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How Do I Know It’s Time for Strategic Planning?

BY: Third PlateauON: 11.02.2022

Alice: “Would you tell me, please, which way I ought to go from here?”

The Cheshire Cat: “That depends a good deal on where you want to get to.”

While this Lewis Caroll quote from Alice in Wonderland might remind you of the typical “consultant” response of “it depends,” when it comes to strategic planning, it is a very real response to a very complex question. The Cheshire Cat is not wrong; many leaders skip this critical step in their attempts to set organizational strategy.

In the 12 years that Third Plateau has been working with social impact organizations to set goals and strategies, we have seen the full spectrum of challenges and opportunities that new leaders face when stepping into their role. Many new Executive Directors and CEOs come to us with palpable excitement for the journey ahead, while some already feel the weight of dealing with organizational ghosts from the past. These first moments in your leadership are crucial to your success and the success of your organization, but it takes courage to say: “This isn’t working. We need to try something different.”

To turn that mirror on yourself, you must follow Alice down the rabbit hole, get curious, and begin asking the questions that will lead you and your organization "where you [actually] want to get to.” (Authors' note: It pains us to end a sentence with a preposition, but damn it if that Cheshire Cat isn't spot on.)"

But what are the right questions? While you likely face many questions on any given day, we’d suggest being clear on three questions in particular:

  1. What is our current state? Are we functioning well? Where are we advancing our mission and vision, and where are we just going through the motions? Are my staff and board in alignment about what’s most important? Are we adequately responding to what’s going on outside our organization – in our sector, our region, or our communities?

  2. What is our desired future? Are we clear about what we think is possible and the impact our organization can make in the world?

  3. How do we bridge the gap? Are we clear about the potential path to ultimately achieving our vision? What are we doing – today, next month, next year – to move from our current state to our desired future?

If you get to the third question and don’t have clear answers, it may be time for some strategic help.

How should we answer these questions, and when?

Asking the right questions is one thing; answering them is another. Most leaders are busy tackling the day-to-day and find it challenging to find the time or energy to answer these big questions. They also know they can’t – and shouldn’t – answer them alone. Investing in a strategic planning process can help.

Strategic planning is the process of clarifying your organization’s purpose and creating a strategic road map for how you will get there in a way that authentically engages your community and key stakeholders.

Many people will point to strategic planning as a magic bullet process that you should do immediately, and for good reason. Investing in strategic planning from the offset can help to:

  • Set a clear direction for the organization.

  • Build relationships with new stakeholders (board, staff, participants, funders, community partners).

  • Retool old ways of thinking and doing.

  • Establish new and fresh ideas to kick-start your tenure.

When done right and the timing is right, great strategic planning will help you capitalize on the most exciting opportunities and navigate the most intimidating challenges. Whether you’re stepping into a new leadership role or have been at it for years, knowing where you’re going with the people who make your organization tick can be an extremely effective and rewarding process worth exploring.


Jonathan Kaufman is Co-Founder and Principal

Somoh Supharukchinda is Vice President of Strategy

If you're unsure about strategic planning and interested in learning more about Third Plateau's philosophy and approach, click the button below and let's find a time to connect.

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