The Compassionate Leader's First 90 Days Checklist
Not another generic onboarding guide, the specific things that actually mattered for me.
I feel like most “First 90 Days” content is written for leaders who had time to plan for the transition.
If you’re reading Altitude, there’s a good chance you didn’t get the luxury of planning. You were excellent at your job and someone put “Manager” in your title or made you a technical leader in some capacity and here you are trying to figure out what you’re actually supposed to be doing as the actual work stacks up.
This resource is specifically for you. Not a generic onboarding checklist from a business book; a specific list of things that made a difference in my management / leadership journey and that I’ve seen matter for the leaders I’ve coached since. The commentary below each item is the point since a checklist without context is just a to-do list.
☐ Meet 1:1 with every person on your team in the first two weeks
Don’t wait. Don’t do group introductions and call it done. One-on-one time with each person is the fastest way to start building individual trust and those first conversations set a tone and foundation for your relationship.
Ask four questions in each one: “What’s going well?”, “What are the challenges or roadblocks we’re running into?”, “What ideas do you have for how we could improve?”, and finally: “What’s one thing I could do to better support you and the team?”
That last question will feel vulnerable to ask but I’ve gotten some of the best and most useful answers from asking it 🫶🏻
☐ Build your stakeholder map
At the end of each 1:1 ask two more questions. These two are doing a lot of quiet work: “Who else should I talk to?” and “Who relies on us for support?”
Together, they start to build your stakeholder map: a picture of who the important relationships are, who depends on your team’s work, and who your team depends on in return. You won’t have this picture on day one but it’s essential for your team’s success and your success as a leader at the center of a web of relationships that make the technical work happen effectively. These questions build it gradually, from the people who actually know. 🕸️
☐ Ask your manager to collaborate with you to define what success looks like at 30, 60, and 90 days
This is the ask new leaders are most reluctant to make, usually because they don’t want to seem like they don’t already know the answer. I recommend it since it’s a huge trust building opportunity and establishes a collaborative partnership paradigm between you and your manager 🤝
“I’d love to work with you to define two or three measurable things that would tell us both I’m on the right track at 30, 60, and 90 days” is a completely normal and valid thing to request.
Most managers are relieved when you ask it. It means you’re both looking at / agreeing upon the same target(s). It also inherently establishes check-in points where you all can talk about your progress toward those target(s).
The alternative (guessing, mind reading, assuming you know the answer) means you are increasing the risk that you and your manager are tracking entirely different definitions of success and you won’t find out until it’s causing tension and conflict later on.
Early alignment between you and your manager is a smart investment. 💸
☐ Follow up on feedback. Tell people what you heard and what you did (or plan to do) with it.
This is the most underrated item on this list.
You’re going to collect a lot of input in those early 1:1s: ideas, frustrations, suggestions, hopes. What happens next determines how much people trust you with future feedback.
If you heard something and made a decision based on it, say so. “After our conversation I decided to do X — here’s what I decided and why” is a trust-building sentence. It tells people their input has value and drives real world results. Most new managers collect feedback and go quiet. Don’t be most new managers. 🎯
☐ Tell your team and your manager how you prefer to communicate and ask how they prefer to communicate
This one might be the most skipped item on this list and in my experience it’s one of the most important.
You have preferences about how you receive feedback, information, and recognition. Your team members have preferences too.
Most of us default to the style that feels natural to us and never actually say it out loud which means at least some of those conversations are landing wrong for at least some people and nobody acknowledges it.
This applies to your manager just as much as your team. Early in my career I learned to adapt how I communicated to match how my manager actually processed information, and it changed everything about how effectively we collaborated. It’s not performing someone else’s style, it’s more like translating for your audience. Communication is only useful if it actually lands.
One question that opens the door: “Is there a way you prefer to get updates from me?” Most managers appreciate being asked.
☐ For in-person teams: create a small ritual for celebrating wins
This one sounds silly and obvious, but it’s harder than you’d think.
It’s easy to get swept up in the day to day hustle of calendars and emails and project updates without pausing to recognize the incremental progress we make each week!
For my current teams, we have a cowbell ceremony. Literal cowbells. Every Friday, we ring the cowbells for every task we completed as a team that week: big wins, small wins, all of them.
It sounds like a small thing but it created a stable, recurring moment where the teams can count on celebrating their own progress together instead of just moving on to the next thing. Not everyone attends every ceremony, but every person who attends walks away with a smile.
You don’t need a cowbell specifically, but find the version of this that works for your team and build it early. Early momentum is real, and a small weekly ritual that marks it is worth creating.
The through-line across all of these is the same thing: your first 90 days as a leader are not about proving you have all the answers. They’re about making it clear that you’re paying attention, that you’re taking the relationships you are building seriously, and that you intend to earn the trust you’ve been given rather than assume it came with the title.
That’s enough to get started 🙌🏻
The Manager’s Conversation Toolkit (pinned at the top of the paid subscriber section) includes 1:1 conversation templates built for these exact early conversations. Paid subscribers have instant access.
I’d appreciate your support at any level - free or paid - as it helps more leaders find Altitude! Thank you for being a reader and part of this community. You mean a lot to me.
I’d love to hear what’s on your own first-90-days list. Is there something that made a real difference for you, or something you wish you’d known sooner? Leave a comment, send a note, or find me on Substack Notes! I read every comment and reply back.
See you next Tuesday,