How do I Deal with an Executive that Always Says Yes? – Ask an Admin


Welcome to Ask an Admin! This is where any administrative assistant or executive assistant can submit any question they have and your peers can weigh in on the conversation with their advice. There is more than one way to approach a situation or problem so we would love to hear your input!

This week Karen asks:

How do Administrative Professionals deal with an executive who says yes to everything?

Background info: Our new CEO says yes via meeting requests via email, text, LinkedIn, Facebook and many other social media channels and then in an email or other post tags me asking me to set up a meeting. I’m struggling since the new CEO started in November, I have a Google doc with all of the requests have come through, ranked them via importance. He isn’t making it a priority to prioritize his schedule and also he doesn’t look at his schedule, I can email, print out or text meetings and he only wants to know what meeting is next. He can also get upset if he’s not prepped properly, but if he’s not making our meetings a priority how can I prepare him properly for success in his role?

So it sounds like Karen may have a “button masher” (someone that just clicks approve or yes without looking) and isn’t taking the time to prep himself. Wow! This is a tough one…

Well what does Karen need to do? What can she do?


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13 thoughts on “How do I Deal with an Executive that Always Says Yes? – Ask an Admin”

  1. Hello Karen! Joan Burge here from Office Dynamics. I read the responses you have received so far and can’t think of anything I would add. I believe you received several good suggestions. I fully agree with you taking more control and trying to get face-to-face time to discuss meetings and priorities. I wish you the best of luck.

  2. My executive said yes to EVERYONE but he added “contact my office to ensure there are no conflicts”. They would call and there would be a conflict. We were his no button.

    Other options: Chelena handles the calendar and will know better than I if I am available.

    It will take some retraining … but they will appreciate the get out of jail free card.

  3. Hi Karen,

    I think you work for my former CAO! He was the same way. After some frustration, I came to terms with the fact that, that was his working style and there was very little I could do to influence or change him. My better option was to find ways and create tools to better prepare myself and anticipate his folly. I began to take charge of his calendar with little permission and participation from him. I educated myself by reading his emails, so I understood the ‘why’ behind his work and could better determine what meetings were a priority and which ones could wait. If he double-booked himself, I would text him and ask him which one was a priority. If he didn’t answer me or I could determine that myself, I’d call the other party to reschedule their time without his participation. I remember, I used to put meetings on his calendar for me and him to connect under the guise of something else. I’d title it Strategic Plan Discussion or something clever. He would think he was meeting with a colleague and it would be with me to strategically plan his schedule. hahaha! He started to realize it was a priority to speak with me. To prep for meetings, I would print bios and everything he needed and leave it for him the day prior so he could review overnight. Or I would take a pic of it and text it to him day of. I kept him on time by knocking on his door five minutes prior to the end of his meetings, then again at the end time. Then again if he ran over. I knocked twice and walked right in. I didn’t wait to be told to ‘come in’. I didn’t need anyone to acknowledge me either. I just started speaking, softy and respectfully of course; ‘Your next meeting is here’. Most of the time he appreciated it, but at times he got annoyed and would tell me “I need ten more minutes”. That was my queue to not interrupt anymore. I asked him to direct all calendar requests to me before agreeing to them. He told me no. That he wants people to perceive him as having an open door and not difficult to meet with. Because I am comfortable with speaking directly, I told him in a 1:1 meeting that our meetings need to be a priority if he wants that perception to continue and actually happen. Help me, help you kind of thing.

    Sorry this is long, but I totally get it. Hope it helps.

    1. Alicia Sinclair, thank you for your feedback! You provided a lot of tips on how to work with this type of work style.

    2. I couldn’t agree more with all the responses so far, but I can absolutely relate to Alicia’s. I won’t waste time by repeating everything she said, but I have to piggy back on the “take action” vibe that she implemented and possessed.
      Listen, I totally get that we need to treat our execs with the respect they deserve, however, we also need to be taken seriously because the work we do matters. Sometimes we have to be the respectful but firm presence they need.
      I believe you need to dive deep and find that characteristic within yourself the higher up the food chain you go, especially. You can’t be afraid to voice your opinions, thoughts, concerns or yes, even tap on doors and let yourself in for the bettement of their work day flow.
      I’m lucky I guess because I have yet to work with an exec who didn’t either expect that type of behavior upfront or come to appreciate it eventually, seeing how it did indeed benefit their day and workflow. So, speak up! 9 times out of 10 it will be appreciated if not at first, then later down the line.

    3. “Help me, help you” — that’s what it all boils down to! Whatever our executives need from us to make a synergetic working relationship is our goal!

  4. Hi Karen,
    There’s nothing like breaking in a new executive. His enthusiasm is admirable and what he doesn’t realize yet in his short tenure is that he can’t do everything, and everyone wants face time with the new guy. Don’t worry. It should calm down soon. He is building relationships and that includes you too.
    Fortunately you have the power of his calendar! Try this, when he asks what his next appointment is, tell him it is you and go in to help him prepare for the next day or week. I recommend daily. Start a routine that works for both of you. You can prioritize meetings based on your organizations goals and strategy and I would explain to him those reasons when you talk calendaring. You have his and your organizations best interests in mind and this is a great opportunity to showcase your talent and knowledge. Good luck!

  5. Ivory JohnBaptiste

    I would mention what could possibly be detrimental pending the “YES” response to the business. Explain, how the manager’s answer would impact the request whether negatively or otherwise. Or, the importance of reading thoroughly before answering. Outlook has preferences and voting buttons options. So, you could include a drop-down list to select.

  6. It sounds like a managing up opportunity, or that your exec has not had an assistant before so this is a training adventure. I would ask him how he prefers to be prepared for each meeting and see whether he needs time blocked on his calendar for that. If he is a “runner” (running form meeting to meeting), you can create folder for each meeting with the agenda, handouts, etc., that he can just grab and go. If you have control of his calendar, you can reply “maybe” to his meetings, or change his reply to “maybe” and then go over which meetings have priority. Over time, you’ll get a “feel” for what is an important meeting and which are moveable to accommodate those urgent ones.

  7. I think you need to give yourself some empowerment and talk to the guy. Let him know how frustrated you are with trying to keep him organized. Be careful you don’t blame him, just keep it factual. He is new to this role, so may still be in a learning mode as well. Talk to him about his priorities, can you take responsibility for replying rather than him?

    I would also make a standing meeting in his calendar first thing each morning, or at least twice a week, for you to meet with him and discuss what’s coming up. You are as much a priority as any other meeting, but we so often put ourselves on the back burner.

    Good luck.

    1. Hi everyone. Joan Burge here… Office Dynamics founder…. I have read all the comments on this issue. Great job. Melissa, I like your comment about empowerment. It’s ironic you would mention that as I just hosted a webinar with Lisa Olsen on this topic. It was a very interesting webinar and we got lots of questions from assistants about empowerment. It just so happens our administrative conference theme this year is The Empowered Assistant. Empowerment has a lot to do with feeling confident, taking risks, and initiative.

      Here is a little piece of what Lisa Olsen said about empowerment. ” Believe it or not, but empowerment is really about building self-confidence, effective communication, exercising judgment and being willing to build personal awareness.

      The definition is “authority or power given to someone to do something.” That does presume an action on the part of the person being given the authority to do something. That can be confusing for some people. I’ve talked to many assistants who say their managers don’t empower them. In reality, and in the research I’ve done, no one can really empower you.

      Empowerment, like motivation, must come from within. Someone else can create the environment, remove barriers, encourage, but the employee must step forward.

      The reason for some employees’ reluctance is that they don’t really want the responsibility that true empowerment brings. The hard work of empowering employees means teaching, coaching, sharing information and trusting them. But, the employee must embrace that and understand the responsibility attached.”

  8. Since your boss says yes to all meetings I would set up a meeting with both he and I and let him know you are here to help and want to make sure he has everything he needs for his upcoming meetings. I would set up some sample guidelines and ask him to work with you on tweaking them to fit his agenda.

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