"Be interested, Not interesting" is touted as a way to get people to like you and open to you. It is perceived as a great wisdom to get to make friends and to build rapport among your subordinates. The great self-help guru, Dale Carnegie also said the same thing.

But, all these self-helps tactics are only good if the other party is willing to talk to you freely, which, in workplace environment, it is quite hard to attain. On one hand I want to be interested in my subordinates and who is showing empathy, on the other hand, inquiring too much on other people's private life is not only meddlesome, but also disrespectful and offensive depending on the situation and culture ( Just imagine asking your subordinate who is on leave yesterday, "where have you been? Anything happened?" It's very awkward!!)

I would like to add that based on my experience, conversing about common topics such as sports and holiday plan is only good if the other party is already willing to share...and I think most are not, especially to a total stranger and workplace boss. In fact, getting people to open up when I express interest in them is very hard.

The problem is not that I don't know how to ask opening questions, I do. But the problem is that when I ask, the reply from my subordinates tend to be just a one-liner, or conversation killer, like when I ask "anything interesting happening during weekend", they reply "fine". That's it. Conversation just ends there because it's pretty hard for me to follow up

How can I be "more interested" in someone without offending him/her?

Edit: I hired them and so they view me as their boss ( not merely a team lead). I guess it is very hard to be friend with your boss.

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    How long have you worked there for & been there manager? Have you come from outside their team or have you risen to there manager from being one of them? It can be depend on who you are to them, a manager or their friend. Commented Jul 8, 2013 at 14:39
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    @JoeStrazzere, I hired them, so as to whether they had bad exprience in the past... I honestly don't know and can't know until they open up to me
    – Graviton
    Commented Jul 8, 2013 at 15:00
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    Why do you want to be friends to them? Should they not fear your tread upon the carpet, your eyes upon their work? Should sweat not fall from their brow at the thought of inconveniencing you?
    – bharal
    Commented Jul 8, 2013 at 15:37
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    @bharal you're kidding right? Commented Jul 8, 2013 at 15:39
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    " On one hand I want to appear as a good boss who is interested in my subordinates..." This statement may divulge part of the problem. You need to be interested in your subordinates, not appear interested; if all you are doing is trying to look interested, people will see through that and - since you're being insincere - they won't trust you.
    – GreenMatt
    Commented Jul 8, 2013 at 17:32

7 Answers 7


Not all types of interest are suited to all types of encounters. I think Dale Carnegie has a great blanket rule, and most folks can improve their relationships by taking it to heart, but it's something where the same techniques can be applied generically to any situation.

Particularly with bosses/subordinate relationships, I think you're right to be a bit cautious and aware that the line between interested and supportive boss and creepy interrogator is a boundary that is best avoided. Here's some tips that work for me.

Personal Questions - Limited and Open Ended

Particularly in the beginning, keep it light and as open and judgement free as possible. As a person with a non-standard home life, I particularly appreciate questions that don't involve a need to address particular details, for example, good questions include:

  • How was your weekend?
  • How's it going? ( Particularly great for all times in the day - and I can talk about work or personal stuff - my choice)
  • Any fun plans coming up?
  • How is the (thing you mentioned before)?

Stuff that's worth avoiding until a detail has been shared willingingly include:

  • How's your family? (if we've been estranged for 10 years.... this will be awkward)
  • Any assumptions about family connections - even when there's obvious clues (pictures, a wedding ring, etc)
  • Assumptions about religion - granted, in the US, it's pretty standard to ask in December "what are your plans for the holidays?" - since even the folks who don't have a religious connection to the season are hopefully enjoying a point in the year where the pace slows a bit.
  • Is that (thing you mentioned) finally fixed/finished/disposed of/etc? - there's an implication (possibly unintended) that it should be complete by now.

Stay Positive & Respect Privacy

In my experience, it's not always about asking questions, but about being open when the information starts to flow. For example "Hey, great poster/painting/picture/art/toy/desk gizmo" - is pretty safe (no touching! - don't play with other's toys unless invited) - hopefully they wouldn't display it in public if they weren't willing to own up to having it.

I've gotten quite far in getting to know folks that work for me by being rigorously open to whatever comes my way - the first time a person comes to my office full of tension I know I've got to be as un-judgemental as possible. While I can't say "yes" to everything, being willing to admit that the person is entitled to their desires is very important. It's a good time for things like "I'm really glad you asked, but..."

A key thing is to find a way to follow up when something comes your way. Whether it's something light, like the admission of a love of a certain interest or hobby or something serious - remembering who told you what and finding an appropriate way to check in is usually a good way to show you care. Be respectful of privacy. When you first hear of something, take note of how publicly it was shared, and remember the privacy "settings" for future conversation. Examples:

  • medical/family stuff - generally keep it private - even if it was broadcast at the big company meeting. Exception: Asking about babies and child-cuteness - pretty much every new parent wants to and expects to show off baby pictures.

  • deeply held beliefs - be aware of who was there when it was shared - it's probably OK to politely inquire with that group, but possibly not the general public.

  • Hobbies, interests - generally not a big deal to bring up in public, but be aware that some folks are super private, and if it was only ever shared with you, don't be the first to mention it.

Cultural Boundaries and Power Distance

Realize that "power distance" - the separation between people of authority and people who are subordinate can vary widely and have many implied norms that aren't obvious if you are new or foriegn to the other person's dominant culture. Western culture, espeically in the US is very low power distance. Asian cultures can be very high power distance, although global culture means that many in foreign countries will defer to Western norms here.

Or at least that's the anthropological way to say it.

What that means is that many of the attributes that you might summarize as "deferential" are more prominent and firmly grounded in some cultures than others. For a given individual, mileage varies considerably - some are happy to be rebels and join in the typical aspects of the dominant corporate culture, others will not stray from what they learned in their own cultures.

This can matter a great deal in the sense of informal sharing between team members and their manager. What one person interprets as flattering interest from a manager can confuse another person entirely.

This fits in a lot with how much question asking or joking is workable... lower power distance people/cultures will probably volunteer more information and participate in more peer-to-peer like communication with their managers than people with an expectation of a high distance/more formal communication.


A really useful tool as a manager is to let a person work through the issue on their own, instead of instantly telling - that fits here, but it's usually best done privately - in a one on one. I suspect you can coach a team, but it won't come off as taking persona interest the way a 1 on 1 coaching will.

The general trick is to ask about something, listen, restate the answer in your own words, and ask a simple and very open ended question back. Generally the person can answer their own questions, but having an external ear really helps.

Probably best with work stuff, but I've used it a few times when I was in over my head in the realm of health care. Obviously if you aren't a medical doctor, you're likely, as a manager, to hit health care issues with employees that are beyond your realm of expertise. While your HR can help with the "is this reasonable?" question, the initial moment when the employee comes to your office and drops a big scary health issue on you is a great time for reflective listening. Particularly since most people involved in a serious health issue don't know the whole outcome yet, it's a great time to just help gather information and then take time to map out a plan for the person and the work they are doing later.

Talk less than you listen

Probably the hardest for me. You can tell personal stories once and a while - being the one to go first sometimes sets the tone - doing only asking and no sharing is creepy. Offering some light stories about yourself can set the tone for what's OK for your team to share.

Telling a story or two breaks the ice. Telling more stories than you listen to is the danger zone.

Addendum: Humor

An office with no humor in it is rarely anyone's idea of a good time. But just like it's important that you listen, it's important that joking be mutual. How you crack a joke is very much a matter of personal style, and an inauthentic joke simply isn't funny, in fact it's painful and awkward.

That said, here's some general joke guidelines:

  • You're the boss, not a standup comedian. Expressing work needs in a funny way or a quick humorous story or parable is fine. But if you find yourself going for the joke as the only form of positive feedback you get from your team - back away.

  • Stay away from sore spots or anything "below the belt" until you know people very well. Joking about yourself is usually safe, funny technical humor is usually safe (think of the site ThinkGeek.com), and anything you might read in Reader's Digest is probably safe. Jokes aimed at people on your team are chancy, jokes aimed at the upper management are politically riksy, jokes aimed at any protected characteristics will get you in trouble fast. The best humor is common humor that is safe for everyone to join in and laugh.

  • It's as important to laugh yourself when other's make a joke - it's a relationship builder. I often find that the ice is broken when someone else on my team makes a good joke and cracks me up. It shows it's OK to be a bit informal.

  • Some relationships never get to a joking point - joking is a form of interpersonal chemistry. There will be people on your teams that just don't share your sense of humor. Leave it be. As long as you get work done well together, accept that it might not happen.

  • Realize that some folks LOVE clowning around, and others hate it. The ones hating it may get quiet and withdrawn rather than say "this bugs me, I'm here to work" - so keep it in moderation and find established boundaries. For example, the end of a team meeting is fine... the middle is a big distraction unless it's breaking tension. Friday afternoons and days before holidays tend to be a lot more fun-filled than mid-day Monday.

My biggest rule of thumb is that I ask "Are we joking, or am I joking?". If my whole team is riffing on a funny idea, and I'm a part of it - great - we need those moments. But if I'm the only one making the humor, it's not the bethlakshmi show.

  • Thanks for the great answer. Sorry for not mentioning enough information in the question. The problem is not that I don't know how to ask opening questions, I do. But the problem is that when I ask, the reply from my subordinates tend to be just a one-liner, or conversation killer, like when I ask "anything interesting happening during weekend", they reply "fine". That's it. Conversation just ends there because it's pretty hard for me to follow up.
    – Graviton
    Commented Jul 9, 2013 at 9:22
  • @Graviton - In addition to what bethlakshmi says: Never tell your subordinates jokes, unless you want the joke to be an instructive parable. Otherwise, your sense of humor will falter and you'll become addicted to flattery. Commented Jul 9, 2013 at 21:12
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    @DeerHunter, Otherwise, your sense of humor will falter and you'll become addicted to flattery -- I don't understand this logic at all. Why is it so? Joke is a powerful form of technique I use to crack ice with strangers.
    – Graviton
    Commented Jul 10, 2013 at 2:39
  • @Graviton - your subordinates will laugh not because the joke's funny but because you're "da boss". A slippery slope. Commented Jul 10, 2013 at 3:48
  • @DeerHunter, without jokes, without laughter, all the small talks and personal questions are just interrogation that your subordinates have to answer and endure. I don't think this is a good way to build rapport
    – Graviton
    Commented Jul 10, 2013 at 3:54

Culture is one factor here but so is what habits have been established. Some examples:

  1. How often do you talk to your subordinates? Are there common "Good morning" and "Good night" messages sent around the office from you to them? This can be useful in leading into the "How are things?" question that you may want to ask though if you spring it on someone out of the blue, it can be quite awkward, sure. Some bosses I've had would manage by walking around and some would just leave things alone giving a bit too much autonomy to the subordinates, in my opinion. However, the point here is that if my boss comes to my desk how confident can I feel that it is an, "Uh oh, I'm in trouble..." situation.

  2. Do you have an "open-door" policy with your subordinates? If they bring something that you see as rather trivial how is this treated? This can be where your receptivity is tested in a sense as depending on how things are received would determine if I'd often bring things to my boss or not.

  3. Are there team lunches with your subordinates? Within Canada and the US from what I've seen this can happen and can be useful in building that initial bond. Sometimes the boss would pay and sometimes not, though the idea here is to have some time to chat in a sense.

  4. While you may have your preferred channels, how well do you what channels they prefer? Some people may prefer to talk, some prefer to text, some may prefer e-mail, some may prefer instant messages. This is something to consider as some people may prefer written communications over verbal ones.

  5. When expressing interest, there is something to be said for what kind posture and attitude do you project in this situation. There are people that express interest in a way that they appear to be a ravenous dog that just found a steak which could get people to clam up as if I feel that I'm about to be eaten alive, I may well just shut up at that point. The other side is to give those nods and "Uh-huh" messages that while it may appear you are listening, I can question the authenticity of that listening since there isn't any feedback. While there is the starting point of initiating a conversation, there is something to be said for keeping it going. Some people may often come back with a one upping story that can also lead some to shut down. If I tell a story that only leads you to tell something better that happened to you, how often do you think I'll let you get away with that?


You can start off with very casual things such as if you see one of these people waiting for the elevator or standing at the water cooler, try engaging in small-talk, such as:

  • "Hey, how's it going?"
  • "Boy it's hot out today!"
  • "Going out to lunch? What's a good place to eat at for pizza/Thai/sandwhiches/etc...?"
  • "That movie/play/show that just came out looks good - have you seen it/heard anything about it?"
  • "Man, these elevators are SLOOOOW!"
  • "Did you see they opened a new coffee shop across the road? I heard they have better coffee than the place next door/in the break-room/where-ever. I think I'll check it out tomorrow".

Not all of these topics might be relevant, but hopefully they can provide examples of what works in some workplaces. Since I don't know the details of your workplace and surrounding environment, I can't be 100% certain that these topics will be appropriate, but I imagine you can use these as a guideline to formulate your own topics if necessary.

Topics that are not work-related, and pretty uncontroversial are good to start with. Try to start with things that pretty much anyone can relate to, such as the weather, and slow elevators. Movies/entertainment/sports teams only work if the person you're talking to is also interested in such topics. Coffee is usually good, unless you're talking to someone who doesn't drink coffee.

Avoid topics that are potentially controversial and polarizing, such as religion, politics, sex, and money/personal finances.

If they respond to this, carry the conversation further. If you have regularly scheduled one-on-one meetings with your employees, you can try this there too.

This may warm people up to you, and eventually let them be more willing to share about other topics that you want to discuss so that you can appear "interested".

You may have to do this for a while before you'll get it to work. Not everyone will open up right away, it might take numerous conversation attempts to make them feel comfortable enough to talk. It also needs to be done often. Don't think it will work if you try it once a year. If your employees all use the same water cooler/coffee maker/break room/smoking area/common gathering point and you use a different one, try using theirs more often (maybe once or twice per day).

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    @bharal: These are examples taken from where I work, and have been appropriate for all but one of the places I have worked at (one place was a 2-story building and didn't have an elevator). The OP should be able to look at this list and determine if they are appropriate for their situation, or if they should formulate new questions, using these as a guideline. Commented Jul 8, 2013 at 15:51
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    +1 because you mentioned that this will be a process and won't be changed/improved immediately.
    – Jeremy
    Commented Jul 9, 2013 at 16:06

Be Interested, not interesting doesn't mean you should never share anything about yourself. The idea is to try and listen more than you talkk and not act like your life is more important, exciting, interesting, etc.

Part of gaining confidence is by trusting the other person first. Be willing to share something about yourself to show that it is appropriate to talk about non-work things. We're people and should have some sort of naturaly curiosity. They put in for vacation, let them know you're planning on a trip to "" and wonder where are they going. It's sharing; not prying.

Of course your topics should be appropriate. This isn't a license to tell everything about yourself. Not everyone will open up on the first attempt. You may have to ask directly or take another occassion to open the conversation.

Having lunch or order in a simple breakfast to break the ice. Unless it is acceptable, I'd avoid alcohol until you are on much more common ground.


I'd try and find some common ground with something not too controversial. Things like sports teams/results, where you're going on holiday etc are all good.

  • That would be only good if the other party is willing to share... and I don't think many are that open to you. In fact, getting them to open up when I express interest in them is very hard.
    – Graviton
    Commented Jul 8, 2013 at 14:31
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    Sometimes it can take time - people not opening up at all at work is not something I've really experienced. Don't try too hard, just try and be nice to them and spark up a conversation every now and again.
    – user319940
    Commented Jul 8, 2013 at 14:45

I work in a very technical discipline and I tend to have managers who don't know anything about my technical skills. I have alot of experience explaining things in english. I have no problem explaining things to management/executives. That being said, 'explain' means, I talk, 'you shut up and listen'. I have had issues with know it all managers who apparently have ADHD and interrupt as soon as I get 3 words out of my mouth. Then make some decision that makes my job harder. They get the '3 word responses'. Everyone else gets as much detail as they want. There is a guy I worked with recently where its '3 words then he spends 10 minutes responding to what he thinks I am saying (its not even close), and then doesn't shut up. He gets blown off.

First off, think about it. Make sure you are NOT interrupting them and then going off in a weird direction that is not germane to the topic. I have had managers do this to me in the past. I say 3 words, they jump on some word that stands out and go on and on about something that is not germane to the topic.

However, if you just want information and they refuse to provide it, you are entitled to the information. Tell them you want details and this is not sufficient. If they won't provide them, get someone who will. Some guys don't like providing details. I can't stand having peers like that. They tend to cause all kinds of problems because they break stuff and don't let the rest of us know what they are doing. People like this tend to be team killers.


Understand their psychological nature (Keirsey temperament for instance.) In some sense its taboo because we don't want to "profile", though gaining insight on the natural "thought strategies" others use can be extremely helpful. For instance, I'm an "INTJ", never ask me a personal question (or anything trivial for that matter), though if you asked me how I thought something works I would open up very easily. I (for instance) am addicted to sharing knowledge or observations. Each has their own and no where else does this manifest more plainly than in a purpose oriented environment (on the streets our mannerisms "average out" in context to the situation).

Ask what they think about various things related to the work you do. Find out how they describe the world and in what terms. This will help you speak their language. You don't need them to friend you, I think you need them to relate to you. Find value in their perspective.

Good luck.

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