A playbook on making difficult career decisions | choosing between Bain and LinkedIn

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Strong decision making is a hallmark of great leaders. It’s one of the most valuable, frequently used, and difficult to master skills.

A leader’s decision-making ability can make or break companies, organizations, and entire governments.

A decision can be anything from a president deciding to implement a sensitive foreign policy, the chief investment officer of a hedge fund deciding to invest billions of dollars into one stock, or a CEO deciding to bet the turnaround of a company on a new product launch.

Decisions are more difficult than discussing hypothetical solutions or making recommendations because you have to live with the consequences of your actions.  

Over the course of your career, you will face many high-stakes, difficult, and multidimensional problems that require decisions. These problems will not be as well-defined and straightforward as your 10th grade math homework.

Instead, these problems will have an endless number of variables to consider, a vague definition of success, and multiple solutions across the spectrum of right and wrong. They will have sluggish feedback loops of months or years, which means you will will not know if you made the right decision for a long time.

A perfect decision maker is someone who is able to consistently make correct decisions given a variety of information. If there is too much information, a perfect decision maker knows how to cut through the noise to focus on what matters. If there is too little information, they know where to invest their time to learn just enough to make the right decision.  

If a perfect decision maker did exist, their value would be priceless. But nobody is a perfect decision maker. In fact, even great decision makers are frequently wrong.

I define a great decision maker as someone who is able to consistently make correct and timely decisions more often than the next smart, capable person.

Decision making is a difficult skill to hone, but if properly developed it will provide you with immeasurable upside in your career. One day you will get to the point where you are in charge of making wide scale decisions that affect many people. But in the near term, there is a more pressing challenge that you will face -- career decisions.

Making difficult career decisions is one of the first experiences you will have with high stakes decision making. With each career decision, your choice will dictate how you spend a significant portion of your time for the next few years or more!

Through helping others with their big career decisions and making a few of my own, I’ve stumbled upon a playbook that can help you with your decisions.

These principles helped me choose between internship and full time offers, and continue to help me today as I explore new opportunities for my career.

Find believable advisors

When people have to make a big career decision, I’ve noticed two common tendencies with how they collect feedback from others.

  1. Some people don’t tell anyone about the decision and quietly make the call by themselves.
  2. Others will socialize the decision with literally everybody and end up with way too much noise to make a sound decision.

Both approaches result in suboptimal decision making. You don’t want to make this big decision on your own. What if you forget a critical consideration?

On the other hand, you also don’t want to put this decision to a democratic vote of everyone you know. This is especially harmful if the “right” decision may not be the popular or obvious choice.

This happened when I had to choose between working at a brand name consulting firm and the relatively new Strategy & Analytics program at LinkedIn. The majority of my peers thought it was crazy to turn down a prestigious consulting firm. And they weren’t totally wrong. I wanted to learn about business strategy and it was generally accepted that strategy consulting firms were the best place to develop that skill.

But the risk of mob mentality is that it misses unique opportunities that are new, because these opportunities are too fresh to have a widespread reputation.

The vast majority of my peers told me this is a no-brainer decision, take the consulting offer. Had I listened to the majority, I wouldn’t be at LinkedIn today.

However, I was able to cut through the noise through a simple thought experiment by asking one question: “What would have to be true for a non-consulting firm to provide a better opportunity to learn strategy and technology?”

Not only did this question help me better analyze each opportunity from the ground up, but it also helped me identify believable people. Anyone who wasn’t willing to engage in this thought experiment was giving me advice based off prestige, hype, or bias -- not first principles thinking.

It didn’t matter how experienced someone was (I spoke with multiple professionals with 10+ years of experience). It was very obvious who was willing to engage in this thought experiment and who was giving lazy advice.

I consider the former believable and the latter non-believable, and learned to weight the opinions of believable advisors 100x more than the opinions of non-believable people.

Find yourself a group of 5 to 10 believable advisors.  

Make sure your advisors represent diverse opinions

Everyone has their biases. When choosing your advisors, select people who represent a diverse spectrum of opinions and biases.

With my decision, I spoke to peers my age, alumni, and professionals with 2 to 20+ years of experience. They represented a range of experience from management consulting, technology, venture capital, and entrepreneurship.

For this decision, I was especially interested in the opinions of ex-management consultants in tech. They had experience in both industries, and I felt that they were best positioned to counsel me on the tradeoffs.

Had I just spoken to current management consultants or only technology professionals, I would’ve missed critical information to piece together the larger picture.

When making your decision, find a diverse group of advisors to gather multiple perspectives.

Career decisions are usually not straightforward, so it’s helpful to tackle them with different perspectives.

Explain the opportunities using facts

Try to keep the conversation grounded when explaining the tradeoffs of each career opportunity. Inform your advisors of the facts, avoid showing your preference, then sit back and hear them out.

If you unintentionally sell them on an opportunity, you’re shooting yourself in the foot by biasing their advice. Try to stay impartial.

These career conversations can be incredibly fascinating. It’s interesting to hear how experienced professionals think about your career tradeoffs. Some of my conversations lasted over 2 hours!

Wash, rinse, and repeat until your gut is leaning in one direction

Have fact-based conversations and gather advice from at least a handful of believable, diverse advisors.

You may start this process totally unsure of which opportunity to take. However, I’ve found that you will start to lean towards one direction after a handful of in-depth conversations.

By my 6th conversation about LinkedIn S&A vs. Bain, my gut was clearly leaning in the direction of LinkedIn.

Some people try to make spreadsheets to quantify different aspects of opportunities for “objective” comparison. This isn’t bad idea when you’re building your fact-base. But don’t make big career decisions just because of what a spreadsheet says. Difficult decisions are rarely objective.

By having multiple fact-based conversations, you should know everything you need to know to make a well-informed decision. After that, trust your instinct.

A few red flags when choosing your advisors

Blanket Advice: Some people love to give blanket advice. This means that regardless of your specific goals, circumstances, and opportunities, they will default to the same standard advice they give everybody.

High quality advice must be thoughtful applied to a specific person’s situation. Blanket advice is a lazy shortcut. You can tell someone is giving you blanket advice when they don’t have a strong rationale behind their advice, and they are not able to adapt their advice as you provide new facts about your situation.

Confirmation Bias: There is a strong, deeply-human need to validate the decisions we’ve made. I’ve often seen advisors and mentors provide advice that is self-serving because it confirms the career decisions he/she has made. In an ideal world, great advice should be selfless. As a mentor, I try to be aware of any confirmation bias I have and adapt my advice to the person I’m speaking with.

For example, working at LinkedIn was the right choice for me and is a great choice for other people with the right background and goals. But it’s not the best idea for everyone. Some people would definitely be better off working in strategy consulting.

You can tell someone has confirmation bias if they are giving blanket advice, telling you to do what they’ve done without a compelling rationale, try to justify their career choices despite having a bad experience themselves (commonly paired with a pay your dues mentality), or fail to engage in the “what would have to be true” thought experiment explained above.

No skin in the game: The best advice also comes from advisors and mentors who feel invested in you. It’s dangerous to give someone pseudo-personalized advice after knowing them for 10 minutes. This type of advice is very prone to the risks I’ve mentioned throughout this post.

You’ll know when you found advisors with skin in the game because they will prioritize your phone call even if they have a busy schedule, listen to all your facts, and spend hours talking with you if needed. They are invested in you and want to see you succeed. Their advice is worth 100x more than someone who barely knows you.

Lastly, commitment is more important than the decision itself

Once you’ve made your decision, push yourself to go all in. There is rarely a right answer and it’s easy to make one decision then questions yourself because of “grass is always greener” syndrome.

I explained how poisonous this attitude can be in my post on the euphoric highs and crushing lows of the professional world. No matter which job you choose, there will always be incredible and horrible weeks. Try to resist spending your limited energy and brain power on doubting your decision.

I believe your ability to commit and crush the job is a far better predictor of long-term success versus making one perfect decision. Do your research, make an informed and level-headed decision, then go all in.

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