The First 90 Days with a New Boss

Lauren Chan Lee
4 min readSep 7, 2021


How to Succeed in a New Regime

Photo by Richard Clark on Unsplash

When you get a new boss, your role doesn’t look like it’s changed. Don’t be fooled — it has. You might have done great work and built a fantastic internal reputation, but if you don’t build a relationship with your new boss, your past successes won’t matter. You should treat a new boss like starting a new job, where you’ll have to prove yourself again. It might not feel fair, but that’s reality.

When your new boss starts, they want to be successful and they need you to help them be successful. In my previous post, I wrote about how they’re looking to understand:

  • How can I drive results?
  • Do I have the right team to get there?

With that key insight into the mind of your new boss, here are the keys to success for starting things off strong.

Nailing the first conversation

#1: When your new boss starts, he or she will want to have onboarding conversations with their team members. Don’t waltz into this conversation blind. First impressions matter. You should prepare for this conversation by anticipating some of the questions that they’ll ask. Deb Liu wrote an amazing post about the Listening Tour that she did when she started her new job as CEO of Michael Watkins’ book, The First 90 Days, is another source that can give you great insight into the types of questions that may come up in an initial conversation. The information that you share will help your new boss get the lay of the land and develop an understanding of what it takes to drive results.

#2: Do some research on your new boss. With LinkedIn, it’s easy to find out information about their past jobs, interests, and maybe even blog posts or speaking engagements. What experiences have they had in the past that speak to you? Where do you think you can learn from them? Instead of expecting your new boss to tell you how they can help you, bring your ideas into the conversation on how you can learn from them. Use this conversation as the starting point on how your new boss can help you grow.

Nailing the first 90 days

#3: You’ll probably have projects that are mid-flight when your new boss joins. Don’t assume that they have context on what you’re working on or why it’s important. Don’t just send them a bunch of links or decks either. Take the time to give them a full walk through on the background of your projects and why it contributes to your team’s goals.

#4: Make sure whatever you say you’ll do, that you deliver on it. Or if something happens, keep your new boss proactively informed. For example, if a release gets pushed back, let your boss and stakeholders know before they ask you about it. They will understand if things change, but they need to know that they do not need to babysit you. Your new boss needs to be able to count on you to follow through.

#5: Loop your new boss in when you’re making a decision. Let them know what the situation is, give your rationale and recommendation, and ask for their input. Your new boss needs to understand how you think and know that they can depend on you to make good decisions.


Putting in a little effort to over communicate in the first 90 days when you get a new boss will go a long way towards success in your role. All of these tactics will help your new boss understand how to drive results and feel confident that you’re the right team member to help them get there. They also serve to build trust between the two of you and, once you’ve built that trust, then most bosses will be happy to let you get back to delivering great work.

Disclosure: This post contains Amazon affiliate links. That means that I may earn a commission if you make a purchase through one of these links (at absolutely no extra cost for you). These funds help me buy my next cup of Philz which, in turn, fuels me to write more blog posts.

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Lauren Chan Lee

Lauren Chan Lee is a product leader who enjoys writing about the connections between product principles and everyday life. Learn more at: