90 Days Before Your First Day Can Make Or Break Your Chances For Success.
By Neill Marshall, Chairman, HealthSearch Partners and Kurt Mosley, Associations Practice Leader, HealthSearch Partners
Jonathan Donahue lives by the principle of “No one cares how much you know until they know how much you care.” As a principal consultant with Lead Effect, he works with CEOs to transform their teams and their organizations to successfully deal with not getting fully unvarnished truth from everyone on the team. He also tackles situations where leaders are more focused on their individual departments and goals rather than overall company objectives. And he bolsters teams who are excited about future potential and want everyone going in the same direction on a clear path to success. Previously he has held executive positions and consultant roles at several firms including Sei AI, InterviewFocus, Ubiquity, WNS Global Services, Conduent, Sutherland Global Services, Synchrony & GE Capital. He earned a bachelor’s degree in Economics and Finance from Rutgers University and a master’s degree in Business Administration in Finance & Strategy from Columbia Business School.
Our continuing series of articles on the first 90 days of leadership generally explores what happens after a leader takes the helm—when the work of observation, relationship building, and cultural alignment begins. But Jonathan Donahue, Principal Consultant at Leadership Effectiveness, sees things through a different lens. He maintains the real foundation for success is often built before the first day on the job.
Donahue, who has spent more than 35 years helping CEOs and organizations build healthier, higher-performing leadership teams, argues that the most impactful 90-day plan starts not with onboarding but with due diligence. He speaks from hard-earned experience.
“The biggest risk is walking into a situation you didn’t see coming,” Donahue told us. “The best way to have a successful 90-day plan is to do the work and invest in the three months leading up to your first day on the job.”
Do The Homework—Prep Like It’s A Final Exam
For Donahue, preparation before accepting a role is non-negotiable. That means more than just understanding the job description and meeting your future boss. It involves mapping out the reporting relationships, investigating who came before you, and assessing any internal resistance to your arrival.
“What happened to the person before you? Did he or she leave or get fired? Who on the team might feel passed over or threatened by your hiring? These are the critical things to ask because you need to know the answers to these questions before you walk in,” Donahue said.
He advocates reaching out to former employees via LinkedIn and leveraging advanced research tools—including multiple AI platforms like Google Gemini—to uncover operational, financial, or cultural red flags that may not surface during interviews.
Push For Full Transparency After The Offer
Donahue believes that many leaders fail to ask tough questions because they’re eager to win the job. But he cautions that rose-colored glasses can quickly turn crimson.
“Once they’ve made you the offer, but before you’ve accepted, is when the most candid conversations should happen. That’s when you ask the hardest questions,” he said.
He recommends inviting key stakeholders to coffee or lunch, off Zoom and away from offices, to probe deeper. Are recent losses being downplayed? Have recent executive departures been adequately explained? Is the organization quietly being shopped? How long is your boss committing to stay?
“Your internal ‘BS meter’ should be turned all the way up,” he says. “If they gloss over serious issues, run.”
Embed The Risks In Your 90-Day Plan
If a new leader decides to proceed despite some concerns, Donahue says it’s crucial to explicitly incorporate those risks into the 90-day plan.
“You don’t ignore them. You make them a priority. You talk to the right people. You build trust by addressing the elephant in the room,” he explained.
He suggests creating action items to stabilize shaky customer relationships, strengthen leadership team dynamics, and clarify go-forward strategies, then measuring and reporting on those early wins.
One More Thing: Listen To The Voice In The Passenger Seat
One of Donahue’s most revealing red flag stories didn’t come from the organization. It came from his wife. After a dinner meeting with the executives of a family-owned company he was about to join, she turned to him in the car and said, “Are you sure you want to work with these people?”
Fourteen months later, he was out. The red flags were there, and he didn’t want to see them.
A Checklist For Self-Preservation
Donahue’s book, Faith-Driven Job Search, includes a complete 90-day checklist built on hard-won lessons. But his core message can be summed up this way:
“Some of the best deals you’ll ever make are the ones you don’t.”
In the race to make an impact as a new leader, Donahue challenges us to start earlier, to make sure the job is as right for us as we are for it. The worst-case scenario isn’t a rough first 90 days, it’s walking into a role you never should have accepted in the first place.
Stay tuned for more insights as we continue exploring the innovative tactics used by healthcare leaders to make their first 90 days count.
If you have adopted this tactic, or any others featured in this series, we’d love to hear from you. Please contact us to share your story.
