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Is your strategic planning process as strategic as it should be?


A sign pointing in three possible directions, this way, that way, the other way.


There is a ton (or two or three) of guidance on how to structure a good strategic planning process, but like most important organizational undertakings, there is no one-size-fits-all solution.


You can buy a cookie cutter process from a consultant, but will it deliver the plan that you want?

Before you buy a cookie cutter, you need to ask yourself whether you are making cookies. You need to ask yourself and those you trust a series of important questions to figure out what meal will be most satisfying for you and your organization.


The desired output of your process will define the process. Figuring out the desired output is question number one.


That’s why it makes me a little craz(ier) when a potential client starts our conversation with, “I want a three-year, detailed workplan that my staff can follow.”


The questions running through my mind, go something like:

  • Why a workplan and not a roadmap?

  • Why develop detailed work plans for a world that is certain to change? Have ever been able to tell where you should focus your time in a detailed way in two years? Three years? FIVE years?

  • Why doesn’t your team have the capacity – skills, abilities, time – to create annual work plans each year?


The best process will turn the word “strategy” from a noun into a verb – from pat answers to a series of probing questions – from 75 pages taking up space on your bookshelf to the center of ongoing dialog about progress toward success.


A strategic plan is an educated gamble that some aspects of the world you are living in today are likely to continue for the foreseeable future. The questions, values, and principles embedded in the creation of the plan will also be your roadmap for the future. When the environment inevitably changes, it will guide you in how best to adapt.


So, let’s dig into the questions that will tell you whether you are making cookies, ramen, or nachos with all the fixings.


Why do you want to begin a strategic planning process?


Strategic planning is a major undertaking. You need to be clear about why you are kicking off the process to build engagement with staff and board.


Here are a few indications you might want to start a conversation with your board president about the need for a new strategic plan:


  • You have nagging questions that need to be resolved if the organization is going to continue maintain or grow its impact. And you sense that your board president agrees with you on what those questions are.

  • There is a persistent misalignment between what you do and how you are perceived by your stakeholders that appears in everything from an inability to attract community members to participate in your services to a lack of invitations to apply for funding for work you do to a failure to be invited to the “right tables” as you define them.

  • There has been some significant change in the world that requires the collective wisdom of board, staff, and all stakeholders to navigate. These type of issues might include major shifts in funding, new political trends, or changes in the population you serve – anything that makes your current direction tenuous or lessens your potential impact and that is likely to affect your organization for at least 2-3 years into the future.

  • The most obvious (although not necessarily most compelling) reason is that you are wrapping up your current strategic plan in one year. Rather than finish the plan and then start the planning process, the final year of a plan is a great time to focus the board, staff, beneficiaries, and donors on thinking about the next stage of impact.


Is it the right time to plan?


Your life is always busy. Your board is pressed for time and a difficult group of cats to herd. You still haven’t hit your revenue targets, and the program team is experiencing higher than usual turnover.


Good time to plan? Bad time to plan?


It’s as good a time as any because those headaches or ones like them are the reality of organizational life. That being said, times of crisis – organizational or environmental – are not. Crises are a time to lean into your existing strategy – to use the current disruption to advance your work in ways you decided last year or the year before. The operational realities of a crisis dictate that the time of the board and staff should be focused there.


Ultimately, the right time is when the executive director and board president agree that it is the right time. Together, you visibly embrace and prioritize strategic planning to fully rally all the voices that must be invested in the future of the organization.


Here are a few things to think about as you force all those ornery ducks to stand in a pretty row.

  • Strategic planning will require no less than three months and likely more like six-eight months to guarantee a thorough process that involves all of the important voices in your work.

  • There should be no other significant organizational activities during that time – no website redesign, no office move, no reorg. A strategic planning process will likely influence any major upcoming initiative – best to wait.

  • Your entire senior team needs to clear the decks along with you. And the board president must ensure the same happens for the board. There will be program graduations, galas, budget cycles, and audits, but everyone will also need the space to dream big with you.

  • In addition to committing significant time, you may want to hire a consultant to lay out and then manage the process, keep you on a timeline, ensure that difficult conversations happen and that every voice is heard, and tell you the truth throughout the process (not what you want to hear). You need time to put together an RFP, interview candidates, and come to agreement on the right consultant.


Like most important organizational undertakings, the right time to plan will never appear. You need to make it happen by building the commitment of all concerned that it is the right time.


It's launch time. What needs to happen?


Your reasoning is solid, and you’ve committed the staff and board time. Here are the questions you will navigate through to plan completion.

  • Who will be in charge? You and your board president will own the process, but you need help. You should appoint a staff lead – a COO or Chief of Staff if you have one. If not, your best strategic thinker and schedule wrangler will do. At the board level, consider having a strategic planning committee to ensure there are regular report backs and input on what board engagement should look like.

  • What questions are we hoping to answer? As you engage board members and staff in the early stages of planning, it is important that they understand what questions you are hoping to answer through this process. You also need to make space for those around you to add their questions to the mix.

  • Who is the right consultant? If you are hiring a consultant, knowing what questions you hope to answer will help you choose the right one. Work with your board strategic planning committee and senior leadership team to identify the ideal attributes and experiences for that person before drafting your RFP.

  • What process will we follow? Vet a process with board and staff leadership to ensure that all agree that it is solid and that all input and analysis is covered.

  • How will we revisit (and maybe rewrite!) the mission, vision, and values? One of the most fundamental aspects of strategic planning is realigning around the mission: what you do, who you serve, and your desired impact. As the world, your team, and board change, the collective understanding of the purpose of your organization can get a bit … shall we say … diffuse. Stopping to ensure your understanding is shared and that you debate those areas that are not shared sets the stage for all the decisions to come.

  • How will we understand the world we are operating in and ourselves better as a result of this process? During the process, take time to name the changes in the world that may affect your business – those things you have no control over but will have to deal with. At the same time, take an honest look within – what are the ways you knock it out of the park and what are the ways you are striking out? And listen. Engage your community of supporters and beneficiaries through interviews, focus groups, and surveys.

  • Are we clear on the problems and possible solutions? After all of this introspection and extrospection, what should surface are a series of decisions you need to make. This step is about identifying which issues you will address during this planning process and which ones will have to wait for the next plan. A successful strategic planning process must include as much clarity on what you will not do as on what you will do.

  • How will we make this official? After all that work, don’t forget to make it official – adopt the strategic plan at a board meeting and celebrate. The ritual is an important one to seal everyone's commitment to the plan's success.


Honestly digging into these questions can turn strategic planning from a boring organizational routine into a galvanizing experience for you, the communities you engage, your staff, your board, and your donors.


Strategy does not exist unless it is articulated and shared. Be sure to introduce the plan to everyone in your community. Understanding where the organization is headed and what role they may play in helping you achieve your goals is unifying and energizing.


For more information on my work in this area, visit my website, follow me on LinkedIn, or schedule a time to connect.




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