Rethinking Strategic Planning

When I first learned about strategic planning, it was based on a top-down business consulting approach.

The old way

  1. You collect some data about the current state of your industry and your organization. Often this is called a needs assessment.
  2. You gather top leadership in the room and you analyze that data. If it’s a new organization, you define your mission and vision (maybe also values) and then from there you decide on your goals / objectives and set performance measures related to those goals.
  3. All of this written up in a plan that gets sent to a Board of Directors or other governing body for approval. These plans are usually written on a 3-5 year timeline and often are reviewed annually. Though the annual review is usually just updating the performance measures and timeline based on the progress that has been made so far.

This model has had many limitations. You may have noticed them: 

  • Long Timelines: The 3-5 year timeline feels too long in a rapidly changing environment
  • Unbalanced Contribution: The leadership team working on the plan can fall into unproductive meeting pitfalls like having only a few louder, more opinionated, or more extroverted leaders dominating the conversation. 
  • Data Doubts: The leadership team can have doubts about the validity of the data they start with. Often leaders will disregard or pick and choose the data they believe to be accurate based on their own experience.
  • Sits on a Shelf: It takes the leadership team a long time to develop the plan and after all their time and investment, they often don’t have the energy and money by the end to invest in communicating and implementing the plan they just created. The finished plan sits on the shelf and doesn’t actually change everyday actions or results.

Despite efforts to innovate, many organizations still struggle to create impactful strategic plans. Why?

Why these problems persist

First, the traditional planning process lends itself to analytical thinking and hierarchical thinking. The idea that if you can just come up with the “right” approach and write it into a plan, the rest will follow. All of the value is placed on the thinking part of planning.

How can we work smarter?
Be more innovative?
Know the problem so well that we can design a perfect solution to solve it?

I wish that was possible, but the idea and the clarity of thought, while important, are only one small piece of success.

Success isn’t just about brilliant ideas; it’s about execution and persistence. Often the greatest changes come from very boring actions done consistently. 

In a large organization, this becomes even more challenging, because it requires the alignment of all of the moving parts. You need a lot of individual employees to all take collective action in pursuit of the new idea.

The challenge with implementation

1) Employees are humans who like to have autonomy. They want to pursue what they think is best.

Best case scenario, you have employees who believe in your mission and are talented and skilled enough to do that work. Even if with those two pieces solid, you will still have the challenge of collective action. Especially unsexy collective action, such as filling out a new form and entering it into a database on time, every time. Many strategic goals break down into the implementation of repeatable processes and the creation of systems. But if employees don’t complete those processes accurately and consistently, or if they don’t use the new amazing systems, then your strategy fails to launch.

Worst case scenario, you have employees who resent you or don’t believe in your vision and they are actively undermining the new approach.


2) Changing behavior is challenging, even when the person doing it believes in the change. Ask anyone who has ever written a New Year’s resolution that they wholeheartedly wanted and then failed to follow through.

Belief in the “rightness” of a new approach is not enough to change behavior. One approach that has been used by leaders trying to manage large scale change projects is to just fire anyone who hasn’t been able to make the change in their behavior within a certain period of time. I believe we can do better.

By studying how habits are formed and reformed and how people make significant changes to their behavior, we can design an implementation plan that gives employees the support they need to do things differently. I believe that when we build that type of support into a strategic plan roll out it will also lessen the amount of resistance and resentment that leads to employees disengaging and to employee burnout.

So, what’s the solution?

A New Model for Strategic Planning

  1. Simplicity and Speed: Lead a rapid prototyping process that will allow a team to design a strategic plan in a short time frame (2 days?) so that they can move from thinking to doing and have more time for supporting implementation, learning from their results, and funneling that new information back into the plan.
  2. Fundamental Questions: Stick to the 3 most important questions that you need to answer in this process
    1. Why do we exist?
    2. What do we want to create?
    3. How can we fulfill stakeholder/customer needs?

Here are those three questions outlined with the important criteria for how you can answer them with your team:

Why do we exist?

  • Customer / Community focused – What evidence do you have that a need or desire exists that you can address?
    • This is where it is important to gather relevant information and data. 
    • A mix of quantitative and qualitative data that includes talking to real customers or real people who have experience with the need or desire.
    • Try to avoid talking about what you do at this stage. Avoid discussing your organization’s strengths, history, assets. This is the “we exist because we exist” trap. You justify your actions based on the need to keep existing because you have employees, shareholders, or history. 
    • Methods at this stage:
      • Customer conversations
      • Observation and ethnography
      • Reviewing reliable data sources that address needs or desires of the population you serve
      • User experience fishbowl
      • Celebrity interview
      • 9 whys
    • Pitfalls at this stage:
      • Moving to problem solving or creation before you fully understand the need or desire and before you have heard from real people who have lived experience with that need or desire
      • We exist because we exist
      • Looking at only one type of data and seeing an incomplete picture (for example speaking to an unrepresentative sample of customers and not validating those experiences with qualitative data about the size and scope of the need or desire they are sharing with you).
      • Large bureaucratic organizations often have a broad or multi-focus mission that makes it hard to answer these questions. Some government entities for example are mandated to exist by law and may not relate to the idea that they exist to address a need or desire. 

What do we want to create?

  • At this stage it is critical to take the information you gathered in the Why stage and be able to sift and sort it and pull in different perspectives from your planning team. 
  • Surface and test assumptions
  • Be able to spell out your logic model — based on the need or desire you’ve identified, what approach are you going to take to address it? What do you think the results and benefits will be for the population you serve? What makes you think that? How will you know if it’s working?
  • What is within your sphere of influence to address this need or desire? Within than, where are your strengths. What unique skills and experience can you bring to this that will differentiate you in the market?
  • Methods at this stage:
    • Asset Based Community Development / Asset Inventory
    • Appreciative inquiry
    • Min specs
    • Wicked questions
    • Improv prototyping
    • Visual problem solving
    • 25/10 crowd sourcing
    • Critical uncertainties
  • Pitfalls at this stage:
    • Group think / unhelpful group dynamics that prevent all ideas from being heard
    • Falling too quickly into how – focusing on the ways you want to get the work done instead of what work you intend to do
    • Slipping back into just doing what you like to do or what you have being doing recently instead of looking at what can be done in response to the WHY with fresh eyes.
    • Focusing on problems to be solved or reasons why things won’t work instead of answering the question of what you want to create.

How can we fulfill stakeholder needs?

  • Now you can finally talk about how you will do the work. At this stage it’s important to align with current reality of what your assets are, what your current resources and skills are. Constraints breed creativity, so rather than having pie in the sky conversations about what would you do if you had all the money in the world, it is actually more effective to look at the limited resources you have and challenge yourself on what you can build with what you have.
  • More Apollo 13, less Field of Dreams. 
  • If your approach requires you to behave a certain way you need to make sure you are working with real behavior, not presumed logical behavior. Many creations have failed because they assume that people will act in their own self interest or that people will go for a cheaper option of similar quality if one exists. Go back to naming your assumptions and be ready to test those assumptions.
  • Methods at this stage:
    • Basic action planning templates
  • Pitfalls at this stage:
    • Not being specific enough. Saying something like – we’ll design an afterschool program for teen girls, does not go far enough. You need to be able to answer the question of how will you know if it’s successful? To answer that question you need more details about the program design.
    • Someone slips in a program or product to this section that is something you already do or is a pet project that does not align with the first two stages. They just want to put it somewhere in the plan so it doesn’t get cut.

Implementation: Bridging Strategy and Action

Now once you’ve handled the 3 strategic planning questions, you can move to the implementation plan side of the equation.

One question that I haven’t seen before in traditional models, but that I think is critical is:

What behavior will have to change in order to achieve the result we say we want?

  • For these behaviors, you then want to look at the structures that are currently supporting that behavior. Let’s take the example of energy savings in an organization who wants to become carbon neutral. Perhaps there is a lot of utilities use in the organization’s offices. In addition to looking at individual behavior change, such as unplugging devices or turning off lights when people leave, this is the time to zoom out and look at the system more broadly. Technical solutions, such as light timers, where all lights will go off if no one is present in the building for a certain period of time. Policy solutions, such as a change to the work from home / teleworking policy so that employees are allowed or encouraged to work from home instead of the office whenever it makes sense for them to do so.
  • Pairing desired new behaviors with a change that is already required. So for example, if your organization is changing location (perhaps downsizing square footage now that more employees are remote), look into locating near mass transit, or creating bike lockers, onsite showers, and other structural supports at the new location that would encourage and enable alternative means of transportation. It is easiest to form new habits when you are already starting new routines or making a big change.


Successful strategic planning isn’t just about crafting brilliant strategies; it’s about execution and adaptability. By embracing simplicity, focusing on real needs, and aligning actions with desired behaviors, organizations can navigate the complexities of strategy implementation and thrive in an ever-changing landscape.