Guest Blog

Your Culture Is More Important to Strategic Planning Than You Think

Stephanie Freeth

As a strategic planning consultant and executive coach, I’ve read a lot of strategic planning Requests for Proposal (RFPs) over the past two decades. I choose not to bid on 99% of the RFPs that I come across. Why? Because most RFPs tell me that strategic planning isn’t what that organization needs. What they need more often is to build a high trust, low drama, and high learning culture before jumping into long-range strategic issues.

For organizations that have achieved this foundational prerequisite or are at least close to achieving it, strategic planning is great at addressing quantitative and qualitative steps toward progress and growth. A few of those are:

  • Intention-setting and creating alignment of goals and objectives
  • Getting actionable feedback from stakeholders
  • Reaching consensus around things to start, stop, and continue
  • Surveying the current internal and external conditions in dynamic times
  • Assessing current strengths, weaknesses, opportunities, and threats (and noticing when threats are opportunities)
  • Increasing communication and interaction across usually siloed parts of the organization
  • Documenting the steps needed to create sustainable and desired change
  • Tracking impact and success with measurable outcomes
  • Having a trained facilitator to hold the space for “hard” conversations 

If you are looking to do these things, then strategic planning could be a good choice for you. Just don’t expect your strategic planning process to address issues like these unless you specifically identify and ask for support around these cultural symptoms:

  • Low-trust cultures with rampant gossip
  • Lack of self-aware leadership
  • Lack of healthy candor in meetings
  • Low psychological safety
  • Tepid creativity due to pervasive fear and distrust
  • Lack of transparency and clear communication
  • Lack of cooperation and coordination across the organization
  • Closed mindsets rather than growth-oriented mindsets 
  • Staying perpetually busy while also having meager results and impact

If these things are showing up in your culture, they will also show up in your strategic planning process with sub-par outcomes.

Einstein said, “A problem can’t be solved at the level of consciousness from which it was created.”

Applied to strategic planning, it takes a shift in consciousness from looking at problems through the lens of fear, doubt, and worry to shifting to an orientation of curiosity, wonder, and learning even to see new possibilities. (This quote is featured in a video called “Locating Yourself: A Key to Conscious Leadership” from the Conscious Leadership Group. I reference this video throughout every strategic planning process that I do.)

When these cultural elements are addressed, the likelihood of a successful strategic planning process increases immensely. So often, the “strategic” issues facing an organization may arise from the often unconscious mindset of the leader and leadership team. I like to say that “The inner game runs the outer game.” This means that the consciousness of the leader(s) shows up in the strategic options and choices of the organization. Without understanding the internal fears and unconscious lens the leader uses to see the world, it’s hard to unpack and develop real strategic options for the organization. 

Before you write a strategic planning RFP, use these questions to assess your own cultural readiness to generate successful strategic planning outcomes:

High self-awareness

  • How self-aware are your leaders, especially in how their actions may affect others?
  • Do leaders walk their talk?


  • Do you have a high-trust, low-drama environment?
  • Do your employees trust each other enough to be vulnerable and authentic?


  • How much candor is present in your meetings? 
  • Is there a safe environment to raise even controversial viewpoints in a constructive manner? 
  • Do your employees have the skills to speak candidly, compassionately, and directly?


  • Is information highly guarded in your organization?
  • Is gossip a primary backchannel of information flow?

Integrity and agreements:

  • Do people do what they say they will do?
  • Do you have clear agreements of who will do what by when?

You will get less than optimal results if your organization enters a strategic planning process without self-awareness, trust, candor, transparency, and integrity. 

You may be looking at these questions and wondering, if strategic planning isn’t the process that will address these cultural factors, what else is there?

My favorite frameworks and tools are Conscious Leadership and the Enneagram to help build high trust, low drama, and high learning cultures. I will only start a strategic planning process if I’ve done executive coaching work using the Enneagram and conscious leadership fundamentals with the leader first. Even after doing a strategic planning process with an organization, I’m also using these tools as training and practices during the implementation of the plan.

As a preview, I like to use the Enneagram to make explicit the implicit worldview and internal landscape of the leader of the organization (and ideally the leadership team charged with strategic planning as well). For example, there are nine archetypal profiles in the Enneagram that show up in strategic planning. Even with the same set of supposedly objective data, a leader who is a Loyal Skeptic (type 6), a Considerate Helper (type 2), or an Enthusiastic Visionary (type 7) will see the “same” set of data through a very different lens and with very different implicit and often unconscious assumptions. It’s human nature, and the Enneagram is one of the most efficient and robust ways to make these assumptions more explicit rather than implicit.

If you are about to write an RFP for strategic planning, I encourage you to be honest about your culture, needs, and your own perspectives as a leader first. I welcome conversations with leaders and organizations considering strategic planning at a very early stage–before your RFP is fully baked and you don’t even know how much you are missing from a cultural perspective. 

If this blog intrigues you, schedule a complimentary 25-minute consultation with me. I’m happy to listen and help you determine your most efficient and effective path to building a high trust, low drama, and high learning culture AND an actionable strategic plan.

If you’re not ready for a conversation, start with my free strategic planning readiness checklist below to see how ready you are for this journey.


Stephanie Freeth

Stephanie Blackburn Freeth is an executive coach and Founder of Stephanie Freeth Coaching. She brings more than 20 years of experience working with leaders and teams on leadership development, strategic planning, fundraising, marketing, and building conscious organizational cultures. She has worked across industries including health care, start-ups, manufacturing, technology, higher and secondary education, arts and culture, social services, and philanthropy. Stephanie is based in Ann Arbor, Michigan.

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