30 Day Challenge to jump start your strategic planning journey

Join this 30-day strategy challenge to start your learning journey. Set time a side every week to watch a weekly video and follow the challenge represented. At the end of the 30 days you should have new information and tools that will make you a more strategic, connected, and effective organization.

Week One: What do you want from a strategy?

Watch: Why you want a - good - strategy 

You always want to start a new process by first taking stock of where you’re at. With strategy this means reflecting on your own strategic plan (or, perhaps, the lack of having a strategic plan) to understand how it’s helping or hurting you as an organization.

Do you have a strategy?

If no…

Get out a pen and paper and write down the answers to the following questions:

  • Why not? What’s prevented you from having one?

  • Can you think of a time where you were glad to not have a written strategy?

  • Can you think of a time where you wished you had one?

  • In both cases, write down why you felt the way you did.

Now go for a walk (15 minutes) and think about what you’d want a strategy to do and what you’d want it to not do for your organization. When you return from your walk, write this down. You’ve now drafted guidance on how a strategy development process should work for you.

If yes…

Get out a pen and paper and write down the answers to the following questions:

  • What is your general feeling about your organization’s strategy?

  • How has it been useful for you?

  • How has it not helped you?


Now go for a walk (15 minutes) and think about the following: 

What do you  want a strategy to do for your organization and what do you want to avoid? You’ve now drafted guidance on how a strategy development process should work for you.


Week Two: Know your why

Watch: knowing your why - why why matters

Have you ever gotten half-way through something - maybe a work project or an activity you’re doing at home - and you stop and question yourself, you think “why am I even doing this?” That same thinking and questioning applies to the work of your organization: you MUST know WHY you’re doing what you do. Why do you exist? What is your core purpose?

We love Simon Sinek’s Golden Circle diagram, which positions “why” at the core of three key organizational strategic elements: “why, how, what.” If “why” is at your core, then it will shape the “how” and “what” you do with clear purpose - and that’s strategic. 

So...what’s your “why”? WHY does your organization exist?

  • Why did your organization get started in the first place?

  • Why are we doing the work we are doing? And then ask why again until you feel you have reached the very fundamental reason you exist. 

Another favourite writer is Jim Collins who recommends using the “five why” approach. It's usually not enough to simply ask “ Why do we exist?”. The answer may not be very inspiring or really reach to the root or fundamental reason. 

Collins recommends that a more powerful approach is to begin by asking “why should we continue to exist?” Once you have answered this question in a short statement, then drill down by asking “why” a further five times. As Collins says. “Even though you already have a purpose, it's nonetheless a valuable exercise to think through the question: what exactly is our purpose? 

And he adds “...once clarified, it ascites as a test for all decisions: is this action consistent with our purpose?”.

And finally, we highly recommend this short video on knowing your why (even better, it’s by a comedian!):


Week Three: You can’t do it all, do what you’re great at

Watch: Do many mediocre things or do a few excellent things

Organizations have a choice - they can choose to focus on some great things and excel at those, or they can choose to try to do many things and likely, at best, ‘get by.’ Great organizations know their purpose (see last week’s lesson on knowing your why) and the value they offer to bring about lasting change.

This week we want you to reflect on all that your organization does and ask yourself the following questions:

  • What are we great at?

  • What do we do that we’re not great at?

  • Is everything we do true to our purpose?

Challenge: Take a look at your annual work plan(s) - identify work that seems absolutely true to your purpose. Now, identify work that seems less important and less aligned to your mission.

While you might not be able to cut out work now due to donor constraints, use this exercise and thinking as you develop future proposals and work plans.

We also recommend this quick read about the hedgehog and the fox: Hedgehog Strategy

‘A fox knows many things, but a hedgehog one important thing.’ -Archilochus


Week Four: What guides you 

Watch: The importance of values

Values are what guide an organization’s actions, behaviors, and decisions. When an  organization is clear on their values, then decisions are easier to make. When values are vague or generic  – something we see often with organizations – they lose meaning and influence and can become quickly forgotten. Strategic planning is all about making tough decisions, so it’s incredibly useful to identify values  early on with an organization and to continue to return to their values throughout the process.

Find a colleague or two and ask for 15 minutes of their time. Go for a walk or grab a virtual coffee with them. Each of you should take 4 minutes to share a story that you feel really represents who you are as an organization. Make sure to share specifics and details - e.g. how you or others felt, decisions that were being made and how they ended up being made, etc.

Once you’ve all told your stories, take a moment to think about them all together:

  • What stands out?

  • Were there any similarities or commonalities?

  • What do you think these commonalities tell you about your organization?

  • Were there any actions or behaviors that you can identify that drive you as an organization?

List down no more than 5 descriptors (single words or phrases are okay).

Now think - are these your guiding values? Are these what guide your decisions and actions as a team? If so, write them down, define them even more, and share them with the rest of your team.

Learn more here: Purpose, Values with Action


We hope you’ve enjoyed this strategic planning challenge and that you’re feeling more confident to tackle hard questions, whether they relate to a project or to big picture thinking for your organization. 

Thank you for putting in the time to become a more strategic thinker. This will benefit you, your organization, and ultimately, our planet! 

Jessie Davie