Four Questions Leaders Must Ask Themselves

Published: Jan 24, 2019
Modified: Mar 25, 2020

By Stephen A. Miles

The best CEOs and senior executives I work with are always learning. The certainties of today—whether it’s relying on a particular business model or banking on a “category killer” or operating under a particular regulatory framework—can be upended and disrupted tomorrow. Corporate leaders who internalize this reality are best equipped to steer their companies through disruption.

As a coach to CEOs and boards worldwide, I ask executives and directors to regularly examine their own leadership style to see what is working and what is not.

Here are four questions for I believe every leader should consider this year:

  1. Are you enrolling your employees—or conscripting them? “The command-and-control” leadership framework has tremendous strengths, which is why the military has employed it forever. In particular, it can deliver outstanding results in high stress situations. But outside of those situations, leaders need to go beyond this conscription model to “enroll” their teams and organizations.


    Effective enrollment—through engagement, clarity of strategy, and communication—is a powerful retention tool. Compensation will always matter, but feeling sufficiently enrolled in the mission of an organization leads employees to go the extra mile and do the additional work needed to achieve the mission.


    • Connect company strategy with individual tasks: Have a clear, unifying strategy that translates into something that employees throughout the organization can buy into, understand, and repeat day-in and day-out. This will increase productivity and results.
    • Bring in the “power brokers” within the team or organization: Engaging both the formal and informal influencers early will have a multiplying effect, as these people can act as disciples and “preach” your mission.
    • Use all of the communication channels available to you: Reaching today’s multigenerational workforce requires a multichannel approach. Make sure that you reach out to employees via all of the effective touchpoints, including newer communications options like social media.
  2. Are you becoming complacent? When a CEO enters the top role for the first time or joins a new company (or both), the discomfort with being new causes the CEO to ask more questions, double check and triangulate information, and seek out others’ opinions. For the vast majority of people, discomfort creates an accelerated learning environment. Over time, the CEO finds his or her feet and gradually gains greater confidence. This, combined with a natural inclination to become efficient (and the resulting lack of diligence and inspection) means that leaders tend to start asking fewer questions, verifying less, and making more assumptions. This is the paradox of “role mastery.” As one’s confidence level goes up, one’s discomfort in the role goes down, until that dreaded moment when a negative surprise leads back to discomfort.



    • Assemble the “uncomfortable team”: Building a team around you that is excellent and diverse will increase the likelihood of debate and avoid a rubber-stamp, group-think mentality. Make sure the team has a safe and supportive environment for discussion and debate and, if you are not getting it, jump in and play devil’s advocate.
    • Listen for content: Have the patience to listen for content versus confirmation, and continue to triangulate multiple data sources. This means asking questions and engaging on the topic instead of trying to win the interaction and move on.
  3. Do you tolerate mediocrity? The disease of “generalized mediocrity” is rampant in companies today. Mediocrity is insidious and tends to be tolerated a long time because it is not extreme in any way; it becomes hard to pinpoint exactly what the issue is. Too many executives tolerate unprepared people, poor work products, and anecdotal information, which all lead to wasted time and unnecessary meetings and follow-up.


    Eliminating mediocrity requires high levels of engagement, discipline, follow-through, and openness to tension. It can also call for CEOs to self-diagnose when they are compensating or taking the path of least resistance. Setting very high standards, not just for oneself, but for every single person the CEO engages with, is the important first step (CEOs spend the majority of their time in meetings,so they need to be highly productive). If the CEO is leading a meeting, assigning project work, or reviewing a business, the preparation and the quality of the thinking and work that goes into the pre-reads, and then the engagement, needs to be high.

    Leaders must set and communicate the standard and then be disciplined enough to hold to it, even if it means stopping a presentation because the inputs are not high enough quality or the presenter has not adequately prepared, or canceling a meeting if the preparatory materials came in too late or are substandard. In order to ferret out habitually average people, CEOs need to use a set of processes and tools and they need to apply them in an relentless and uncompromising way.


    • Set expectations high for preparation: Make it mandatory that pre-reads for meetings be well thought-out and data-driven (vs. anecdotal) and are distributed X number of days before a meeting. Jeff Bezos at Amazon is famous for having executives write a well-constructed and thought-out white paper (no more than six pages) that the entire executive team sits and reads together, then discusses and debates. The white paper helps eliminate any presentation bias, so form never wins over substance.
    • Demand accountability during and after meetings: Set the expectation that everyone is expected to contribute. Train executives to build on a point, versus simply restating points that have already been made. Always ensure minutes are taken, complete with assigned accountabilities for follow-up. Assign a directly responsible person for each action item, then manage your “DRPs.”
  4. What kind of general are you? The year 2013, just like the year before it, will demand leaders to be flexible.  No matter what the size of your business, different situations call for different styles of leadership, and each has its time and place. Determine whether a situation calls for you to be a “field general” or a “Pentagon general”:


    A “field general” teaches someone to lead from the front, often in very operational situations that require ruthless focus and prioritization. This style is about strong decision-making abilities in the field and being willing and able to make decisions with speed and imperfect information. A field general typically utilizes more of a directive approach involving smaller, but very focused teams and there is often a clear mission. These leaders reach down and touch a lot of the organization.

    A “Pentagon general” makes the strategic decisions that often are less reversible, so heor she has to think through the second- and third-order effects. This type of leadership is about slowing down and managing to an outcome—even if the route to get there is a zigzag rather than a direct straight line between point A and point B. It’s about understanding the direct and indirect constituencies and what is in it for them. What trade-offs are you willing to make, and what are you not willing to give up on? It is also about dealing with higher levels of ambiguity. Are you able to formulate a point of view when there is no right or wrong answer? A Pentagon general utilizes those around him or her as true advisors who can help shape their thought process, and they triangulate this information for the purpose of making more informed decisions and having a generally broader perspective.

    Many CEOs excel at one leadership style, but the trick is to be able to integrate both into one’s leadership process, depending on the situation.


    • Identify your own leadership style. This can explain a great deal about how you motivate people in different situations and where there might be room for improvement.
    • Push your comfort level with a leadership style that isn’t “yours”: If you tend to lead at a field general level, consider a more strategic, long-term approach for steering the company into the future. If you are more of a Pentagon general, step into a more operational, field general approach when the situation calls for it, as your hands-on leadership will be required. The key is to understand your own foundational approach and then have cues to identify when you are in a field versus a Pentagon decision so that you can “go to manual” and use the most effective approach for a particular situation.

About the Author(s)

Stephen A. Miles is the founder and CEO of The Miles Group (, which develops talent strategies for organizations, cultivates high-performing individuals and teams, and ensures effective leadership transitions.