Avoid a Classic Mistake: Don’t Be a ‘Try Hard’

I've written before about how your relationships at work are everything.

If your bosses like you, you get better assignments, more favorable reviews, honestly you even get paid more and promoted over co-workers that probably deserve it more than you do (on work merit alone at least).

Such is life. Favoritism is not a new thing. And it is very, very common on Wall Street.

So a lot of junior level employees reaaaaaally want to make deep connections with their higher-ups.

And they screw it up big time.

Imagine this:

You're a partner at a firm. You have co-workers you've known for years that are legitimate friends of yours. You have calls and meetings that could make you seven figures in one day if things go well. And you have a junior level employee that's constantly hounding you and trying to force you into conversations you don't want to be in.

You're going to HATE that person. And you're going to distance yourself from him/her as much as you can.

This exact mistake actually cost me a full-time offer after my first summer internship, and was what caused me to start studying psychology and persuasion in the first place.

(I know this because they told me so to my face. Ouch!)

So that's what we're going to avoid :-)

I can sum it up in 5 words:

Don't Be A 'Try Hard'

Vague advice right? So let's dive into exactly what that means.

The first thing you want to avoid that makes you a 'try hard' is forcing conversation.

This is the one I was most guilty of as an intern.

One example I can still remember vividly almost 10 years later. I was at a company event, walking by two of the partners talking about basketball.

This is a topic that I loved, a sport I played and watched religiously. It should have been easy for me to connect on it.

But instead of storing that information away - knowing I could bring it up later and it would go well - I jumped in with "Oh, are you guys talking about basketball? I love basketball!"

I was INCREDIBLY over eager...

That is the first thing I see people screw up a lot and that's the lesson I had to learn myself.

When you're talking to senior people about topics besides work, you want to talk to them like they're people - exactly like you would with a new friend.

(Minus the swear words and slang, depending on your friend group...)

It's okay if you're excited some of the time but if you are constantly being effusive like, "Oh, you love fishing? That's so cool!" "You love golf? That's amazing!" It's going to be off-putting.

View post on imgur.com

Liking you and respecting you are two different things. If your behavior reminds people of this little dog, you're going to have trouble moving past being a mid-level employee...

Tons of people like golf. Wait until you learn something about them that's actually amazing before you say, "Wow that's amazing."

Does blowing smoke up someone's ass work? Yes.

Does it work if they know that you're doing it? Not nearly as well.

So hold back on that over-eager, constantly excited suck-up style of conversation. Treat your bosses like people, instead of like somebody whose attention you aren't worthy of.

Those are the three keys of it - don't force conversation, don't be over eager, don't overreact.

So what do I do?

Alright, so it's easy to tell someone what NOT to do.

The tough part is, what SHOULD you do?

And the answer is - ping for their interest.

Especially when you're talking about your own life or your own hobbies, but even if you're talking about theirs, don't go into a 10-minute monologue uninvited.

Without any hints from them that they want to talk to you right now, if you just launch into a 10-minute story about your violin concert or your MMA competition, you run the risk that they're not going to be interested.

Maybe they're busy, maybe they just don't care. Either way, they'll get bored and want to escape the conversation, and then they're going to try to avoid you in the future so they don't get trapped again!

View post on imgur.com

We've all seen this in friends or in the office. When there's a person who doesn't quite know how to read interest and they trap you, all you want to do is get away as quickly as you possibly can.

How to ping for interest

The key here is to read the other person.

Their interests

For example, imagine that someone says that they really like golf. Simply ask them a question about it or make a statement about it. If they give you a short one-sentence response, then don't keep plowing down that conversational thread. Just let it go for now.

If you get an excited response, or a multi-sentence story about it, then you can start to open up and engage in a back and forth dialogue about it.

Your interests

If you want to ping for something that YOU have interest in, wait until you get asked the inevitable Monday morning question of "hey, how was your weekend?"

Now is your chance to toss several seeds out there and see what plants. Something like "Oh, this weekend was awesome, I did [x], [y], and [z]".

That's it, you're done. No huge stories, no 5-minute monologues. By throwing out multiple topics, you're basically making it a 'choose your own adventure' for the other person. If they're interested in any of those 3 topics, they can ask you more about it. And if they ask you more about it, then you have the green light to start to elaborate :-)

(Note: if this is someone you already have a great pre-existing relationship with, then obviously feel free to give a longer immediate answer. Once you're close with someone, you don't really have to manage individual encounters like this. This mostly applies to relationships that are in their early stages)

And if they DON'T ask any follow up questions - let it go for now. Nothing lost, no harm done. You can even bring the same topic up a week or two later and you might get a different result, depending on their mood.

Remember, these are long relationships. You don't have to force everything to happen in one conversation.

In Sum

  1. Don't force conversation
  2. Don't be overeager
  3. Don't overreact
  4. Ping for interest before diving into 10 minute stories with people you don't know well

Do this and you'll avoid being a try hard. As a bonus, these types of dynamic back and forth conversations feel much more natural, and will lead to a stronger connection than simply forcing conversation.

By the way, let me know in the comments if you guys like posts like this and I'll do more! Otherwise we'll stick to YouTube videos :-)

Comments (23)

Best Response
Sep 9, 2016

I'm amazed people need threads on how to speak to someone.

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Sep 9, 2016

Took the words right out of my mouth. If you're over 22 years old and don't know how to talk to people then you should probably step back and reevaluate yourself. It is really strange how many forums I see like this or "how to talk to girls" "where to meet girls", etc.

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Sep 9, 2016

"where to meet girls", etc.


Sep 9, 2016

People even need life coaches these days

Absolute truths don't exist... celebrated opinions do.

Sep 9, 2016

Really?? You must have a rare group of Wall Streeters haha. I'd actually bet that there are just as many people who don't get promotions or top bucket bonuses based on "fit" (inability to connect well) as there are people who miss it due to lacking the technical skills or work ethic

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Sep 9, 2016

I'm amazed people need threads on how to speak to someone.

You beat me to it.

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Sep 9, 2016

You wrote an in-depth guide on not being a try-hard. Odd.

Sep 9, 2016

Isn't this common sense? Like 5 years on an elementary school playground would teach you this shit. Then again, anything social comes rather unnaturally to our baller 125 lb analyst class.

I think- therefore I fuck

Sep 9, 2016

To be fair I've seen plenty of VPs at investment banks try too hard to impress their partners or their peers on the buyside. I think social struggles affect a % of people at all ages

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Sep 9, 2016

The interesting part about this thread is that initial interviews are gauged to see if you'll be a fit for the environment and the people in the area.

Boy oh man, how did you manage to screw it up? All you had to do was show up on time and get crap done, say hi to a few people and do whatever you're told. Performance eval's are base on these criteria.

Sep 9, 2016

Because a good chunk of people aren't good at showing their true selves when they feel nervous or under pressure. So they might be able to do well in an interview, but then try to hard to connect with their bosses, instead of just being comfortable being themselves in what they perceive as high pressure moments.

Same reason some people don't do well on dates, or giving speeches, or presenting in meetings, etc. Most people do well 95% of the time but drop the ball in the situations they most want to do well in.

Same way a basketball player can miss an easy shot when the game is on the line.

In my case, intern Ben interviewed really well but felt pressure to impress to get the offer. It wasn't until I was locked into a full time role that I didn't feel pressure to force a connection onto my bosses.

It isn't just young people that display this behavior. I've seen multiple VPs that tried way to hard to impress their partners

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Sep 13, 2016

Most people do well 95% of the time but drop the ball in the situations they most want to do well in.

Sep 9, 2016

Is trying not to be a try hard like a double negative, or something?

Sep 9, 2016


Sep 9, 2016

Good stuff

Sep 10, 2016

People are pretty hard in the comments. I find this post was quite good - I am sure you are all innate masters of the art of making it into banking and the wallstreetoasis audience is a bunch of 30 year old MDs. For the ones that are not quite at that level well done for writing this. I am sure it will be helpful.
Agreed on everything you said, and also good on them for giving you brutal feedback it helped you think a bit.

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Sep 13, 2016

You'll notice the classic disjoint between the Cert. Users who's general response is "nice write up, good points for the younger chimps out here," and the anonymous dudes trollin with their "who on this site doesn't know the finer points of conversing with superiors."

Edit: the use of your name was completely incidental, albeit hilarious.

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Sep 13, 2016

Conversation 101 for socially retarded undergrads.

Sep 15, 2016

People are putting you down for no reason whatsoever. If you spend even a few minutes at a networking event, you can definitely tell that a LOT people need to read your advice. Good stuff man.

Sep 15, 2016

Be nice to people, and having an interesting hobby helps, too. If all else fails, work in a socially awkward geek-tolerant field like quantitative finance or machine learning.

I'm tempted to troll Ben on this, but as the self-appointed rustbucket-driving Suze Orman of WSO, I also find myself repeating the same obvious advice that 50% of members don't get and the other 50% either vociferously disagree with (don't live in Manhattan if you don't have to your first year or two, go in-state to avoid student debt) or think is mind-numbingly obvious, obnoxiously self-evident,, and boring (get your 401k match).

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Sep 16, 2016

I actually found this article highly useful and something that needs to be shared at the intern / fresh grad level. We sometimes tend to forget the mistakes we've all made at the beginning of our own career and can be extremely hard on our juniors. Social skills for some are innate and for some require practice - in this case, most of those who already know what Ben wrote are simply not the target audience.


Sep 17, 2016
Sep 18, 2016