Getting to the Heart – Weekend Reflections for Leaders: September 22, 2018

Bringing new people onto a leadership team is never easy. We could all probably share a few stories about decisions we made to fill key leadership positions that did not turn out well.

Poor decisions on filling critical leadership positions have enormous costs that go well beyond the financial statements.

Whether it is bringing in leaders from the outside or finding strong internal talent to move into a needed leadership position, the challenge is the same. Identifying the needed skills and experience is the easy part. The most difficult challenge is getting to the heart of a candidate to see if they will be an asset or a liability on the culture that is needed for the team to reach its full potential.

Many organizations and leaders spend a great deal of time and money on the well-studied executive psychology assessments, the expert questions to dive deep into experiences, and ensuring the guard rails are in place so questions don’t get too close to certain areas of life. These steps, although helpful, leave many gaps in assessing the heart of an individual to ensure a strong fit to the culture.

As we look to build and sustain a healthy, highly effective business, here are two areas that successful executives assess deeply to get to the heart of a leader before extending an offer to join the team:

(1) Problem Solving: What have been the most difficult problems you faced? How did you solve them?

We need leaders who focus on solving problems, not creating them or hiding from them. An orientation towards solutions is needed to grow customers, retain employees, and deliver financial results.

This question helps to get to the truth about personal ownership and accountability to find a needed solution as opposed to riding the wave of the team. People who take ownership of problems and the accountability to ensure they get solved can speak clearly about these experiences as they usually are memorable.

(2) Dealing with Failure: What have been some failures in your life? How did you handle them and what did you learn from them?

This question helps to understand integrity, responsibility, and risk taking. Individuals who are striving to reach their full potential have all fallen short at certain times.

We need leaders who are self-aware to recognize when and where they fell short, take accountability for failure (don’t play the blame game), share learnings and have the resilience to keep moving forward.

Many times, these two questions enable candidates to share more than their business experience and give insight into their humanity, which is an important component to building a healthy team as we learn to appreciate and care for each other as human beings as opposed to just cogs in the machine to drive growth and profitability.

These two questions are used by effective executives in identifying talent to fill leadership roles and as routine questions during one on one meetings with top talent throughout the organization. These two questions help effective executives get to the heart of leaders on their team and provides another vantage point to assess the health of the culture they are creating.

What if I were to ask you, “What is the most difficult leadership challenge you are facing today?” What would you say? Here are a few resources to help:

  1. Download the FREE resources at
  2. Contact me. Email: (M) 269-370-9275
    David Esposito