Monday, March 23, 2026

Ask Better Questions During Complexity

Right now, because of issues related to dealing with complexity, many leaders are pushing their teams for more action, and more effort. They want 200% commitment, and perfect execution. In short, they want all of the time, focus, and energy they can get from the team, and they want it, morning, noon, and night. 


What interests me the most about this form of leading people is that very few leaders are actually focused on outcomes. Instead, many tell me that they want success. When pressed on what this means, it often translates into achieving the goals as defined in the strategic plan, or someone’s annual performance plan. 


I often respond to this line of thinking with a simple question: “So, what difference will that make?” Once the goal is accomplished, we all know that the company will set new goals. There will always be new expectations, and there will always be more things to get done than time available. So, what is the outcome of all this action and effort? 


This is a simple question on one level. Yet, as I visit with more and more leaders and managers, I have come to realize that few, if any, can articulate the line of sight from the goals that they are trying to accomplish to the mission or the vision of the organization.


I believe that the current intense focus on action and effort reflects leaders feeling pressed for time. I also believe it reflects leaders holding unrealistic expectations when it comes to execution. This is happening, in part, because the definition of success is binary, namely done vs not done. There is no connection to mission or vision. There also is no understanding that in order for action to be successful, it actually needs to be successful over time, namely that it happens again and again, quarter after quarter, year after year. 


BrenĂ© Brown in her book, Strong Ground: The Lessons Of Daring Leadership, The Tenacity Of Paradox, and The Wisdom Of The Human Spirit (Random House, 2025), understands this perspective when she wrote: “Our job is not to move things off our desk and our to-do list, but to think strategically about systems and to anticipate…. Strategic thinking is more about asking the right questions than finding perfect, strategic plans.”


Jim Collins in a conversation with BrenĂ© Brown, as shared in the aforementioned resource, said: “Sound strategy is impossible without clear vision. Muddled strategies flow from muddled vision; clear strategies flow from clear vision. If you want to have a good strategy, you need to first understand with piercing clarity what you are trying to achieve. A good strategy determines how you will achieve your BHAG [Big Hairy Audacious Goal], guided by your purpose and consistent with your values. Vision then strategy then tactics.” 


At this time period, I think we have lost the vision, mission, and the core values that should be guiding action and effort. I also think we have lost a great deal of strategic thinking. Instead, we are just doing a lot of strategic reacting. 


I get that most leaders want perfect plans, and perfect execution. But, in reality, they need to be asking better questions. As Dr. Sarah Lewis, award-winning art and cultural historian, author and professor at Harvard University writes: “The mental discipline and flexibility required to sustain excellence is different, and often harder, than the exertion it took to get there in the first place.” With this in mind, we need more mental discipline and flexibility if we seek to create on-going and sustainable levels of excellence. And this begins with better questions such as What is mission critical right now?, What are we trying to achieve right now, and why?, and What will be the outcome of our actions?.  


With clarity of mission and vision, we can be successful over time even in the midst of complexity. It will take great effort and hard work, but when there is clarity around the outcome, and direct line of sight from action to goals to strategy and ultimately to vision, then the results are impressive. This week, I urge you to ask better questions and create clear lines of sight. 


© Geery Howe 2026


Geery Howe, M.A. Executive Coach in Leadership, Strategic Planning, and Organizational Change

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