On-the-Job Experience Plus Deliberate Practice

It’s rare for major business journals to talk about experience-based leadership development. So I was pleasantly surprised to see an interview with Cynthia McCauley of the Center for Creative Leadership in Strategy + Business. McCauley describes why on-the-job experience, rather than formal training, is important to developing leadership:

Leaders who step into new situations face challenges that call for untested abilities. They continue to develop their capacities and successfully take on higher levels of leadership responsibility. That’s consistent with what we know about adult learning and development, too: People learn how to do things when they’re put in situations where they have to do them and practice doing them.

This may sound obvious, but few organizations build leadership development around on-the-job experience. Instead, they offer formal training and possibly mentoring or coaching. Therefore, there is a great opportunity to improve leadership quality by matching leaders who are good at learning with experiences that teach them what they need to learn. McCauley provides four tips to organizations interested in doing this:

Master difficult conversations

Learn my best tips for staying cool under pressure and elevating your leadership in complex times.


  1. Plan initiatives carefully, monitor learning carefully, and track executives as they move up the organization.
  2. Customize learning experiences to each individual.
  3. Invest disproportionately in supporting leaders during times in their careers when they need concentrated development. In addition to on-the-job experience, provide peer learning, coaching, and related training.
  4. Provide experiences that cross organizational boundaries.

This is great stuff. To strengthen it, I’d suggest three powerful complements:

  1. Identify pivotal new conversations. Conversations are the building blocks of leadership. When leaders take on new experiences, they have an opportunity to enter new types of conversations with new people. What are these specific conversations and what does it take to do them well? For example, let’s say you’re a line manager who has managed organizations of 500-1000 people and you’ve been asked to take on a staff role that reports to the GM of your business. You now have three direct reports rather than ten, and most of the people you need to influence to get things done are outside your authority and unaware of your past track record. What kinds of conversations do you need to have with these people? What prior conversations with your direct manager, the GM, will set you up for success? These are questions worth asking at the outset of any new assignment.
  2. Deliberately practice these conversations on the job. In Practice Greatness, I describe the four elements of the on-the-job practice cycle: preparing, acting, reflecting, and getting feedback. In this interview, McCauley mentions reflecting but doesn’t explicitly suggest preparing or getting feedback. All four elements are essential to accelerating learning from experience.
  3. Deliberately practice these conversations with a coach or mentor. I think leaders would learn much faster if we offered them opportunities to practice speaking and listening outside the pressure of everyday work. What if practicing leadership conversations looked like practicing tennis: you say a few things, reflect on how it felt, get quick feedback, adjust, and try again? This is how my coaching clients and I spend one third of our coaching sessions. Although this approach is an outlier in the leadership development field, it is mainstream for other endeavors in which people are consciously practicing for high performance.