10 Things You’ll Wish You Had Known About Your New Job

Take these steps now or you may experience buyer’s remorse later - Issue #22

There are obvious things that people focus on when deciding whether or not to accept a job offer. The big factors tend to be title, role, salary, bonus, stock options, benefits, vacation days, commute, and a few other personally meaningful items. During the 23 years of my career in Silicon Valley Tech, it really wasn’t these big factors that ended up influencing my happiness with a job though.

We sometimes become too focused on those factors and overlook important issues that can make or break your satisfaction with a new role. A great salary doesn’t mean much if the company fails and lays everyone off within a year. All of those perks won’t make you happy if your boss is a psychopath.

While it is possible to accelerate your career with smart job hopping, you don’t want to frequently quit jobs simply because you didn’t do enough research before saying, “Yes.” I experienced this the hard way a few times during my career. I overlooked red flags that I have since learned to recognize.

So, don’t forget to ask good questions during the interview, spend some time doing your research and due diligence, and get information about the following:

  1. The corporate cultural norms

  2. How your performance will be evaluated

  3. How employees feel about the company

  4. How employees feel about your boss

  5. How people work in the office

  6. Flexibility in office hours

  7. The work from home policy

  8. The company’s financial situation

  9. Why your position is available

  10. A business SWOT analysis

1. Corporate cultural norms

Every company has a corporate culture. But, what is printed in the company handbook and plastered on corporate posters across campus can be very different from the cultural norms that are expressed and rewarded at the company.

  • Do the best ideas win or are a lot of politics involved?

  • Is it a collaborative environment or highly competitive?

  • Is it informal and fun or serious and stuffy?

  • Is there a strict leadership hierarchy and deference to authority?

  • Are people expected to work long hours and put in a lot of face time?

You will learn a great deal by observing behavior in the office when you go in for your interviews. Take note of how people behave, talk with each other, and talk about each other. Ask questions about decision making, teamwork, collaboration, who gets promoted, work-life balance, etc.

2. Your performance evaluation

We sometimes assume that the evaluation of our job performance will be relatively straightforward. But, you might be surprised. One of the worst things that can happen to you is to be held to a standard you were not anticipating. You may find out that there are unreasonable expectations for your performance, and now you’re being held to that.

I know a few people who had that unfortunate experience. Now they are dealing with an upset boss and potential damage to their career. They’re struggling to reset those expectations, but it’s much harder once you are in the job.

Ask your potential boss detailed questions about the role and the expectations for your performance.

  • When I take this job what will my top priorities be for the rest of this year?

  • What do you think my biggest challenges will be in this role?

  • What does success look like for someone in this job?

  • In 6 months, how will you know that I’m doing a great job here?

  • What data and information do you prefer to use to evaluate performance?

3. How employees feel about the company

You’ll be interviewing with current employees at the company. Candidates tend to think of this as a one-way street, but don’t forget to interview them right back. You need to get answers to your questions, so play detective. Pay close attention to their body language too.

I was once in an interview with an employee grilling me. But, after about 20 minutes the tone of the interview flipped. He decided that he wanted me on board and started pleading with me to join the company to help fix all of the bad issues they were experiencing.

It is also very helpful to talk with ex-employees you know and trust. Sometimes old employees have an axe to grind, so take the information with a grain of salt. However, if it is someone you know and trust, then you are in a better position to evaluate what they tell you.

4. How employees feel about your boss

It’s obviously challenging to get current employees to really open up about your boss. They know that they risk career suicide if they are too honest and it gets back to him or her. But, much like the previous issue, watch their body language as you discuss the boss’s management style.

Again, it can be very helpful to talk with ex-employees who used to work for this person. You’ll get varying answers depending on how that work relationship ended, of course.

The other thing I’ve learned over the past two decades is how small an industry can be. In Silicon Valley, everyone knows almost everyone else, or they know someone who knows that person. Leverage your network to do deeper research on your potential boss.

Talk with people who worked with him or her in the past. You can learn a lot about people from the way they climbed their own career ladder. I’ve known people who are admired by almost everyone who came in contact with them. I’ve also known people who’ve burned bridges left and right, and earned quite a few enemies as they advanced in their career.

5. How people work in the office

During your interview process, find out how people really get work done at the company. Is it an open office plan, cubicles, private offices, or some hybrid model? Observe people working alone, or in small groups. Take note of the meetings you can see.

For example, open office plans are clearly making some people unhappy and even impacting productivity. They are ok for certain professions and activities, but they wreak havoc with others (e.g., designers, engineers, writers). Some of Apple’s employees are so unhappy with their new $5B campus that they are finding other places to work.

Make sure that the company’s model fits with how you do your best work. If you’re forced into a situation that doesn’t work for you, your performance will suffer. It’s hard to change that once you’ve accepted the job.

6. Flexibility in office hours

Some companies have very strict policies around acceptable work hours. You have to be in the office by 9 AM and you’d better not be seen leaving before 5 PM. In Silicon Valley, we wish that we had 9–5 jobs, but that’s an article for another time.

Get clarity from your potential boss around the expectations for this. If there is no flexibility in start time, this may put you right in the middle of the morning rush hour every day. Be prepared for the pain of a grueling commute or negotiate a more flexible working schedule as part of the offer negotiation process. You may decide to pass on a job for a different one that won’t steal so many precious hours from your day.

7. The work from home policy

Depending on the company and the job, being able to work from home may or may not be a reality for you. If you’re going to be a barista at a coffeeshop, you’re going into the business every day whether you like it or not. But, if your work is mostly performed online or over the phone, then you can have a lot more flexibility in where that work is actually performed.

Related to the previous section, a flexible work-from-home policy can greatly improve your satisfaction with a job. Some companies excel at offering remote positions, some will let you have a dedicated work-from-home day, and some have really clamped down on it. Know where your potential employer falls on this range.

This also ties back to the first point about a company’s cultural norms. A company may say that they support working remotely, but then you notice that the only employees getting promoted are those who put in face time. Research by Kimberly Elsbach found:

Employees who work remotely may end up getting lower performance evaluations, smaller raises and fewer promotions than their colleagues in the office — even if they work just as hard and just as long.

8. The company’s financial situation

Research the company’s current financial situation. Public companies in the U.S. must publish quarterly and yearly earnings reports. Usually, you can find these reports on the company’s website.

I also find it helpful to look at the stock transactions for the executives at the company. Are they buying or selling? Is there an overall trend (e.g., the execs seem to be dumping stock)? For example, many of us raised our eyebrows recently when the CEO of WeWork dumped $700 million in stock ahead of their expected IPO.

Of course, insiders are only allowed to trade during specific time windows. So, their activity is concentrated and can be a clue about what is going on within the company.

Nejat Seyhun, a professor at the University of Michigan, found that a stock tends to outperform the market by 8.9% over the next 12 months when execs buy shares in their own company. But, when they sell shares, the stock underperforms by 5.4%.

“The insider has only one reason to buy: to make money”
- Peter Lynch

9. Why your position is available

One of the most important questions that you can ask is, “Why is this position open?” Find out if it is a new position. If not, did the last person quit or was he fired?

You may not get a straight answer if the person was fired. But, you’ll learn a lot from how your potential boss answers that question. As you’ve probably noticed, I’m a big believer in improving your ability to read others and interpret body language.

If you can, track down the last person who held this job and meet over coffee. I’ve done this before, and it was extremely valuable. As I mentioned earlier, Silicon Valley is small and I knew the person who had been in the position before me. We met and I learned a great deal about the dynamics of the organization, political issues, and who could be trusted.

10. A business SWOT analysis

The traditional SWOT analysis is far from perfect. But, researching the company’s business means that you are at least going into the job with a better understanding of the potential upside and risks.

You won’t have all of the confidential information and data that an internal employee has access to, yet. So, you’ll have to do the best you can with what you know about the company, its strategy, the competitive landscape, trends in the industry, etc.


  • Everything the company is doing well to be strongly positioned relative to the competition

  • For example, a strong product and engineering team, executive team, board, IP portfolio, and customer base


  • Issues with the company that put its business at a competitive disadvantage in the marketplace

  • For example, a product or service that is inferior to a competitor’s offering, an antiquated technology stack, or an ineffective sales organization


  • Any factors that represent an opportunity for the company to acquire new customers, grow revenue, expand operations, move into new markets, etc.

  • For example, a competitor’s missteps, a move into a significant market, or an acquisition that enables the company to expand into a new product line


Basically, is the company successfully focused on an opportunity that has longevity or are they clinging to a dying industry? Are they strongly positioned for growth in the market or is a competitor eating their lunch?

The last thing you want to do is hitch your career wagon to a sinking corporate ship (two metaphors for the price of one).

No regrets

No decision can be made with 100% certainty. No company is 100% perfect. No job is going to be your 100% dream job — unless you create it yourself. But, you should be fully aware of the situation you will be getting into before you accept a job offer.

Perform your due diligence and you will greatly improve your odds of being happy with your new job!

What I’ve Been Reading

  • Here are some good suggestions for getting outside more often during the day; 10 Ways To Spend More Time Outdoors During The Workweek. It helps clear your head and makes you feel better to escape those fluorescent lights. One of my favorite tips is to have walking meetings. I used to do that when I was working for a company as a consultant. It was such a welcome break!

  • Relocating for a Job? 5 Things to Consider. Did you know that more than 3 million people in the U.S. move for work every year? I’ve moved for a job a number of times during my career. Some of the moves were big (e.g., Texas to California) and some were smaller (e.g., Livermore, CA to Santa Clara, CA). When you move for a job — especially when it’s a big move — you have to know what to expect. One of the biggest things you’d better research is how easy will it be to find your next job in that location? Some people move to a company town with one big employer, lose their job, and then struggle to find another one.

  • In Confessions Of A Former Corporate Recruiter, Dawn Graham admits that the recruiting, interviewing, and hiring process is broken. If you are currently interviewing, you are already aware of this. Have you submitted a job application and never heard back? Have you interviewed with a company and they ghosted you afterward? Unfortunately, this is all too common. It’s why I recommend that you bypass that entire mess, find an inside champion, and land a job in a completely different way.