Getting the boss to communicate his schedule

Question: I’m an executive assistant to the president & CEO who, in his 23 years of business, never really had an assistant before. He’s mentioned once or twice that he doesn’t know how he ever did it without me.

I think he understands the benefits of having an assistant, but he still does not “keep me in the loop” as I expect he should, mainly concerning his schedule. I sit in a room directly behind the receptionist and next to his office. He’ll walk right by me and tell her where he’s going to be. I thought maybe it was because she’s been here for so long, but he also does that with the temp who is currently filling in for the receptionist.

From the road, he’ll call everyone else—rarely me—and tell them what he’s doing for the day. I have told him that to successfully perform my job duties, I need him to communicate his schedule to me. I even set us up on a shared MS Outlook calendar to make it easier. He said he would try harder to keep me informed, but it’s not working. I’m thinking about calling him every morning to check in. Is there anything else I can do?? Please help! — A.S.


I think your boss must feel like having his shared calendar with you is enough communication, and that with your responsibilities, he may feel that telling someone else in the office you will know if you have to. Sometimes bosses don’t like to be kept track of like you are his mother and enjoy the freedom of just letting someone know where he will be(whoever he chooses) if he thinks he needs to other than what he has put on his calendar. I would let it go and not worry about it. You probably have enough to do and just assume that he has let someone know in the ofice on how to reach him if it is not on his calendar. If you quit asking, he may just tell you where he will be instead of the others one day.

Maybe if you ask him to sit down with you each morning to review his calendar – explaining that you need to be aware of his whereabouts in case clients/employees are trying to contact him. Explain that you feel a need to do this because you are still not being included. This might get to the point so that he starts sharing immediately and the meetings can be eliminated after a while.

I agree that he just probably isn’t use to having someone ‘assisting’ him, but you need to keep selling the idea to him – that you are an asset to him but it will only work if you know what is going on. He may not think he needs a ‘gatekeeper’ now, but the day may come and you need to be prepared – he is showing you a disservice and this could reflect badly on both of you if you can’t answer a question of his whereabouts.

I think it is very helpful for you to know his schedule, especially if you receive his calls when he is out. People frequently come to me as the person who should know when he will be in, etc. If he could leave you a voice mail of his weekly schedule that would be helpful, even if it does change day to day. At least you will have a general idea of what is going on for the week.

I print off my supervisor’s calendar for the next day about an hour before the business closes for the day. This gives her an opportunity to see and to comment on what the next day looks like. This would be a good time to ask if there is anything that should be added. A lot of times meetings get scheduled as a result of a phone call. Since the boss set it up, you may not hear about it. Habits are hard to break. Give your boss time to come around to a new way of operating and be willing to help along the way. It’s something you believe in.

I had the exact same problem when I started working at my present position. Realizing that if it continued I would never get to fully do my job, I became assertive and told him I was taking the first five minutes of his day to go over his schedule and discuss upcoming tasks or projects. It was uncomfortable at first, especially when he had nothing to share. However, with persistance, he has now come to rely on these exchanges and on me, making my job a lot more fulfilling.

He probably trained himself long ago to use the receptionist to manage his day, so he’ll continue to do just that. I would ask him if he would mind the receptionist keeping you up to date. He may just think that is the perfect solution.

Be a good, and I mean GOOD listener. When your boss informs everyone else of his plans for the day, be sure and keep an ear open. Then you know where he’s headed.
If he has a blackberry, send him emails of his telephone messages as you receive them.
If he has an appointment, and he is on the phone, you can always send an email reminding him of his time constraints. (EX: “Your next appointment begins in 5 minutes)
Make a standing appointment once a week to have a sit-down meeting with him and take your calendar in with you. Go over everything he has going on for the week, and anything beyond that he brings up.
If he travels, make sure you offer to organize all his travel for him, even down to offering to book his wife into a spa or special retreat if she goes with him and will need something to do during the day.
Make note of all his important dates, wife’s birthday, his birthday, bosses’ day, etc.
Once you quietly make those moves, he will get used to you being there, and will rely on you more than the others.
A word of warning, don’t get caught in the trap of feeling angry that he is not doing what you want him to do. Believe it or not, it can show, and make him less likely to come to you with anything…so be careful and be patient. Do a good job and be consistent.
Good luck!

It may be helpful if you have not done so to have a brief meeting with your boss and the receptionist to have a clear understanding of everyone’s expectations and roles. Monthly 15-20 minute meetings between the two of you will ensure you are meeting his expectations & ward off any surprises or mishaps. Since he did not have the privilege of an executive assistant for 23 years (which is an extremely long time) I’m sure part of his mindset may continually to do business as usual although things are different. Even though you are valuable to him, perhaps things were not broken enough for him to see the greater significance as quick as you need him to. Also, take a breather and concentrate on other aspects of your role because if needed you can find him via the receptionist. Work on managing her role in a sense and all the tasks to be done and not so much his every move. Also, most executives on his level probably prefer saying things to one person and one time. Your situation should move you to think outside the box and find a balance that will create a “win win” situation for the both of you and the receptionist. Just remember with patience your ship will sail!

I think that it may take him a while to break his old habits. I agree with the brief meetings in the morning, go over his schedule and ask if anything has changed. If nothing has changed wish him a good morning and go back to work. Keep it short and sweet. I had the same problem, eventually things will work out. Until things change talk to the receptionist and ask her to either call you or email you when he leaves. I don’t think he’s trying to keep you out of the loop.

He hasn’t gotten used to the fact that he has an assistant. He just needs some time to make the transition. Several years ago, I had the same problem, but if you keep being persistant like you are he will definitely come around. Believe me.

I have experienced the same situation. I found that the direct, proactive approach worked best for me. I didn’t wait for my boss to talk with me. I scheduled a regular 1 on 1 meeting for every Monday morning for about 20 minutes and asked specifically what he knew was happening with him during the week (e.g., “What should I know about your schedule this week?) and what he anticipated happening. I also reminded him to call me with any changes and thanked him for making my life easier and my job of supporting him more effective.

Another method I used to help the situation was to make sure that I was the only person who scheduled his meetings and that I was copied on all of his meeting requests.

Because I had a good relationship with my receptionist and other coworkers, I asked them to direct him to me when he started talking about his schedule (e.g., “Thanks for telling me that. Does Jane know that, too? Maybe you should let her know.”) After a few weeks he became better at passing on information to me but reinforcing the behavior was an ongoing effort on my part.

I don’t agree that letting it go and not worrying about it is a good solution. Inevitably, something important in your boss’s life will be scheduled (a meeting with his boss, a flight to another location, etc.), you won’t know about it, your boss misses something important, you don’t look good and, more importantly, your boss doesn’t look good. After all, isn’t part of your function to help keep your boss on track and “assist” him?

Who receives your bosses phone messages? In our office, our staff rings me with messages for my boss. This keeps you aware of what is currently on his plate. If he is in, I buzz him with the info of who the caller is and to what it refers; if he is out, I take the message. Sometimes, I can give the caller the info he’s looking for without any interruption to my boss. As his assistant, you should be able to be his buffer. In order to do that effectively, you’ll need to know his whereabouts. Initiate this with the receptionist and explain to her why it is necessary. Before long your boss will realize how well you shield him from a lot of time consuming return telephone messages, you won’t have to make a plea for better communication; he’ll willingly and without a thought share with you his daily itinerary.

You’ve gotten good advice. Always remember that if you give good value, if whatever routine you work out adds a positive benefit and makes his life easier, he will eventually commit to it. Tactful persistence is what you need. P.S. Always be discreet about his schedule if you sense it’s necessary.

I also work for a boss who was not used to having an assistant. (Previously, I worked for someone who relied on me a great deal, so this was quite a change.) At first, this made me quite uneasy, because I felt like I wasn’t doing a good enough job. I decided to sit down and talk to him about it, which really helped. It took some time to develop our working relationship, which is now great!

My boss prides himself on being “low maintenance,” but I have learned how to work with this situation. I check in with him several times a day (often just popping my head into his office and saying “What can I help you with right now?” He’s getting much better about delegating things to me (after six years!) but is still quite self-sufficient. Fortunately, this has freed up a lot of my time, and I have been able to take on more responsibilities in other areas (such as Human Resources).

First thing every Monday morning I “borrow” my boss’ personal calendar and make sure mine matches his for the week. Before closing time each day I type out and give him the appointments I have for him for the next day. This gives him an opportunity to let me know of any added appointments I may not be aware of.

I let my staff know that I need to be aware of where they are in case an emergency with their family or at the office should arise. They seem to understand that better than just asking them where they will be.

I too worked for a boss that had not had an assistant for 18 years of his career at the same company. He had no idea what he wanted me to do or what I could do for him. I had to be proactive and look for things that made his work day better. I needed to know where he was because people came to me looking for him for signatures etc. I printed his calendar from outlook everyday for me and him. Soon he was asking me to make appointments for him and sharing his whereabouts. I had to make a big deal about knowing where he was before he got used to letting me know. It takes a while for a person who has not been assisted before they realize how valuable an assistant can be. I hope you find the perfect balance for you both.

You need to retrain your boss to deal directly with you and no one else. To do this, ask the receptionist to re-direct him to you when he approaches her about his schedule. Also, when you see him walking by your office (as if he’s on his way out the door), stop him before he can get to the receptionist’s desk and give him the opportunity to tell you where he’s going. When he’s out of the office and calls in, instruct the receptionist (or anyone else who receives his calls) to direct those calls to you. After doing this for a while, he’ll be retrained.

I have a hard time with that also, but I double as Administrative Assistant/Receptionist. I send an email out every Monday asking everyone (I have three people to keep up with) what their schedule is for the week. Or you could try talking to the Receptionist and ask her to inform you whenever he tells her what he will be doing.

The answer to the new supervisor managing new employees, Get to know them individually, have a mini staff meeting for everyone to introduce themselves, what their functions are to run each day smoothly. Offer how you and everyone else can assist them in down time. To set a positive note from the get go…