The First 90 Days (Ch 1): Prepare Yourself
How to effectively onboard to a new position while navigating common challenges


“Joining a new company is akin to an organ transplant - and you’re the new organ”
In this week’s post, I share some summary sketchnotes from Chapter 1 of The First 90 Days. (For a summary of the Intro, check out this post here.)
Highlights From Chapter 1
Here are a few highlights from Chapter 1 that stood out to me:
The First 90 Days seems particularly geared toward senior-level leaders.
I see myself as somewhere in the middle with an eye toward growing into a more senior leader. In my current situation, not every piece of advice is directly applicable to me. It is helpful to get a window into the kinds of problems senior leaders consider, especially when they transition.
For example, one of the described common challenges is “Rethink What You Delegate”. When working with a team of 5, the new leader can be more hands-on to delegate tasks; with a team of 5000, the new leader needs to rely on their direct reports to own products, platforms, or full businesses.
My takeaway is - for whatever challenge I am working on at my current level, I can keep an eye for what I can learn to set me up for the next level. For example, I have a tendency to be a very involved manager, and I have more to learn on how I can give my direct reports room to manage themselves.
Other challenges that stick out to me are: Exhibit the Right Presence and Communicate More Formally.
I wear my heart and head on my sleeve, and it’s hard for me to not say directly what’s on my mind. As I accumulate more experiences, I can see how this approach may not always be appropriate based on the situation.
In contrast, sometimes I have been frustrated with leaders when it seems like they are providing canned responses, cold and sanitized.
I had the opportunity to work more closely with senior leaders and learn how they approach leading an organization.
I started to realize the weight their words have, and how easily they can take on different meanings to different people. One ambiguous word, and the organization can lurch into uncertainty and disarray.
Regardless of whether you are a formal leader, pay attention to how your words could come across and potentially be misunderstood by other people. It takes time to craft thoughtful words, but I would rather spend this time up front than waste painful time later trying to walk back or re-explain what was said.
My final highlight focuses on assessing one’s vulnerabilities, relearning how to learn, and not retreating into one’s comfort zone
When you start at a new organization, it’s a given there will be new knowledge and skills to acquire.
But people may underestimate how much learning they’ll have to do. A successful transition depends on more than learning the ins and outs of how the business works. It also includes observing how people work together and understanding the unspoken rules that govern their behavior (see the parts on the Culture Pyramid).
And fewer people still may anticipate that an onslaught of learning may crash through walls holding up insecurities and reveal areas of incompetence.
If you notice yourself feeling despair, frustration, or imposter syndrome, do a quick assessment of what you’re doing and how much it’s new to you.
I bet there’s some element of the situation that isn’t familiar to you.
After all, if the problem and solution is familiar to you, you would know what to do and it wouldn’t be so difficult.
The First 90 Days advises identifying what one’s preferred problems are.
What problems do you like to solve? That you feel good about when you are solving them? That you feel reflect and build off of your strengths? Those problem areas can be a source of quick wins.
They can also serve as a safe haven when times get tough - which comes with benefits and drawbacks.
Retreating to one’s comfort zone may assuage feelings of incompetence in the moment, but it won’t help you learn or create new solutions that may be better at solving the problem than your tried-and-true solution.
You may also risk avoiding problems that need to be addressed in your new organization.
As uncomfortable as it may be, keep an eye on where you are putting your energies at work. If you find you are avoiding some tasks or problems, consider whether you’re doing it because you are afraid. If that’s the case, try in little ways that feel comfortable to you to push and nudge yourself out of your comfort zone.
Managing Fear Using Advice from The First 90 Days
I believe that so much of making a transition is about managing one’s fear. And that much of that fear is related to anticipating what the future may look like. Sometimes this is an adaptive response. Oftentimes, the brain can go in overdrive as it flashes down different paths, trying to predict potential scenarios and prepare you to tackle the various challenges. Being prepared is important, but not if it’s causing you to be short of breath and unable to sleep.
The First 90 Days provides advice and ideas to keep in mind as you encounter situations that often arise when transitioning to a new role. It addresses the “what” you can do to meet the content of a situation.
I like the idea of pairing these examples with “how” to manage a big change, especially when anxiety emerges. Sometimes when you are in the situation you’ve been playing out in your mind, instead of feeling prepared, all the doors I your mind that lead to helpful nuggets of information slam shut. All you can feel is the pounding of your heart pulsing in your ears.
This happens to me. And for a long time, I tried to fight through the tightening around my throat that wrapped around my chest. I would hide behind a smile and try to squeeze some semblance of a coherent thought through constricted neurons.
Now if I find my vision start to blur, the first thing I tell myself is to breathe. To take in a big belly full of air so that I can flood my brain with oxygen.
When I take that brief second to breathe, I give my neurons a chance to relax enough to fire off thoughts. I try to label my emotion - “I feel afraid. I have no idea what I’m doing” - followed by a new reframing of that fear - “I feel afraid because I’m learning something new.”
I feel afraid because I am learning something new.
Once I take that breath and reframe my fear, I can feel the gates around my brain creak back open. Tidbits of information from sources like The First 90 Days start to flow toward my prefrontal cortex.
Then, when I ask myself, “What can I do in this situation? What can I learn?”, I can access advice from The First 90 Days and successfully navigate new and unpredictable waters.
Very helpful to those who start a new role or even a new job