Reader question: “What to do once you’re inside?”

Reader question: “What to do once you’re inside?”


Newsletter reader recently got a new job (congrats SD!) and sent me the following email:

“I’ve joined a startup in NYC as a Product Specialist. First week in so far and I really like it. Question: I feel like there’s a lot of writing out there about getting what you want, but once you get it… Then what? Once you’re in a new organization, what should you look for? What things should you keep in mind? How should you behave?”

I like this question because it illuminates the education we lack about marrying being a good employee with growing as an ambitious and independent professional. The reader understands that if he neglects these questions, he will fail to leverage his new partnership. He wants to exceed expectations of himself and his employers so he can be rewarded with more skills, money, respect, autonomy, and optionality, both in his new job and in future career opportunities.

Some caveats before I jump into the advice:

  • I don’t know what the conversations and negotiation between the reader and his employers was like before being hired. The specific expectations from both sides may vary depending on the reasons both sides decided to invest in each other.
  • James Fallows says that the question that distinguishes tactics from strategy, when you consider any move, is “how does this end?” I don’t know what the reader wants for his life in the end. It may be short term income to transition into his own startup six months from now. I will dispense some ideas assuming that he wants to grow in the company.
  • I assume the company is average, with average employees. While most of this advice is universal, one may be spared a lot of office politics nonsense working for some great companies like Google.

So, how to grow in a company once you’re inside? Some thoughts:

  • You are an investment who was brought in to solve a problem. Your minimum obligation is to solve that problem without requiring additional investing (i.e., be problematic, lazy, etc.). Better yet to discover and solve other problems too, because you will be seen as a great investment. Clean the kitchen, fix the company’s website, bring clients, it all helps.
  • Ask about the vision and direction of your team and the company. Understand the intricacies of the problem the business is trying to solve, and why it’s doing it in its particular way. Work hard to understand the customers, because that’s what your bosses are thinking about: your customers’ needs. The sooner you join them in seeing the big picture, the faster you will join them in upper levels of the hierarchy.
  • Try to understand your bosses’ personal and professional goals inside and outside the company. Be subtle with personal questions! Help them achieve those goals. If you can be an ally for them as individuals, they will want to keep you close no matter what they do. That’s how you develop a network of allies.
  • Forget about trying to win arguments and proving people that you are smart. Fuck being right. You were not hired because of your wiseass skills.
  • It’s all about appearances. Be the first to come and last to leave, even if you are checking Twitter for the first and last hour.
  • It’s all about appearances. Don’t let people see your computer desktop if you are not working. Grab a bunch of papers and walk quickly around the office if necessary. Go relax where no one can see you, or relax when others are relaxing too. It’s all bullshit, obviously, but people’s judgements are emotional. If they see you alone in the bean bag chair, they will associate your face with bean bag chairs as opposed to hard work.
  • Be seen with different people, don’t hang out with the same coworkers all the time.
  • Try to understand what your coworkers like or care about, so you can find more ways to bond.
  • Put yourself in situations where you can play with others, or work hard and achieve milestones together, so people associate you with fun times or with achievement.
  • Shower and brush every morning, and put some perfume. Nothing worse than a smelly coworker. Make sure your clothes are clean too.
  • Ask your boss out for lunch and ask them about the industry, their experience, and career advice. People like to be heard and respected. Do the same with your coworkers (they have been in the company longer, so respect that).
  • Promise and deliver EVERY TIME. No excuses. You want to be seen as reliable, and more importantly, someone your superiors don’t have to worry about. Peace of mind and mental bandwith are the most precious gifts you can give to your bosses.
  • Think twice before going to your bosses with questions. Make sure it’s not a dumb question. If it’s not a dumb question, DON’T avoid asking it; it will make you look smart for asking a smart question, and you will avoid making mistakes out of stupid pride.
  • Leave your craziness and dramas at home. Act as if you have your shit together.
  • Take notes of everything, especially of advice someone gives you. Be seen as someone that writes down everything important. Don’t risk forgetting anything, since nothing is more annoying than having to tell someone something twice.
  • If someone gives you advice or tells you to read/watch something, follow up on it. Tell them how you applied it for last few days/weeks. Tell them about your impressions. Send them links related to what they told you. Show them that giving you advice is not a waste of their time.
  • Eliminate as much friction as possible and hand-hold people through every request you make. Tell your boss you will send him some ideas to bring more customers, how you will execute those ideas, and that the only thing you need is his permission. Don’t ask for him to sit down with you to think ideas together. Tell your coworkers that you will make a reservation for happy hour at the bar around the office at 6 pm. Don’t ask where everyone would like to go.
  • Don’t talk too much or dominate any conversation. If you want to be interesting, be interested. The more you listen, the more you can understand the dynamics, incentives and power plays within the organization.
  • The sooner you can understand “how we do things around here,” the better. You may modify the culture and create new habits eventually, but you can only do it once you’re seen as a member.
  • Always be aware of who else is listening. Should you be including them in your conversation? Should you not say certain things in front of them? People are unaware that most of life is a podium, not a 1-on-1 conversation. People talk to each other about what they hear. Take advantage of your audiences and be careful about who you may neglect or offend.
  • Praising others, working long hours, asking many questions, being playful in the office… Great attitudes to have, but if go too far, or display them in front of the wrong peoeple, you may be perceived as an ass-kisser, or a workaholic, or a threat, or a clown. Be conservative while you gauge people’s responses to your attitudes, so you can get closer to that culture’s sweet spots.
  • Don’t obsess about meritocracy or fairness. Other than being a hard worker, life comes down to how you make people feel. If you can combine competence and ambition with people’s trust and likeability, you will have a great career.
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