Year-end and beginning-of-year planning sessions can do more than set priorities. They can help leaders understand what their teams need to execute those priorities successfully. This article explores three conversations that can strengthen clarity, capacity, motivation and shared ownership as teams prepare for the year ahead.
September has its own rhythm in organizations.
Summer schedules are ending. Fourth-quarter priorities are coming into sharper focus. Leadership teams are beginning to think about year-end team planning, offsites and 2027 priorities. Budgets are being finalized, and decisions are being made about where to invest in the people and teams who will be responsible for delivering what comes next.
It is a natural time to ask: What do we need to accomplish next year? But as leaders begin shaping year-end meetings and beginning-of-year planning sessions, I think there is another question worth asking first:
What does our team need in order to accomplish it?
Those are not the same questions.
A strong strategic plan can identify where the organization needs to go. It cannot, by itself, create the clarity, capacity, connection and shared ownership required to get there.
And for many teams, those conditions deserve some attention right now.
The Team Entering Next Year Is Not the Team That Entered This One
Think about what many organizations and their people have been absorbing.
AI is rapidly changing how work gets done, creating new demands on teams and how they work together. At the same time, organizations are navigating growth, restructuring, shifting priorities and continued pressure to accomplish more with finite resources.
Some people are energized by what is possible. Others are tired. Many are both.
Middle managers may be translating another round of change while simultaneously keeping work moving and supporting their people. Employees may be hearing about new priorities before the previous ones have fully left their plates. Teams may be adopting AI at very different rates, creating new efficiencies in some places and new friction in others.
That makes a year-end or beginning-of-year gathering more than an opportunity to review objectives.
It can be an opportunity to understand what is actually happening inside the team system before asking that system to carry another year of ambitious work and before unclear priorities, hidden friction or depleted capacity begin showing up in execution.
Three Conversations to Include in Your Year-End Team Planning
1. What matters most now?
One of the most useful things a team can do together is distinguish what is important from what is most important.
In busy organizations, priorities accumulate. Initiatives that once made sense remain on the list. New opportunities appear. Customer and stakeholder needs shift. Leadership makes new commitments. AI introduces possibilities that did not exist a year ago.
Eventually, nearly everything can begin to feel like a priority.
A facilitated planning conversation can help a team step out of the day-to-day long enough to look outward and ahead. What value do our customers, partners and other stakeholders need from us? What value do we want to be creating for them in the future? And, given that direction, what is most important for us to execute now?
That can lead to a different set of questions:
What will create the greatest value for the people we serve?
What has changed around us that should influence our priorities?
Where are we spending energy that no longer serves the strategy or the value we are trying to create?
What needs greater attention now, and what can we consciously stop, postpone or simplify?
That clarity is not simply a planning exercise. It helps a team connect today’s choices to the value it wants to create tomorrow, while protecting capacity for the work that matters most.
2. What could get in the way?
Once priorities are clear, another conversation becomes possible.
What might prevent us from delivering them?
Sometimes the answer is technology or process. Sometimes it is unclear decision-making, weak handoffs, competing incentives, insufficient resources or roles that have evolved without being redefined.
And increasingly, AI is exposing those underlying team dynamics.
When AI changes a workflow, for example, it can quickly reveal where ownership is unclear, where information is siloed, where people do not feel safe experimenting, or where teams lack common expectations about how technology should be used.
These are not simply AI problems. They are team-system questions.
Bringing them into the room gives the team a chance to address barriers while there is still time to change how the work gets done, rather than discovering them six months later in missed goals, stalled initiatives or exhausted people.
3. What will help this team want to move forward together?
Motivation rarely comes from a slide announcing next year’s targets.
People are more likely to engage when they understand why the work matters, can see the value their team is there to create for its stakeholders, understand how their own contribution connects to that larger purpose, and have some voice in how the team will accomplish what is being asked of it.
That does not mean every decision becomes a group decision.
It means creating enough space for people to understand the direction, bring in the voices and needs of customers and other stakeholders, surface what they are seeing, contribute their own knowledge, and help shape how the team will work together to create value.
Sometimes that conversation uncovers frustration or fatigue. Sometimes it uncovers ideas leadership has not heard. Often it reveals strengths the team can build upon.
And sometimes people simply need an opportunity to reconnect with one another and remember what they are capable of together.
Don’t Start With the Workshop. Start With the Team’s Need.
I believe strongly in interactive workshops and facilitated team conversations. But the starting point should never be, What workshop should we do?
It should be: What does this particular team need right now?
For one team, that might mean clarifying three priorities for the coming year.
For another, it might mean understanding why execution keeps getting stuck between functions.
Another may need to examine how AI is affecting workflows, roles and team dynamics.
And another may need to rebuild connection and shared purpose after a demanding year of change.
The starting point is not choosing a workshop from a menu. It is understanding what this particular team needs in order to do its most important work well.
The format follows the need.
Sometimes that means a focused facilitated session. Sometimes it becomes a series of conversations or a broader team-coaching engagement that helps the group work on real business priorities while strengthening how it works together.
The goal is not to create a memorable workshop.
The goal is to help the team leave more capable of doing the work that matters.
Turn Your Year-End Gathering Into Forward Movement
Later this month, Abby Hopper and I will be putting this kind of facilitated inquiry into practice with clean-energy leaders at the WRISE Leadership Forum in Chicago.
Rather than arriving with a predetermined list of answers, we will be facilitating conversations to help leaders surface the most significant challenges they are encountering as they work to create enterprise value from AI, identify approaches that are already working, and learn from one another’s experience.
What emerges from those conversations will come from the leaders in the room.
That is one of the things I value most about well-designed facilitated work: it does not assume the answers live with the facilitator. It creates the conditions for the knowledge, experience and perspective already present in the system to become visible and useful.
As you begin thinking about year-end gatherings and 2027 planning, consider asking one additional question alongside the strategic and financial ones:
What conversation would help this team move into next year with greater clarity, capacity and shared ownership?
That answer may tell you more about the gathering you need than any off-the-shelf agenda ever could.
If you are beginning to shape a year-end or early-2027 team gathering, that is a useful place to start. And if you would value a thought partner in designing the conversation your team most needs to have, I would be glad to explore it with you.
