Strategic Doing — Book Summary

Ten Skills for Agile Leadership Book Summary

Today’s world is a complicated one, and there’s a lot of more wicked problem around that needs solving. Hence, this is what Strategic Doing aimed to assist and explains.


Strategic Doing: What’s a wicked problem?

Wicked problems are ambiguous, and we may lack crucial information when we try to solve them. They change constantly, and attempts to solve them might produce unintended consequences.

“Strategy has to be a team effort, and the more complex the environment, the larger the group – the network – that will need to be engaged.”

“In meeting adaptive challenges, we learn by doing.”

In a hierarchy, a leader sets the agenda and people report up to him or her. In a network, members align themselves toward an objective. A “tight core” of people manage networks, which form around assets or resources. A porous boundary separates who is “in” and who is “out.” The problems they address may be complex, but their strategy process is not. The necessary skills are simple, but not easy.

To use strategy in a networked world – think, behave and perform differently.

Frame your strategy by asking: Where are we going? How do we get there? Strategy in a networked world can’t rely on one decision-maker.

For the strategy to work, people must collaborate meaningfully by linking and leveraging their assets, building capacity and moving toward mutually beneficial, shared goals. 


Skill One: Establish a safe environment for deep, focused conversations.

Groups must cultivate in-depth, focused conversations to determine their goals.

  • Deep conversations nourish and satisfy, but they require cutting out all distractions. 
  • Set aside time and create the right space. 
  • The optimum size for this discussion is seven people.
  • The best place is neutral ground.
  • Select a location where people feel safe communicating and where they believe they’re being heard.
  • Being civil helps people feel secure, so they can take more risks with each other. 
  • An agile leader allots time equitably and understands that fostering this kind of conversation in a group setting takes time.

Skill Two: Frame these conversations with the right questions to address complex problems.

An agile leader designs an appreciative framing question – one that has many answers, that is complex and that demands engagement. You can use technical and adaptive questions.


  • Technical questions have clear rules and outcomes.
  • Adaptive questions are more ambiguous: The strategy for addressing them is iterative. The solution arises from a learn-as-you-go process. 

Grand, brave and exciting framing questions help the group address wicked problems most effectively. They draw people to express diverse viewpoints which invite in-depth discussion. An agile leader forms compelling questions about a future that is still out of sight with the goal of provoking innovation.

Wicked problems conversations should not centre around the problem itself, but should explore opportunities. Such conversations have more emotional impact. Hence, instead of asking, “What can we do to minimize customer dissatisfaction?” ask, “When have our customers been happy, and how can we build on that success?”

These questions compel people to act. By addressing them, the group discovers that it can create shared value. Furthermore, the right question prompts people’s interest to join the conversation.


Skill Three: Identify your assets to create new opportunities.

“Perfect knowledge is not possible, so the best option involves testing ideas.”

Hierarchies usually held and allocated resources, but that doesn’t happen in a networked world. Assets and resources are everywhere, and the odds are no one is in charge of allocating them.

So, identify your resources which also include:

  1. Physical assets such as real estate and equipment, and commodities.
  2. Skills and knowledge assets such as writing, design, data, public speaking and research.
  3. Social assets such as professional associations, academics and politicians.
  4. Capital assets such as financial resources and anything that you purchase with money.

Focusing on what you have keeps you action-oriented and more attentive to available opportunities, and not problems. Look to your network to see what assets you can share to everyone’s benefit. You won’t know right away what to do with your assets. You may not have enough to do everything you want. So, think about what you can do right now, with what you have, to open more opportunities. Look to try to do more with less.

Leverage your network!


Skill Four: Leverage and link these assets.

Agile leaders don’t just help identify and allocate resources, they also find linkages, leverages and alignments among them. Build a powerful platform by combining assets that can help you solve complex problems.

Think horizontally when seeking new ideas; other domains can offer knowledge and insights through connections. An agile leader starts by identifying three or four assets and devising ways to combine them.

At times, all you need to unstuck is to look at the problem from a different angle

Skill Five: Use the “Big Easy” matrix to identify easy opportunities with big impacts.

Examine your options, and move forward on the one that has the most likelihood of success. Select choices that are easy and have the biggest impact.

  • Being big is exciting.
  • It motivates people.
  • Selecting something relatively easy is practical.
  • You avoid getting bogged down in big ideas that are hard to execute or doing the expedient thing that inspires no one.
  • Small efforts attract attention and draw more support.

Then, your network will expand, and you can tackle more complex tasks.

The Big Easy matrix helps guide that intuition. Take small steps with your Big Easy, and start over if it doesn’t work out. Even if you choose the wrong activity to begin, you’ll learn from the failure. Facing hard facts together builds trust. Some doubters may not want to move forward without all the information.

Delay erodes trust. You will never have all the information. You will know what to do only when you actually work to carry out an objective. Generate, consume and analyse data as you move forward. Choose an opportunity that motivates the group to act. Opportunities will connect over time. Your speed will increase as the network grows.


Skill Six: Measure your progress so you can convert ideas to outcomes.

“Emotion – not vague vision statements – is what drives people to action.”

When considering the future, ask:

  1. If we are successful, what will we see?
  2. What will we feel?
  3. Whose lives will be different, and how?

Imagine prospection. Prospection draws you to emotionally invest in the process. Brainstorm the future you imagine, then deepen the conversation to iron out details while addressing inconsistencies.

notes: Prospection means reminiscing forward

Measurable Metrics

Almost no one likes metrics, but they are essential for determining value. You must be able to measure and compare to gain perspective about success. Everyone needs to use the same language to avoid miscommunications. If you can agree on a standard for success, you are off to a good start.

What matters most is aligning the group toward a shared outcome.

  • Avoid disagreements, which erode trust and produce apathy.
  • Have the deep conversations early on the process.
  • Try to craft three statements about the outcome, and
  • Name two ways you would measure its success.

With a shared vision and agreed-upon metrics, the group can feel confident about taking action.


Skill Seven: Get started on a project even if you don’t have all the information. 

You won’t know all the conditions without experiencing them. The same is true of any plan. You must start doing something to find out what to do next. If you don’t start, you might get overwhelmed. Analysis paralysis kind of thing.  

In identifying the best starting project,

  • Evaluate whether it is short enough or needs permission. Projects that are too long or have a long approval process risk losing momentum and failing.
  • Determine if your project engages everyone on the team and create a buzz with a forward-looking narrative that excites people of the possibilities. 
  • Consider whether the project tests key assumptions, so you can draw new insights that propel it forward. Testing key assumptions will give the project more meaning and impact.

Skill Eight: Follow an agile strategy with shared leadership.

The collaborative shared leadership model allows more flexibility and suits complex problems better than single-leader models. Trust is the most important factor in successful shared leadership. To build and scale trust, ask for commitments to small, achievable goals that fit the bigger organizational picture. Everyone should leave a meeting with a task. Use a feedback loop to make sure the agile strategy stays on track. Take what you learn from your activities to determine their success and how they move a project forward.


Skill Nine: Hold 30/30 meetings to gather data and adjust.

Definition: A meeting where the participant discussed what they’ve learned in the past 30 days and decide on what to do in the next 30 days.

  • Holding 30/30 meetings maintains the feedback loop.
  • Frequent and predictable meetings increase trust.
  • Nudge when appropriate, reinforcing positive momentum. They also explore other networks to find connections that align with group goals.
  • As the group grows, divide it into smaller groups.
  • Transfer the knowledge necessary for autonomous operation while staying connected to the larger goal.
  • Promote the group successes to build group commitment and enthusiasm.

Skill Ten: Implement Strategic Doing and share leadership, because no one person possesses all 10 skills.

No one can master all 10 skills for agile leadership. Strategic Doing does not work in a hierarchy. Since

  • Each member of the group brings a different strength.
  • Diversity matters when you’re confronting wicked problems because it brings together different viewpoints on the situation. 
  • No one person can guide the rest.
  • Shared leadership to optimize the network’s potential.

Ask: Where are we going, and how do we get there?

A plan that answers these questions will yield a worthy strategy. It is iterative and improves on itself as it develops. Whether in your personal life, a small group or a large, bold project, Strategic Doing can provide the 10 skills you need to tackle even the world’s greatest challenges.

Further reading with the similar topic might be “Maximize Your Potential” and Ray Dalio’s Principle.

9/10 ★



Author: Muhamad Aarif

A notorious book addict by night and an oil and gas executive by day. As Mark Twain said, "The man who doesn't read good books has no advantage over the man who can't read them." So, read, read, and read some more.

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