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Preparing to Plan (for individuals, teams and organizations)



Preparing to plan…the step before we actually start thinking forward and planning requires us to make time to look back in reflection and review. This step is almost always overlooked, and can be a huge source of insight and inspiration. It requires us to pull out of the day to day and dig deep to think about and explore questions like: Where are we? Where are we going? What needs to change? What can’t change?


When we step back to consider planning more holistically, we realize there are 4 steps:

  • Preparing to plan

  • Planning

  • Executing the plan

  • Managing the plan

Executing the “preparing to plan” step effectively gives us a lot of data points and a solid foundation upon which we can consider our future. In addition to reflection and review, this step includes things like gathering information and reporting, as well as gaining insight and input from others.


When we skip this step, whether as individuals, teams or entire organizations, it can be easy to miss things that will drive success or failure in our future plans. For instance, if I set a goal as a salesperson to sell 35 widgets, it will be important for me to review whether or not I actually hit that number (seems obvious but many of us don’t have systems in place to actually check in on ourselves) and understand what contributed to the success or failure before making plans for the next year.


When we reflect as a team or as a whole organization, there are so many factors we need to consider related to our internal environment like our strategy, systems, structures and people and there are several external factors like competition, economic, political, legal, environmental and other pieces that impact our goals and plans we need to evaluate.


Teams that ignore this step typically keep doing what they’ve always done and continue to experience frustration, or we scrap some of the things that did make us successful by shifting our entire approach vs. digging to find the nuance of what is working and what isn’t. This step can save us time, money and energy and accelerate our success.


One of the main questions we get asked is, “With things changing so often and so quickly, why should I plan? Isn’t that just a waste of time?” To address that question we like to refer people to our friend Jim Collins (one of the most well-respected teachers of what makes companies great). Here is an excerpt from an interview where he is sharing how the great companies think about and execute their planning process:


…let’s ask the next layer of question down, “Was there any difference in the way they did it? What might account for some of the difference?” Well, I would actually go to a couple of pieces as to how it was different. First of all, you’re right. One of them said, “Planning is priceless; plans are useless.” That was the quote he used. He took it from Eisenhower, who basically said, “We have to have immense plans for D-Day, but once it actually starts, the plans become a lot less useful because things unfold in ways that we can’t predict.” So, planning is priceless; plans themselves are useless.


So, they didn’t do plans and then get stuck on them. Their strategic planning process was not a rote exercise. It was a mechanism for stimulating disciplined thought. If we get the right people on the bus, engaged in a rigorous, vigorous debate and disagreement, leading to the best insights—a mechanism to gain understanding. And from that understanding comes a series of decisions.


So, instead of being a rote exercise followed by rote implementation of decisions, effective planning involves vigorous debate, infused with the brutal facts and insight seeking, from which comes an iterative series of decisions that add up over time. It requires discipline and rigor. One thing that really stood out to me about the process, the feel of these companies as they did their planning, was the extent to which it was driven by a search for the right questions more than a search for the right answers.


If you still aren’t convinced that investing time in a planning process is important, then you can stop reading.


If you are convinced, then here are some good questions for you (and your team members) to reflect on as individuals to start the process. We do start with this reflection process as individuals because organizations and teams are made up of individual people having both an individual and collective experience, and so that individual perspective shouldn’t be skipped.


Questions that Support Individual Preparation (for planning)

  • What is meaningful and valuable to me right now?

  • What have I learned this year?

  • How did I grow this year?

  • What’s going well?

  • What is challenging?

    • What is behind these challenges? (how have I changed, how the world has changed, etc.)

    • What is something that is on my mind consistently that should be addressed?

    • Where do I need help or support that hasn’t been communicated yet?


Other Frameworks that Support Individual Preparation In addition to these reflection questions, you could use a Wellness Wheel (there are many different forms so find one that speaks to you) to evaluate where you are in different aspects of your life and wellbeing. You could also ask family, friends, colleagues, mentors and others for feedback. We like requesting they provide one thing each you could start, stop and continue doing. This framework is simple and gives clear direction.


Preparing to Plan as a Team and Organization Instead of only focusing on what we are doing, we encourage you to make some space to think about how you’re doing as a team. Even when the vision and goals are clear, making them a reality can be very challenging. Do we have the right people? Do people understand meaning? What human systems are working and which aren’t? (decision making, executing, learning, development, communication, performance management, teaming, etc.) How we are together is just as important as what we do together.


You can have the perfect framework and set up for planning but if we have interpersonal issues or inner-personal issues, we won’t talk about the right things to get to the right place. The following are some good questions to help the team prepare to plan.


Questions to Prepare the Team and/or Organization for Planning

  • When it comes to functioning as a team/org:

    • What is going well?

    • What is challenging?

  • What are we best at?

  • What are our non-negotiables?

  • What needs to change?

  • What can’t change?

We often see teams and organizations so focused on the future and what needs to change, that they lose sight of and stop focusing on what makes them great. Consider this additional concept from Jim Collins: Preserving the Core While Stimulating Progress


Enduring great organizations exhibit a dynamic duality. On the one hand, they have a set of timeless core values and purpose that remain constant over time. On the other hand, they have a relentless drive for progress—change, improvement, innovation, and renewal.


Great organizations keep clear the difference between their core values (which never change), and operating strategies and cultural practices (which endlessly adapt to a changing world).


Just as important as what needs to change is what can’t change. Build upon the foundation you already have!


Additional Ideas and Frameworks to Help You Prepare as an Organization

1. Perform a Formal Initiative Review

  • Where did we set out to be with goals and where are we? Why did we meet and why did we miss? What did we learn?

2. Keeper Test (from Erin Meyer)

  • Who can we not afford to lose and what are we doing about it?

3. PESTEL analysis (political, economic, social, technological, environmental, legal)

4. SWOT analysis (strengths, weakness, opportunities, threats)

5. Client and employee surveys

6. Direct feedback from clients and employees

  • What outcomes are most important to our business and how are we doing?

  • What systems and processes are critical to our business and how are those working?

7. Market research

8. Engaging outside perspective and feedback on your services, ideas, approach


The last step in preparing to plan is to consider the process and system(s) you will use to execute the planning process, and then to implement and manage the plan itself. If we don’t have a system, then all of our planning efforts will likely be lost. We have to have a way to keep the plan visible, to check on and celebrate progress, to pivot and to provide accountability to get things across the finish line.


If you want individual, team or organizational support in preparing to plan, planning, or implementing and managing your plan, The Restoration Project would love to support you! Cheers to being more intentional in your life and leadership!


Written by: Lindsay Leahy, Dream Builder at The Restoration Project

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