More Effective Questions – Weekend Reflections for Leaders: September 8, 2018

In order to effectively compete in today’s hyper-competitive markets, we have developed efficient systems to measure performance against key objectives and frame those objectives into specific results that can be tracked and monitored. These tools are incredibly helpful to align our teams around the critical tasks and provide an efficient starting point to discuss performance at the team and individual level. These tools, if used properly, can also provide early warnings to changes on the periphery of our markets that may become disruptive if not addressed.

As we strive to be effective executive leaders in the workplace, we need to efficiently use these tools to take routine performance management a few steps forward beyond the simple insight of:

  • “Did we hit our volume and sales goals?” why or why not?
  • “Are we on time and within budget on the new product launch?” why or why not?
  • “Is employee turnover within range of our expectations?” why or why not?

Beyond the routine performance management process, effective executives and top talent move their teams forward with a few additional more effective and thoughtful questions:

What did you learn?

How can we apply those learnings today to be more effective tomorrow?

As we look to build and sustain a healthy, highly effective company, executive leaders and top talent need to move beyond just the simple numbers and understanding of what happened.  Leaders need to consistently reinforce the importance of individual and shared learning to support the long-term health of the company.

There is no doubt that the task needs to be completed, the product needs to ship on time, the cash flow needs to turn positive (at some point), but it is the ongoing learning that builds the foundation for greater impact down the road.

As effective executive leaders and top talent prioritize discussions about the learnings gained in the process, below are a few of the upsides:

  1. Reinforce personal growth. Continual growth is the foundation for building a brighter future for us as individuals and teams.
  2. Lessen the risk of getting arrogant and fooled by short-term, great accomplishments. We typically only gather learnings when disaster strikes. Maintaining some level of discipline to discuss specific learnings when we overachieve will help us avoid the all too common path of arrogance proceeding the fall of a once great organization.
  3. Demonstrate to others that we care more about them than just the numbers and the benchmarks. Ensuring others know that we care far more about them learning rather than just accomplishing results, we will keep the door open for genuine, healthy, and meaningful relationships in the workplace.

Being intentional about creating a continual learning organization is a worthy endeavor for executive leaders and top talent.  In the stress and strain of hitting benchmarks on a performance dashboard that is reviewed each day, week, and month, it will take some discipline to reinforce to our teams the importance of understanding what they learn in the process of delivering the results.

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 FREE resources at  
  2. Contact me. Email: (M) 269-370-9275

David Esposito

Difficult Conversations – Weekend Reflections for Leaders: September 1, 2018

Social researchers in academia, human resource consultants, and our own personal experience would say that the vast majority of us avoid and delay having the difficult conversation to address lingering frustrations in the workplace.

As leaders in the workplace, we often delay having the difficult performance discussion or avoid addressing the occasional behavioral problem with an employee until it is just unavoidable, and the team or project has been significantly impacted.

The reality of leadership is that we will have a steady flow of opportunities to have difficult conversations. 

To ensure the optimal health of an organization, the wisdom of experienced executives and top talent would say having the courage to put the difficult conversation on the table sooner rather than later is the most effective choice for the individual, team, and sustainability of the business.

Below are some habits of successful Executives and Top Talent who are effective at having the difficult conversation today rather than tomorrow:

  1. Acknowledge the Truth. It is not easy to effectively have these types of discussions. The work environment is often complex, disruptive, and painful. Addressing difficult issues does not come with paint-by-numbers instructions. It is not perfect, but it needs to be experienced, not avoided.
  1. Begin the Dialogue. When we avoid addressing the problem, we often create more problems. Unresolved issues do not go away, they just rear themselves in other ways. As leaders, we learn and grow as we address challenges, so get started.
  1. Shared Accountability. Effective executives and top talent acknowledge both parties have behaviors that contributed something to the problem. As leaders, the willingness to acknowledge our own shortcomings in a situation is often a helpful start to a productive discussion.
  1. Intent, Understanding, and Behaviors form the Foundation. (A) It is important to be genuine in our intent to move the relationship forward in a healthy way to achieve the long-term goals of the team and the individual. (B) Seek understanding first as we do not see the world as it is, but we see the world as we are, and our experiences and attitudes bring about a host of preconceived notions and biases. (C) Be clear about addressing the behaviors without making a sweeping condemnation of the individual’s character or potential. 
  1. Set the Example. As a backdrop to having these individual difficult conversations, we may often find ourselves in a tough spot in the overall business which adds to the pressure and urgency around having a difficult conversation. We will learn and grow through addressing difficult issues and even if they don’t get adequately resolved (which many may not), we will be setting a great example for others to follow in that we don’t give up.

Executives and Top Talent who delay and continue to avoid having the difficult conversation will be less effective in leading their teams to sustain top performance in the marketplace.  We all need to muster the courage to have the difficult conversation sooner and build a healthy environment for our teams to reach their full potential. 

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 FREE resources at  
  2. Contact me. Email: (M) 269-370-9275

David Esposito

Training & Development – Weekend Reflections for Leaders: August 26, 2018

In our hypercompetitive and rapidly changing marketplace, it is critical for all of us to be intentional and relentless about continuing to learn and grow.  It is essential for our survival in the workplace.

Many traditional businesses rely heavily on the training department or human resources/leadership development teams to package together well-rehearsed programs to support a generic brand of leadership training, conflict resolution, job-specific skills, and team building.  If some business unit is falling short, most often one of the responses from operational leaders will be “we need more training” and then here comes the ½ day curriculum to make us all feel good that some action was taken to address a gap.   

Many of these top-down programs do provide a helpful channel to reinforce corporate values and priorities to keep the team aligned and on track to deliver on company objectives.  However, the idea that top-down corporate training and development programs can create the kind of nimble and effective leadership teams needed to effectively address today’s challenges is a false-hope. 

Today’s marketplace demands a radical shift from the one-size fits all, sit down and “feed me” top down development programs to remain competitive in the marketplace. Executives and their Top Talent need to expect and embrace a more effective way to remain individually relevant and forward-thinking in their roles and to be contributing in a manner that can help the team be more competitive.

The three behaviors below frame the mindset and routine practice of successful Executives and Top Talent who are intentional about learning and growing to add value to their teams and organizations.

  1. Search. Beyond the top-down training curriculum, they are searching for resources that speak to them personally at their individual areas of need and interest.  There is an amazing amount of free content online from some of the foremost global thinkers and doers.  They read, they make time to interact with others outside their industry and they remain engaged in the search for the best and brightest ideas in areas that are relevant to them.   
  2. Share. As new insights and resources are found to be helpful to them, they don’t hold their findings to themselves like some trade-secret to further their own personal agenda. They thoughtfully share helpful findings with others around them. They share what worked for them with a degree a humility that it was helpful them and may be of help to others.      
  3. Impact Others. Overtime, the information and resources they find and share have a measurable impact on individuals and teams in a meaningful and relevant way to make them more effective. Others begin to proactively seek them out for quick, nimble solutions rather than requesting “more training” and scheduling another ½ day training session. 

Executives who still lead their teams by orchestrating top-down training and development vs fostering an environment for independent search and sharing will be less effective in leading their teams to succeed in today’s hypercompetitive marketplace.

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

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

David Esposito

Why Lead? – Weekend Reflections for Leaders: August 25, 2018

Being an effective leader in today’s marketplace is not easy.  The pace of competitive threats and marketplace disruption from global innovators has threatened all aspects of companies operating in a traditional framework.

As the demand on leaders continues grow in complexity and intensity, we all will, at some point, come to that reflective moment and ask ourselves, “Why I am still doing this and do I really want to continue to lead in this environment?”

Here are a few thoughts to help keep the fire within burning bright during some dark part of our leadership journey:  Answering the question, Why lead?

  1. Leadership helps others. Beyond the pressure of the business, the competition, and the money, leading others provides us with a unique opportunity to connect with and make a positive impact into the lives of others. Leaders can make the world a better place, one person at a time. Life is designed to be in community with others and leadership puts us in the forefront of connecting with others to make life better. Our leadership can support a purposeful life as connecting with others is what gives life meaning. 
  2. Leadership is for the long-term. Our leadership is not defined by a near term failure or success in the business. Today’s bonus check and write-up in the paper may define the short-term impact, but our leadership is defined by the long-term personal impact we make on others.  When our actions consistently build a foundation based on trust, respect, and commitment, we prepare our teams and business for success over the long-term which will define our leadership legacy.  
  3. Leadership chooses the hard things. As President John F. Kennedy tried to rally the nation to the cause of going to the moon, he said, “We choose to go to the Moon…and do the other things, not because they are easy, but because they are hard; because that goal will serve to organize and measure the best of our energies and skills…” As leaders we need to choose to do the hard work in order to set an example for others and lead our teams to reach their full potential. It is the most effective choice and most of us would prefer to be remembered as having done the harder right rather than taking the easy way out.

As our business gets more challenged, leaders rise to the occasion and whether we want to continue or not in our role, the reality is, we are leading regardless of whether we acknowledge it, embrace it, work on it, or just plain check-out. Our presence and actions influence those around us for the positive or the negative, regardless of title or position.

I wish you all the best to keep moving forward in your leadership.

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

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

David Esposito

Introduction – Weekend Reflections for Leaders: August 25, 2018

We all cast an influence on those around us.  Whether we embrace it or not, those with influence lead others and we all have the potential and the opportunity to lead more effectively.

The purpose of Weekend Reflections for Leaders is to provide leaders with:

  1. Practical tools and concepts to be a more effective leader
  2. Moments to pause and reflect on the larger personal leadership journey we are all on
  3. Encouragement and support for leaders to be the best for those they care about most – Top Talent who are leading an organization forward

The content for Weekend Reflections for Leaders will be posted on LinkedIn and no surprise, on the weekends.  The reason for the timing is two-fold:

One: Despite the practical reality of 24-7-365 communications in our highly connected workplace, there are moments in the work cycle when there is time taken to pause, recharge, and reconnect with others outside of the day to day grind of work.  For most developed economies, there is some moment over a typical weekend that can provide a momentary pause to reflect and recharge.

Two: For most leaders, there is always that moment during the weekend when our mind begins to ponder the “list” of the upcoming week’s demands, our stomach may begin to churn, and the restful weekend mindset begins to turn to a bit of anxiousness toward the work responsibilities ahead.  These writings are designed to help lessen the anxiousness of the week ahead by providing encouragement, insight to deal with leadership challenges more effectively, and a moment to put the week’s challenges in perspective of our larger leadership journey.  These steps have personally helped me be more effective in addressing the Sunday late afternoon and evening concerns of the week ahead.

My hope is that this content will speak to you in the most personal and relevant way in order to nourish you along the journey to reach your full potential as a leader.

The encouragement of those whom I have worked with in the past and those of you who have been readers of my weekly blog Character Creates Opportunity (inert link) were the sources of motivation for me to begin to share some thoughts on leadership. As for as my qualifications and expertise, I don’t want to turn you off, but I claim no unique skills and I have no formal license or accreditation to do anything. Here are just a few insights into my 25+ years of professional background and experience:

  1. I have stepped “into the ring” of leadership in large corporate environments, mid-sized privately held companies, entrepreneurial start-ups and combat in Iraq.
  2. I have experienced some big successes and some very painful failures in business and leadership.
  3. I have been a mentor to many and have been mentored by some amazing leaders.
  4. I have been intentional about placing a premium on learning and growing continuously throughout my own leadership journey.
  5. I am still actively stepping “into the ring” of leadership in the marketplace today.  

What I hope to share in these writings are some observations and practical action steps for the things that matter most in helping us be more effective leaders, inspiring others to lead, and laying the groundwork for even greater impact in the marketplace.

The focus on these writings will be on leadership in the workplace because meaningful and purposeful work most often brings out the best in us, encourages others, and along with education can be a gateway to improving the lives of others.

In addition to the Weekend Reflections for Leaders, here are a few resources to help:

  1. Free resources at
  2. Contact me. Email: (M) 269-370-9275

I wish you all the best.

David Esposito

Standing In the Gap Leadership Programs from Harvest Time Partners

Learn & Grow – Weekend Reflections for Leaders: March 23, 2019

There is no doubt that the marketplace continues to get more complex and uncertain. The pace of innovation continues to accelerate along with the ongoing rise in globalization that brings competitive threats from every corner of the world. In addition to the human capital that brings pressure to the marketplace, the rapid adoption of machine learning and artificial intelligence is reducing cost and time at amazing rates across all industries.

As senior executives and the top talent on their teams strive to be more effective in their roles to lead their teams and drive growth in the business, they need to be intentional about their efforts to learn and grow. Maintaining a consistent effort to draw clear learnings from experience and rapidly apply those learnings to be more effective in the future is critical for leaders to remain relevant in the marketplace.

Much of today’s documented learnings in business that are accumulated inside senior executive teams and boardrooms are around applying new technologies to be more efficient, emerging competitive threats, and innovative service offering to expand impact in the market. The continual learning in these areas are all important to the near-term and long-term health of the business.

However, what is not always well documented and discussed inside senior executive teams is the personal leadership learnings that would demonstrate individuals are increasing their leadership effectiveness to keep pace with the demands of the environment. As senior executives and the top talent are their teams strive to improve their leadership effectiveness, here are a few areas worth reflecting on to ensure they are continuing to learn and grow to remain relevant:

  1. Difficult Conversations: What have I learned about my ability to raise the difficult issues quickly, clearly, and effectively in order to drive action? How am I applying those learnings to my next set of challenges?
  2. Talent Management: What have I learned about my ability to place and assess talent in the most critical functions of the business? Am I sharing those learnings with others?
  3. Risk Taking: What have I learned about my willingness and ability to assess risks and to take risks in the business and our people?
  4. Communications: What have I learned about my ability to effectively communicate to stakeholders around critical aspects of the business such as mission, goals, behaviors, recognition, etc.? How have I applied those learnings to be more effective going forward?  

Many times, leaders focus discussion on the shared learnings around process and technologies to demonstrate they are building “learning organizations.” These types of learnings are important to the business. However, leaders need to create the space to think about their own personal leadership learnings in order to ensure they maintain their effectiveness in a constantly changing environment. Leadership effectiveness is the differentiator for companies to drive growth in a complex and uncertain future.

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 FREE resources at
  2. Contact me. Email: (M) 269-370-9275

David Esposito

Middle aged woman looking out of the window in the boardroom

Veteran Transitions – Weekend Reflections for Leaders: March 16, 2019

There has been a great deal of progress over the years in supporting military veterans as they pursue employment opportunities after transitioning from their active duty service commitments. 

As Senior Executives and the Top Talent on their teams work to build high performing teams with a diverse set of skills, I wanted to share a few thoughts that I provided to a friend who asked me, “What were some of the key learnings that you carried from West Point and the Army into your career in the business world.” My friend is a leadership consultant and he was preparing for a client meeting to discuss the importance of culture.

I thought the principles contained in my response maybe helpful to others as we all continue to build and strengthen our leadership. The below is basically a “cut and paste” of some points from the email:

Set the example:

  • At West Point we all lived the “Follow Me” mindset (US Army Infantry motto is “Follow Me”). You must be willing to stand up and lead when everyone else is scared, tired, confused, and bullets are flying. The simple and courageous act of “modeling the way” by standing up and leading into the fire to accomplish a goal was a day in, day out lesson we all learned by doing and by watching others. The reality is that with the noise, confusion, and extreme chaos on the battlefield, the only effective means of communicating and leading a team is to lead by example and that means moving forward into fire to encourage others to move on to the objective with you.
  • In terms of transferring that to corporate life, much of the above holds true. People need to see the leader who is leading the way in terms of making principle-based decisions, treating people with dignity and respect, and giving their full, committed effort to accomplishing the objectives. In the corporate world, the inevitable atmosphere of “politics”, “perception”, “turf wars”, etc. will always be there as a potential hindrance to serving customers and getting things done.  However, it has been my experience that the leader who humbly and persistently sets the example by mere day in, day out actions, will ensure the team achieves their objectives more times than not. All the great memos, corporate communications, and employee briefings are important, but it seems the daily actions of a leader will always be the element that will rally a team to deliver.
  • Continuously learn and grow (remain teachable):
  • At West Point, there was a tremendous amount of regimented process as you would expect, but inside that regimentation, the situation was always changing and you had to be committed to learn and grow otherwise you would not survive. As a plebe (freshman) you had a constantly changing set of assigned tasks to support your company. As upperclassmen, you were given new leadership assignments constantly so there was always new people and new situations that you had to deal with to accomplish the objectives. In addition, you had a front row seat to constantly observing others in leadership positions so you could be aware of learnings to apply when you were in those positions. Regular Army training and the experience gained after graduation gave additional learnings. Situations in combat can be very fluid and leaders need to be prepared to adjust plans and techniques to accomplish the mission. You are learning in both success and failure. The environment keeps you humble, and humility is critical to remain teachable.
  • In the corporate world, there is a whole field of study around the “change management process” because it is so difficult for people to understand the need to change, embrace it, and then effectively deliver on the needed change. However, most veterans thrive on change as it became a way of life in the military. The business world continues to grow in uncertainty and intensity. Competitive threats emerge so quickly, business plans can become meaningless in a matter of months, not years like in the past. Leaders must be insatiable in the desire to learn, grow, and adapt to a very fluid marketplace. Without a humble and proactive willingness to learn and grow, one’s leadership effectiveness and one’s business may die a quick death in today’s hypercompetitive and fast-moving global marketplace.
  • Service to others and a cause greater than oneself:
  • The entire military experience falls under the umbrella of “service” to our nation and very tactically, service to others in our squads, platoons, and companies. There is so much written today about having a “true north” to guide personal growth and organizations. Service to our nation was that “true north” at West Point and it solidified the sense that our entire journey of life is about something bigger and greater than ourselves. Tied very directly to that sense of service was sacrifice. You cannot have one without the other. Sacrifices daily that then ultimately prepared one to give the ultimate sacrifice on the altar of freedom.
  • In the corporate world, there seems to be a more consistent drumbeat from leaders about the aspect of service to their people, teams, and customers. However, there is still a strong gravitational pull to “my title, my paycheck and my accomplishments” that undergird personal motivation. Some very practical realities like paying bills, supporting personal responsibilities, etc. make those motivations important. However, when leaders place those things above the call of service to their people, customers, and the cause of the organization they lead, they are missing a critical element to achieving a sustainable, high performing business.

The principles of effective leadership transcend industries and markets. Senior Executives and the Top Talent on their teams may utilize various techniques to accomplish business objectives given the many variables in a complex marketplace. However, just like in the military, techniques can change given the situation, but principles should not be violated.

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 FREE resources at
  2. Contact me. Email: (M) 269-370-9275

David Esposito

Feeling Safe in the Workplace – Weekend Reflections for Leaders: March 09, 2019

There has been slow, steady progress over the years of the industrial revolution to improve the physical safety of workers. At the time, the assessment of company leaders, unions, and government agencies continued to demonstrate the fact that when employees feel physically safe in the workplace, their work improves and operational efficiency of the business increases.

Fast forward a generation or two into the current environment of the knowledge worker where the pace of change and disruption in the marketplace continues to accelerate, and we see the emergence of a new kind of need for safety in the workplace that can drive improved performance. Academics and business consultants studying leadership effectiveness would document the need for individuals to feel mentally and emotionally safe to share different points of view, raise topics without fear of repercussions, and have difficult conversations in a timely manner as the new, critical areas of feeling safe in the workplace that will sustain improved business performance.

There is solid evidence for senior executives and the top talent on their teams to ensure team members feel safe to speak up and address key issues head-on without a significant fear of being viewed as “not a team player” or more directly, being labeled as a pain-in-the-ass that slows down the process and most likely will be passed over when the next talent review is conducted to support various internal promotions.

The business issues continue to get more complex and senior executives can’t be on the front lines in all sectors. It is important for senior executives to have people on the ground with a sense of safety to quickly raise key customer challenges, emerging competitive pressures, or indications when the original annual plan is coming off the rails to ensure the survival of the business. Toxic internal/HQ environments can also disrupt the long-term health of the company as we have witnessed over the years with accounting irregularities that were never surfaced or the revelations that the #MeToo movement has brought to boardrooms in every business sector.  

Ensuring team members feel safe in routine meetings, operations reviews, strategic planning sessions, talent assessments, etc. is critical to the long-term strength of the business. Here are a few ideas to ensure senior executives and the top talent on their teams create an environment where team members feel safe:

  • Set the Example: There is no greater action step than leaders demonstrating the courage to raise key issues and put difficult topics on the table. We must “walk the talk” as leaders if we want others to follow.
  • Different Viewpoints: Leaders need to acknowledge the truth that we all see the world as we are, not as it is. Ensuring we gather a wide, diverse set of viewpoints is critical to making the most effective decisions on complex business challenges. Teams comprised of everyone having the same viewpoint will soon miss some major shifts in the market.
  • Recognition: Leaders need to consistently take time “in the moment” to recognize team members who make courageous attempts to speak up on relevant topics. We would all love difficult topics to be raised in a respectful and thoughtful way. However, in the workplace, just like life, things can get messy at times. Leaders needs to recognize issues being raised even when they are not done in the “approved company protocol” as there is a greater risk of continuing to sweep critical issues under the rug vs not abiding by the company protocol. Over time, some coaching and training can help team members with the company protocol, but for now, priority should be given to getting the issue on the table.  

Modeling the above behaviors will help senior executives build the healthy culture that companies need to ensure team members feel mentally and emotionally safe to effectively contribute to the long-term health of the business.

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 FREE resources at
  2. Contact me. Email: (M) 269-370-9275

David Esposito

Real life businesspeople shot on location. Since these locations are the real thing, and not shot in an “office studio”, high ISO levels are sometimes needed to catch the moment. The ISO range is between 250-600 so it should be fine for most usage cases. Most people won’t notice anything really, but if you are a nerd like us, you can see a little noise.

The Assessment of Top Talent – Weekend Reflections for Leaders: March 2, 2019

Most large organizations put a great deal of effort into managing their top talent and much is written about the war on top talent in competitive markets.

Top talent are an essential element to the growth of a business. They provide the energy and initiative to get the work done today combined with the hunger and openness to learn what is essential for the company to succeed in the future. Their names are in the “top box” to become the future senior executive leaders of the company.

There is often a unique relationship between senior executives and the top talent in their organizations that (a) creates the energy and ideas to raise the bar on all aspects of near-term company performance and (b) drives the forward edge of innovation to build and sustain long-term value in the marketplace. This relationship is critical to the value creation of companies.

There are a variety of academic instruments and structured programs that are used to assess talent and categorize them on a consistent grid for company leaders to understand their bench-strength and ensure there are solid plans in place to keep top talent engaged and further developed to fulfill larger roles in the future.

Many of the traditional rubrics uses to assess talent are quite extensive and capture the essential leadership qualities in addition to applying a heavy hand on the objective results delivered to demonstrate someone can effectively deliver positive business results over time.

In having participating in many talent assessment sessions across large and small businesses, I have experienced that there are two skills that are not always well assessed well in these standard rubrics and these skills are critical to becoming a long-term successful senior executive.

  1. A strong intent for teamwork that is driven by humility. As the marketplace continues to grow in complexity and uncertainty, the business issues are difficult…all the easy ones have already been solved or will be solved soon enough with machine learning. Through the lens of humility, successful senior executives realize there is not one person (and it certainly is not them) that can brilliantly solve these complex problems. Diverse thinking, well-functioning teams are essential to business survival. Quite often in our top talent assessments, we look to the individual’s “smarts” or “critical thinking” and don’t adequately assess their desire for teamwork that is driven from their own humility in realizing the complexity of our situation.      
  2. Resilience to overcome failure.  Most business plans don’t work out as brilliantly pitched during some annual operating plan/budget approval process. Business events, some planned for and some unforeseen, will bring our original plans completely off the rails at some point.  Successful senior executives have learned to quickly put the situation on the table, get teams involved sooner rather than later, and bounce back with a plan and a renewed energy to keep moving forward. Quite often in our top talent assessments, we look to discuss the individual’s successes and don’t spend adequate time assessing the times they failed and how they handled those events. Another driver of not digging deeper into a top talent’s failures is the dominant, prevailing challenge for most large organizations which is their inability to appreciate failure as a means to learn and grow stronger. Most large organizations would still prefer to sweep failure quickly under the rug and get back to the less difficult, more positive discussion around some other event in the business that went particularly well.     

I have found that there are two helpful lines of questioning that can bolster the efforts of senior executives to better assess top talent in the two essential areas highlighted above:

  1. Teamwork driven by humility. Assess problem solving: “What were the most difficult problems they (top talent) faced and how did they solve them?”
  2. Resilience to overcome failure. When did they experience failure? How did they (top talent) handle those events and what did they learn from them?

In addition to understanding the specific responses to these questions, there is a hidden gem in the responses (or lack of response) to these questions which is the broader assessment of how hard are these supposed top talent pushing the limits of innovation, seeing around corners for competitive threats, and risk taking that are all critical skills for successful senior executives.

Senior executives and the top talent on their teams face significant challenges in building a long-term healthy business. It is important for all of us to recognize the underlying essential behaviors that deliver over the long haul.

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 FREE resources at
  2. Contact me. Email: (M) 269-370-9275

David Esposito

Shot of a businessman giving a presentation in the boardroom