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Illustration by iStock; Security Management

Why Security Executives Should Lead with Doubt

Leadership is the basis for success, it is the imperative in the security industry. Security executives, including chief security officers (CSOs), lead in good times and bad. We must be far-seeing when we lead and be prepared by looking over the horizon for details others do not see or want to see. It is our experience that allows us to anticipate and to excel when it is difficult.

Leadership is really about success. No one wants to follow an unsuccessful leader, but in this world, how do you leverage against not being successful?  Doubt has its place in leadership.

Successful leaders need to have four types of problem-solving people in their inner circles when making decisions with quality outcomes. Each characteristic contributes to the finished product.

  • Dreamers are simply big thinkers and dream up the idea—they do not focus on details.
  • Designers are detail-oriented and generally map out the task from “Point A” to “Point B,” and beyond.
  • Doers are the executers and are tasked with assignment completion.
  • Doubters provide the expertise, have intricate knowledge of the task, and serve as the subject matter expert (SME). The doubter is the person that is raising their hand saying, “Hang on a second, we're missing something here. I see a problem.” Doubters are a critical key to success because they often prevent failure.

How does a leader cultivate these types of problem-solving characteristics within their team to drive success? It requires three-dimensional relationships with team members. The three-dimensional relationship embodies clarity of purpose, commitment, and time. Time is the most critical. The three-dimensional relationship affords the leader opportunities to establish relationships beyond one-dimensional Zoom, Microsoft Teams, or Facetime calls. In a three-dimensional relationship, the leader can develop positive and real relationships, fostering “relationship deposits” with people by connecting with them on a personal level. Much like deposits into bank accounts, the more time and relationship deposits you make, the more the professional relationship grows and over time.

The investment of time into the professional relationship invites trust between both parties and empowers team members to put more of their personal insights and views into the collective work. The more empowered they feel, the more motivated team members will be to listen, process, and act. Successful leadership is truly about relationships. But this is not always easy.

In my experience, the doubter takes a little more time to cultivate the personal relationship because there are intrinsic obstacles to overcome. Doubters are frequently the SME on a topic, and by knowing that topic, they are the ones who will most likely find the problem, whether it be a software code, idea, task, or operation. It is absolutely worth the time investment to allow the doubter to do the due diligence to arrive at the problem—they are the person you need to listen to and address objections or questions.

By committing to knowing all the parties, three dimensionally, the dreamers, designers, doers, and doubters create a formula for success. By having these groups set up and structured, the leader can prepare for success of the project, task, initiative and company.

Can the doubter sometimes be misunderstood, marginalized, or not included? Yes. Successful leaders will learn how to factor them into more decisions without throwing teams off balance.

All entities and organizations want to avert catastrophic events, but the drive to execute more efficiently, faster, and cheaper can lead to group think, where the group thinks everyone is on-board with an idea because they are looking to appease the leader. In this situation doubters are overlooked or dismissed because they are perceived to be standing against the leader or the majority.

The goal is to achieve group agreement, but not through group think. There is a big difference.

As security leaders, we must strive for and demand group agreement and avoid group think because it is a recipe for disaster that eliminates the margin for error by isolating or marginalizing the doubter. Group think can lead to a phenomenon known as “self-organized criticality,” where everyone is on board with the idea no matter what the cost according to Ted Lewis, author of Bak’s Sand Pile: Strategies for a Catastrophic World.

In a group agreement setting, by comparison, all parties have equal input and typically group agreement is a secondary action when all parties’ concerns, obstacles, and doubts have been addressed, ultimately leading to success. The success is really being inclusive of all thoughts and opinions because all opinions should—and do—matter.

At the end of the day, leadership and management are more art than science, but at their root they are about people—leading them and giving them the confidence to be able to stand up and safely voice an objection or concern without fear of retribution.  

Former U.S. Secretary of State and Chairman of the Joint Chiefs of Staff General Colin Powell wrote Thirteen Rules of Leadership. In my opinion, the value of the doubter resonates throughout, especially in these six takeaways that could resonate especially deeply for security professionals.  

  • Rule #1: It ain’t as bad as you think! It will look better in the morning.
  • Rule #4: It can be done.
  • Rule #8: Check small things.
  • Rule #9: Share credit.
  • Rule #10: Remain calm. Be kind.
  • Rule #13: Perpetual optimism is a force multiplier.  

Time and again throughout history marginalizing the doubter has had catastrophic effects to projects and initiatives. In the 1986 Space Shuttle Challenger disaster, engineers stated it was too cold to launch and that the rockets’ O-rings would fail. Leaders didn’t listen to the doubter, and the Challenger broke up into pieces over the Atlantic Ocean just 73 seconds into its flight.  The doubter checked the small things—as listed in Powell’s Rule 8—but no one listened.

Being the leader means being visible. It takes strength, dedication to task and focus on all team members. In the 2016 movie “Hacksaw Ridge,” U.S. combat medic and Medal of Honor recipient Desmond Doss is shown repeating the phrase “just one more” as he continually puts himself in harm’s way by going back for the injured at the Battle of Okinawa in 1944; Doss’s actions are credited with saving 75 men.  CSOs must be similarly focused on “just one more” to be sure that everyone is safe—it is up to us to lead.  

I have been very fortunate to work alongside and learn from great leaders throughout my career. Recently, at the International Association of Chiefs of Police meeting in Dallas, Texas, I met with a friend who retired from the FBI as an executive assistant director. He shared a story of an operation whereby he was the “responsible person in charge.” When he was briefing the operation, a member of the team stood up and said, “If we do this, someone is not coming home.”  My friend paused and rescoped the operation with input from the doubter. Once group agreement was established, the operation was executed and was successful. 

Years later, he shared his leadership principles with me, and they bear striking importance to a CSO seeking to find balance between all four characteristics within a team. A few pertinent ones here include:  

  1. Take care of YOUR people.
  2. Don’t be afraid to lead.
  3. Accept total responsibility for everything you and your team does or fails to do—you are the leader.
  4. Don’t lie or slant the truth, ever!  No spin.
  5. Don’t make the same mistake twice.
  6. Doing things sequentially is easy. Learn how to make several things happen at once.  It is synchronization, not multitasking.
  7. Get the right person, in the job right now.
  8. Leadership is a privilege, not a right.

Early in my career I was responsible for a significant task and the team was completely on-board with the project.  We worked long days and several weekends in a row. This was taking a toll on the team’s personal lives. We discussed as a group, and we decided to make time for families for several weekends in a row.  This really energized the team for last push.  We could have finished early, but at the expense of the team members’ families. We decided to finish on time instead and give some work-life balance back to the team.  We didn’t try to “spin” not finishing early; we told the truth, and team appreciated it.

Leadership is your chance to do things right; we must and should engage when presented with the opportunity. As a CSO you will not have an opportunity for a do-over. We need to get it right the first time and every time.

At the end of the day, leadership is about success. No one wants to follow a leader who is unsuccessful. Being a successful leader is an absolute marathon of a journey. To be successful it takes time—including your personal time—to grow yourself and others. Grow your influence by listening to all leaders, good and bad. Sometimes you’ll find your gold nuggets of wisdom lying on the ground, and sometimes you might have to dig for them, but it is worth it to make a difference.

It is true that leadership is a privilege, not a right.  It is earned by listening to everybody in the room— dreamers, designers, doers, and the ones who disagree with you, the doubters.


Keith A. Waddell, CPP, is the director of security—Americas for Jacobs, Inc. Waddell is a member of the ASIS CSO Center Board of Directors and has been a member of ASIS since 1987. Waddell earned a Master of Science in Administration degree with an emphasis in security management from Central Michigan University and a Bachelor of Criminal Justice from Louisiana State University in Shreveport. He has primarily worked in the aerospace and defense industry throughout his career. 

For more about how to develop key skills as a CSO, ASIS CSO Center members can access an exclusive library of resources on ASIS Connects.