How to Hire Exceptional Leaders
A Comprehensive Guide

JD Saint-Martin, Lightspeed President
•
April 14, 2025
Hiring great leaders is both an art and a science. The right leader can elevate an organization, inspire teams, and drive success. But the wrong hire? It can be a costly mistake, setting your organization back significantly.
In this article
Here’s a streamlined guide to finding and hiring exceptional leaders who will make a lasting impact. Benchmarking against the following principles when building your leadership team will increase your odds of success:
1. Assess Loyalty, Longevity, and Cultural Fit
A candidate’s work history tells a story. Look for signs of loyalty and longevity over excessive job-hopping. Leaders with a track record of staying power have likely navigated challenges and seen initiatives through to completion.
Cultural fit is equally critical. Ask yourself: would you enjoy sitting next to this person on a 10-hour flight? If you’d dread the experience, they might not be the right fit. Leaders spend significant time with their teams, and their interpersonal dynamics can make or break relationships.
2. Seek Role-Relevant Experience and Data-Driven Mindset
Great leaders have walked a mile in the shoes of the role you’re hiring for. They’ve faced the challenges, navigated the complexities, and know what success looks like. This lived experience enables them to lead with empathy, clarity, and confidence.
Additionally, look for leaders who understand the value of a data-driven approach. Great leaders know you cannot manage what you cannot measure. They bring a clear understanding of what great looks like and identify the right key performance indicators (KPIs) to track progress, ensuring measurable success.
3. Find Leaders Who Raise the Bar
Exceptional leaders elevate everyone around them. They inspire teams to aim higher, think bigger, and achieve more. Assess whether the candidate has a history of bringing top talent with them to the table—former colleagues or proteges are strong indicators of leadership success. Do they already have great people in their network that will join the journey? Look for signs that they will challenge the status quo, see problems as opportunities, and push for innovation and growth.
4. Look for Adaptable Problem-Solvers with a Customer-First Approach
Avoid leaders who come in “guns blazing” with a pre-baked playbook. Every organization is unique, and leaders must adapt to the specific context and challenges they’ll face.
Great leaders ask thoughtful, probing questions and approach challenges with curiosity and creativity.
Sales leaders, in particular, must invest in understanding your product and customer base. Audit whether they’re demonstrating a commitment to learning the product, analyzing the customer experience, and understanding the pain points your organization solves. Leaders who immerse themselves in the customer journey are better equipped to drive meaningful results.
5. Balance Internal Promotions and External Hires
Striking the right balance between promoting from within and hiring externally is critical. A good rule of thumb: aim for 60% internal promotions and 40% external hires.
The devil you know is often better than the devil you don’t know.
Internal candidates bring institutional knowledge and cultural alignment. An organization that fosters internal development and that recognizes and grows talent from within will increase its longevity.

On the other side, external hires offer fresh perspectives and challenge entrenched norms. Be aware, however, that external hires carry risks—it is not unusual to see 50%+ that don't work out. Invest significant time and energy in vetting external candidates to minimize this risk and ensure you’re hiring the right person. Incorporating case studies into the interview process will reveal how candidates think, problem-solve, and approach real-world challenges. Seasoned executives are exceptional at selling themselves. Find ways to catch them off guard to see the true nature of what they bring to the table.
6. Avoid Leaders With Massive Corporate Mindsets
Leaders from massive organizations like Google or Microsoft may struggle in smaller, resource-constrained environments.
These candidates often rely on vast support systems and may lack the hands-on experience required to "roll up their sleeves" and execute in leaner organizations.
Seek leaders who are comfortable working in "less is more" environments and thrive on resourcefulness.
7. Guard Against the Cost of a Bad Hire
A bad hire can be detrimental, draining resources, morale, and momentum. Prioritize getting the right person over filling the role quickly.
The wrong leader can set your organization back significantly, so take the time to evaluate candidates thoroughly.
By aligning your hiring process with these principles, you’ll position your organization to secure leaders who inspire, innovate, and deliver measurable results.
Remember: great leaders don’t just fit into your organization—they make it better.
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