How Do I Speak With The CEO Minus His Secretary?


I work in an executive level position for a company CEO. Our office has three persons – the CEO, the secretary, and me. The secretary reports both to the CEO and me, but I rarely use her services. The secretary and boss have adjoining offices at the front of our building, while my office is close by, but not directly adjoined to the CEO’s. The secretary and boss converse frequently because she answers his phone, schedules his appointments, etc. Because of the location of my office and the nature of my work, I talk to the boss less frequently than the secretary does, but still meet with him several times a day.

My problem is this. Nearly every time I try to have a friendly, casual conversation with the boss in his office (about something non-work related), the secretary immediately jumps up from her desk and stands in the doorway to listen. She does not do this when any other employee is in his office. Overall, she is a nice person, but she does not seem to understand or respect personal boundaries. I am sure she is just interested and wants to join in the conversation, but it is disconcerting and irritating. I think part of establishing a good working relationship with your boss is being able to have informal, friendly, one-on-one chats, as well as more formal, work-related conversations. I don’t seem to be able to do this without his secretary immediately walking into the room.

Now, the boss accidentally calls me by his secretary’s name much of the time. He catches himself immediately and is very embarrassed, but

her name slips off his tongue whenever he starts to address me. I think a big part of the reason is that he talks to her all the time, but when I am in his office, she is standing right behind me. I feel like I have a conjoined twin!

This is harder to address than you might think. The secretary is a very sweet, naïve person whose feelings are easily hurt. I don’t know how to address this without making her cry and humiliating her. I have dropped very strong hints, I have walked out the office in a huff, I have given her the evil eye, but she absolutely doesn’t “get it.” Any suggestions? This has been going on for a long time and I am at wit’s end. Thanks for your help.


Assistant To The CEO


Dear Assistant To The CEO:

I can imagine this is frustrating and irritating–and particularly difficult if the secretary seems to mean well. Obviously I do not know your complete situation, so some of my response may not fit your workplace. However, perhaps it will give you a place to start.

1. First, do a general assessment of the situation to make sure you see the big picture. Could there be some other reason the secretary comes to the door when you are talking and stands right behind you? You say she is very nice and sweet and that may be true, but could she have a different feeling about the boss than you think, and as a result, not want you talking to him alone? Does the boss have different feelings for the secretary than you think and that’s why he calls you by her name on occasion? I’m not judging that or implying anything! That is probably far from the truth of the situation. I just think it’s wise to be look at the situation from every possible perspective.

Do you generally get along with the boss? Is there a reason he would not want to have a non-business conversation with you? That may sound like a foolish question, but it’s worth thinking about. Perhaps the secretary thinks she is protecting him in some way.

Is your relationship with the secretary very friendly the rest of the time? Could it be that the real reason she comes over when you’re talking is because she wants to talk with you? Does she assume you are automatically including her when you have a non-business conversation? Are the topics you discuss of a nature that she would naturally be interested? Does she contribute to them when she stands there or does she only listen? That would say a lot about why she is interjecting herself in that way.

How long does she stand there? Does she leave if she is not included in a few minutes? Does the boss include her in the conversation or does he seem to resent it or find it strange as well? One way you can tell is if he looks over your shoulder at your conjoined twin and smiles as he talks, to include her.

Have you ever questioned her presence? Have you ever mentioned it to the boss? Would you say she is much closer to him when it comes to that kind of honest talk?

So, that’s the first thing to do: Figure out how it happens, what seems to be going on in her mind and his mind when it happens and what you do when it happens. 2. Here are some possible things to do–any, all or none of them might work. But, maybe you can adapt them.

*Set up a lunch date with the CEO on a semi-regular basis, if you have that status and the company works like that. Talk about the things you normally think you’d be talking to him about in his office. Suggest it as an every two week or so event for a while. That might establish your role more firmly in the secretary’s mind and also remind the CEO there is more than the secretary in the office with him.

*Make an appointment with the CEO to come in and talk about a specific work issue. If your office works like this and it is comfortable and acceptable, ask him if he wants a cup of coffee or a soda and bring one in for each of you. The meeting automatically becomes more casual that way. Discuss business, and then segue to the more friendly conversation.

*Start using the secretary more for delegated work, if she reports to you. Establish that you are more than an office friend, that you are also a supervisor, whatever your title or organizational role in relationship to her. The next time you want to have a private conversation, bring her a small project or task and ask her to do it. Then, go to the boss’s office and have your personal conversation. If she comes up behind you, you are in a better situation to ask her if the work is done. If it isn’t, you can say you need it in a few minutes or whatever. That might send her back to work. *Set the stage for a while by asking the secretary to let you know if your phone rings because you’re going to be in a conversation with the CEO. This will require you to have something to say besides “Hi.” But, it will put her in the position of needing to stay at her desk.

*When you’re going to talk to the CEO, don’t just stand at the door as though you are only popping in for a few seconds. Ask if you can come in and sit down. Make it a formal casual conversation! That might be less to seem like an office chat to which everyone is invited.

*When you want to have a conversation with the CEO, do not chat with the secretary first, head straight for the CEOs door. As it is now, the secretary may think you intend for your conversations to be between the three of you because you have smiled at her and now you’re standing in the doorway and easily can be heard by her.

*If she walks up behind you or in the doorway, stop immediately, as though she interrupted you, and say, “Mary, did you need to see Jim?” If she says no, ask if she needed to see you. That will force her to explain and she may say she was just interested in your conversation. Smile a big, friendly smile and say, “Oh. Well, I’ll be finished here in a few minutes and I’ll come over to your desk and chat about it. Thanks!” That’s pretty blunt but doesn’t sound mean.

*Converse about more casual things, by email. That way you can get his personal comments and have personal contact, THEN, mention his email in the conversation when you’re talking to him. That way if you’re interrupted you’ve at least shared thoughts.

3. The secretary may be as nice as you say, but it is not your responsibility to feel embarrassed that she doesn’t have the wisdom or courtesy to let you have a private conversation or even just a casual conversation, without interjecting herself into it. This is particularly true since you and the CEO are apparently higher in status than she is. Likely the CEO has been so friendly that status has been forgotten in the friendship of the office. I’m not big on status, but I am big on keeping a separation in business.

If you have left in a huff or given her the evil eye even once, you can bet she knows you were resentful for some reason. So you have to ask yourself, if she is an intelligent person, why she wouldn’t pick up on that? That brings me back to my starting questions.

4. If you conversed more with the secretary, apart from when the boss is around, do you think that might help? It’s possible she is interested in building a better relationship with you and is trying to achieve that.

5. According to how well you know the CEO and how comfortable you are with him, ask for his help with this. Explain that you like the secretary and wouldn’t want to hurt her feelings, but you would like to be able to have a personal conversation with him without her jumping up and coming into the room. Ask him if he has insight about it. He won’t want to get in the middle of it, you can bet and may say it doesn’t matter. But, you might ask him if he’d do you a favor and next time ask her if she needs something. Ask him if he would do that every time until she gets the hint that you’re having a private conversation.

6. This last is scant consolation: You are probably right that she doesn’t think a thing of it. She may consider herself part of your team to such an extent that she figures you want her in there and would include her by choice. As I wrote this I thought about the times when I have likely done the same thing, thinking everyone was one big happy family so of course they’d want me to be part of their fun talk!

I think you’re correct in wanting her to allow you some one-on-one time. Still, you don’t want it to be you and her grappling over him! So, it all needs to revolve around a business reason for wanting to have uninterrupted conversations. Be prepared to make a one or two sentence statement about what you want and why, just in case you ever have the chance to say it!

I hope these thoughts will help you find a way to deal with this. Otherwise, it will end up being the drama you are trying to avoid. Frankly, I’d tolerate it before I’d create an issue with it. You will feel constrained around her forever if you confront her and ask her to stop doing that. If it gets so bad you must approach it that way, so be it. But, it would seem that would be truly a last resort.

If you have the time and wish to do so, let us know what develops with this. Who has access to the boss, is not so important as is the sense of we’re in this boat together. That’s what our signature WEGO means.

Tina Lewis Rowe

Tina Lewis Rowe

Tina had a thirty-three year career in law enforcement, serving with the Denver Police Department from 1969-1994 and was the Presidential United States Marshal for Colorado from 1994-2002. She provides training to law enforcement organizations and private sector groups and does conference presentations related to leadership, workplace communications and customized topics. Her style is inspirational with humor.