How To Be Strategic with Your Goals: What’s the Hope, What’s in the Way, and What’s the Path



“Study the past, if you would divine the future.” — Confucius

I picked up my copy of Being Strategic, by Erika Anderson, and randomly flipped to a page in the book.  On this page, was a simple picture of a castle at the top of the hill.

At the bottom of the hill was an “X” to mark the starting point.  And there was a line up the hill to show the path to get to the castle.

The castle represents the hope.

The process outlined in the book started with “What Is”, but it’s the following words that echoed the most in my mind:

  1. “What’s the Hope” …
  2. “What’s in the Way” …
  3. “What’s the Path”

So simple.  So sticky.  So powerful.


Because it reminds you to figure out what you want, figure out what the obstacles are, and figure out an effective path to get there.

Being Strategic to Achieve Your Goals

Andersen uses a simple definition for strategy:

“Consistently making those core directional choices that will best move you toward your hoped-for future.”

With that in mind, let’s take a deeper look at how Andersen shows us how to be more strategic and move our lives in the direction of the future we hope for, in her book, Being Strategic.

The Castle on the Hill is Your Vision of the Future

You can use the castle on the hill as a visual anchor to help you think through what you want, what’s in the way, and how to get there.

Andersen writes:

“’X Marks the spot — that’s where we’re starting from.  This castle on the hill is our vision of the future. 

And the obstacles are the steep parts of the mountain, and the trolls hiding in the cracks.’

I then draw an arc from the X to the castle and continue, ‘And now we’re going to define our path from where we are to where we want to be by first agreeing on our core directional efforts — our strategies — and then filling in that path [at this point I usually sketch in a few ‘cobblestones’] with tactics.’”

What’s the Hope

When you envision your  future, or your “castle on the hill”, and try to answer, “What’s the Hope”, Andersen recommends that you use the following framework:

  1. Pick a time frame for success.  Pick a point (a specific date) in the future that will allow you to have made substantive progress on your challenge.   Anderson recommends no more than 3-5 years in the future, otherwise it becomes a confounded experiment with too many variables.
  2. Imagine yourself in that future.  Anderson recommends using some form of, “OK, now it’s the __ of __, __ (the day, month, and year you’ve selected).  You’ve come back together to celebrate the fact that you’ve addressed the challenge, and to share what’s happened in the future you envisioned.”
  3. Describe what success looks and feels like.  Get firmly grounded in the future date (If you’re not sure, ask yourself, “Are you there? Is it April 17, 2015?”.)  Reflect on the following, “What have you accomplished relative to the challenge? How does it look and feel to be in this successful future? What are others seeing and saying about you?”  Write it down.
  4. Select the key elements.  Extract the headlines from your envisioning of this successful future.  Pick the five or six elements that are most important to you, and write one of them on each of your sticky notes, and call them “cards.”

Anderson provides an example of six headline “cards” using the Union Square Hospitality Group:

  • Bucks County: Enjoying the rewards of profitability.
  • Good Bones: Structures and systems that support our growth.
  • WAH-full: Living balanced and satisfying lives.
  • Home Run King: Best-in-category – again and again.
  • Gen Next: Current and future leaders create our success.
  • Grand Crew: Employees who live – and love – the vision.

Notice the simple label up front, and then the longer headline.

What’s in the Way

When you figure out “What’s in the Way”, Anderson recommends the following framework:

  1. Be a “Fair Witness”  Being a fair witness is a mental skill that requires being able to observe and report without a lot of interpretation or judgment.  Just report the facts – what do you see, or what do you hear.  For example, “this sweater is too small for me”, is pure reporting.  “I look horrible and fat in this tight sweater” is interpretive and judgmental.  Anderson recommends that before you begin thinking about the obstacles to achieving your vision, become conscious of any unhelpful self-talk you may have, either about looking at obstacles in general or about specific obstacles that you may be either resisting or over-emphasizing.   Pick out the one or two self-talk statements you think could make it hardest for your to be a Fair Witness in looking at the obstacles to your vision.  Write them down, and then revise them to be more objective.
  2. Pull back the camera.   Now, with your “Fair Witness” self-talk in place, you’ll think about the obstacles to your vision.  Mentally “pull the camera back” so that you can see the whole picture: where you’re starting from and where you’re trying to go.  What’s likely to get in the way? That is, what difficulties, constraints, or challenges are you going to have to get over, around, or through in order to move from where you are now to your vision of the future?  It’s helpful to look at the obstacles outside you (in your company, with other people, etc.) and the obstacles within you (lack of skill or resource, self-doubt, etc.)  Using your “Fair Witness” self-talk to keep yourself honest and balanced, write down the obstacles outside you, and the obstacles within you.
  3. Sort for impact.   Review what you’ve written and circle those obstacles you believe have the highest potential to derail you from moving toward your vision and that therefore are most essential for you to overcome.

You can use this process to catch yourself when you limit yourself or get stuck.  Andersen writes:

“Think about a current situation in your life where you’ve stopped yourself from moving forward because you felt overwhelmed by the obstacles.  OK, now take a few minutes to recognize, record, and revise your self-talk about the obstacles in this situation.

Then pull back the camera and look at the situation as though you’re someone else: a neutral third party, a Fair Witness. 

As this other person, not you, note the starting point,t eh hoped-for future, and ‘what’s in the way.’

As you observe the situation from this third-party vantage point, note any changes in your perception of the obstacles and their impact.”

What’s the Path

Anderson recommends using the following framework to figure out “What’s the Path”:

  1. Be a “Fair Witness”.   Get as objective as possible.
  2. Pull back the camera.  Step back from the details to take in the whole picture.
  3. Sort for FIT.  “FIT” stands for “Feasibility,” “Impact,” and “Timeliness.”  It’s a great way to determine which strategies will best move you toward your desired outcomes.  Feasibility simply means deciding whether you can actually make a given effort.  Impact focuses on whether or not the proposed strategy is a good use of your resources.   Timeliness focuses on two things: ordinality and opportunity.  Ordinality means the order in which things have to be done.  Is this strategy something that needs to be done now, or are there other things that need to be done first?  Opportunity is about having the chance to do something:  is this strategy one that needs to be done quickly  before the window closes.

Anderson reminds us that twelve to eighteen months is generally an appropriate time frame for crafting strategies.  Focus on the strategies that make the most sense to accomplish in the next year to year and a half.

Andersen writes:

“Once you’ve gotten clear about where you are and where you’re trying to go – how you envision your “castle on the hill” – and you’ve gotten a reasonably good handle on what’s in the way, it’s a huge temptation to just start running up the hill with tools in hand. 

Stop yourself! 

This particular point is the beating heart of being strategic. 

You have the opportunity here to select strategies that will form the core of your effort, instead of dissipating your hard-won clarity in a flurry of activity or worse, a flurry of argument about which activities are best.”

Think Roadway, Then Asphalt

When you figure out your path, think “Roadway First, Then Asphalt.”    Strategies are core directional choices.

Andersen writes:

“That’s what strategies are: core directional choices.  And tactics are the specific actions that you’ll take to implement these core directional choices. 

Think about it this way.  You’re at point A and you want to get to point B.  So you need to find, while getting around, over, or through the obstacles. 

Strategies are the road you choose – the path you’ll take.  Tactics are the road graders and asphalt you’ll use to build that road.”

By getting clear on what you want to accomplish, figuring out the obstacles in the way, and creating a smart path to get there, you can be more strategic.  Being more strategic will help you get more out of the time and energy you put into things, and ultimately help you shape your future more successfully and consistently over time.

Remember that “hope is not a strategy.”  But, figuring out your core directional choices is.

Whenever you get lost, simply go back to the basics and remind yourself of the mantra:

“What’s the Hope” … “What’s in the Way” … “What’s the Path”

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    • Trolls aren’t so bad when we expect them and acknowledge they are there.

      I think the worst scenario is when we get surprised by them.

  1. Hmmm. Its true being a “fair witness” helps one to understand the situation without any bias and probably also helps him to take the right decision in a right way.

    • Being objective takes a lot of emotional intelligence, but it pays off in terms of self-awareness and insight.

      It helps us stay out of our own way.

      • So true but in either way …… being self aware helps one to be objective and also being objective improves one’s self awareness..

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