Bringing in the right executive is a major win, but it’s only the beginning…
Onboarding shouldn’t be conducted as a formality or a checklist.
It’s a structured, intentional process that determines whether your new leader builds momentum—or gets stuck in the fog.
When onboarding is done well, it speeds up alignment, builds credibility, and sets a solid foundation for performance.
When it’s rushed or treated like an afterthought, even the best candidates can struggle to gain traction.
Here’s how to make onboarding thoughtful, strategic, and human!
Make Self-Awareness the Starting Point
Leadership performance is directly tied to self-awareness.
Yet only 10-15% of leaders are actually self-aware.
That gap is a risk—and an opportunity.
Early in the onboarding process, invite your executive to engage in a facilitated Enneagram session.
We love leading these for our clients.
It is important to note that this is not about labeling, rather, exploring how they show up in a room, what drives their decision-making, and what they look like under stress.
Then take it a step further.
Bring the team into the conversation.
Not to dissect types, but to ask the question: Who do we need to be to get to where we want to go?
This reflection builds empathy, trust, and a shared language for growth.
Focus on the First 90 Days
The first three months are about learning, adapting, and building credibility.
The way your executive approaches this window will shape their long-term impact.
Use the STARS framework from Michael Watkins to guide them through different types of leadership transitions:
Help them identify the nature of their specific transition so they can act accordingly.
Small, visible wins early on are crucial.
These don’t need to be flashy.
They just need to show traction, good judgment, and strategic clarity.
Give Space to Observe Before Acting
There’s a natural temptation for new leaders to prove themselves immediately…
Resist that pressure.
Encourage your executive to slow down and absorb the environment.
They should spend time listening and observing before making significant decisions.
This includes understanding how culture, people, and power dynamics actually operate—not just what’s written in the org chart or values doc.
The onboarding process should create intentional space for this.
Carve out time for one-on-one conversations, peer lunches, deep dives with functional leaders, and direct exposure to customers or users if relevant.
Build Relationships, Fast and Intentionally
Trust is earned quickly—or not at all.
Successful executives don’t just understand the business, they build genuine, productive relationships across it.
In the first few weeks, make it a priority for them to meet with key stakeholders: their manager, peers, direct reports, and cross-functional collaborators.
Set these meetings up in advance.
Include context on what matters to each person and how they’ll be working together.
A well-connected executive moves faster, collaborates better, and navigates challenges with more nuance.
Align Early with the Hiring Manager or Board
Misalignment at the top is one of the fastest ways to derail even the strongest executive.
That’s why it’s critical to negotiate success with whoever they report to, before assumptions calcify.
Schedule a working session within the first two weeks.
Use that time to clarify expectations, define success metrics, discuss priorities, and talk through working styles.
If your new hire is working with a board, include a separate conversation around how to manage communication, decision-making, and reporting rhythms.
This avoids the “wait and see” dynamic that often turns into frustration on both sides.
Make the 90-Day Plan Tangible
A thoughtful onboarding process should culminate in a clear 90-day plan.
This is a living strategy that gives your executive a confident runway.
That plan should include:
Make sure this plan is co-created.
It needs to feel like something your executive owns, not something handed to them in a binder.
Evaluate the Team, Set Expectations
If your executive inherits a team, they’ll need to assess quickly and objectively.
That means evaluating skills, alignment, and behavior—not just performance metrics.
Sometimes that also means making tough calls.
Support them in this process.
Give them tools for structured evaluations and feedback conversations.
Encourage honest dialogue.
Then help them set clear expectations with the team so everyone knows where they stand.
Keep the Support Going
Just because the calendar hits 90 days doesn’t mean onboarding is over.
The most effective executives keep adjusting, reflecting, and learning well into their first year and beyond.
Keep your feedback loop open.
Offer coaching, peer support, and space to reflect on what’s working and what isn’t.
Make sure they know where to bring questions and how to access continued development opportunities.
And don’t forget to check in regularly.
Not just for status updates, but to ask:
What do you need?
What’s in your way?
What would help you lead even better right now?
Final Thoughts: Set the Foundation, Get the Return
A well-integrated executive doesn’t happen by luck.
It happens by design.
Set them up thoughtfully, support them intentionally, and they’ll return that investment in ways that ripple across your culture, your results, and your team.
Well, this is the end of our Hiring Series blogs.
Thank you so much for following along with us, month by month.
I hope all of the takeaways learned will allow you to feel more confident and empowered as you continue your recruiting journey!
Blog written by Catherine R. Bell of The Awakened Company.