A Leader’s Guide to Strategic Planning with Your Team
- Courtney Haynes
- Jan 21
- 5 min read
A practical approach to combating the post-holiday slump and creating real buy-in for the year ahead
I have always loved New Year’s Eve for the nostalgia, reflection, and sense of reset it brings. I still get teary-eyed when I hear Auld Lang Syne followed by New York, New York. For me, it’s an evening of appetizers, bubbly, kisses, snuggling my kiddos, watching When Harry Met Sally, and then the ball drop — all while thinking that the people standing in Times Square freezing their butts off are absolutely crazy.
That feeling of reset doesn’t always translate to the workplace. January can be a tough time. People are trying to get back into a routine. Colleagues are “circling back” (nooooo, not the circle back!) after projects were paused for vacations and time off. It’s dark, it’s cold, and frankly, we all just want to stay in our warm beds.
As leaders, though, this is when momentum matters most. Losing traction during these winter months can have a real impact on the year ahead. Instead of pushing through with business as usual, I use this time to reflect and reset by engaging my entire team — especially junior employees — in building our annual strategic plan.
Early in the year is when people are most open to being included, heard, and invested in the future of the department. That sense of reset isn’t just personal — it’s a powerful leadership opportunity.
Why Engaging Junior Employees in Strategic Planning Matters
A common leadership mistake is treating strategic planning as “high-level” work that happens behind closed doors and is later communicated down to junior employees. This approach misses several critical opportunities.
Junior employees often have the clearest view of inefficiencies within their roles and day-to-day processes.
Inclusion increases accountability and follow-through. Your team will be executing these goals every day — their buy-in is essential.
Exposure to strategy develops future leaders. Involving junior employees builds strategic thinking skills and prepares them for growth.
When people help build the plan, they are far more committed to executing it.
How I Approach Strategic Planning Each Year
Below is the framework I use to engage my team and build a strategic plan that is both realistic and motivating.
Start with the Agenda and Ground Rules
Schedule at least two full days in person, when possible. While it may feel like a lot of time away from production, the realignment and clarity gained far outweigh the short-term pause.
Send an agenda in advance and set clear expectations. This may be the first strategic planning session some team members have ever attended.
Build in structured email check-in times (first thing, mid-day, and end of day), and ask employees to disconnect from work-related messages during other sessions.
Communicate with other leaders that your team will be offline. True emergencies should be filtered through you as the department head so you can determine what needs immediate attention.
Reflection: Reviewing the Previous Year
The first session focuses on reflecting on the prior year.
Ask the team to:
Revisit last year’s strategic plan and identify what was accomplished (checking things off feels good).
Call out meaningful work that wasn’t originally on the plan.
Discuss the most significant challenges.
Celebrate the most significant accomplishments.
This reflection provides critical context for the year ahead and ensures lessons learned are not lost.
Learning & Development: Setting the Cultural Tone
Dedicate time to learning and development around a concept that reflects the culture you want to promote in the coming year. Examples might include:
Exceptional customer service
Increased productivity
Stronger cross-departmental partnerships
This signals what matters — not just what needs to get done.
Goal Setting: From Input to Ideas
Using everything gathered so far, present:
Employee survey results
Relevant employee feedback
Notes from team meetings throughout the year
Company-wide goals and priorities
From there, begin the brainstorming process. Depending on team size, this can be done individually or in small groups before sharing with the larger team.
Guiding questions for brainstorming:
What would make your individual work better this year?
What would improve employees’ or customers’ experiences?
What are must-haves for the coming year?
What are nice-to-haves?
How does our department contribute to company-wide goals?
Initial Goal Setting: Create a Safe Space
This is the time to throw everything at the wall.
When the group reconvenes:
Collect all ideas without filtering.
Encourage creativity and ambitious thinking.
Explicitly reinforce that this is a safe space, especially for junior employees.
Invite “crazy” ideas and ensure every voice is heard.
Once the full list is visible, revisit company and departmental values to help ground the discussion.
Ask each team member to:
Identify three personal work-related goals for the year
Identify what they believe are the three most important team goals
Whittle Down the List
Refocus the team by asking:
Does this meet organizational needs?
Is it aligned with company and department values?
Does it meet the needs of the team?
This is when you begin “parking lot” ideas — explaining clearly why they aren’t the right fit right now. Emphasize that these ideas are valuable and will be revisited in future planning sessions.
Formalize the Plan
With a refined list in hand, help the team understand what is realistic within the year.
For each initiative, identify:
Priority level (high, medium, low)
Time requirement (high, medium, low)
Who needs to be involved
As a group, discuss how many initiatives of each level the team can reasonably take on per quarter. As the leader, ensure expectations are realistic and no individual is being stretched too thin.
Note: Personal goals can be saved for one-on-one meetings later, but employees should keep them in mind as they help shape the team’s plan.
Build Momentum with a Working Session
Select one goal that can be started — or even completed — during the planning session itself. Working on something tangible together builds momentum and leaves the team with a sense of accomplishment as they move into the new year.
Finalize and Align
Following the session:
Take the next week to finalize the strategic plan.
Share a draft with the team for feedback and corrections.
Prepare to present the plan to Executive Leadership.
When team goals are visible and aligned with leadership priorities, employees know they have support — and that their input mattered.
As leaders, the way we invite our teams into the future determines how committed they are to building it. What strategies are you using to lead your team into 2026?
“When we strive to become better than we are, everything around us becomes better too.”— Paulo Coelho
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