The First 100 Days: How to Set New Executives Up for Success

By Tony Cinello, Founder – Anthony Andrew

The offer’s signed. The exec accepts. Everyone exhales—job well done, right?

Not quite.

What happens next will determine whether your new hire becomes a high-impact operator… or a costly false start. And in mid-market firms, there’s very little margin for error.

Studies show that 40%–60% of externally hired executives fail within 18 months (Harvard Business Review, 2022). Not because they lack capability—but because they walk into environments without clarity, support, or alignment.

In this article, I’ll walk you through what a high-performing First 100 Days framework looks like, why it matters more in mid-market and PE-backed environments, and how retained search partners should support far beyond the hire.

Why Executive Onboarding Is Broken

Here’s the uncomfortable truth: most onboarding programs are designed for employees, not executives.

They focus on paperwork, systems access, and HR orientation. They don’t focus on:

• Strategic alignment with the board and CEO

• Managing cross-functional expectations

• Defining early wins that matter to the business

• Navigating legacy politics, people, and power dynamics

And when those elements are missing, even the most talented leaders struggle to gain traction.

What’s at Stake

When onboarding fails at the executive level, it doesn’t just affect one person. It ripples through the organization:

• Strategic initiatives stall

• Team engagement drops

• Political fractures deepen

• The company loses confidence in its hiring judgment

  
  

According to the Corporate Executive Board (now part of Gartner), executives who receive a structured onboarding plan are 58% more likely to meet performance expectations in their first year (Gartner, 2023).

That’s the difference between momentum and missed opportunity.

The First 100 Days Framework: What It Should Look Like

We’ve helped mid-market companies launch hundreds of executives into new roles. Here’s what a First 100 Days framework includes—especially when stakes are high:

1. Pre-Day One Alignment (Before the Clock Starts)

• Align stakeholders (CEO, Board, CHRO) on expectations, success metrics, and timeline

• Provide context on the team’s culture, key relationships, and political landscape

• Review org chart, operating rhythms, and decision-making norms

• Clarify what not to change in the first 30 days

  
  

Too many execs walk in blind. Pre-boarding prevents early missteps.

2. Day 1–30: Learn the Business, Earn the Trust

The first month is about building relational capital, not launching initiatives.

Priority actions:

• Conduct 1:1 meetings with direct reports, peers, and key influencers

• Shadow key operations or customer-facing activities

• Attend board or investor meetings as a listener

• Identify quick credibility wins (but avoid big moves too early)

Tip: This phase should be structured but not rigid—flexibility is key to learning dynamics on the ground.

3. Days 31–60: Pressure-Test Assumptions

This is the diagnostic phase. The leader should begin to:

• Audit their function’s current state (people, process, priorities)

• Identify gaps, overlaps, and potential team misalignment

• Draft a 12–18 month strategy and align with CEO/CHRO

• Socialize early thinking with key stakeholders

  
  

Too often, new execs jump straight to implementation. This phase builds buy-in and avoids misalignment later.

4. Days 61–100: Execute Early Wins, Lock in the Plan

This phase turns momentum into movement:

• Begin to implement visible early wins

• Finalize strategic roadmap (with cross-functional input)

• Deliver a "100-day readout" to executive leadership and/or board

• Establish operating rhythms and feedback loops with the team

By Day 100, the exec should be trusted, calibrated, and aligned. That’s what sets the tone for long-term success.

What Role Should Executive Search Play?

At Anthony Andrew, we don’t believe our job ends when the offer is signed. In fact, that’s just the beginning.

Here’s how we support our clients post-hire:

• Help build First 100 Days plans with CEO/CHRO

• Align stakeholders before Day One

• Provide onboarding advisory check-ins at 30/60/90 days

• Pair new leaders with external coaches when needed

• Ensure feedback loops are built in early—not after problems show up

  
  

Because we don’t just place executives. We launch them.

The Mid-Market Angle: Why This Matters More Here

In large enterprises, mis-hires can be absorbed. In mid-market and PE-backed companies, the risk is magnified:

• Fewer layers of leadership

• Shorter runways for performance

• Boards and investors watching every move

• Cultural dynamics that can’t be navigated from a playbook

That’s why First 100 Days planning isn’t optional. It’s a multiplier—or a liability.

Final Thought

If your last executive hire felt like a coin toss—or your onboarding process is built for employees, not leaders—it’s time to rethink the playbook.

Your executive hire cost you time, money, and political capital. The First 100 Days is your best chance to make that investment pay off.

If you’re preparing for a leadership transition—or already onboarding someone new—I’d be glad to help you build a plan that works.

Because the hire is just the beginning.The success? That’s in how you launch.

—

Tony Cinello Founder | Anthony Andrew Retained Executive Search | Leadership Advisory

References (APA Format)

• Harvard Business Review. (2022). Why So Many New Executives Fail. Retrieved from https://hbr.org/2022/09/why-do-so-many-new-executives-fail

• Gartner. (2023). First 100 Days: Executive Onboarding Best Practices. Retrieved from https://www.gartner.com/en/human-resources