Three Ways to Move Ahead in Your Career at BigCo

In which I discuss career development in large organizations and three strategies that can help anyone looking to get ahead when they’re feeling stuck.

I recently caught up with a close friend the other day about the “bamboo ceiling” mentioned in the Paper Tigers article by Wesley Yang. We’ll call him Dan. Dan is an Asian-American guy working in a large organization – he has been there after finishing graduate school awhile back. He’s been trying to move into a different position for a while – he’s currently working as a data analyst but wants to be doing something closer to policy development since that’s what he studied in grad school and it’s what he’s really passionate about.

Dan has been rejected a few times when applying to more policy-oriented positions within the department and thus feels that he is hitting the “bamboo ceiling”. Now there may or may not be an anti-Asian sentiment in his department but I don’t think his situation is hopeless. I believe my friend Dan is lacking the “political sense” needed to move up.

As an aside – I grew up hating the idea of “playing games” – whether it came to dating girls, negotiating scholarships or other “political” stuff. It annoyed and frustrated me to no end. As I’ve gotten older and wiser, I’ve learned the lesson that management guru Tom Peters has hammered home – “Implementation is about first, middle and last about politics – that is, dealing with your fellow human beings”. And as a guy who likes to make things happen – I’ve begun to study and sometimes relish the art and science of the political game, which, it turns out, is less “dirty” that I originally thought.

I think there’s a whole blog post or three to be written about what “political sense” means but for the sake of brevity, let’s call it: understanding how you can get people to help you reach your goals.

But let’s cut to the chase – after a long conversation, we identified three things that Dan could do to move ahead in his career, and I’d like to share those ideas with you here.

Note: I haven’t worked in a large organization (mainly startups and small businesses) but like Sebastian Marshall writing about getting a raise, my thoughts here are based on observation, reading lots, and talking to people who’ve been successful. Take them with a grain of salt.

Identify and Observe The People Moving Ahead

Dan has seen some people that he’s felt were at his level / similar to him that earned promotions or exciting new positions while he hasn’t. Whenever I hear about a situation like that, I treat it like reviewing the results of an experiment – you started with more or less the same but got different results. What caused it?

Dan noticed two things in particular that these people who moved ahead did:

  • They went to Happy Hour and made friends with other folks in the department. Dan is a little uncomfortable with going to Happy Hour – he doesn’t know what to say, who to talk to, what to drink, etc. So he doesn’t go.
  • They left positions they were unhappy / dissatisfied with. For a variety of reasons that include needing a steady paycheck to support his family and simply lack of courage (his words) Dan has stayed in his current position even though he isn’t quite thrilled about it.

I think he’s noticed two interesting things already that he could potentially use to increase his chances of getting the promotion. If Dan went to Happy Hour – . But we’ve just started. Let’s keep the advantage stacking going.

Ask Them For Advice and Bring Them to Your Cause

You can learn only so much by looking from the outside. I encouraged Dan to reach out to his colleagues who have moved on to bigger and better things and take them out to lunch – so he can hear directly from them what they felt made the difference in their careers.

Dan isn’t sure about this because he doesn’t know these colleagues that well and doesn’t feel he can trust them. I think he’s a little scared of getting rejected (which is totally normal) but that the consequences of reaching out are high upside no downside.

Imagine getting emailed by a distant coworker or acquaintance with something like

Hey (their name),

I’m Jason Shen, from Department X at BigCo. We’ve met briefly a few times and I’ve been a big fan of your work – especially on Project B. Michael from my team also always has good things to say.

I’m looking to add more value at BigCo and advance my career – and you seem like a great person to talk to about this. I was wondering if I could take you out to lunch sometime this week or next and just learn more about how you’ve been able to do so much good stuff at BigCo. I’d really appreciate it.

I’m free Tues/Thurs/Fri this week and Mon-Wed of next week. Let me know if that works for you.

Looking forward to hearing from you,


I find it hard to imagine someone who wouldn’t be flattered and impressed by an email of this sort. Even if they end up not taking you up on the lunch, you leave them with a great feeling about you.

And if you DO get the lunch? Bring a notepad, have some good questions laid out in advance, take copious notes, ask if they know someone else you could talk to, pay for lunch and follow up! After doing this for a couple people, look at the things that several people said helped them and that make sense for you and then DO THEM.

Again, no experience working in BigCo or Gov’t but I imagine you’d agree that doing this would be greatly beneficial to your career.

The benefit of this is not only in the new things you learn and do, but also the connections you’ve made. If you work hard to stay in touch with these new lunch buddies and tell them what you’ve done after your conversations – they will naturally become your friends and supporters – and that can be invaluable in more ways than one.

Dan did think of one colleague in different department that he feels comfortable reaching out to and I’m looking forward to hearing how this goes for him.

Volunteer to Lead a Special Project / Visible Extra Work

I can’t take credit for this idea (nor really can I take credit for the other ones either … they’re all pretty straightforward) but this one in particular – comes from the awesome Charlie Hoen – a twenty-something guy who, after struggling to find a job as a promising recent grad, has gone on to work for Seth Godin, Ramit Sethi and Tim Ferriss in some unbelieveably awesome gigs – and helped make Four Hour Body a megahit.

Anyway, this is from his presentation called Recession-Proof Graduate – which has been viewed over 76,000 times:

Now pay close attention to what I’m going to say next, because I’m about to mess you up with the truth.

In terms of rapidly advancing your career path and finding work that you actually care about, there is one option that stands above all the rest. That option is…

Free work.

Charlie goes on to give some great advice about emailing employers and offering to doing free remote work on a small project and blowing away the potential employer, paving the way for real work in the future.

We can adapt this to Dan’s situation easily – he could reach out to someone influential in the policy department and make the same offer – he wants to take on some additional work and learn more about how this team operates and would be happy to take on some work that needs to get done.

It’s ok if the first job includes a lot of grunt work or very small in scope – this is a get-the-foot-in-the-door technique. Now that he has this little project, he has an excuse to connect with other people on the team to get feedback or necessary information to complete his task. Because of the low expectations, Dan can over-invest in the project and hand back WAY more than anyone expected. That’s going to make him look really good next time a position opens up in policy because:

  1. The other members of the team know who he is and is comfortable with him vs a stranger
  2. He did a killer job on project X and knows how this team works

Those two facts are going to be his twin cannons as he blasts his way to a great new position.

Look none of these things are particularly hard though but they require taking initiative and doing things that are outside your job description. Many Asian Americans, as I mentioned in my post Loud. Arrogant. Rebellious. Asian., have been taught to keep their head down and do what they’re told – which usually does not result in an advancement.

I hope this (rather lengthy) dissection of my friend Dan’s career is helpful to you. Let me know if you have any thoughts or other useful ideas for him in the comments!

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