The Art of Working Backwards

January 11, 2019

The Art of Working Backwards

In 2002, I joined Teach for America and taught 6th grade students in Houston’s fifth ward. That year was undoubtedly one of the hardest years in my life – I couldn’t keep up with the demands of teaching, getting certified in the evenings and praying that my students would simultaneously behave, learn and love me. Every day, I was faced with some form of emergency – students disrupting class, hungry students, fights, drug use, family illness – that would take all of my energy and focus, leaving me unprepared for the next day. I couldn’t break out of the cycle.

I needed a plan.  The planning process took a month during the summer – but I knew that a couple of weeks of careful work would literally make or break the next year. I knew that my students needed to hit certain learning targets by the end of the year, so I broke down my planning into quarterly, monthly and weekly objectives with clear metrics that would lead to achieving the annual learning goal.

Working backwards paid off. With a clear end goal and plan in mind, I had a weekly guide to plan lessons that aligned with learning objectives. I could also stay focused during crazy emergencies and started to say ‘no’ to optional time commitments that interfered with my priorities and goals.

Now, as a consultant who coaches mission-driven organizations to create long term strategies and align team members on these goals, I use this same process of starting with the end (a long-term strategy) and working backwards to define short term goals and milestones.

Sometimes, I get some pushback: “How can I find time to think about the future when I am putting out fires all day in my current role?” The answer: investing time upfront to envision a future and work backwards will make your priorities crystal clear and will actually make your days more focused and less hectic. Here are some questions to consider as you work backwards:

  1. Where do you need to be? In my example, I forecasted one year out – but for growing organizations, I coach clients to think about their five or ten year plans. If it seems hard to think that far out, look back to your organizational vision and mission for inspiration – what is your organization’s purpose for existing? Where do you want to ideally be in ten years? What impact do you need to make?
  2. What are the major milestones you need to hit? Working backwards, divide your journey to your long-term plan into four phases, and then get more and more granular as you approach the current year. Include SMART goals in each of these phases that encompass metrics that are crucial to your organization – many times with mission-driven organizations, this is a combination of financial goals, as well as specific ways to measure your organizational impact.
  3. How will you get there? In each of your phases, think through to the people and resources that you need – and strategically align timing with effectively developing relationships, securing funding, etc. It’s also necessary to anticipate obstacles that could hinder your progress and make contingency plans to stay on track.
  4. How will you ensure accountability? This is the hard part – actually doing the work and honoring your plan! I recommend communicating and investing your team, codifying the strategy and using the plan to drive team check-ins on a recurring basis.

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