I am the first to admit that as time goes on, it is becoming increasingly more difficult for me to be patient. In my professional life, that is far more true than in my personal life. That is likely the case because of the perceived timeline over the horizon. I have entered the 2nd quarter in my current job, and though no one knows how much time is left on the clock of a military career, I can safely say that the amount of time I have left to serve in the Navy is much shorter than the almost 24 years I have served. As the time gets shorter, so does my patience. I don’t think that makes me different than most, but I may pay more attention to time than anyone else I know. One indicator is the response I often get when I tell a teammate how long I have been in my current job (227 days as of this post). Because I want to make every day count, I find it helpful to count each day. For the same reason, I have a need to continually remind myself and others of the progress we have made and the next outcome we are committed to delivering. I am not saying that such behavior is necessary, it’s just who I am and it works for me. In fact, the team with whom I lead now makes it a point to publicly “acknowledge our wake” and “chart our course” every two weeks – Accountability inspires progress.

Leaders who are committed to progress tend to be much bolder than managers of the status quo. Leaders committed to shaping the world of tomorrow are far less cautious than managers focused on preserving relevance today. That boldness inspires many and it puts off others. For that reason, it is important that those of us committed to truly changing the order of things (the real call of leadership) are Cautiously Bold. In both my primary duty and in the execution of a few side projects I am having to temper my boldness. There is little choice but to take a more measured approach than I would like. This approach is necessary if there is any chance of winning the hearts and minds of the managers of the status quo. To borrow a term I learned from Adam Grant in his book, Originals, I find myself doing more strategic procrastination than ever before.

Adam uses the term strategic procrastination to describe a situation when we have a vision for the future and are ready to make it a reality only to realize the world around us is not. Whether it be technology, culture, or something else, we acknowledge that others are not yet ready to own the vision and partner to make it a reality. Instead of boldly communicating the desired end-state, we take a cautiously bold approach that deliberately shapes the environment for the next steps, molds the minds for the big leap, and makes what seemed like a crazy idea last month the obvious next step today.

Just Friday, I was talking with a teammate who communicated a bold vision to which I am fully committed, but I had to take the wind out of his sails, “Josh, unfortunately, the world around us is not ready for such boldness. Key stakeholders are not yet able to see what we see. Egos and self-preservation will ensure others sabotage the very idea we are advocating.” I have every reason to believe that if we do our jobs properly, the world will evolve to a point where others will be championing his very idea – the same people who would choke on it and deliberately undermine it today. One of our many challenges is that bold leaders are not prevalent in our world, while cautious managers are abundant. The bold leaders are changing the world, the cautious managers are leading us toward irrelevance. Many bold leaders are taking their skills elsewhere, leaving many cautious managers behind to preserve the status quo and compete for promotion. Leadership is a team sport and the “Coalition of the Doing” with whom I partner regularly live on the bold side of the pendulum. Our duty is to counteract the cautious careerists who prioritize personal ego over the good of the team.

As General Michael Hayden shared in his recent book, Playing to the Edge, “Caution isn’t always a virtue. Not if you’re serious about doing your duty.” I refuse to be cautious – I prefer to be bold – I choose to be Cautiously Bold. For cautious boldness is the way to help a team evolve and ensure the culture you are helping to create lives long after you depart.

  • Where do you fall on the Bold – Cautious pendulum?
  • Have you ever met a cautious person who inspired change in an organization?
  • Have you worked with someone so bold that they completely turned off the rest of the team?