has anyone run into this before and figured out a way to “fix” the communication between you and your executive? I go home wanting to cry every day because I feel like I’m not performing at my best. I know I’m a great executive assistant, but my new executive doesn’t understand that we need to be a partnership. And I can’t get him to communicate.

A Very Frustrated Admin

Wow! A failing partnership between an executive assistant and a CEO can be a very tough thing to repair or establish but I know many of you out there have succeeded in accomplishing this so, let’s try to help this Very Frustrated Admin. Give us your thoughts below!


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16 thoughts on “Communicating with your Executive – Ask an Admin”

  1. I, too, support, not enable, a non-communicator. Due to being at a certain point in my career with my agency, leaving is not an option. I took her actions/non-actions very personal for a very long time. In hindsight, the negativity was even affecting my personal life! Not cool!
    But, I decided to invest in myself–the one thing I can “control”–and CHOSE to do my best at this new challenge. The first action I took was to “google” ways to communicate professionally (Thank you Office Dynamics!!!!). When the derailments would happen due to lack of communication, I would go to her office, state clearly the facts and urgency created from the current situation, then provide a revised timeline to complete the rest of my responsibilities. As I grew in confidence, I took charge of my performance by being proactive–prompting conversation after a meeting she had attended (amazing what I learned!); keeping a folder on my desk with her name on it (old school tickler file) and placing documents, notes, etc. in it needing her attention (She now will glance through the folder as she passes my desk, usually on a daily basis!!!). And, thanking her, yes, thanking her for supporting me through her actions and communication. She has even owned a couple of the derailments because of a lack of communication. Baby steps to be celebrated…
    I end my work days knowing I’ve performed my job at the level I expect of myself. And, if there’s a silver lining, this challenge keeps my days exciting and I’m building a great career portfolio!!!
    Hang in there!!!

  2. Successful communication between you and your boss is critical to your performance and his/her’s success. They work in tandem….nothing new here – you’ve heard it all before. At some point, you have to ask yourself what is the return on your investment? Are you being set up for success? Are you doing your best work under the circumstances? Is his/her behavior a reflection of the value he/she feels you bring or something else? Do you feel respected and valued?

    After you ask yourself these critical questions, evaluate your answers to determine if you are having an equitable return on this investment. You have choices. Stay and do the best you can under the circumstances, stay and try to coach him/her a different behavior OR decide to take your skills and immeasurable contributions somewhere else where they will be cultivated, valued & RESPECTED accordingly.

    I’ve worked with managers like your boss. They don’t often change but on the rare occasion, you do find a few who are clueless to the impact their behaviors/choices are having on those around them. Remember, they need us more than you need them. Sometimes the right move is to vote with your feet. Life is too short to not be valued.

    Good Luck!

  3. I so understand where you are coming from. My first thing is maybe your executive views text and email as informational only. That is my current boss. So unless I title it action required and mention it to him they don’t usually even get a glance let alone answered. He is a face to face or phone call communication person. So I have had to learn to change how I go about my communication style. He is also not the best communicator, that is partly his personality. I have a meeting with him every morning at the beginning of the day we go over his calendar any other questions and anything he may need to sign. I never just leave stuff for him with out first telling him before hand in a face to face meeting or a phone call. Sounds like he isn’t likely to change his ways, so you would be best to try different approaches to get to something that works for both of you. Your probably going to have to do the biggest changes. Could you possibly talk with a former assistant or someone who has worked his I’m a while to get some ideas on how to handle things. I have one of those people I can talk with and it has made a world of difference in my frustration level. Wish you the best of luck!

  4. There are some really great comments and feedback on here! I like the suggestion of putting a pending to-do list/agenda on his desk each day. I also agree with the first commenter that you’re going to have to accept this is how your executive rolls, and it’s not personal. He’s a terrible communicator and I imagine others share in your frustration. Do you have access to his email? I wouldn’t know 3/4 of what our CEO was up to if I didn’t skim through his emails several times a day. He forgets to tell me about upcoming trips, meetings, out of office time, etc. as well. I would also recommend dumping on his calendar a weekly one-on-one meeting to go over his calendar, etc. for the week. He clearly needs a lot of nudging. Good luck to you!

  5. Yes, I do understand, I am in a very similar boat. I keep putting myself on my executives calendar (once a week, not even once a day) and get bumped off, answering emails is hit or miss and even text get or get not answered. S/He is also not competent in technical things and will not get any advice (I think s/he might be embarrassed, which doesn’t help with learning) so sometimes misses changes on email or the calendar system we are using .

    My only advice is to keep on trying and be the best I can be under the circumstances.
    I can only change myself and no one else, so I am trying to be as excellent as I can be and hope that eventually things will change. I am proactively looking for opportunities to demonstrate what would be easier/helpful. We do talk a little bit more (18 months and counting), the missed opportunities are often painful, though. I am still hoping for the best…

  6. I wish I had advice, but all I can give is empathy since I’ve never had to deal with such a big disconnect. I do know how exasperating it is to be stuck, waiting for answers and clarification, wondering how hard to push to get his attention, questioning my methods, trying to read his mind. You’re in a really tough spot because, you’re right, delays and last-minute changes can reflect badly on you, despite your best efforts. That’s maddening and embarrassing, especially since you’ve had such success with your other executives and you know the value of a true partnership, and what a joy it can be. I think it comes down to trust and respect. How can you trust him when he doesn’t respect you (or your role) enough to communicate regularly? Perhaps that’s how you approach it.

  7. My reply might be a little different today. I’ve been living in your world for about a year and have learned a few things that might help. First, continue to do and be the best you can every day. You will be judged by your consistency and your trustworthiness and not necessarily by your manager’s challenging behavior.

    Second, do not share your frustrations in even the slightest way with anyone in your professional setting. No eye-rolling, no comments like “IF I get an answer from him” or any other indication that he is the slacker and you are at the whim of his response. That never shines poorly on anyone but yourself. Also, do not make promises to get back with anyone by a specific time that you cannot actually commit to do to his actions – let them know you will respond or share the information when it becomes available.

    Finally, do what you can to alert him to your needs. And then leave it at that. For example, if sending an email, ensure the subject line very clearly expresses your need. Use a consistent alert when an urgent response really matters. For example, there might be an email string from several executives discussing a conflict and instead of simply replying and using the same email subject line (which will not differentiate it from all the other replies) I will change it by pushing the subject line to the right and replacing the start with “?? Need response re today’s conflicts”… with the original subject line following that but pushed slightly to the right.

    I will start email subject lines with very specific flags. LIke the two question marks used above. Or “NEED RESPONSE” followed by a quick description of need. Or “Time Sensitive Today”. Reviewing your example, and having another executive tell you your manager was not going to be in on a day that you thought he was, I would try to assess who had the freshest information. Since the executive seemed to have the fresher information, I would have immediately sent an email with “?? Moving YOUR Tuesday’s meetings” and used the body of the text to outline that you had heard his plans had changed and that you would be moving the scheduled meetings before leaving at the end of day unless he responded with different instructions. Then you would have communicated your need for information, your action steps that you were going to take if you didn’t get an update and expressing your proactive solution to what you were sensing was an important change to his schedule. Taking action can drive a response. If there is any frustration that you moved the meeting – it will generate a discussion (which is your desire). If it worked out, you were the magical executive assistant with her ear to the ground understanding the ever moving needs of her manager. Win win.

    Finally, get over it. This was the most difficult part for me. It’s a relationship and we all know you cannot change people. Once you know who they are, that IS who they are – so accept him. Do the things you can. Don’t fret over the things that he is not fretting over (he would respond if he was). And remain professional, proactive and positive. You will shine and he and others will be greatful for your consistency and professionalism. Try really hard to accept that this is the situation and it likely won’t change. That alone will feel very empowering. Good luck.

    1. Wow, Chris. Some very practical, broadly-applicable advice. I can tell your insights are hard-won, perhaps learned the hard way. Thank you for sharing, and for advocating to always take the high road. I am grateful for this community, for being able to share our unique struggles and take comfort that we’re not alone.

    2. chris this was right on the money. i don’t necessarily have this same problem, but i liked your email subject line suggestions as they can pertain to anyone at any give time or situation.

      thank you also for your frankness at the end. getting over it is sometimes the best advice to give and hear.

    3. Hi Chris! Joan Burge here! You gave very good advice to our frustrated Executive Assistant. Thank you so much for taking the time to share from your experience. Very sound, practical, usable advice. I agree with your final statement. We can try to change people but ultimately every adult does as he or she pleases. During my administrative career, I was able to get a few executives to change some behaviors. There were one or did who just would not change their ways. So I either lived with it and adapted accordingly or, in one case, I left the company. It just was not worth it to me.

      1. Thank you for the feedback. As soon as I read the question I was surprised at my strong desire to respond with guidance. I was having a truly busy day and yet thought I absolutely needed to take time to share my point of view and learnings. I had just gone through a transition to a manager that sounded very much like hers and was reminded of my sleepless nights, the fretting and frustrations, and most acutely, the feeling of personal angst in being seen as less than efficient/proficient/professional due to his actions. I appreciate that others are finding my guidance to be actionable and sound. I’m in a much better place and hope it will help “A very frustrated Admin” find her way with her manager.

  8. I too have a problem with communication with the manager I report to. If I ask for time off she never responds until I send her a few more e-mails or stop by her desk..
    If I ask if I can work from home tomorrow in case it is icy or do I have to take paid time off, her answer is “I don’t know what the weather will be like.”
    Recently a headphone set was missing from a cube. No one gave me a consitent answer as to how to order the headset. When I told the other manger who was requesting the headset that I have reached an impasse and could she intervene, she took a headset from an empty desk and reported me to my manager. My manager said I should have never involved that manager. I should have come to her and she would have given me a headset. I asked her to please let me
    know what the proper procedure it to order a headset. I reached out to the other executive
    assistants to see if they could point me in the right direction. I copied my manager. She then sent out an e-mail telling the other executive assistants to hold off replying. She would do some research. Today I asked her if she has gotten any information. She proceeded to take out a headset from a drawer filled with headsets! I said why didn’t you tell me you had a supply of headsets. She said “I thought you had taken care of it.” I am at a loss to explain her behavior. I spent a lot of time sending e-mails to try to find out the proper procedure when she could have just handed me the headset.

    1. Sharyn — That’s insane. She’s playing games with you and you’re never, ever going to win because she makes the rules up as she goes along.

  9. I have a standing weekly meeting with my executive to review his calendar for several weeks out as well as to catch up on travel needs, staffing requirements, and anything else that requires attention. I also scan to see if there are opportunities to work remotely that he may wish to take advantage of and mention those so I’m not blindsided by last-minute changes. By keeping tabs on family birthdays, celebrations (when I know about them) and discussing scheduling needs with him, he’s very aware of keeping me in the loop of his plans. For more urgent issues, I will speak directly to him as appropriate, or email with “Urgent” and the requirement in the subject line so he can see immediately what I need. I know others who meet daily, but this has been working well for us. You just need to see what will work so he can see the value of getting his schedule right the first time, most of the time.

  10. I also work for a non-communicator so I can only pass along something our CEO’s EA passed along to me. Create a live word doc that you keep adding things to that you need from your executive. Outstanding documents, answers to questions, etc. put the date in the left column. Provide this to the executive every day. Remove completed tasks to another document but Every day or two that something doesn’t get answered or completed, gets added to the TOP of the list with the following day’s questions and it is in red text, He may still ignore it….mine does the majority of the time, but maybe you can draw his attention to what you’re waiting for.

  11. I have no suggestions for you other than look for a new job.

    My manager is much the same; they do not perceive it as a problem and you are unlikely to get them to change. For your own sanity, find something new.

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