Leaders, Cultivate Your Initiative Environment

by Brian Disque

As a leader, have you ever wished your team would “take more initiative?” Or perhaps you personally have wanted to take more initiative and were unsure of your options? Have you ever reflected on what it really means to take initiative and how it occurs? Maybe you have been considering how to assess and encourage the degree to which your subordinates display initiative?

Ask any leader what personal attributes they value, and most will list “takes initiative” near the top. Initiative is “the attribute of an empowered individual, armed with the knowledge of a greater plan and purpose, who inherently makes decisions on their own accord and takes action to contribute to a mission.” The attribute of initiative is desirable in almost all workplaces – and frankly, the military will require more initiative at all levels to win future wars. 

To truly maximize a team’s performance (and your own), one should consider the initiative environment we create and operate within, and how to assess the level of displayed initiative.

When it comes to defining your initiative environment, avoid setting lower expectations. Often, initiative and discipline are confused. Operating without direct supervision is a form of discipline, “doing the right thing when no one is looking”. The space and ability of a team member to operate within broadly-scoped guidance and maximize opportunities is a more productive way to consider initiative theory. In other words, leaders should concentrate on acting deliberately and creating an optimal initiative environment for team members to seek and find opportunities. The classic Harvard Business Review article, “Who’s Got the Monkey,” offers five degrees of initiative:

Using these categories, we can create an initiative environment for ourselves and those we lead.

Level 1: Wait Until Told

If “wait until told” describes you or your team, likely you are either not confident in which action to take, or you are excluded from taking initiative by policy or some other means. In this case, waiting until you are told what to do might not be negative. For example, if you are new to a position or lack situational understanding, caution is a good approach. A well-intended, less informed attempt at initiative may not be desirable, especially if your job possesses a high potential for negative consequences. As you gain experience and confidence, you should progressively move up the “initiative scale.”

Level 2: Ask What to Do

As a subordinate, observe your leaders and other experienced Soldiers, ask questions, and confirm you are receiving necessary information, especially with new personnel. As a leader, assist your team with clear and concise communication to encourage growth and risk-taking where necessary.

A distinction exists between “asking what to do” and “asking to do something.” If you are confident enough to mention an idea as a question, consider stating it as a recommendation. Making recommendations is an outward display of your confidence and critical thinking. As a leader, recognize this nuance, and appreciate the level of confidence required to recommend rather than ask.

A lack of empowerment often represents greater problems in one’s subordinate leaders, including distrust and ignorance. In my experience, empowerment comes from two main sources: knowledge and trust. A subordinate leader demonstrates knowledge when they understand both the higher intent and desired end state of the mission. A subordinate leader who maintains the trust of their senior leaders and understands the mission will be empowered to take initiative. A good leader will discern which subordinates understand the mission and will analyze how to empower them appropriately. On the contrary, a breach in either trust or knowledge is antithetical to inspiring initiative.

If your team is experienced already and, as their leader, you want them to take more initiative, the first place to look is in the mirror. Increase communication and be careful about what messages you send regarding how much you trust them. This can include subtle behaviors such as nonverbal gestures or expressions, or asking microlevel questions not normally associated with your position that indicate you might be micromanaging. These seemingly small behaviors can have a degrading impact on the initiative environment you are working to cultivate.

A primary reason leaders seem hesitant to extend trust to and empower subordinate leaders is because of the “no-fail” culture within the military. Leaders worry that they must accomplish their mission and, therefore, cannot allow their subordinate leaders the opportunity to grow. The balance of failure and trust can put leaders in an uncomfortable position, but if you want to lead an empowered team, being uncomfortable is something to get used to. 

As a leader, prioritize team building and developing trust and confidence among your leaders, rather than seeking results in the early stages of a command relationship. Short of a combat operation or significant risk to personnel or property, our tolerance for mistakes should be relatively high. Increased confidence and trust should be a primary outcome of every team event or operation, rather than emphasizing that teams execute individual tasks perfectly. Building subordinate leaders who possess resiliency and problem-solving skills is far more beneficial than developing teams who cannot adjust fire when the mission changes.

I can recall a situation where I failed to demonstrate that I trusted a teammate. I was a Platoon Sergeant, and my unit was undergoing a Joint Readiness Training Center (JRTC) rotation, a demanding training event meant to prepare units for combat deployments. We were in the midst of dynamic missions, with little notice or planning time. My company commander called me over to his Humvee to give us our next mission. He specifically called for me, not my young platoon leader. My relationship with this commander was built on mutual confidence, trust, and respect. We had worked together for over a year and we were both very confident in each other, a good place to be for both of us.

We huddled around the humvee as he showed me the plan on the map. I was aware of my platoon leader behind us, somewhat boxed out, trying to see what we were looking at. I was also aware of a cadre of observers/controllers furiously scribbling in their green books. We broke the huddle, I went back to the platoon, executed some quick troop leading procedures, and we were off. To be honest, I can’t even remember what the mission was or if we were even successful (probably not).

Afterwards, we had a chance to reflect. My Commander and I realized we had completely missed the point. We were so worried about “getting an A on the test” that we denied this young officer a chance to lead and learn. Reflecting was good, and I realized exactly what I should have done. My commander and I had a laugh about it, but it disappoints me to this day that I missed the mark so badly. Out of that entire JRTC rotation, this vignette might be the most important thing that I learned.

To trust a subordinate enough to fail is one of the greatest extensions of trust a leader can grant. Moreover, how a leader deals with failures and setbacks can have a stifling or encouraging impact on the team’s initiative and the level of trust within the unit.

A perfect example of how a leader’s reaction to failure can improve trust and empowerment occurred early in my career as a freshly promoted E-5 Sergeant and the arms room NCOIC for my platoon. Our battalion commander was inspecting our company arms room. Somehow, he managed to find one of those pesky “unassigned” weapons that was in an abysmal state of repair. Thoroughly embarrassed, I expected to undergo a thorough “chewing out.” My company commander must have expected it as well because he stepped in to offer excuses. My battalion commander stopped him, smiled, handed me the weapon, and said, “I’m not worried about it – that’s why we have SGT Disque.” He walked off, leaving me with the weapon, my dignity, and initiative intact. Although this event occurred 26 years ago, my battalion commander had such an impact on me that I still remember it vividly.

I’ve been fortunate that most of the leaders I have served with created positive initiative environments where I have felt empowered and trusted. I can only think of a few leaders who failed to grasp how critical this concept is. Instead of extending trust to and empowering their subordinate leaders, these few leaders would add cumbersome limitations that inhibited initiative and indicated severe distrust in their subordinate leaders. Consequently, the poor actions of these few leaders discouraged an initiative environment, causing the subordinate leaders to resent and distrust them.

To grow yourinitiative environment, you must present your expectations to your team. Outlining the situation, intent, end state, and your appetite for risk allows them to understand their limits and where they should and should not take initiative. Furthermore, you must resist the urge to “over lead” and micromanage by providing too much guidance or problem solving for your team. Yes, you are more experienced and likely have dealt with the task at hand, but if your goal is to improve trust and confidence, let your team solve the issue with their initiative intact – do not constrain them unnecessarily.

Lack of confidence is another telltale sign of one’s hesitancy to take initiative. I have seen many commanders ask for permission to do something they already had the authority to do. Such requests indicated that, if they weren’t willing to act within their own authority, it was unlikely they would be able to take bold initiative during a decisive moment.

In one situation, I observed a battalion commander speaking with a company commander who was asking permission to do something within their command authority. The battalion commander told them, “Hey…you are the commander. Go lead your Company…I trust you.” The Battalion Commander did not answer the question or even acknowledge it, leaving the young officer to deal with the matter on his own terms, with his own initiative. Moreover, the battalion commander was subtly reinforcing their trust in the subordinate’s decision-making, indicating that they, the battalion commander, would underwrite the risk to develop the junior officer’s confidence. 

Seeking guidance and approval for an intended course of action is different than asking for permission. As a follower, you should try to implement the former, seeking guidance for an intended action. As a leader, you should consider the situation and lead with confidence. When in doubt, confirm your authority and ensure you are operating within the higher intent, and then execute and report.

If you have confident and knowledgeable Soldiers who you can trust and empower, you are well on your way to building a high performing team. If you do not have such a team or you do not feel comfortable empowering them, you may still accomplish a mission, but your team will never perform to their fullest potential.

Levels 3–5: Recommend, Act & Advise, and Act & Report

The highest level of initiative, to Act & Report, is where we must set our sights. Information and decisions will present themselves at a rate that makes a cumbersome and laborious reporting and authorization chain ineffective. Moreover, any lesser form of initiative will result in missed opportunities, unrealized gains, and, potentially, an increased exposure to risk.

The ultimate goal within our units should be to create an initiative environment where our leaders execute and report, where our leaders continue to execute in a manner that places the unit in a position of advantage, while keeping their senior leaders informed. Such initiative cannot occur unless commanders and leaders, up and down the chain of command, operate in and promote a total-initiative environment.

Recommending, the third level of initiative, is a productive step toward the ultimate goal of Act & Report, the fifth level of initiative. Recommending demonstrates that you are thinking about the situation in terms of options and opportunities and have considered the best action. Initiative operates in tandem with one’s ability to generate options and opportunities. Always organize your team to create options and opportunities and provide outcomes for unit and mission success. To accomplish such success, however, one must recognize when opportunities to take initiative are present. 

Often, opportunities to take initiative manifest in resource-scarce or time-constrained environments. Empowered leaders are problem solvers and will find ways to maximize and create opportunities, even where no good options seem to exist. In fact, during these circumstances, personal and team initiative can mean the difference between mission success or failure.

A recent example occurred during the Afghanistan retrograde in the summer of 2021. I was part of the Area Support Group in Kuwait. Our role in the big picture was to “support” everything from billeting, to meals, to essential services. Our higher headquarters was faced with the challenge of a rapid evacuation of tens of thousands of people, including U.S. military troops, U.S. government personnel, and Afghans. All these people needed food, shelter, and other life support. The situation in Afghanistan was developing very quickly, carrying with it a great deal of uncertainty.

At the time, our living and working areas were dispersed across our bases and we were operating at half-capacity due to COVID concerns. Our team huddled, and as we analyzed the situation we felt that consolidating was prudent, as we anticipated extra billeting and services would be needed.

This idea was not without some risk. Not only is displacing troops from living areas inconvenient, but displacing work areas and command posts is disruptive, and we risked a COVID breakout from tighter living conditions. Moreover, we weren’t exactly sure if we even needed the space, since there was no decision regarding the location to where these personnel would evacuate.

Nevertheless, the impending events would prove this decision to be prudent indeed. As we reported billeting capacity, our higher headquarters selected our bases to support Soldiers as they retrograded. Our team’s initiative and willingness to accept some risk created options that helped our higher headquarters solve a problem.

Although we assumed some risk by taking initiative, our inaction was not risk-free either. Had we waited and just reported our current capacity, our higher headquarters, located 6000 miles away, might not have known that we could consolidate, and they would have developed a less optimal course of action. By being proactive, executing, reporting, and taking some risk, our team was ready when called upon.

Key Takeaways

Initiative is important. Do an honest evaluation of your team and your own initiative, using the above scale. If you are not satisfied, do some analysis. Initiative is not intangible. You can observe, measure, and improve team initiative.

1. It starts with trust and knowledge – every action or event should improve confidence and trust as an outcome. If you come out of an evolution with less confidence or trust, you missed an opportunity (or made an error). 
2. Initiative is about maximizing and creating opportunities that place your team in a position of advantage. If you cannot think of an opportunity or action to take, you haven’t thought hard enough.  
3. “Execute and report” is the gold standard for initiative. The modern battlefield demands this type of empowered leadership.
4. If you are not satisfied with the level of initiative displayed by your team, it stems from the initiative environment you set.

We as senior leaders create the environment and set the conditions for our Soldiers and junior leaders to take initiative. Use these criteria to evaluate your unit’s culture and create an initiative environment that allows your leaders to accept risk and take decisive action within your higher intent.

Brian Disque is an Army Sergeant Major with 28 Years of service. A light Infantryman by trade, he has served as a Command Sergeant Major at the Battalion and Brigade Level, as well as other senior leadership positions. He currently serves with Army Futures Command.