Onboarding Senior Executives: What CEOs Get Right—and Wrong

In this edition of Chasm Conversations, ChasmLead Executive Coaches Jen Person and Christine Britton discuss what they’ve learned from onboarding senior executives placed by Chasm Partners—and what CEOs can do to set these new leaders up for success.

About Jen Person

Jen Person is an executive and leadership coach for ChasmLead, as well as a designer and facilitator of leadership development experiences. She partners with mid- to senior-level professionals to sharpen their leadership skills and expand their capacity to lead and thrive in fast-paced, uncertain, and complex environments. An ICF-certified Integral coach and expert in Emotional Intelligence and Adaptive Leadership, she is the founder of Boundless Horizon, LLC.

About Christine Britton

Christine Britton is a ChasmLead executive coach and advisor specializing in leadership development and organizational effectiveness. For over 30 years, Christine’s career has been defined by her work as a consultant, coach, and trusted partner to senior leaders across a wide range of industries and functions. As a leader in corporate and advisory roles, she has supported executives through complex organizational challenges, transformation efforts, and periods of growth and change. At Chasm Partners, Christine provides executive coaching for senior leaders and conducts executive assessments to support due diligence for the firm’s investment clients. She is also the founder and principal of Christine Britton Coaching and Consulting LLC.

Given the large amount of onboarding work you have done at ChasmLead with executives, what are some key insights you’ve gained from onboarding senior executives that would be helpful to the CEOs leading them?

Christine Britton:

One of the biggest opportunities starts even before the executive joins. Once you have found your final candidate and are preparing to make an offer, there’s real value in opening the transparency aperture as much as you feel comfortable.

Share more than you typically would during the interview process—not just the strengths of the business, but the challenges they’re walking into. That might include team dynamics, revenue or margin pressures, or areas where you’re hoping this person will make an impact.

When new executives walk in and what they see largely matches their expectations, they have a real advantage. They can assess, prioritize, and start contributing much more quickly.

Jen Person:

Building on that, a pattern I consistently see is that leaders assume senior hires want lots of autonomy immediately and don’t need much direct attention.

But the reality is that no matter how experienced someone is, dedicated one-on-one time with their executive leader during the first two or three months gives them exactly the foothold they need to be successful in the long term.

It doesn’t have to last forever—but that regular cadence of focused one-on-one time in the first month or two makes a huge difference.

What difference do those early touchpoints actually make?

Jen Person:

That’s a great question. There’s so much context in any organization—especially in smaller, private equity–backed companies—that tends to be underestimated. 

Those early conversations are where a new leader learns the history, the informal dynamics, and the “why” behind how things work. Without that, the first few weeks can be full of landmines as they unintentionally make missteps.

Consistent early check-ins with their executive leader help shortcut that learning curve. They give new executives context faster, helping them avoid unnecessary mistakes while creating the confidence to ask bold questions, propose new ideas, and move faster because they’re not guessing.

Christine Britton:

With that foundation in place, they’re able to hit the ground running more thoughtfully. They can better make sense of what they’re hearing as they meet people, learn the business, and come back with better questions. And it helps them build stronger relationships as well.

Going back to the hiring stage, what else should CEOs keep in mind related to more effective onboarding?

Christine Britton:

In addition to transparency, there’s real value in sharing not just the challenges, but why you’re excited about the capabilities and experience this particular executive brings to the table. 

It helps connect the dots for them—here are the challenges, and here’s why we chose you to address them.

That combination creates a lift. It turns what could feel like a vulnerable moment—walking into a messy situation—into a moment of clarity and purpose.

Jen Person:

Yes, and it also normalizes the messiness of the work ahead. No organization is perfect, and acknowledging that upfront builds credibility.

When a new executive understands both the real challenges and the reason they were chosen, they come in with a clearer sense of purpose. They’re able to say, “These are the expectations, and here’s how my experience applies.”

Trust is critical in the early stages of a relationship. What actions are most important to build it from the outset? What happens if that trust is not created?

Jen Person:

It’s critical—and often underestimated. Another consistent theme I see is how long it actually takes to build the trust needed to lead change.

The executives who make the fastest strides are the ones who invest early in organizational relationships—not just with their direct boss, but with peers, direct reports, the board, and other stakeholders.

One of the most important, yet counterintuitive, actions I coach new executives on is to listen first and resist the urge to act. The pressure to demonstrate value quickly is real, but the executives who build the deepest trust are the ones who spend their first 30 days observing, asking curious questions, and reserving judgment. When people feel genuinely heard before change happens, they become partners in it rather than resistors to it.

Around the two-month mark in our onboarding coaching, we invite new executives to complete a Chasm Partners proprietary Stakeholder Analysis framework exercise. By then, the executive has enough context to honestly assess their key relationships—who they've connected with, who they haven't, and where the gaps are. The quality of that conversation tells me a great deal about how trust-building is going. 

My advice to hiring leaders is to explicitly give new executives the space and encouragement to focus on building “relational intelligence” across the organization—even more than building technical or industry knowledge. That investment pays off much faster than people expect.

Christine Britton:

That reminds me of the old saying that people don’t care what you know until they know that you care. Prioritizing that relational foundation actually accelerates everything else.

Without trust, senior executives tend to have lower commitment to the enterprise and can be more vulnerable to accepting calls from competitors or search firms.

How do you see that relationship-building play out in your coaching work?

Jen Person:

During our discussions about the Stakeholder Analysis tool, we ask questions such as: What do your key stakeholders care about most? How do they communicate? What does a mutually beneficial relationship look like?

The executives who have invested early in building trust are much better equipped to answer those questions in a far more meaningful way. It’s often a clear signal that they’ve done the hard work to set themselves up for success.

Christine Britton:

This framework is incredibly valuable and serves as a pivot point midway through the coaching engagement. It takes the executive through a series of questions about the progress of building relationships with the CEO and their peers, including considerations such as motivation, communication style, and mutual value. 

Beyond onboarding, it provides a structured way to track and deepen key stakeholder relationships over time and maintain alignment between the new executive and the rest of the organization. It also helps measure the impact of onboarding activities such as listening tours and 1:1 time with peers.

What consequences have you seen when onboarding is not properly managed?

Jen Person:

The most common and costly pattern I see is the executive who arrives in a vacuum. No comp plans, no defined goals, no clarity on authority, and sometimes not even a proper announcement that they've joined. They walk in ready to lead, only to spend their highest-value weeks — that irreplaceable time when a new hire brings a valuable “outsider’s lens” and organizational optimism — firefighting and building the basics from scratch. When organizations fail to prepare the basic infrastructure a new executive needs, they inadvertently consume the very asset they hired for.

What makes it worse is that the vacuum rarely comes alone. It's almost always paired with misaligned expectations. The executive was hired to build and lead, but the board is demanding results before the foundation even exists. Or the role boundaries were never clearly defined, so the executive is constantly decoding what success actually looks like while the target keeps moving. That ambiguity erodes confidence and produces work that misses the mark — not because the executive is incapable, but because no one took the time to set them up properly.

The organizational cost is real and compounding. The ELT disengages. Revenue timelines slip. The coaching investment shifts from growth to damage control. And perhaps most telling, the organization questions the hire rather than questioning the conditions. The pattern repeats with the next executive, and the next. What I've consistently seen is that these organizations hired well and onboarded poorly — and, in doing so, converted capable executives into struggling ones.

What happens if the new hire gets off to a rocky start? What are some actions the CEO and the organization can take to course-correct?

Christine Britton:

This is where the ChasmLead coach can be very helpful as a sounding board and advisor to the new executive. Because the coaching is confidential, the leader can feel free to share the real concerns or challenges they are facing. Talking them through with the coach helps the executive feel much more motivated and prepared to take those issues or questions directly to the CEO or other key stakeholders. 

My advice to the CEO is to preempt a bumpy start by spending regular quality time with the new executive to draw out these insights directly – asking good questions about their experience, listening well, and being open to the valuable feedback that a fresh set of eyes can bring. 

Final thoughts—what ultimately drives success in those first few months?

Christine Britton:

And there’s nothing more satisfying than seeing that alignment take hold—when capability meets need, and momentum builds.

That early traction benefits both the executive and the organization. It’s where you really see the impact of getting onboarding right.

ChasmLead helps healthcare organizations and investors strengthen leadership performance, team effectiveness, and culture through executive coaching, psychometric assessments, and consulting services. If you'd like to learn more, let’s connect.