New CEOs Have 60 Days to Get Stakeholder Outreach Right

Between 12 and 13% of CEOs are new to their position in any given year, and roughly 28% of those arrive from outside the company, according to Equilar. That share of chief executives starts the job with no real feel for the culture they have inherited, let alone the strengths and weaknesses of the business itself.

The first 60 days decide whether that gap closes or hardens into blind spots that follow a CEO for years, according to a recent Entrepreneur analysis. The early window of listening and assessment ranks among the highest-leverage periods of an entire tenure.

Yet new CEOs routinely overlook key stakeholders during onboarding. The analysis argues that mistake costs them crucial information — information that should inform strategic planning, the skills and structure required to build a leadership team, and how the company refines its messaging and go-to-market approach.

The obvious stakeholders still matter

Most chief executives focus on the mission-critical, obvious stakeholders. The real opportunity, the analysis argues, is to move past surface-level questions and go deeper faster.

With the board chair and key investors, the priority is understanding their strategic aspirations, risk tolerance and definitions of success. Every board has its own communication style and cadence. Pay attention to how they operate, not just what they say. These conversations also serve as a chance to both educate and be educated.

With the executive team and direct reports, a new CEO should assess capabilities, spot the silos and identify early adopters who already align with the vision. The analysis flags two warning signs: a hero culture, because it will not scale, and detractors and excuse generators who keep pulling the organization back toward legacy habits.

Phrases like "we've always done it this way" or "we tried that, and it didn't work" are red flags. So is a leadership team that struggles to set priorities or complains about workload instead of building a roadmap to get there.

The listening should not stop at leadership. The analysis recommends focus groups with individual contributors and mid-level managers to get a ground-level view of morale and execution speed — also one of the fastest ways to build trust and transparency early. Influencers and culture carriers exist at every level, and they determine how new thinking gets adopted.

Existing clients deserve time in the first few weeks too, both to build confidence and to ask the kind of basic questions that would seem uninformed coming from a CEO six months into the job.

The relationships most new CEOs skip

Few people know the pitfalls of the job better than the person who held it before — particularly if the departure was not amicable. A former CEO can speak to what worked, what is still in progress and what fell short, along with insights into the culture, the clients and how the board actually operates.

Partners in tech, data, platforms or agency relationships tend to offer the most neutral read on where the company stands in the market. Ask them directly what your reputation is, when the market turns toward you and when it turns away, and how your leadership team is perceived. If they are not familiar with the brand at all, that is useful information too. Sales teams in particular trade in this kind of intelligence, so building a relationship with them early pays off.

Conversations with recently exited clients and recently lost pitches can be uncomfortable, but the analysis calls them often the most revealing. Ask open-ended questions, avoid leading the witness and cast a wide net.

New CEOs should also set aside office hours where any employee can reach out directly. Enthusiasm is often the earliest signal of a change agent.

How to read what you hear

Gathering information is a critical step, but knowing how to read it matters more. The analysis outlines five things to watch:

The faster-horse instinct. Notice where executives and employees are more attached to the familiar process than to the outcome it is supposed to produce. That reluctance is often mistaken for institutional knowledge.

Patterns over volume. Weigh the themes that repeat across departments more heavily than whatever the loudest person in the room is pushing.

Cross-functional friction. Ask specifically where the bottlenecks occur and where processes break down for customers. Friction between teams is usually a structure problem — unclear ownership or roles — not a personality one.

A scorecard, not a gut check. Build one early, based on real KPIs, and go in with a hypothesis to test rather than a blank slate.

Earned authority. People follow leaders they trust. Restructuring or criticizing too early risks alienating a team before the CEO has proven an understanding of their day-to-day work.

The analysis closes with a caveat. None of this replaces the strategic work ahead: the plan, the team and the go-to-market decisions still must get made. But that work is only as good as the picture it is built on — and the picture is only as complete as the range of people a new CEO is willing to sit down with in those first 60 days.