How to Start a New Job: Handling Career Transitions Like a Boss

July 7, 2015
Year On TeamFuture of Work

Original post by Chris Kelly

The transition from the safe academic bubble to the professional world is a tough one. In fact, so is jumping from one job to the next. Luckily, our friend, Eric Jorgenson, has made his latest edition of Evergreen a deep exploration into how to make this difficult transition successfully.

For those of you who haven't read one of Eric's Evergreen articles before, they are designed to feel like short books; let yourself meander and spend ~3 hours on this topic this week. Save some of the links found within the article for deep diving later and leave this week smarter than you started!


“Do you know what’s waiting for you… beyond that [first 90 days on the job]? Immortality! Take it, it’s Yours!”

A new job can feel like stepping out into a whole new adventure — a fresh chapter in life with new people, new challenges, and new opportunities. It’s also nerve-wracking, gut-wrenching and insomnia-inducing. That whole first-day-of-school feeling, but with prestige and a paycheck at risk.

This collection is designed as a guide to that transition, to help you make the most of this treacherous period where there are so many moving parts, and so much at risk.

If you know someone going through a career transition (starting a new job, their first job, a promotion, or considering a move), send this collection their way as a gesture of support — we worked hard to make it helpful for people in their exact position.

Here’s what’s coming up in this Edition of Evergreen:

  • Cultivating the Right Mindset — How to think about this change
  • Doing the Research — What you need to know before you walk in
  • Getting a Head Start — What to do before day one, to start out right
  • What to do on Day One — The most important things to remember
  • The Two most Crucial Books to Read 

Cultivating The Right Mindset

The first step to a successful transition is to cultivate the proper approach by getting into the right mental space. By keeping a set of simple ideas in mind, you’ll be much more effective.

Know Yourself

Before studying your new context (company, culture, people) you must understand yourself. How do you work best? How to do you communicate best? Who are you likely to work well with?

"Knowing where one belongs can transform an ordinary person — hardworking and competent but otherwise mediocre — into an outstanding performer."

This quote is from a short essay by Peter Drucker, called Managing Oneself. It’s a short read — Here’s a link to it HBR, and I bought this nifty little pocket version.

It’s full of good ways to understand yourself in the context of your new environment, and explains how people work differently. Ask yourself:

  • What are my strengths?
  • How do I learn?
  • How do I contribute?

Many people never spend time getting to know themselves. By skipping this step, you’re making any other research meaningless. Without understanding the shape of your puzzle piece, how can you expect to know where you’ll fit?

A Transition For You is a Transition for Everyone

One of the great (but easily overlooked) points from the book The First 90 Days is that if one member of the team is new, it means the surrounding members are in transition in their own way as well.

"The fact that you’re in transition means they are too. They quicker you can get your new direct reports up to speed, the more you will help your own performance. Beyond that, the benefits to the organization of systematically accelerating everyone’s transitions are vast."

In an even broader sense: have empathy for the changes that your team is going through. A new person is always a meaningful change, and it’s easy to lose sight of that if you’re the one undergoing the main transition.

Do Your Research

It’s a rookie move to show up on day one without any knowledge of the industry, company or team and expect to learn all of that on the job. You’ll have a lot to learn as it is, so it would behoove you to do your research ahead of time to spread out the amount of new information.

For my first job, I created flash cards of 30 people I’d be working with, so I knew all of their names, backgrounds, and what we had in common before I showed up. This was a noticeable advantage and time well spent.

Know Your Organization

To start with, learn the obvious stuff. This would include the history of the company, and it’s products. How did it become successful?

Next, learn about the strategy of the company. What are it’s competitive advantages and how does it fit into the landscape of comparable companies?

Beyond those basics, it’s also helpful to understand the culture of the workplace you’re about to join.

 This image is from the Slideshare presentation linked below.

There are multiple types of organizations, and the culture and behaviors change for each kind. Know which type you’re joining, and you’ll understand what they might expect of you.

There are two [very different] resources that can teach you this in detail. If you’re into books and Greek Mythology, read Gods of Management, which uses the archetypes of the Greek Gods to explain the types of organization. Alternatively, Stephen P. Anderson created a slideshare that riffs off this book using different bands and musical groups. Thanks to Matt Dononvan for this suggestion!

Know the Context of the Transition

In any new job, you’re coming into a unique situation. Each new position is begun in a specific context — what has happened before it, and the current mindset of your new team. There are a variety of possibilities, each of which require their own emphasis.

This paper from CEB, suggested by Sam Whiteman does a great job of breaking out the various situations:

"Smooth Sailing— The leader moves into a position according to a previously arranged transition plan under normal business conditions (3% of leadership transitions).
Replacing an Icon— The leader’s predecessor was very successful in the job (18%).
Following a Train Wreck— The leader’s predecessor was not successful in the job (27%).
Jump Start— A static environment where the performance of the leader’s predecessor wasn’t particularly strong or weak, but the organization needs to quickly move in a different direction (19%).
Breaking Ground— The leader assumes a newly created position (31%)."

To understand what each of these situations will demand of a new entrant, check out this paper. Do your research to find out exactly which of these environments you’re going to find yourself in, and fine-tune your approach.

 Dive in Headfirst!Dive in Headfirst!Dive in Headfirst!Dive in head first!

Getting A Head Start

If you want to impress your new co-workers (and you should), then getting a solid head start is crucial. Work hard before your first day to get yourself up to speed.

Learn the Business (& Your Role) from First Principles

Starting a new job is full of snares that will trap your thinking, from multiple sides. It’s common to fall into one of two sets of errors:

Assuming that your predecessor was doing everything right, and follow her lead exactly as instructed. Assuming that your previous successes are directly applicable and replicable in this new environment.

The antidote to both of these sets of errors is the same: Reasoning from First Principles. As Elon Musk says:

"What reasoning from first principles really […] means is boiling something down to the fundamental truths, or what appear to be the fundamental truths, and reasoning up from there, and then having a good feedback loop."

In order to reason from first principles, you must understand the company, it’s strategy, and the role you play in the creation of value. I love how James Whitehurst puts it in this post on Linkedin:

"Deeply understand how the business creates value.
Obviously you need to learn how to do your job well, but more than that you need to understand the company’s competitive advantage and underlying value proposition to make sure those things happen.
Don’t assume your predecessor did.
Don’t assume the way you did your old job, or the way your new job was done before, is the way it should be done now."

Start Meeting & Befriending Co-workers Right Away

An under-appreciated challenge of starting a new job is adopting an entirely new social circle. This is an important part of the transition, to ensure happy working relationships and productive alignment.

Building relationships takes time, and can’t be rushed. As the real work piles up during your first few months, you’re going to be happy that you worked ahead to build relationships before day one.

CEO & Co-founder of Hotel Tonight Sam Shank wrote a great post where he talks about his attitude toward this aspect of starting a new job, and his advice for new employees:

"Looking back on the early days of my career, I didn’t spend nearly enough time getting to know my coworkers. I spent more time focused on the work itself, and when I did build relationships, I often built them upward, which was a mistake."

As he notes — make sure you get to know your reports and your co-workers in addition to managers and other adjacent superiors. Shank also has advice on just how many people you should get to know:

"Building relationships is key, but don’t wait for your first day. Between when you accept a job offer and when you start, reach out to future peers and begin to build relationships. […]
By Day 90, you should have introduced yourself to the 50 most relevant people in the company (or all of them if the company is under 50 people): know their names, what they do and ideally one personal fact about each of them.
These may be superiors, peers or people in junior or supporting functions, but all of them will be influential in your career and your day-to-day life at work. Try to get to know at least one person from each team."

One more thing to consider here is that you have a perfect window to do this when you’re fresh at the company. It gets harder to say “I’m new and would like to meet, let’s grab coffee” as you stay with the company.

Even though there will be a lot going on, make this a priority, and try to get a head start while you can to make the transition smoother.

What To Do From Day One

Now to the hearty stuff — what to do when you show up on your first day. With an overwhelming amount of things to learn and do, let’s sort out where to start — the most important things. Right after these short posts, we’ll get into the two most important books for starting a new job.

Goal One Is to Prove Sanity

Ryan Holiday has a collection of advice for young people starting out their first job. I don’t agree with every point, though he covers some basics that every other resource seems to have overlooked. Here are some favorites:

“Calm down.”
“Assess the terrain. Sit there and observe. Figure out who the dominant personality types are, what makes them tick and how things really work. Don’t act, don’t give your opinion, don’t do anything until this has been done. When you understand the people, politics and the business (eg, the terrain) then you can begin to get to work.”
“Always say less than necessary.”
“The point isn’t just to prove that you’re capable, but also that you’re sane. In fact, if you had to pick between the two, being well-adjusted is the better one. You can teach people how to do things. You can’t make them normal. In other words, leave your crazy at home.”

This last point about sanity is a fantastic one. Be sure and provide copious evidence of being sane and well-adjusted. [As a corollary, do your best not to display any evidence to the contrary.] If you accomplish nothing else during your first few days, this is the most important thing to convey.

I also appreciate Holiday’s point to assess the terrain. Your first instinct should not be to open your mouth. To get started, just shut up and listen.

Feedback Is a Gift

You cannot expect to improve at your job and learn and the pace that you need to without Feedback. In cultivating the beginner’s mindset and opening yourself up to be managed, you can begin to see Feedback as the gift that it is — even if it stings in the moment.

Here is a post that excerpts Pam Fox Rollin’s Book for new Leaders. Below are my favorite ideas, steps to cultivate your own feedback channels:

"As we say regularly at Stanford in courses focused on interpersonal skills and leadership capabilities, feedback is a gift. And yet, Pam writes, new leaders 'can’t count on informal feedback, as many people fear annoying anyone in power. You may not even receive formal feedback, as review cycles are disrupted by job changes — including yours.' So Pam suggest that it’s your responsibility to 'Forge your own feedback channels' through the following steps:
Ask: 'What am I doing that’s helping you accomplish X?' 'When am I a roadblock to you and your team?' 'How might I screw this up?' 'What issues or people should I be giving more attention?' The higher up you are, the more you have to ask for it…
Initiate it yourself: Don’t wait for an annual process to receive upward feedback. If you can’t hire an executive coach, arrange for a trusted peer to interview your team and summarize key messages back up.
Respond tremendously well: The fastest way to kill your feedback channel is to downplay the feedback, even slightly, verbally or non-verbally.

Unfortunately, not all working environments are well-practiced at crafting and delivering helpful feedback. That doesn’t mean that it’s ok to not get it. It does mean that you’ll have to work harder for it.

Brush Up on Your Internal Communication Reading

At the risk of being self-congratulatory, we did an Evergreen Edition on Internal Communication that seems to have been helpful for some folks.

Taking on a new working environment is an opportunity to re-set rules and expectations around work communication, so now might be a good time to read it and see what could be applied in your new place.

Read ‘True Professionalism’

Being a ‘True Professional’ is something anyone in the business world should aspire to. It’s the moniker for those who are always honest, capable and engaged — they’re the people that we always look forward to working with and hope to work for.

“Real Professionalism is about attitudes, and perhaps even about character.”

True Professionalism is a book by David Maister, a consultant formerly of Harvard Business School, which dives into the details of mindset, conduct, and character of the true professional. I’ve now read this book twice at various points in my career after a thorough recommendation by Bo Fishback, and get something new and valuable out of it each time.

Are You Willing to be Managed?

To get anything whatsoever done, professionals must voluntarily approve and accept new accountabilities. They must willingly vote (or at least consent) to give up their jealously guarded autonomy. They must agree to be managed.

This is such a fascinating concept to me. A clear set of expectations at the beginning of the working relationship can set you up for success in your new role — you must agree to be managed, and understand exactly what that means.

If people are not prepared to be held accountable for what they do, it is unlikely that they will achieve much. Without accountability, most of us will ‘cruise along’ at a level far below our real potential.[…]To choose a goal without being prepared to be accountable for progress towards it is to choose nothing.

As new members of a team, we should readily accept management, agree to it, and make that contract with ourselves. We should view active management as an athlete views a coach — a forcing mechanism to get us to achieve all that we’re capable of, even if it hurts to push ourselves through hard times.

This mindset has the power to reframe nagging reminders or painful feedback into welcome discomforts that we know are meant to make us stronger, smarter, and better.

Why Should Anyone Follow You?

I love this question so much. It might sound like an affront if someone asked you directly, and that’s what makes for such a potent thought experiment. If your new role is as a leader of any kind, you better have a good answer.

Maister has a strong set of answers in True Professionalism that all leaders can look to as a guide. It’s hard to see yourself through the eyes of those you’re expected to lead, and this framework can help.

Here are what Maister lays out as the 4 tests of leadership:

"Motives: 'I will accept your direction only if you give me evidence that you are primarily committed to the success of the group or institution, rather than your own self-aggrandizement.'
Values: 'I will accept your influence, guidance and direction if (and only if) I believe that you and I share similar goals. I want you to have a personal philosophy of practice that I can be inspired by and share.'
Competence: 'If I am to listen to you, I not only expect but require that you have constructive new ideas on how to improve things.” […] “Telling me that I should do better but not telling me how isn’t leadership — it’s merely offensive. Be substantively helpful to me, and I’ll listen to you.'
Style: 'If all of the previous tests have been met, I’ll be interested in your style. Good leaders must be effective coaches, helping both me and my colleagues to stretch and fulfill goals.'"

Two points that Maister hits throughout the explanation of these ideas:

  • These concepts cannot merely be given lip service. If you’re not living them, your team will see right through any hypocrisy and you’ll lose authority. Your history counts. Previous records will be evaluated and taken into account. If you aspire to lead, start living these ideals now. Don’t expect to get a leadership position if you’re not, and don’t think you’ll be successful as a leader until you do.
  • There is a whole chapter that breaks these ideas down further and expounds upon them, and it’s critical reading for any leader, present or aspiring.

While Maister crafted this book specifically for the Professional Services sector (Accountants, Lawyers, Consultants, etc.), the most important lessons are relevant for all of us. (A mental shift to position the client as your employer and yourself as the service provider reframes this book well). The first section of the book is universally applicable, and something any employee would benefit from reading.

Read the first half of this book during your transition and you’ll find yourself sharpening up your professional life, and see the results immediately.

Read 'The First 90 Days'

This is the book that is designed to answer this “How to start a new job” question. Written by Michael Watkins, an absurdly qualified academic and consultant who has dedicated his life to answering this question, it is the must-read from this collection. Thanks to Clay Patterson for the suggestion.

If you start a new job tomorrow, go buy this book today.

The first half of the book is relevant for 99% of people starting new roles, while the second half is more focused on managers and senior leadership in transition.

We’ll pull out some of the most potent ideas…

Avoid These Common Failure Points

Before you worry about what to do, always know what you have to assiduously avoid.

Here’s Watkins’ list of Transition Traps:

"Sticking with what you know: You believe you will be successful in your new role by doing the same things you did in your previous role, only more so. You fail to see that success in the new role requires you to stop doing some things and to embrace new competencies."
Falling prey to the 'action imperative': You feel as if you need to take action, and you try too hard, too early to put your own stamp on the organization. You are too busy to learn, and you make bad decisions and catalyze resistance to your initiatives.
Setting unrealistic expectations: You don’t negotiate your mandate or establish clear, achievable objectives. You may perform well but still fail to meet the expectations of your boss and other key stakeholders.
Attempting to do too much: You rush off in all directions, launching multiple initiatives in the hope that some will pay off. People become confused, and no critical mass of resources gets focused on key initiatives.
Coming in with 'the' answer': You come in with your mind made up, or you reach conclusions too quickly about “the” problems and “the” solutions. You alienate people who could help you understand what’s going on, and you squander opportunities to develop support for good solutions.
Engaging in the wrong type of learning: You spend too much time focused on learning about the technical parts of the business and not enough about the cultural and political dimensions of your new role. You don’t build the cultural insight, relationships, and information conduits you need if you’re to understand what is really going on.
Neglecting horizontal relationships: You spend too much time focused on vertical relationships — up to the boss and down to direct reports — and not enough on peers and other stakeholders. You don’t fully understand what it will take to succeed, and you miss early opportunities to build supportive alliances."

How many of these have you seen happen in your organizations before? Have you felt the pain of a new leader who had made one of these mistakes? Use this short list to keep yourself on track, and check against if often.

Get a Cultural Interpreter

One of the ideas that was subtle but that jumped out at me was deliberately learning about the language, habits, history, and culture of the new organization. This is an idea expanded from this passage from First 90 Days:

"If you have been hired from outside, ask for help in identifying and connecting with key stakeholders or finding a cultural interpreter. These people often are natural historians who can give you insight into how the organization has evolved and changed."

You want someone to get you up to speed on the informal institutional knowledge (and the inside jokes) as soon as possible, so find yourself a ‘Cultural Interpreter’ and bombard them with questions until you feel like a natural. There’s a wealth of knowledge in institutional knowledge — what has been tried before, what has failed, and why things are the way they are.

Every organization has their own languages, and learning to speak it as soon as possible is a good investment of time, as you’ll learn and move faster as soon as you can keep up with the lingo.

The Three Main Goals

There are entire chapters in The First 90 Days dedicated to each of these topics, so these are far more fleshed out in the book, but it’s worth pulling them out in basic form in this post because they’re each such crucial aspects of nailing your new job.

Each of the three is below, with some of the most definitive excerpts for each idea, to give you an idea of what is intended by the author.

1. Accelerate Your Learning:

"The first task in making a successful transition is to accelerate your learning. Effective learning gives you the foundational insights you need as you build your plan for the next 90 days. So it is essential to figure out what you need to know about your new organization and to learn it as rapidly as you can. The more efficiently and effectively you learn, the more quickly you will close out your window of vulnerability.
The starting point is to begin to define your learning agenda, ideally before you formally enter the organization.
There is much that bosses, peers, and even direct reports can do to accelerate your learning. However, to enlist their aid you need to be clear about what you’re trying to do and ask how they can help. Critically, you need to be willing to ask in the first place and not feel that you should know everything and be in complete control from the moment you walk through the door."

[In my personal opinion, that last excerpt is the most crucial piece of advice in this entire collection.]

2. Negotiate Success

"Negotiating success means proactively engaging with your new boss to shape the game so that you have a fighting chance of achieving desired goals. Many new leaders just play the game, reactively taking their situation as given — and failing as a result.
Be conservative in what you promise. If you deliver more, you will delight your boss. But if you promise too much and fail to deliver, you risk undermining your credibility. Even if you accomplish a great deal, you will have failed in your boss’s eyes.
Even if you’re sure you know what your boss expects, you should go back regularly to confirm and clarify. Some bosses know what they want but are not good at expressing it. You don’t want to achieve clarity only after you have headed down the wrong road. So you must be prepared to keep asking questions until you’re sure you understand.
Assume that the job of building a positive relationship with your new boss is 100% your responsibility. In short, this means adapting to his style."

3. Secure Early Wins

"Because your earliest actions will have disproportionate influence on how you’re perceived, think through how you will get connected to your new organization in the first few days in your new role.
As you strive to create momentum, keep in mind that your early wins must do double duty; they must help you build momentum in the short term, and lay a foundation for achieving your longer-term business goals.
An early win that is accomplished in a way that exemplifies the behavior you hope to instill in your new organization is a double win."

Conclusion: Put In The Work Before Work

The prevailing attitude to starting a new job seems to be to coast into day one — to show up empty-handed and empty-brained and just take it from there. This is not a recipe for impressing your new team.

Putting in some work before day one to get your mind in the right place, and to get organized as to how you’re going to join this new organization is time well-spent. First impressions matter and remember you’re holding others back until you reach the point of net positive contributions.

By working to make the best of your first weeks on the job (and prepping for it a few weeks before), you’re going to stand out amongst everyone else, and it will quickly set you up for bigger and better things.

Get after it.


If you enjoyed this, you’ll get more like it every week by joining Evergreen.

Donating = Loving

Bringing you Evergreen takes dozens of hours each week. If you find anything helpful and interesting here, please consider becoming a Supporting Member with a donation of your choosing, between a coffee and a good dinner. Thank you very much! ❤ ☺

Thank You

Massive appreciation for who suggested pieces of content (or wrote something new) for this Edition of Evergreen: Matt Donovan, Joe Bayley, Mahesh Bhatia, Sam Whiteman, Alberto Villa, Matthew Frost, Tim Harsch, Clay Patterson, and Bo Fishback.

Many thanks for being a part of this project! Not every suggestion is able to make it to the final edit, but every single suggestion is read and appreciated.

Never Enough

As my Father always says: “There’s always room for the best.” There’s always a better resource out there. These collections can always get better, and I hope that they do. If you can think of anything that was missed, I welcome you to share it.

To share your thoughts, improvements or additions: Email or Twitter.


This Edition of Evergreen, along with all of my others and the ideas behind this project, is inspired by the excellent content created online every day. To name a few that hold particular places in my heart:

Learn more about Year On.

Start charting your own educational path. Subscriber to learn more about Year On and get exclusive updates about our gap year programs.

Thank you for subscribing! Keep an eye on your inbox for the latest Year On updates.
Oops! Something went wrong while submitting the form.

Related Posts