In every career there are both milestones and plateaus, which are alike in that they take effort and new skills to hurdle. The single biggest challenge, however, is letting go of what I call the transactional level of leadership.

Remember how hard it was to learn to delegate in your first management job? You were in charge of a unit; suddenly you found yourself leading the organization. You stayed actively involved in the day-to-day transactions. After all, you had been the best salesperson, technologist or whatever in your particular field. You had made it this far on those skills. Therein lay the next challenge?and the key to advancing your career up the proverbial ladder. The things that made you successful in the past could be the very things that retard your growth to the next level.

I once worked with the president of a large company who had earned his stripes as a marketing executive before taking the top spot. Chaos reigned almost immediately. He did not fill the marketing position; he drove his staff through multihour meetings late into the night. He was literally working around the clock. He could not let go of the tasks that had made him successful. During one midnight conversation, I cautioned him, "You cannot do 37,000 jobs, but you can fail by trying." He gradually grew into the job but not before imposing a lot of pain on his organization and himself.

The challenge of letting go of transactional leadership exists at every level in organizations: when moving from a team member to head of the team, from manager to executive, from departmental executive to CEO. To be successful in these moves, you must move yourself from a transactional style.

There are several challenges that one must overcome in order to move through that transactional level of management to a big-picture leadership style. The term "transactional" as used here may differ from the academic definition, but it suffices to describe the conditions I have observed in real companies.

Letting go of the tasks that you have enjoyed doing and that led to your success may be difficult, but if you don’t, you will remain mired in your experience rather than benefiting from what you have learned. Consider the question: "Do you have 10 years of experience or one year of experience 10 times over?"

A former colleague depicts a leader as a juggler, with more and heavier balls being added as you move up the ladder. Even the best jugglers will eventually drop a ball. Reaching for the lost ball, the juggler drops more balls and thus begins a cascade.