Strategic planning is an opportunity to shape the kind of organization we’re becoming. Who will we serve? What will we build? How will our people grow? What good will we contribute?
After leading Strategic Planning sessions for dozens of organizations, over the past 15 years and having spent thousands of hours facilitating these sessions in board rooms, I’ve observed a number of common mistakes teams make.
In the Appreciative Operating System, strategy connects the whole organization. Our 9 Elements of a Fully Flourishing Organization are designed to do just that: Destiny, DNA, Design, Decisions, Delegation, Data, and Delight. Our direction, culture, structure, and daily practices need to work together.
An appreciative approach begins by discovering what gives an organization life and what becomes possible when those strengths are developed intentionally. It also requires honesty about what needs to change.
Here are fourteen mistakes that can undermine that work, and practical ways to improve the process.
I believe a strong planning process can itself be a catalyst for building culture, gaining momentum, and engaging your people.
1. Skipping the pre-work
Without preparation, planning becomes a conversation shaped by incomplete information, recent frustrations, and whatever happens to be on everyone’s mind.
Try this: Gather meaningful data, customer feedback, and perspectives from across the organization beforehand. Ask people about moments when the organization was at its best, what made those moments possible, and what needs attention. Give everyone a short briefing and time to reflect.
2. Getting lost on rabbit trails
One operational issue can consume an entire morning. The conversation may feel productive while the decisions that matter most remain untouched.
Try this: Build the agenda around specific strategic questions and decisions. Capture unrelated issues, assign a follow-up owner, and return to the question at hand. Allow exploration, then deliberately make choices.
3. Underestimating the importance of facilitation
A gifted facilitator notices what is happening beneath the conversation: hesitation, confusion, unspoken disagreement, and voices that haven’t been heard. That requires skill and attention.
Try this: Choose someone who can ask thoughtful questions, navigate tension, synthesize ideas, and guide decisions. Give them permission to challenge the room, including its leaders. Whenever possible, let the leader participate without also managing the process. Give facilitation as much thought as you give outcomes.
4. Leaving without clear commitments and ownership
People can leave the same meeting with very different understandings of what was decided. Enthusiasm fades quickly when responsibility is vague.
Try this: Document each priority, its intended outcome, one accountable owner, the resources required, and the next milestone. Have owners explain their commitments back to the group. Aim for shared clarity while naming the uncertainties you still need to test.
5. Mistaking tactics for strategy
“Launch a campaign,” “hire a salesperson,” and “redesign the website” describe activities. They don’t explain whom you will serve, the distinctive value you will create, or why your approach should work.
Try this: Make the strategic choices first. Identify your ideal customers, the value you can deliver especially well, the capabilities required, and what you will decline to pursue. Then select the activities that support those choices.
6. Avoiding constructive conflict
A room full of agreement may contain plenty of unspoken reservations. An appreciative approach makes room for difficult truths and competing perspectives.
Try this: Invite people to test assumptions respectfully. Ask, “What might we be missing?” and “What would have to be true for this to work?” Explore disagreement without making it personal. The aim is better judgment, not conflict for its own sake.
7. Letting the loudest or most powerful voice decide
Confidence, position, and volume can crowd out insight. Leaders may unintentionally narrow the conversation simply by sharing their preferred answer first.
Try this: Start with individual reflection, then give everyone space to contribute. Ask senior leaders to speak last. Agree on decision criteria beforehand and evaluate ideas against evidence, purpose, and values.
8. Failing to create trust and openness
People assess whether honesty is welcome by watching how leaders respond to it. A request for candor means little if disagreement brings defensiveness or embarrassment.
Try this: Establish clear agreements for listening, curiosity, and respectful challenge. Begin with a meaningful story of the team at its best. Leaders should acknowledge their own blind spots and respond to concerns with questions before explanations.
9. Focusing on the work while neglecting relationships
Every strategic commitment depends on people coordinating, asking for help, sharing information, and keeping promises. Strained relationships make even straightforward work harder.
Try this: Include time to understand one another’s strengths, pressures, and support needs. Discuss where collaboration breaks down. Ask, “What do we need from each other to make this possible?” Make those relational commitments explicit.
10. Treating a good strategy as the finished work
A strong plan still needs time, resources, leadership attention, and repeated follow-through. Without those, it becomes another document competing with daily demands.
Try this: Translate priorities into manageable commitments and schedule regular progress conversations. Review outcomes, remove obstacles, and adjust based on learning. Decide what existing work will stop so the new priorities have room to succeed.
11. Spending the whole session on issues and fires
Urgent problems deserve attention. But when they consume the agenda, there is little room to develop the people, capabilities, and systems that could prevent the next round of problems.
Try this: Protect time for proactive development. Ask, “What should we strengthen now to make next year healthier?” Study where things already work well and identify the conditions worth extending. Pair necessary repairs with investments in future capacity.
12. Building the plan entirely from the top down
Leaders have a valuable perspective, but so do the people closest to customers and daily operations. Asking employees to execute a finished plan misses their insight and their opportunity to help shape it.
Try this: Engage people across levels and functions through interviews, small groups, and working sessions. Invite them to identify possibilities and test feasibility. Be clear about who makes final decisions, then show how people’s input influenced the direction.
13. Forgetting Your Mission and Values
If strategic planning and leadership is an act of stewardship, and I believe it is, then it’s surprising how often teams completely forget their Core Values and Mission while making strategic plans.
If our values and our mission aren’t a guiding light for all decisions, a filter, then what are they even there for? We would have to ask ourselves, “Are these even our real values?”
Try this: For years, I’ve asked each leader in the room to write down the mission and values of the organization on the white board. Then, each leader is given full permission to point at the mission/values and say, “How can this impact our decision?”
14. Forgetting Critical Stakeholders
Just as common as forgetting mission and values, I’ve found it surprising how often key stakeholders (team members, clients, vendors, partners) are not considered when making plans and decisions.
Try this: Next time you gather for a planning or decision meeting, write the names of actual stakeholders in your organization. Often times, this ends up being clients, customers, team members, vendors, and partners. Then, put them in an empty chair at the table. Give them a seat at the table, and keep their perspective and goals in mind as you make decisions.
Done well, the process itself helps build a healthier organization: people understand the direction, contribute their strengths, work through differences, and take responsibility for what comes next. That is how a shared vision begins to become a flourishing reality.
Remember. Every conversation, every meeting, every interaction is where you are either building a flourishing culture, or something else.
–Chris Cloud / Master Facilitator and Founder of CloudNINE
