Episode 30: With Retired Lieutenant Colonel OAKLAND McCULLOCH, on challenging your leadership approach

E30 Oakland McCulloch

As the title suggests, this podcast is all about unearthing a new perspective on risk.

My guests are experts in their fields where they impact risk either directly or indirectly. My interviews aim to lift the lid on risk and rip it apart to give you a whole new perspective on it.

My name’s Lisa Sisson and I am founder of risk consultancy, Unearth. I’m also becoming known somewhat as a “Risk Rebel”.

At Unearth we believe that risk starts and ends with people. Equally, we believe that opportunity starts and ends with people. So if you’re not looking at risk with, through and by your people, then you are not only leaving your organisation exposed to risk, you are also not opening up the opportunities that a people-centred risk strategy will deliver.

If you looked at your leadership style (or your managers/executives), on a scale is it authoritarian or chaotic? At the authoritarian end, you may find intimidation and micromanagement are present, whereas the other end of the scale, it is somewhat chaotic, where you have given your people the tools and mechanisms to create some magic, even though it might appear to many outsiders as somewhat messy. Perhaps you are somewhere in between.

My guest this week is Lieutenant Colonel Oakland McCulloch, U.S. Army (Retired) and one of the points we discuss is the authoritarian to chaos scale. Oak is incredibly passionate about leadership and knew early on in his life that he wanted to step forward into a leadership role. Oak’s 23-year career in the Army saw him hold numerous leadership positions in the Infantry and Armor branches. He also assisted in disaster relief operations for Hurricane HUGO in Charleston, South Carolina, and Hurricane ANDREW in south Florida.

Even though Oak and I may reside of different sides of the world, we are both seeing the issues associated to lack of leadership and trust within business and government. Not to mention that employee disengagement at an all-time high, and the risks associated. A call for strong and courageous leadership is needed to help turn the tide.

Oak and I openly discussed some of the different styles of leadership and how the military are often viewed as a ‘command and control’ style of leadership. Oak shared his own experience of how it was his team, his people, that helped shape his leadership style.

To help provide some context of Oak’s journey, during his time in the US Army, some of Oak’s deployments included Operation Desert Shield/Desert Storm in Saudi Arabia and Iraq as a Generals Aide-de-Camp, the Congressional Liaison Officer in support of operations in Bosnia and the Operations Officer during a Peace Keeping deployment to Kosovo.

Oak then stepped forward to help develop future leaders, as he took on various positions within the US Army and Charities, like Bay Area Food Bank and Mobile Rotary International Club.

In October 2013, Oak became the Recruiting Operations Officer for the Eagle Battalion Army ROTC program at Embry-Riddle Aeronautical University where he more than doubled the size of the program in 6 years. Cadet Command selected LTC Oakland McCulloch as the top recruiting officer, out of 274 recruiters in 2019.

In February 2021, Oak published his first book, “Your Leadership Legacy: Becoming the Leader You Were Meant to Be”.

During our discussion, Oak and I also touched on points like:

  • Where your best ideas can come from – “somebody who you think is a superstar will give you some stupid ideas, and somebody who you think is your weakest link in your organisation is going to give you an amazing idea.”
  • How fear associate to risk management and control can impede your people.
  • Fear associate to making mistakes… then how do people learn?
  • Risk adverse and micromanage… stifles creativity and people taking initiative.
  • Why the saying “that is the way we have always done it” hits a nerve.
  • Difference between mistake and failure to learn.
  • The only way to achieve a result of your mission or objective is with and through your people.
  • Are you setting people up for success or failure?
  • Pitfalls around culture.

With future challenges, threats, and risks ahead of us, now is the time for strong and courageous leadership. It is only by uniting and engaging people that we can deliver our best. Our future is begging for courageous leaders to build a path towards it. The leaders we need are not called to leadership by a job title, but by what they hold to be important. What matters to them that they are prepared to make a stand on. This is leadership that requires courage and vision and a clear sense of identity. Are you ready to step forward?

Connect with Oakland McCullouch

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