Pictures And Connections

In the world of strategic planning, there are two common phrases. The first phrase is “leaders need to paint the big picture.” The second phrase is “leaders need to help people connect the dots, not just collect the dots.” Both phrases reflect a mindset about planning that is common. I also think both phrases need significant unpacking in order to be useful. 

The first phrase, “leaders need to paint the big picture”, often refers to the idea that a leader and a group of people involved in planning need to step back from day to day operations in order to understand the world in which they are delivering their goods and services. Once they have stepped back, it is the role of the leader to describe “the picture” of what is happening in the world. 

The difficulty of this phrase is that most leaders describe “the picture” like it is a framed painting. They tell the group all that they see in the picture. Rarely do they ask others what they see in the big picture. There is the assumption within the phrase that the leader is all-seeing and all-knowing when in reality a leader often only sees part of the picture due to their own biases and normal blindspots. 

At the same time, the world in which goods and services are being offered is not a big framed picture. Instead, it is in constant motion. It is more like a movie that is continually evolving.

Therefore, the best way to understand what is happening in the world is to understand the Heisenberg Uncertainty Principle. This principle states that we cannot know the position and speed of a particle, such as a photon or electron, with perfect accuracy. The more we nail down the particle’s position, the less we know about its speed and vice versa. 

For me, painting the big picture comes with an inherent uncertainty because most leaders paint it in a static form, i.e. we nail down the particle’s position. However, we do not know it’s speed or direction. Therefore, I think a better way “to paint the big picture” is to illustrate the emerging trends that are taking place within the world in which goods and services are offered. Within these trends, we can see the speed of change and the possible direction of change, e.g. think of the changing demographics within the USA. 

Furthermore, we need a diversity of leaders to share the trends that they believe are significant. This is why I advocate for a PESTEL analysis which stands for political, economic, social, technological, environmental, and legal trends analysis. The aggregate of these trend lines give a more holistic understanding of what is happening in the world, and what is happening over time. I also encourage leaders to read the following article: “Your Strategy Needs A Strategy” by Martin Reeves, Claire Love, and Philipp Tillmanns, Harvard Business Review, September 2012. It will be good food for thought and generate important sharing amongst a group that is engaged in strategic planning. 

The second phrase, “leaders need to help people connect the dots, not just collect the dots,” is an interesting one. While I have referenced it myself many times, I think the phrase also needs to be unpacked in order to access the truth within it. 

First, the phrase assumes that those who are involved in the planning and the subsequent execution are aware of the “dots” and the need for them to be connected. The problem that many leaders miss is two fold. One, the integration of the dots assumes the process of separation has already taken place. Two, that there is an awareness that the dots need to be reconnected. I think the challenge is that most people have not consciously separated the dots. Instead, I believe most people are completely unaware that there are dots. And if they are aware of the dots, they had no idea how they are connected, or why they would need to be reconnected. Therefore, connection and integration wouldn’t be possible or warranted. 

The missing clarity within this phrase revolves around two leadership skill sets, namely the ability to synthesize and the ability to integrate. For our purposes here today, synthesis is defined as the combining of multiple sources of information in order to form a new and unique perspective or comprehensive understanding of a concept or topic. Synthesis involves critical analysis and interpretation of information to develop this new understanding of something. Integration, on the other hand, focuses on merging different elements into a cohesive whole, often without generating a new insight or perspective. Integration means bringing parts together to function as one unit.

What most leaders do in planning, and why many of the problems occur during execution of the plan, starts with a lack of synthesis. Few leaders want to spend the time combining multiple sources, i.e. think trends, to form a new and unique perspective or comprehensive understanding of what is happening in the world. Furthermore, few leaders know how to do critical analysis and interpretation of information that has been synthesized in order to develop a new understanding based on the trends. 

One big reason leaders struggle with this part of planning is that they want to create a document that lowers the level of disequilibrium within the organization, i.e. think the feeling of things being chaotic, out of control, or not predictable, in order to create or maintain a level of SOP.  However, the desire for predictability does not take into account the potentially disruptive elements surfacing within the PESTAL analysis. These adaptive challenges, which are normally found when studying the emerging trend lines, are typically complicated, complex, or both complicated and complex. Thus, a singular goal, objective, or strategy can not solve them

Furthermore, with these kinds of adaptive challenges, defining the actual problem is part of the problem. Plus, these kinds of problems call into question fundamental assumptions and beliefs about the business. They also can call into question past strategic choices and current systems. In short, connecting the dots and integrating the dots may only represent a maintaining of status quo in a world that has, or is continually evolving away from the company’s core business strategy, e.g. think of the evolution away from cable TV to someone choosing a variety of customized streaming platforms. 

Therefore, I think leaders need to spend more time helping people to synthesize and integrate the idea of strategy. By lengthening the planning process to more than the normal 1-2 day strategic planning retreat, and instead encouraging regular and in-depth strategic dialogues over a 90 - 120 day planning cycle before document creation begins, we will then have the time and space to think about the proverbial “old” dots and consider the possibility of “new” dots. The sum of these two actions has the potential to create more clarity and new ways of thinking about the core mission of the company. The outcome will be two fold, namely more ownership and more thoughtful execution. 

When one unpacks the previous two phrases with their team and does the subsequent work connected to them, they will discover the profound and important insight: strategy is a part of everything we do on a day to day basis and that everything is connected back to strategy. As leaders realize this level of interconnection, they can then show how strategy is a part of everything and that everything is connected to it. In short, they can paint the picture of the interconnected networks throughout the company. And along the way, they can paint the picture of the relational networks, too. Because in the end, the successful execution of strategy, which is the desired goal of all strategic planning, is always more relational than analytical. 

© Geery Howe 2025

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

Even If Just For A Moment

Over the last couple of months, I have returned again and again to the following lines in Louise Penny’s most recent book, The Grey Wolf (Minotaur Books, 2024): “In lives so unpredictable, they found sanctuary in certainty. Even if just for a moment.” I love the phrase “they found sanctuary in certainty.” For me, the power and importance of daily rituals, and the certainty that comes from these daily rituals gives me solace in the midst of life’s challenges. 

For example, I love making coffee in the morning. I like filling the pot with water and pouring it into the coffee maker, and then inserting the paper coffee filter. Next, I delight in the measuring of the roasted beans and putting them in the grinder. Then, I enjoy pouring the freshly ground coffee into the filter, closing the lid, and pushing the start button. I know there are faster ways to do this and fancier machines that will make it easier, but I like the slow rhythm of making a fresh pot of coffee in the early morning. 

I also like the daily ritual of sitting down in my favorite chair with that first cup of coffee, and a stack of inspirational books and my daily devotional material. Our youngest son and wife call this “slow coffee” time, and I treasure it because the hustle and bustle of the day has not kicked into full gear. With the first light of the sun rising in the east, a warm cup of coffee by my side, and a good book, I pause and take stock of myself and the day, remembering that in the midst of all this unpredictability, I can, “even if for just a moment,” find sanctuary. 

I think the challenge of this time is that we are not creating enough space in our lives to find sanctuary in certainty. Every day, we are swamped with lists, e-mails, and text messages. All which need responding. So, our lives have become nothing more than one long reaction to everything and everyone. 

Therefore, I suggest we pause this morning, and find the answers to the following three questions:

- Where is the place that you find sanctuary in certainty?

- Where is the place that you find peace?

- Where is the place where you feel home and safe?

Given current events, we need to create and/or find the places in our lives which offer comfort and restoration in an ever-changing and turbulent world. We also need to create and maintain a sense of community, a place that offers love, acceptance, and support during the challenges of life’s journey. 

As Louise Penny continues, “Life was, after all, made up of tiny choices. Like a pointillist painting, no one dot, no one choice, defined it. But together? There emerged a picture. A life.” Thus, we need to find places where the pain and the sorrow, the stress and the grief can be released and healed. We need to find places where peace can be found and experienced. We need to find places that are a balm to our hearts, minds, and souls. We need to find places where we rediscover the sacred in the ordinary, and revel in it. 

For me, one other, powerful place to discover the sacred in the ordinary and sanctuary in certainty is to witness the sunrise each morning. In this simple action, I am reminded that each new day is a gift, and that each new day has the potential to be filled with many blessings. With this in mind, I can be present to the day, and experience the sacredness of a new beginning at dawn. 

This week, I hope you can create some slow coffee time in your life. I also hope you can find sanctuary in certainty, and the sacred in the ordinary. 

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

Chart Your Path - part # 3

Three Critical Choices

Next, we need to grasp the following statement: In order to lead the change, we must participate in the change. This is much easier said then done, because most leaders want everyone else to change. They believe they are just fine as they are and that their leadership style works perfectly, if not elegantly. However, in reality, if one seeks to chart a path, then one must commit to the path. And this level of commitment always involves personal and professional change. For in the beginning, there are three critical choices that need to be made, and they will significantly impact planning and executing a plan. 

The first choice is to understand the difference between the following two concepts: individual competences and organizational capabilities. Individual competencies refer to a specific person’s knowledge and skills required to fulfill specific role requirements. Organizational capabilities are collective abilities of the firm required to execute the business strategy. During planning, we sometimes work at the competency level and other times we work at the capabilities level. Given current events, I suspect we will work at both levels.

During the preparing to plan stage, we need to reflect on our own individual competences and on our own organizational capabilities. I remember one day sitting with a hospital CEO, discussing this very idea, when he said to me: “I cant get there from here. I don’t have the capacity to plan and the capacity to execute the plan we create. My team is dysfunctional. Our middle managers can not take on any more change, and I don’t have the stamina to keep pushing myself. I’m afraid I will break.”

I sat quietly with him as he paused and reflected. I think he surprised himself. He just sat there and let it all sink in. Then, he looked at me and said, “I think I need to do my own work before I am ready to engage the whole group process.” I nodded in agreement and then we discussed what he needed to do in order to chart his own path. 

The second choice relates to the planning process. Many leaders want a well defined and well-structured planning process. They want everything to be preset before engaging in the work of planning. Other leaders want a process that is not all planned out. Instead, they are seeking a process that is more emergent, i.e. one that is unfolding and evolving through dynamic and less structured processes. These leaders are typically guided by their firsthand, day-to-day experiences, and their gut for lack of a better term. The former focuses on structure and the later focuses on dynamic interactions and the feeling of flow. 

During the time of reflection when one prepares to plan, understanding our own level of comfort with the choice between structure and more unstructured planning is critical. I have sat with many leaders of all different ages who are not clear about this element. And when this happens, I know that once planning starts they will quickly move in one direction or another, causing massive trust and communication issues amongst all the participants. By reflecting and clarifying this in advance, particularly if they grasp that leading a planning process means they have to participate in it rather than oversee it, and if they recognize that they will need to change, not just that others and the organization needs to change, then the process will be more effective. And then people will own the plan not just execute the plan. 

The third choice relates to execution and a leader’s style of leading. Many leaders, upon experiencing the normal chaos that comes with executing a new plan, will default to a a top-down and unidirectional style of leadership. This is best summarized by the “I lead/You follow” mentality. Others will choose a more participatory form of leadership which involves a wide diversity of people and a process that is multidirectional in nature. Rather than focus on control and order, these leaders choose to focus on alignment, ownership and empowerment, which by the way can appear, at first glance, to be very chaotic. While each path has it’s pros and cons, the key is to choose which way you are going to lead before you engage in formal planning. And that is why preparing to plan is mission critical to planning. 

How Do I Begin?

Ryan Holiday in the aforementioned book on Monday’s blog post states that we need to do the following things: “be fully present, empty our mind of preconceptions, take our time, sit quietly and reflect, reject distractions, weigh advice against the counsel of our convictions, [and] deliberate without being paralyzed.” I like these key points as a starting place for creating time and space as one prepares to plan for change. 

At the same time, I’ve had many leaders ask me privately, “But what do I actually do when I sit quietly and reflect? I am not someone who is just going to sit there and do nothing.”

“I agree,” I respond. “In the beginning, I want you to write or type out the answers to the following two sets of questions. Here is the first set: What do you do at work? I want you to define your role. Next, what are the priorities in your life and work? This will help define your focus over time. Finally, what do you do that matters most at work and at home? This will clarify your sense of purpose or mission. 

Here is the second set of questions: Why is this important work to do? Is this work meaningful? Is it worth doing? All three of these questions are designed to make you think deeply and broadly about your life, your role, and your work.

Once you have written out these answers, it is time to share them with an ally, confidant, mentor, or executive coach who you trust and know will offer insights and perspective. The subsequent dialogue will be very helpful.” 

Creating time for reflection is important. When doing this, I am reminded of something that Kevin Cashman wrote: “As you believe, so shall you lead.” What we are doing during this stage of pre-planning is clarifying what we believe. 

At the exact same time, we need to remember one other point, namely as they believe, so they shall follow. Doing your prep work first helps you lead the team and the organization. It also helps you role model and communicate better too.

And when people take time to sit quietly and reflect, and when they make time to answer the above questions, they generate insights into how to move forward as a person, and a leader. In short, they feel better prepared for the work and journey of strategic planning. 

The Curious Paradox

Carl Rogers, one of the founders of humanistic psychology and one of the most influential psychologists of the 20th century, once wrote: “The curious paradox is that when I accept myself just as I am, then I change.” And this is why preparing to plan is so critical to short and long term success. It helps us to accept ourselves when we seek to chart a new path. 

At the same time, meditation instructor and journalist, Jeff Warren notes: “The reality of where you are, is always more important than the ideal of where you imagine you should be.” When we choose to prepare for planning through in-depth reflection, we sort out the difference between the should-be expectations, typically placed on us by others, and the could-be potential that is generated from our own, internal clarity and alignment.  Then, with this level of clarity, alignment, and acceptance, we have already started to change, and we have already started to chart a new path.

 As Brene’Brown so clearly stated, “You either walk into your story and own your truth, or you live outside your story, hustling for your worthiness.” When we prepare to plan in a thoughtful manner, we not only walk into our own story and own it, we also create and role model a process that others can follow. For the curious paradox of charting your path is that when you do this and you change, then others can do this and they can change, too. 

© Geery Howe 2025

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

Chart Your Path - part # 2

A Good First Step

I remember a day when the CEO of a large company and I were sitting in his office after a full day of training on strategic planning. We had about forty-five minutes before the team met for a group dinner. This was to be followed by a discussion about lessons learned after a day of training. He was sitting in his chair and looking out the window. I sat quietly with him. When the time was right, I asked him a question: “Are you ready for strategic planning?”

He responded, “I know we need to do this and everyone is expecting it to happen. My board wants to know where we are going, and my team is eager to have a plan too.”

“I get this,” I replied. “A lot of people have expectations of you as the CEO. But my question was focused on you, not the company. Are you ready for this level of work?”

There was a long period of silence and then he quietly said, “No. I am exhausted. With the pressure to perform, and the hard work of raising a couple of teenagers at home, my tank is empty. My battery is drained. Some days I just want to step away and do something else. Some days I wonder if I am no longer the right guy for the position. Some days I don’t know what to do next.”

I just sat there with this deeply personal statement and realization. This was not a moment to speak. Instead, it was a moment to be present, and to acknowledge the pain that led to this moment. 

After a bit, I shared. “That’s a hard place to be. I know it both personally and professionally. It hurts on so many levels. It’s beyond stress management level techniques. It’s the feeling of being overwhelmed and not knowing where to start.”

He nodded his head. 

“So,” I asked, “what is one thing you can do this evening that will slowly refill your empty tank?”

He pondered this for a moment, and then said: “I think it is time to share with the team that I don’t have all the answers about what to do next. That I need them to work with me to co-create the plan rather than just follow me and do what ever I think up. I need them to know that I am struggling and that I am not Superman. I am just a guy who wants to do good in the world and wants to make a difference.”

He paused, and then asked me a question, “Is this asking too much?”

“No,” I replied. “Your team cares deeply about you and about this organization. Many of them are struggling too. How about creating a plan that does not try to solve all of the world’s problems, but instead gets you and the team back on solid ground? How about creating a plan that does not result in any more burn-out at work or at home?”

‘“I’d like that very much.”

“Good. Then let’s begin this evening by creating a safe space for in-depth sharing and dialogue. Being a leader and planning for the future should not result in complete burn-out.” 

So, that evening after dinner, we made time and space for sharing. It was a good first step.  

Afterwards, as he and I walked back to our respective cars, he to home and I to the hotel before the next day’s meetings, he stopped and said, “Thanks. That was very important and very special. It helped.”

“My pleasure to be of support.”

“So, I have one more question. What do I need to do in the morning before heading to work?”

I smiled, and said, “Turn off the computer, Luke. Trust the Force.” 

He chuckled, and I continued. “Really. Don’t start your day doing e-mail. Instead, pause and do the following. First, find a quiet place in the house and read something that inspires you or helps you put things in perspective. I suggest a passage from the Bible or some other book related to your faith tradition. Second, write down three to four things that you are grateful for in your life. Counting our blessings is important. Third, think of someone who has made a positive difference in your life. Take a moment in prayer to thank them, or write them a brief note of thanks. Finally, eat a good breakfast. Ideally with your spouse and family. The e-mail can wait. Now is the time to slowly refill your empty tank, or recharge your battery. You choose which metaphor is best for you.”

“I can do that, Geery.”

“Good. See you in the morning at 8:00 am.” And each of us headed out for the night. 

Creating time and space for reflection and healing is hard work. We need to be patient with ourself and with others. We need to remember and to understand that the path we take to the destination we seek is the future we will experience. We also must recognize that charting our path is an on-going personal growth and development process. Still, the first step is to reconnect with ourself before the actual planning begins. 

To be continued on Wednesday. 

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

Chart Your Path - part # 1

Introduction

This morning, I have been thinking about a line from Ryan Holiday’s book, Stillness Is The Key (Portfolio/Penguin, 2019), where he states the following: “We are overfed and undernourished. Overstimulated, over scheduled, and lonely.” When I step back and look all around me, I see a lot of people who fall into this description. 

In particular, I see people in leadership positions dealing with this, and struggling with how to move forward given so many things in their life and work feel unclear, uncertain, and unknown. They want to create a work plan, and then they want to execute it. They also want a plan for their personal future. The challenge is that they are overfed, undernourished, overstimulated, over scheduled, and lonely. So, they feel stuck about how to begin the whole process.

The phrase, charting a path, is how one decides upon a destination and a route. It is an old naval term where you use charts to navigate your way. When one does it correctly, it prevents them from arriving at some unintended or undesired destination.

Whether we are doing this at sea or on land, charting your path typically involves three general steps. The first is orientation where you identify and clarify your destination, i.e. your overall goal. The second is way finding, where you make a plan for how you are going to get there, i.e. think planning your itinerary. This can also include making a map or using a map to figure how to get to you destination. The third step is journeying, where you actually walk the path you defined in the previous two steps. 

As we know, all three of these steps will involve stepping outside your comfort zone, and experiencing moments that feel chaotic and uncomfortable. But with the right framework and the right kind of support, we can chart a path and in the process transform the route from being chaotic to being a challenge. The key is to know where to begin. 

Preparing To Plan

Having spent decades helping people and organizations plan for the future, and having spent decades teaching people how to plan for the future, I like to use the following five part framework: preparing to plan, planing the plan, preparing to execute the plan, executing the plan, and evaluating the plan. While the aforementioned three part framework, i.e orientation, way finding and journeying, may work for an experienced planner, I find that many people don’t know how to begin the process of planning. And when they do begin, they often get lost in the prep work and in the planning. This then creates a cascading of problems which results in getting lost in preparing to execute the plan and in executing the plan. As the old Irish saying goes, “a good beginning is half the journey.” Same goes for planning. A good framework for charting your path makes a world of difference when you walk the path. 

From my perspective, the most critical step to charting your path is preparing to plan. And I believe most people skip this step in their rush to create the plan, i.e. the actual document, and to execute the plan. Nevertheless, just because most people skip it does not mean it is unimportant. Instead, I believe it is vital to success, because to chart your path means to find your path and this takes time and self-reflection. 

When we feel overfed, undernourished, overstimulated, over scheduled, and lonely, the idea of taking time for reflection seems worthless. However, I agree with the French mathematician, physicist, and philosopher, Blaise Pascal who wrote in 1654, “All of humility’s problems stem from man’s inability to sit quietly in a room alone.” It is in the creation of unstructured states of being, i.e. creating time and space for reflection, that we discover a great deal about our self and our path, past, present, and possibly the future. 

When we create time and space for reflection, we create a window into discovering what’s most meaningful and fulfilling in our work and our life. We also discover whether or not we are willing to follow it whole heartedly. We even create a window into whether or not we have the capacity to plan and the capacity to execute the plan. 

John Paul Lederach in his book, The Moral Imagination: The Art and Soul of Building Peace (Oxford University Press, 2005), notes that most people “want to build a tunnel [i.e. a linear pathway] through the problems/obstacles they are currently experiencing.” But Lederach ask us to consider a the following question, “How do you tunnel through an active volcano?” The choice to build a  tunnel creates “tunnel vision” and the outcome is that we lose “peripheral vision.” As he explains, “the capacity to situate oneself in a changing environment with a sense of direction and purpose and at the same time develop an ability to see and move with the unexpected” is very difficult because “people with tunnel vision can only see forward.” As he continues, successful leaders can see “forward, backward, and sideways.”

And for me this ability to see holistically begins when we create time and space for reflection, i.e. unstructured states of being. Here we stop rushing forward. Instead, we pause and reflect on what got us to this point in our life, and whether or not we have the time, the energy, and the right support network to move forward. But this is deep end of the pool work and it is challenging. 

To be continued on Tuesday.

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