Coaching is one of the most difficult challenges facing leaders today. For starters, it places many outside of their comfort zones because they view it as “an additional requirement for which I have no expertise”. They might also view it as an added requirement at a time when they are already overburdened and resent an additional requirement being placed on them. What most do not grasp is that by effectively developing your subordinates, they can lift burdens off your shoulders. By doing your ten dollar an hour work, you have the bandwidth to do a $500 or $10,000-an-hour job.

When I was selected to be the US Secretary of Defense’s number two assistant, I was thrown into a pressure packed office and nobody had the time to coach me. I was disheartened and frustrated and almost quit until I started to train myself to “think like my boss.” My boss was the Senior Military Assistant and a two-star Army General. It was the same job Colin Powell had when he was a two-star. I observed the General every day and tried to anticipate his decisions to prove that I could think like a two-star. When I made the same decision the General made, I realized I could think like a two-star. When the General made a different decision than I would have made, I would sit back and try to see where my training needed to be improved so that next time, I would make the correct decision. When I couldn’t figure it out, I would find a quiet moment and say to the General “I’m trying to understand how you made that decision. Could you please share with me your thoughts so that I can be better prepared the next time?” Over time, my decision-making ability improved. At the same time, the General started to trust me more. He started to shed some of his responsibilities to me which eased his stressful job. I went from being an individual contributor to being responsible for the trip planning teams, the security detail and the communications group.

What made this coaching model successful is that we both had something to gain. I learned how to think like my boss and he had burdens lifted off his shoulders. It would not have been successful if I did not feel comfortable enough to challenge him at an appropriate time and say, “I don’t understand. Can you please explain to me your thinking on this?”

I took this model with me to USS Benfold. I put the onus on my officers to start thinking like their bosses. I also made sure we were approachable so they could ask us if there was something they didn’t understand. It wasn’t an additional burden or program but it became ingrained in our culture and how we operated. Along the way, I tried to groom these young men and women to be able to command their own ships some day and to this day…have the highest percentage of junior officers from one ship to command their own ship.