Lead with the best version of yourself.

How to Leave a Legacy


By Ryan Kenny

When you look back at your contributions throughout your career what will matter most to you? How will you judge yourself and expect to be judged? Too often, as leaders, we do not ask ourselves these simple questions throughout our everyday lives. We wait until the end. Then we examine the tough questions. Did I do all I could? Did I put enough energy in the right areas? Did I make a difference? Instead, we should pose this question all the time.

What will be your legacy and how will you achieve it?

Legacy Principles and Lessons Learned

Discipline your leadership energy (Do first things first). We all have limited time and energy. Therefore, it is essential that we remain disciplined in executing our priorities. Prioritize, communicate your priorities, and hold yourself and your team accountable to these goals. Resist distractions. Do first things first and be ruthless with your time, money, and workforce.

Understand operational factors and how they affect legacy – Establishing a plan for your legacy requires thinking like an operational planner. The operational factors of time, space, and force play as much of a role in determining one’s success in establishing a lasting legacy as they do in determining how best to manage fights in complex battlefields. Be deliberate in organizing your approach and start with looking at your time horizon. I recommend breaking up your time assessment into three phases – Learning, Execution, and Transition.

Learning – In the learning phase devote enough time to capture bottom-up concerns and ideas. Your plan coming in will not survive first contact with your organization, and that is a good thing. Being agile enough as a leader to adapt to your unique operating environment and the talents of your new team will prove crucial in your ability to develop a realistic set of objectives. This phase typically takes the first quarter of any timeframe.

Execution – This is the phase in which you will achieve the brunt of your objectives. It is also the phase in which you will be most susceptible to distraction. Changes to your operating environment, personnel, and perspective will cause you to question your original plans. This is where employing disciplined leadership energy matters. You will be tempted to chase other objectives, but if you wish to achieve your legacy goals, you will have to temper those desires by applying balance and knowing when to eliminate efforts as sunk costs. This phase should consist of roughly half of your time in a given position.

Transition – For real impact, leaders need to invest as much energy getting ready to depart as they did coming in. From what I have seen, this phase, by far, is the most overlooked by leaders. Military service is a pick-up game. We all must be ready to jump in and contribute, and in turn, pass the ball. Great organizations and teams recognize this. For example, Ray Dalio, in his book Principles: Life and Work writes about his announcement, 10 YEARS ahead of time of his pending departure from Bridgewater, one of the most successful hedge fund companies over the past 40 years. He and his leadership team developed a long-term strategy to offload key management roles and responsibilities and adequately train successors. They began this work a decade before his planned departure. I believe you should devote the last quarter of your time in a position, for preparing for and executing a fantastic transition.

Schedule your priorities – We often strive to “prioritize” our schedules to make sure we get all the work done. Instead, schedule what matters to you the most – avoid the rest. Begin by backward planning from key objectives and deliverables. Deliberately place milestones in your calendars. Avoid canceling these events even if they are not fully ready for prime-time. These meetings, briefs, etc. serve as forcing functions for others to take time to prepare and participate. Organizations know their leaders’ priorities by how they spend their time, money, and workforce.

Keep your eye on the prize by deploying trust and encouraging “Satisficing – Leaders of other leaders will discover quickly they do not have the time to remold direct reports in their image. Focus only on what matters and deploy some trust. Great senior leaders recognize that building systems solely to meet their idiosyncratic needs comes at great cost to time and resources. Furthermore, these efforts rarely lead to any lasting change within the organization – therefore they do not impact your legacy bottom line. Understand that others will solve problems differently – and every product may not get an A grade. That is It is more important that the content of your top 3 to 5 priorities receive high marks. Leaders must be willing to assume risk and defend those decisions if they want to leave a lasting mark.

Nest for success – Some leaders either forget or lose sight of the fact, that 50-66% percent of their organizations time and energy will be used in accomplishing a higher echelon’s priorities. Still, they will plot out long-range calendars as if they had 80-90% of their time available to pursue their goals alone. Truly exceptional leaders are masters of killing multiple birds with one stone. They understand time management, and they take a realistic view of their resources. Next, they do their homework. They read training guidance across echelons. They snoop calendars. They keep their ear to the ground for signals of shifting priorities. Then, they modify their plans and timelines accordingly. All throughout they take a methodical approach. They are masters of executing their primary objectives systematically across their higher headquarters lines of effort. Those that can do this will not only side-step distractions – they will find a way to elegantly gain some capacity by nesting their objectives throughout the net of events their organizations will have to navigate.

Maj. Ryan Kenny is the executive officer of the 30th Signal Battalion, Wheeler Army Airfield, Hawaii. A Signal Corps officer, he has primarily served in the 82nd Airborne Division and the special operations community and has deployed multiple times to Afghanistan. He has created an online forum to foster discussions on emerging technologies at www.militarycommunicators.org.


1 thought on “How to Leave a Legacy”

  1. I always believed that my legacy was not anything that I accomplished, but rather what those who followed me accomplished. That is what I am most proud of, like one of my LTs who is leading the charge to use social media as a leader development tool for the entire Army. That is a legacy to be proud of.


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