Strategy Execution as a Learning Process

Concept to ExecutionI’ve been teaching the idea that the strategic initiative leader (the program manager) functions in the role the Chief Learning Officer (CLO).

Here are three essences of the CLO role:

  • Establishing an attitude and culture that is friendly to learning. The CLO role regards the statement of “I don’t know” as an opportunity to discover useful information. Ignorance is not a weakness.
  • The leader leads by asking questions. One of the best is this: What don’t we know? When problem-solving, the question “How might we ___?” often opens up the conversation.
  • Use experiments and probes to increase the learning. In particular, in areas of complexity, watches for emergence. If an experiment is working out, the leader moves to amplify its positive effects. If the experiment is not delivering benefits, the negative effects are dampened.

When it comes to strategic initiatives, I find that a mindset of efficiency gets in the way of success. I recently found some support in an article by An Kramer. The following table summarizes some of the reasons that we think of strategy execution as a learning endeavor rather than one of efficient deployment.

  Execution as Efficiency Execution as Learning
Leaders Have a “fund of knowledge” that is selectively dispensed Establish general direction
Employees Valued because they follow directions Valued because they discover and adapt
Methodology Set in advance Tentative
Change in work flow Infrequent, seen as costly Continual, organic
Feedback Typically 1 way: boss to worker 2 way
Problem solving If unsure, the worker asks leader for information Constant problem solving. Info flows freely to workers
Fear Does not harm quality of execution and might even motivate those facing a dull task Inhibits learning, experimentation, discourages sharing, lowers awareness of options

I find that most people in my seminars greatly appreciate the idea of setting the climate for learning in the team. However, they struggle and often are held back by traditional mechanistic notions of organizations that are focused on efficient production.

References. The above table is an adaption (by me) of An Kramer’s article “Ready for the Future: The Four Principles of Nomadic Learning,” in the journal, On the Horizon (2013). Kramer  credits Amy C. Edmondson (2008) for the distinctions.

How have you practiced the idea of “execution as learning?”

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Why I favor a mental stance of disorder

Disordered StanceThis article will be of particular interest for those readers who want improve their strategic thinking. The advice for you is straightforward: Assume you don’t understand the situation that you’re in.

The dangers of the K.I.S.S. Maxim.

For most, this is difficult advice to follow. The reason is that their own natural predisposition, magnified by the culture of operational thinking, draws to “Keep It Short & Simple.”

A stance of simplicity is inappropriate for most strategic initiatives. Here are two examples:

  1. A company wanted to improve its new product development capabilities. It hired a large training firm with an established “best practices” project management curriculum designed for information technology practitioners. The methods and skills taught were irrelevant to the company’s product development process, and everyone involved ended up frustrated and in a blame game.
  2. As a result of declining demand, a company went on an aggressive cost-cutting program. Any proposal that involved expense was met with an answer of “no.” The cost-cutting program didn’t address the organization’s core strategic challenge that it’s once strong strategy had been disrupted by competitors.  It needed to focus and invest, instead the managers found it easier to decentralized and tighten the belt. The organization never addressed its core challenges and the result was that the company became smaller and weaker. Because of simplicity, it was absorbed by a competitor.

Strategy is often oversimplified as vision, mission, and values

Many people equate the concept of “strategy” with “plan.” As a result, they misunderstand strategy as ordered and specific steps that get them to their desired outcome. They are ignoring the several pertinent facts:

  • No one can predict the future. Unexpected things emerge and cause adjustments.
  • It is hard work to get people to agree on the issues that face the organization
  • People spend more time arguing over proposed solutions and visions rather than understanding their strategic situation
  • Good strategy often hurts people’s feeling as causes difficult choices about where to invest scarce resources and where to disinvest

These oversimplifications (coming from a mental stance that values simplicity) explain why organizations flounder and resign themselves to bad strategy.

Your mental stance

When you are in your physical stance for a sport, your body is positioned to anticipate and react to the game. The mental stance is similar, how your mind is positioned to anticipate and react to information.  The mental stance is the way you filter or amplify signals coming from outside of yourself. To hold a disordered stance is to look at the data as a set of uncategorized signals.

Cynefin’s region of  disorder

I’ve been interested in Cynefin framework for years, but it wasn’t until I wrote this earlier article on VUCA that I really began to understand its genius. You can find out more on Cynefin elsewhere. For this article, I’ll simply point out that the framework is composed of five regions: simple, complicated, complex, chaotic, and disordered.

In the Cynefin framework, the disordered region is the condition where people do not know (or do not agree) on the whether their situation is simple, complicated, complex, or chaotic. To be clear, disorder means that any of these could be true (yet, when time has passed, only one of them was correct):

  • The person is unsure of the effectiveness of a so-called best practice or process
  • The person is unsure whether an expert can resolve the problem
  • The person is unsure whether some unanticipated (black swan) event might emerge
  • The person is unsure whether an experimental approach would help

A disordered stance is a better way

Instead of assuming simplicity, you should assume a disordered stance. Stated differently, embrace disorder as the entry point for analysis and decisions. Returning to the two examples above of the excesses of simplicity:

  • Don’t be captivated or convinced by the label of “best practice.” Don’t assume that a performance problem can be fixed by training.
  • Don’t rely on simple rules of cost cutting.

In both cases, a diagnosis of the situation is necessary. Moving past symptoms, what are the core challenges that the organization faces? This is the realm where good strategy is needed.

Some complicated problems are fixable, such as the example of new product development productivity.  The answer is to avail yourself of expertise. Keep in mind that “thinking outside the box” actually means looking in other boxes (ideally as far afield as possible), a process that’s as analytical as it is creative.

For more discussion on the domain of complexity, see this article: Complexity: Four Principles for Program Managers.

I like data

When you favor a stance of disorder, you do these things:

  • You research widely, looking deep inside other boxes
  • You search for interesting things
  • You expect the unexpected
  • You resist “ideal forms” like methodologies and best practices.
  • You dig deep to understand the fundamentals

Basically, you think in an unconventional way. Earlier I wrote that a stance of simplicity is appropriate for most strategic initiatives.  I’d like to clarify that (somewhat) with these words from Richard Rumelt’s excellent book, Good Strategy/Bad Strategy:

A hallmark of true expertise and insight is making a complex subject understandable. A hallmark of mediocrity and bad strategy is unnecessary complexity – a flurry of fluff making an absence of substance.

I tolerate complexity and ambiguity

This quote from Oliver Wendell Holmes, Jr. is one that reflects my advice:

“I would not give a fig for the simplicity this side of complexity, but I would give my life for the simplicity on the other side of complexity.”


Complexity and ambiguity are each a source of anxiety, and that the desire to avoid anxiety explains why many people don’t become competent strategic thinkers.

Do you agree that mental stance is an important leadership attribute for strategic initiatives?

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Critical Asking

Critical Asking Reduces AmbiguityA challenge of strategy execution is that visionary people (executives and managers) have visions, ideas, goals, and solutions; they need others to realize the benefits. Often, the tactical people react to the request with pushback: “That will never work. We don’t do it that way. We don’t have this. We don’t have that.”

For good reasons, much execution flounders because of a gap in communication. Both sides need to be grounded into reality. Martin Rupert, who works on strategic initiatives for a large confectionary company has a great technique for turning vision into action. Critical Asking helps to explore the assumptions, visions, and rationale from visionary and strategy requestors. The word “critical” is used in the sense of finding deeper truths, and not in the sense of being pessimistic. Its purpose is to bridge the gap between the expectations of requestor and those implementing the request. Martin tells us,

“If the communications and understanding of the strategy does not happen, the chances of success are slim.”

Funneling ambiguity into clarity

Strategy is inherently ambiguous. The word ambiguity means multiple meanings, which is to say that any given strategic situation makes sense to people in different ways. The job of the leader is to help others tolerate and work through the ambiguity.

Martin suggests that we picture the situation as funnel where the wide side opens into the haze of ambiguity. The technique involves iteratively meeting with requestors (visionary and strategy) and those “tactical” people who have to design a solution. Martin serves as an intermediary between the requestors and the delivery team.

Martin Rupert

Martin Rupert

Phase 1 – Clarifying the request

People who operate business units are on the front lines of interacting with customers and operations. They have many needs and are exposed to lots of suggestions for improving their business. Those solutions – and the underlying business needs — are often vaguely stated.

Martin starts off the critical asking process with open-ended questions, such as these:

“What are we going to do? What is the impact? What is the end goal? How do you see this working?”

Martin is searching for the “driver” for the need that reflects the strategy’s insight.  He often probes deeper:

“Why do you say this? Why do you believe this?”

His ultimate goal is to facilitate the vision by building a business case based on facts. He knows that eventually there will need to be a discussion and exploration of true financial benefits and costs. He also knows (from experience) that there can be a huge gap between the tactical people and the people with the vision.

He presses on with questions like the following two:

How will we know that we’ve been successful? Martin reports that, “You can see the gears turning in the requestor’s mind on what success looks like.”

What’s the financial benefit?

Phase 2 – Exposing the idea to implementation team members for critique

Martin then takes his understanding of the request to the implementation team. He overviews the request with them, explain the “what and the why” of the request. He then asks for reactions.  He finds that there are any number of issues related to resources, technology, process, regulations, system capabilities, funding. These issues will need further investigation.

As the implementation team understands the request and its rationale, they can better plan the needed project-level activities.

Phase 3 – Further resolving the ambiguity (shuttle diplomacy)

Phase 3 is a further iteration, where Martin shuttles back and forth between the requestor and the implementation team.  He says,

“Each time, you get a little more insight each side is seeing where the other is coming from.”

Phase 4 – Meeting of the Minds

At some point, Martin judges that both parties are ready to get together. Being the intermediary saves time and gets people to a common understanding more quickly. There is an agreed basis on the basic need, challenges, and issues. He reports,

“That is where you really start hitting the jackpot and making some progress.”

Martin acts as a mediator helping the participants see all sides of the issues.

Tough-minded mediation

Of course, Martin gets pushback on critical asking because he is taking valuable time.  People will ask him, “Why are you asking so many questions?” He responds,

“This is a calculated and disciplined process. If we do not get the ambiguities resolved, how will we know where we are going and how we will get there?” I am asking you indulge me and I believe you will see the results of this effort very shortly.

I asked Martin about his personality. He says,

“I have been labeled as the ‘strange guy’ and been told that I’m ‘a pain.’ That’s OK because I know the value of this process and what it can provide. Seeing results makes the effort worth the iterations again and again. I know we will make progress and the light bulbs will go off on both sides.”

Critical asking saves time, churn and frustration. How might you use it?

Note: Do you have an idea that you want to share with my readership? Contact me and we’ll discuss how to get it published.

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Transcending the Status Quo

I was recently asked about the reasons for the status quo, specifically the lack of attention given to selecting, prioritizing, and supporting strategic initiatives. Everyone knows that strategy is important, so how do you get people moving?

Let’s start by describing some concepts that help develop understanding about the sources of status quo.

“Flow” and being in “the zone.” Flow describes the psychological state where a person is absorbed in the task; they have a feeling of energized focus. Time seems to pass quickly. The presence of clear goals and measurable progress seems to enhance flow.

From a strategic thinking perspective, in conditions of flow, people lose their ability to self-consciously reflect upon their situation. They are captivated by psychological flow, an enemy of competent strategic thinking.

A preference for intuition. Intuition is a kind of memory that comes from repeated exposure to a task and the environment. Intuition leads to good decisions most of the time, but is frequently faulted when mistakes are made.

Intuition is also an enemy of strategic thinking.

Regrets and the “negative fantasy.” People tend to imagine more regrets from a choice to act.  They tend to have fewer regrets for staying put. Thus, making choices to act is associated with regret and the resulting cognitive bias is for the status quo.

Further, people are subject to imaging a story about themselves that escalates into an unrealistic, low-probability-but-horrible outcome.  Here is an example that I frequently see: A person is given a vague task.  Rather than ask clarifying questions, they tend to make their own assumptions (which are, many times, poor assumptions). They don’t ask questions because they regard themselves as a subject matter expert. Here’s where the logic and imagination gets slippery: If they ask a question, it means that they don’t know. If they don’t know, then they can’t be an expert. If they are not an expert, they have lost the respect of others and their own self-worth. (Here’s where the negative fantasy really takes off.) Because they have lost respect, they are unlovable, not valued, and unnecessary. Their employer will fire them and their family will abandon them. They will end up homeless and isolated. Our minds exaggerate things and justify our inaction.

Organizational culture tends to preserve and amplify conventional thinking

Here is a fourth reason for why the short-term status quo gets more effort than strategy work:

Strategy imposes a cost with uncertain benefits. Many managers follow an unwritten role of operational-thinking rule: don’t incur a cost unless it yields immediate and preferably economically-measurable direct benefits. Operational thinkers quickly sense that doing strategy work imposes a cost on the organization: taking the time to collect and analyze data about the competitive environment causes people to de-specialize. It moves energy away from the task at hand. That energy has a cost and the easy decision is to defer it to later.

~~ ~~

The status quo bias is a powerful challenge to strategy work. The tendency towards the status quo is a basic feature of human cognition.  This article describes a little bit of the underlying theory and will help you understand why it happens.  The pragmatists want to know: how do you transcend it?

The answers include developing self-awareness of your own thinking, noticing what’s going on around you, and having the courage to speak the truth. If you work in an empowerment culture, you will find it easier to speak your mind than if you work in a permission culture, where you need to find an audience with the powerful elites.

What are the other causes and solutions to the status quo?


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Connecting Strategy to Execution

Strategy road signI was recently asked, “How should the PMO (project management office) connect strategy to execution?”  In order to provide a compact answer, I’m going to sidestep the more-fundamental challenges: organizations have too many projects, every project is important to someone in the organization, and that organizations commonly confuse goals for strategy. My answer is for the ideal case: an organization with a good strategy that is commissioning a strategic initiative to close a performance gap. I suggest these three actions:

Understand the diagnosis for the strategy. 

Strategy is a form of specialized issues management.  A leader should start with questions like these: What is the business problem at the macro level? How will the strategic initiative effectively “move the needle” on cost structures and revenue streams? Is this the first time the organization has faced a similar set of business issues?

These questions are all probes for the ‘why’ and the insights that underlie the strategy.

There are some things to avoid as well: don’t fixate on goals, objectives and dates. Your time is better spent understanding the ambiguity that is certain to be in the strategic situation. In time, you can begin to drive into the specifics.

Understand the guiding ideas of top management

Again, more questions: Who gains and who loses in this strategy? What are the constraints on resources, technologies, and internal restructuring of the organization?

The idea here is to funnel broad policy ideas into narrower guidelines.  A good strategy is not specific on the details but provides guidance on the main points of focus.

Experiment well

Strategic situations are typically complex situations (see last month’s article).  In complex environments you need to experiment: looking for wins (which you will amplify and attempt to chain-link to other wins) and losses (which you will dampen).

Strategy execution, like formulation, requires a mental readiness to understand the situation at a deeper level. Do you agree?

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Complexity: Four Principles for Program Managers

I started writing this article to report and elaborate on eleven useful practices as identified in a 2014 Project Management Institute (PMI) publication titled Navigating Complexity: A Practice Guide. I thought it would be a straightforward project, but it morphed into an article and outlook that I believe will be much more valuable for readers.

As a “practice guide,” the publication was a collaborative project, written and reviewed by dozens of people with expertise in program and project management. You can see those eleven practices are on the nearby graphic (which is an image clipped from the document’s table of contents).


Complexity TOCAs I began to elaborate on each of the eleven practices and their applicability to strategic initiatives, I had a growing sense of discomfort. It started with the document’s weak definition of complexity (page 1), “complexity may be viewed as challenging characteristics of programs and projects that organizations and practitioners encounter in today’s fast-paced, competitive, and dynamic environment.” In other words, the authors regard see complexity as a “challenging characteristic.” That’s pretty inclusive, as something as mundane as a broken photocopy machine, a corporate policy, or an aggressive schedule could be challenging.Navigating Complexity

For purposes of this article, I’ll point you to Neil Johnson’s definition of complexity (from Wikipedia) as

“the phenomena which emerge from a collection of interacting objects.”

The key characteristic of complexity is that it involves emergence: opportunities as well as threats emerge. The specifics of that emergence can’t be predicted in advance. (This article is a case in point: it started out as a straightforward listing and elaboration but transformed into a more sophisticated perspective about the presence of complexity in programs.)

What follows is four principles that emerged for me as I analyzed and synthesized the key elements of PMI’s eleven practices.

Principle 1 – Recognize the role of emergence

In the natural world, complex systems are characterized by emergence. Examples are weather events, epidemics, and even terrorist cells.  The time and place of the specific event are not predictable. In strategic initiatives, emergence can be in many forms: unexpected mergers, unexpected moves by competitors, and so forth.

One of the most useful habits is to encourage everyone on your team to pay attention to small signals, with the idea that they grow to be significant threats or opportunities. Establish a mindset in the program’s culture (especially the communications and decision processes) to expect the unexpected.

This brings us to one of the most important (and subtle shifts) from the traditional PMI mindset towards quality. I wrote earlier that I had a sense of discomfort as I read the document. Besides the definition, it was caused the emphasis on command and control. People preach the commonsense value of preventing defects from occurring in the first place. That certainly makes sense for well-understood and ordered systems. However, the emphasis on prevention tends to begat controls on top of controls, which unintentionally creates yet another layer of potentially-complex behaviors.

In complex systems, consider moving away from emphasizing prevention to emphasizing resilience. The idea of resilience is that some sort of failure is inevitable. It’s smarter to create a culture that encourages early detection of an event, and then quickly respond and remediation. Finally, figure out how to transform the threat to an opportunity.

We use the term integration all of the time in program and project management. I’d like to suggest that integration  –  when in domains characterized as complex – really means the approach that the team uses to monitor the entire system and quickly react to emergence.

Principle 2 – Avoid oversimplification

The practice of avoiding oversimplification is very similar to the first practice of recognizing emergence.

All people like simplicity, but often over-simplification leads to poor decisions. When we are in areas of complexity we recognize that rules of thumb are two-edged: when we use simple rules, we activate our intuition. However, a simple rule can also lead us to missing important nuances. They challenge the assumptions, and accept change as a constant.

Note this quote (attributed to Oliver Wendell Holmes, Sr.),

“I wouldn’t give a fig for the simplicity on this side of complexity; I would give my right arm for the simplicity on the far side of complexity.”

Strategic thinkers look for that simplicity on the far side of complexity. They do this by developing a nuanced understanding of the organization, especially the numerous interfaces with the external environment. You want to err on the complexity because small errors cascade and magnify into greater problems.

This means that managers should be aware of their own assumptions and challenge them. They should see data from the organization.

Principle 3 – Recognize and manage your strategic assumptions

Optimistic executives can often set the program up for failure by not understanding the true nature of the situation. A strategic assumption is an assumption that if invalid, causes cancellation of a key program element or a redirection in it. You can find more on recognizing and managing strategic assumptions at this link.

Principle 4 – Favor expertise over experience in staffing and communication

Experience and expertise are not the same thing. A person may have worked in an area for a long time and accrued much experience. However, an expert is more adept at recognizing the causes of symptoms. Here we can learn something from the academics that have studied experts and novices in fields like chess, counseling, and medicine. They tell us that experts are more thoughtful in approaching the problem. They search for important features and formulate a mental representation of the issue. That mental model contains abstract rules and principles.

On the other hand, novices tend to search for “methodologies” and best practices.  I find it is often because they are impatient to see some results, so they plunge into complex situations without the right mental stance.

You’ll get much better results if you orient your staffing and communications around this question,

“Who has the best ability to diagnose and understand the nuances of this specific situation?”

I’d welcome your comments, especially if you are familiar with Navigating Complexity: A Practice Guide. Do you agree with the four principles and do you agree they reflect the eleven practices?



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Use the PAVER Framework to Assure Strategic Commitments

Promises & Strategic Commitments

As they left the courthouse on the day their divorce was finalized, Mark apologized to his now ex-wife Renee, “I told you I would do some things for the benefit of our marriage. I didn’t do them, and I’m sorry.” Such is the case with good intentions that are taken as promises, and then not fulfilled.

Strategy execution has an important similarity to Mark’s admission: an individual fails to follow through and the desired outcome suffers. I believe that we will get better execution of our strategic initiatives if we become more skilled at making and managing promises. To start, I’d like to introduce you to the PAVER framework (an acronym), which I adapted from an article by Donald Sull and Charles Spinosa, “Promise-Based Management: the Essence of Execution.” (Harvard Business Review, April 2007).

A good promise has five properties.

It is made publicly. All stakeholders can detect — through the promiser’s words and declarations — what has been promised. As you might suspect, public exchanges of promises are more emotionally-binding and transparent, both of which are desirable within strategic initiative team.

Perhaps the most important characteristic of a good promise is that it is an active exchange of expectations. Sull and Sponosa write that promises are active conversations that are comprised of “offers, counteroffers, commitments, and refusals.” That may seem a little formal and rigid, but consider the pain that you’ll avoid later when you try to cajole, plead, and bully non performers.

Let’s contrast that negotiation-oriented style with the more common practice of making mild and oblige suggestions. This also brings forward another important success driver: determining which individuals have authority to make decisions and commit resources.

Sull and Spinoza also note that much of the discourse in organizations is endless assertions about the state of nature; that is, a description of what the true conditions are. Some will say the market is growing, and others will assert that it has peaked. Someone will say that they have heard something from a top management and others will claim to have heard something differently. Here is yet another example: consider the frequent comment that “we’re different” that is used by many stakeholder’s to justify why ideas can’t be accepted in their culture. This kind of conversation is a waste of time!

A third property of a good promise is that it is voluntary. As most of us experience, it is easy for an executive to agree to a request, and defer the consequences of that ‘till later. In many cultures, those who say “no” are labeled negatively. However, the courage to say “no” to any request is a key for making the promise voluntary.

The forth property is that a good promise is explicit. Most people are familiar with the idea of SMART objectives, which makes clear the deliverables, the providers, the budget, and the timing.

Sull and Spinoza call the fifth property mission based, but I prefer the term rationale. When you can answer the question, “Why are we doing this?” you are providing a rationale that forces you to show that you understand the linkages and alignment with strategy. (The question “why” is the first of the four driving questions of radical innovation, and needs to be asked and answered before getting into the following questions of “Who needs to be involved? What are we going to do? When are we going to do it?”)

Too, recall that good strategy is a form of problem solving; your explanation of the rationale must link to the important issues and performance gaps that face the organization. Strategic initiatives exist to close a performance gap, so you need to be clear in describing how the strategic initiative supports changing the outcomes and filling that gap.

~~ ~~

Requests and promises are the basic units of work coordination. They take place in a network of external and internal relationships, most of which are informal.

Realize, too, that resources in organizations are constrained by existing commitments and a shifting set of priorities. I always tell my colleagues that they have the right to change their mind about a commitment, but they owe me a message to tell me that they’ve rescinded their commitment.

 Do you agree that making and managing promises is a useful focal point for building effective relationships with your network of colleagues?

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