The One Question You Must Ask In a New Leader's First 90 Days

Most organizations approach executive integrations with the same checklist mentality they use for entry-level hires: Provide access credentials, schedule introduction meetings, share company documents, and hope for the best.  

But the fundamental reason many executive transitions fail isn't what organizations did or didn’t remember to do during the integration. It's what they forgot to ask.

In our work with leadership transitions, we’ve found that too few leaders ask a critical question: “What will success look like for this new hire in their first 90 days?" Those who do ask it often don’t do so in the most effective way, which in our experience includes having a neutral third party in the room to document the discussion and relieve the pressure.

It may sound mundane. Yet over thousands of integration coaching sessions, this single question, which Modern includes in all our executive search projects, has repeatedly revealed layers of complexity and insight that continue to surprise us. When it’s asked in the right environment, hiring managers provide more support and guidance. New hires ask better questions, experience less anxiety, and get intentional about relationship-building. It reframes the entire conversation, giving everyone permission to prioritize a successful foundation over flashy wins.  

The Stakes for Early Success Have Spiked

The question has proven, time and again, to be an essential launching pad for more successful executive integrations, a process that’s long been fraught with failure. In a study of more than 1300 HR leaders by Michael Watkins, the author of The First 90 Days, nearly 75% strongly agreed that success or failure during the first few months on the job is a strong predictor of overall performance. Estimates of executive failure rates within the first 18 months in a new job range from 38% to more than half, according to the Center for Creative Leadership.

This single question—asked in the right environment—has repeatedly revealed layers of complexity and insight that continue to surprise us.

Today's talent landscape compounds those longstanding realities.  

Organizations are increasingly hiring for competencies rather than traditional credentials, bringing in leaders with diverse backgrounds who may not have worked in the same industry, company size, or business model. This skills-first approach opens enormous talent pools and brings in fresh perspectives but invites more risk. Executives’ ability to deliver value isn't just about their competencies; it's about how quickly and effectively they can apply them within a different organizational context.

At the same time, the urgency for new executives to make an impact fast has never been greater. In an era of exponential advancements in AI and relentless technological disruption, competitive advantages emerge and disappear within quarters. New leaders no longer have six months to a year to find their footing. Failing to find quick success in today’s pace of technological change not only risks new executives’ own careers, it risks enterprise initiatives that define enterprise strategy.  

Envisioning Success, Not Just Setting Goals

When we first started asking this question, we expected hiring managers to have ready answers. After all, they've just invested months in a rigorous selection process; surely, they know what they want from their new hire?  

But while new executives are often asked to set goals in their early days on the job, that's not the same as discussing a vision of success. Goals set in the early days of a job are often too vague, too unrealistic, and too anchored on outcomes rather than process.  

Asking instead about what success looks like in the first 90 days tends to reveal different truths. For instance, recent research suggests that when leaders state their visions and involve employees, it leads to an increase in employee performance.  

In our experience, we’ve found that about half the time the question is asked, there's a long pause, followed by "that's a really good question ... I hadn't thought about it quite that way." These hiring managers aren't unprepared; they're human. They've been so focused on finding the right person that they haven't stepped back to consider what the first 90 days should actually look like.

In the other half of cases, when hiring managers do have specific expectations, the new hire doesn't just nod and take notes. They engage. They ask clarifying questions. They share their initial thoughts and reactions, expressing genuine excitement and curiosity about next steps.

The Magic of the External Voice

But what really makes a difference is not just whether the question was asked. It’s who’s asking it. When a new hire asks their boss "what does success look like?" (or vice versa) it can feel like a test, with pressure to find the perfect answer.  

When a neutral third party such as a coach asks the same question, however, something different happens. The hiring manager relaxes, feels safer, and begins to think out loud in ways less constrained by status.  

When a neutral third party such as a coach asks the same question, something different happens. The hiring manager relaxes, feels safer, and begins to think out loud in ways less constrained by status.  

Indeed, research shows that external or facilitator roles help reduce interpersonal risk, interpret hidden group dynamics, and foster psychological safety on teams by making it safe to raise doubts or explore unexpected options. In these spaces, hiring managers often generate fresh ideas, notice assumptions they had missed, and have genuine “aha” moments, precisely because the coach helps shift the dynamic away from performance pressure toward curiosity and shared understanding.

The more we've explored this question, the more we realize it's not really about defining success at all. It's about creating a moment of shared reflection and intentionality in what is typically a rushed, assumption-filled process.

It forces everyone to slow down and think about what the next 90 days should accomplish. And in that thinking, in that conversation, something shifts. The integration process stops being something that happens to the new executive and becomes something that everyone is actively, thoughtfully, participating in.

Engineering Success from Day One

Every new executive onboarding represents a choice: Will you rely on hope and good intentions—and checklists—or will you engineer success through clear expectations of success and structured support?

The skills-first hiring revolution has given us access to incredible talent, but it's also made successful integration and the investment in new hires more critical than ever. The scale and speed of technological disruption is opening vast new opportunities but only accelerating expectations for new leaders to move fast and win quickly.  

The conversation that determines a new executive’s success or failure happens in their very first week. Make sure you're having the right one, with the right person, asking the right question, and in the right way.