How do I learn from experience?

The American educator John Dewey (1938) stated, “We do not learn from experience… we learn from reflecting on experience.”  That fact remains unchanged (for at least the last 79 years) because it describes the need to reflect on how leaders develop.  For instance, a leadership shortage may be described by demographic shifts (millennials or global diversity), insufficient training (after promotions) or discouraging mindsets (low engagement or trust measures).  In response to that shortage, leaders need to practice desired behaviors more frequently (Kouzes & Posner, 2016).  Consider this example.  When I recently asked a room full of leaders, “How many of you describe yourself as a leader?” only about 10% raised their hands.  My experience is that many potential leaders do not regard themselves as leaders, largely because they do not trust their personal experiences.  Leaders can learn from experiences, but not all experiences are meaningful (Yip & Wilson, 2010).  This short paper explains how the two top processes of leader development can be applied to executive leadership.  Those two processes, 1) challenging assignments and 2) developmental relationships, described 64% of leader development experiences in the United States 24 years ago (McCall, Lombardo & Morrison, 1998) and are just as critical today.


Challenging assignments


As a species, humans have always adapted to environmental stimuli.  As leaders, humans adapt to environmental stimuli with internal change (Schein, 2010).  When I ask leaders to share their “personal best leadership story” the results may range from parenting to global reorganizations.  The unifying characteristic of those stories is that they describe challenging assignments; all leaders model initiative, take risks and innovate new behaviors (Kouzes & Posner, 2016).  One useful framework for practicing more leadership behaviors includes these five steps:  1) model the way, 2) inspire a shared vision, 3) challenge the process, 4) enable others to act, and 5) encourage the heart (show appreciation and celebrate successes; Kouzes & Posner, 2016).  That framework focuses on learning leadership behaviors, like a road map, and consequently I have shared that framework with dozens of executive leaders.  Any leader cited throughout history (in any reference book or in any story) has embraced challenging assignments.


So, what are useful challenging assignments?  Yip & Wilson (2010) list five types of assignments; 1) increase in job scope, 2) creating changes, 3) job rotation, 4) stakeholder engagement, and 5) cultural exchanges.  Examples of an increase in job scope include redesigning roles or responsibilities, adding people or budget to a current assignment, a career succession pipeline or a job succession ladder.  Examples of creating change abound as leaders respond to technological changes, market adaptations, global choices of suppliers and providers, diverse stakeholders, demands for improved efficiency, effectiveness or new outcomes.  Examples of job rotation include formal systems with regular shifts, as physicians and healthcare leaders often do when training, or informal rotations when leaders shadow colleagues in a different work group or culture.   Examples of stakeholder engagement include cross functional teams (sales and operations) or new market negotiations (vendors, clients, government officials) designed to develop awareness of cultural complexity and the need to negotiate desired outcomes.  Examples of cultural exchanges include foreign assignments, foreign responsibilities, cultural awareness assessments, organizational culture development, language skills, and understanding of global leadership behaviors.


The next question may be, “how do leaders increase their probability of success in challenging assignments?”  The answer includes feedback from developmental relationships.


Developmental relationships


       No leader succeeds alone.  We all need meaningful relational feedback such as coaching, peer or group mentoring, or one-on-one mentoring.  Yip & Wilson (2010) list three types of developmental relationships; 1) constructive managers, 2) difficult relationships, and 3) other venerated leaders.   Examples of constructive managers include regular one-to-one feedback sessions, performance reviews, based on critical organizational competencies or developmental states validated by a career development plan.   Examples of difficult relationships are those conflicts or disputes that were handled poorly, remain memorable as instructive reminders of “what not to do next time”, or lessons from unethical or inappropriate behavior.   Examples of relational feedback from other venerated leaders may include a mentoring session from an elder or historically wise leader, or an exemplary role model in a community or organization.


     How do leaders increase developmental relationships?  The most effective answer is to actively seek out wise mentors and regularly ask for feedback.  As Kaplan (2007) states, the person in the mirror may be able to respond to seven key questions with candid feedback.  However, my experience is that executive leaders require external, objective relationships with experienced mentors and coaches who can “speak truth to power” or model new desired behaviors.  The most requested topics for executive coaching engagements have not changed for many years; those topics are (1) executive presence and influencing skills, (2) ability in leading teams and people development, and (3) relationship management (TCB, 2014).  Managers and supervisors may be able to provide insights into those topics, but only executive coaches can observe and recommend new desired behaviors.


     The coach training industry is now estimated at 53,500 global coach practitioners and over $2B in annual revenue, with 115 accredited coach training programs (ICF, 2016). The International Coaching Federation (ICF) hosted the largest global survey (n=15,380, with 38% non-members) of coaching practitioners (internal, external or both) and managers or leaders using coaching skills (within Human Resources, Talent Development, or any line of business; ICF, 2016).  That survey identified the top future obstacles for coaching as (1) untrained individuals and (2) marketplace confusion (ICF, 2016). The survey also identified the top future opportunities for coaching as (1) increased awareness of the benefits of coaching, and (2) credible data on ROI/ROE/outcomes (ICF, 2016).  Those findings suggest a significant need for research on the efficacy of coach training.




When Dewey revolutionized American educational systems, he caused leaders to challenge the status quo and provide developmental relationships for students.  In a similar way, leaders have always accepted challenging assignments and sought candid, relational feedback of their performance.  In recent months I have applied the model from Kouzes & Posner (2016) to several executive leaders because it focuses on frequency of desired leadership behaviors.  If we assume that any leader needs to 1) model the way, 2) inspire a shared vision, 3) challenge the process, 4) enable others to act, and 5) encourage the heart (show appreciation and celebrate successes; Kouzes & Posner, 2016), then we can help more leaders to increase the frequency of desired leadership behaviors.  In other words, we can help leaders practice leadership.


Contact Doug Gray, PCC, for details at 615.905.1892 today.



Dewey, J. (1938). Experience and education. New York: Macmillan.

ICF (2016).  2016 ICF Global Coaching Study; Executive summary.  International Coaching Federation.

Kaplan, R. S. (January 2007). What to ask the person in the mirror. In On managing yourself (pp. 135- 156, 2010). Boston: Harvard Business Review Press.

Kouzes, J.M. & Posner, B.Z. (2016).  Learning leadership; The five fundamentals of becoming an extraordinary leader.  San Francisco, CA: Wiley.

McCall, Lombardo & Morrison (1988).  The lessons of experience; How successful executive develop on the job.  (reference not included in text, but cited on p. 64). In Velsor, E.V., McCauley, C.D. & Ruderman, M.N. (2010). Handbook for leadership development, 3rd Ed.  San Francisco: Jossey-Bass.

Schein, E. H. (2010). Organizational Culture and Leadership (4th ed.). San Francisco, CA: Jossey- Bass Publications.

TCB (2014).  The 2014 Executive Coaching Survey.  The Conference Board, Report #R-1568-14-RR.

Yip, J. & Wilson, M.S. (2010).  Learning from experience.  Pp. 63-95.  In Velsor, E.V., McCauley, C.D. & Ruderman, M.N. (2010). Handbook for leadership development, 3rd Ed.  San Francisco: Jossey-Bass.


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