Strategic Planning and Haircuts

Strategic Planning and Haircuts

Depending on your experience, Strategic Planning is either

  1. your organization’s most important activity every three to five years,
  2. a necessary evil that must be endured even though it totally gets in the way of everything important, or
  3. the bane of your existence to be avoided at all costs – and expensive consultants just make it all the worse.

As a veteran of good, bad, and ugly strategic planning processes, here’s the most important thing I’ve learned about Strategic Planning: Assuming the process has integrity (and that is not a trivial consideration), Strategic Planning takes organizational priorities away from the personal and makes them about the group. In other words, Strategic Planning makes it less likely that one individual will charge (or wander!) off on their own.

I’ve seen two types of organizations work more or less effectively without a Strategic Plan. The first operates under the control of a visionary leader. The Strategic Plan may not be written down, but it very much lives through the personal energy, passion, and drive of this single personality. These organizations often take great pride in being “flexible” and “nimble,” particularly related to larger, more cumbersome organizations and agencies. “We don’t need a Strategic Plan – it’s all in Deb’s head!

The second operates as a collaborative of such individuals who work in silos; and sometimes in relative harmony with each other. These are people wandering off in different albeit compatible directions.

Both types of organizations have the same fatal flaw when it comes to land trust work – neither is a permanent organization, but in fact only survives as long as the visionary leader does.


If you want to go fast, go alone.
If you want to go far, go with others.

– African Proverb


As land trusts, our mission is to go far – to be permanent organizations – regardless of how much we might value “flexibility or nimbleness” and regardless of the urgency we feel in any particular moment. Good Strategic Planning processes are designed to take the entire organization FAR because the process itself involves and engages everyone. This specifically and explicitly includes partners, volunteers, and donors. In this regard, the process is just as important as the product. The larger the organization, the more complex the issues and projects, and the more people involved, the longer it will take to ensure everyone’s voice is heard and everyone will support the outcome. Done well, it takes time – up to six months for small organizations and a year or more for larger groups. But the organizational benefit in helping the entire organization pull together on the mission is incalculable.

This doesn’t mean that everyone agrees with everything. In fact, some might leave if they cannot support the direction preferred by everyone else.

Strategic Planning done well will include the following:

  1. Reflective time spent being honest about where we are right now.
  2. Check in with key constituencies – do they see us the same way we see us? (Don’t skip this part. The consequences of not knowing, or not understanding, the way the rest of the world sees us can be damaging.)
  3. Visioning – looking out as far as we can see, what difference will we have made? What do we look like “out there”? How is that different from the way we look now? These differences, both external and internal, are rephrased as goal statements and serve as the backbone of the plan.
  4. Brainstorming – what are the possible strategies or activities we could engage that would put us on a better path to making our vision a reality? These strategies answer the HOW questions.
  5. Prioritizing – which strategies hold the most promise?
  6. Planning – Given our time frame (3-5 years), how far will we get toward each goal and strategy? In other words, when we look back 3-5 years from now, what will we be able to say we’ve accomplished?
  7. Budgeting – how much will THAT cost? (Remember to include adequate funds for raising money.)
  8. Implementation –The first year of a strategic plan can be detailed in terms of specific actions that will be undertaken, including “by whom” and “by when.” Each year thereafter, the full strategic plan should be formally reviewed, and another year’s worth of activities similarly detailed.

Strategic Planning done poorly often compresses these activities into a shorter time frame to “just get it done” and/or involves just a few people, resulting in a plan that may be efficient to produce but is not inspiring and more likely to be shelved.

Ideally, board members, staff, and key volunteers will emerge from planning with a shared vision and everyone understanding their role in accomplishing it. In my view, the best way to engage and involve everyone is through a facilitated retreat. Do the internal and external check-ins first (survey and telephone interviews) and review the results as a first agenda item at the retreat.

Retreats can be done in a single day, but I don’t really recommend it – planning is exhausting and even the best of us get tired. Instead, I prefer a 1.5 day model where everyone shares a meal together in addition to all the “work time.” Something like Friday afternoon and all day Saturday. Such a retreat could be expected to finish through Step 6, above. The writing of the plan, budgeting, and implementation work can be productively delegated to committees who might take another month or two to complete their work. I’ve worked with several organizations highly dependent on volunteer labor who did the implementation planning as a second retreat just to make sure everyone stayed on board.

With an explicit acknowledgement of my own conflict of interest, let me put in a plug for skilled facilitation. I like to think of facilitation like barbering. You could cut your own hair. Use a mirror so you can see what you’re doing.

You could also cut your neighbor’s hair in return for them cutting yours. Trading facilitation or haircuts has the significant advantage of introducing objectivity.

Both options are functional – they can get the job done. Both use skills that can be honed with practice. In other words, you will get better with practice. AND – any mistakes will grow out in a relatively short period of time.

On the other hand, you could take your hair to a cut-rate barber who will charge you money based on cutting your hair in one of three current styles and using the same techniques s/he uses for everyone – cookie-cutter style.

Or you could go to a stylist who takes the time to learn who you are and tailor what s/he does to your specific and unique needs. There is a difference in cost, of course. But there’s also a difference in how confident you feel and in how others react to the way you look.

Regardless of how your organization approaches Strategic Planning – DO IT. It takes time away from seemingly more-important-in-the-moment activities and can be expensive. But the added costs return to the organization in increased productivity, cost efficiencies, and even improved funding opportunities with donors. I learned the other day that one recent client just completed their annual fundraising event and raised $100,000 more than last year as a direct result of an idea that emerged during Strategic Planning!

* * * * *

Fundraiser’s Almanac
Here’s what I’m thinking about in January. What are YOU thinking about?

  • Communications Theme for 2016 – a theme that will run all the way through your communications for the entire year. It will provide substance for newsletter and website articles; Facebook, Twitter, and other social media; solicitation and thank you letters; and even events.
  • Cultivation Plans for my Top 100 List – A Top 100 (or T-100) is simply a list of top donor prospects. These are people who warrant and deserve your special cultivation attention. In January, for each donor, draft and calendar an individual cultivation plan.
  • Evaluating and Soliciting the Board Members – One-on-one, sit down meetings with each board members to evaluate their experience as directors in general, discuss committee placement, review measurable goals from last year, set new goals for the coming year, and solicit a pledge for their 2016 gift.
  • Saying Thank You – How will you thank your donors this year? Can you get Board Members involved?


* * * * *

More from the A/B test: With most of the results in from the A/B test I conducted (See A Few Thoughts on A/B Testing) using a 4-page letter and a 1-page letter. The 4-page letter is the clear winner with 36 responses and $3,860. The 1-page letter had 24 responses and $2,730.

Surprised? You shouldn’t be. This test validates results that have been repeated in comparable tests for as long as I’ve been fundraising – more than 30 years now. What could you do with a 50% greater response rate and 40% more money from your appeals?


* * * * *

Finally this week, did you think about your three words? Here are mine:

Together – This word has meaning for me in my personal life. Kate’s and my son is completing his four years at the University of Iowa and our daughter is flying high with her job in Washington DC. After years of chasing them around and moving in different directions, we are beginning to think more about how we can do more – together. It also resonates as in “getting my, ah, business together.”

Depth – It seems like my consultancy is changing a bit, and I’m looking forward to the changes. I’ll be working with fewer clients this year but with deeper relationships. Instead of assessing and planning alone, I am being increasingly asked to help with implementation.

Membership – With several of these deeper relationships, I seem to be getting drawn into membership programs. PALTA has asked me to research and design a collaborative experiment in membership building. Housatonic Valley Association is launching a new membership approach. And Aldo Leopold Nature Center needs to grow unrestricted funding rather than continue to be dependent on restricted grants and gifts – in other words, build membership.

For more information about the three word approach to New Year’s resolutions, see Chris Brogan’s Three Words post. Those are mine for 2016. Please share yours as well!





Photo credit: Stream in Winter by Walt Kaesler.


Yes, I can help you with Strategic Planning. I work with two partners at Conservation Consulting Group to help land trusts plan at all levels. To find out more, click here.

Share this!
1 Comment
  • Rick Newton
    Posted at 17:11h, 12 January

    I think the biggest thing lacking in the LTA accreditation process is not having a requirement to have a strategic plan.