Too many priorities
Everything feels important, so the team keeps shifting focus instead of executing the few things that matter most.
Peak Annual Planning Sessions
Start the year aligned, focused, and ready to execute.
A professionally facilitated annual planning session built around your company, your leadership team, and the decisions that matter most.
Clarify where the company is going, decide what matters most, align ownership, build measurable priorities, and leave with an operating rhythm the team can use throughout the year.
Standard two-day format
Fully customizable agenda
In-person, remote, or hybrid
Optional ongoing support
A Peak Annual Planning Session is a professionally facilitated leadership-team planning process designed to create shared direction, focused annual priorities, clear ownership, measurable goals, and an operating rhythm for executing, reviewing progress, solving problems, and learning throughout the year.
Why annual planning matters
The strategy can be clear to you and still be unclear to the team.
A leadership-team annual planning session or offsite creates dedicated space to surface what is not aligned, make the decisions day-to-day work keeps postponing, and create one shared plan for the year ahead.
Leadership misalignment
Leaders leave meetings with different interpretations of the strategy, priorities, or decisions required to move forward.
Unclear ownership
Important work crosses functions, but accountability and dependencies are not explicit enough to create reliable follow-through.
Execution still depends on the CEO
Too many decisions, escalations, and follow-ups continue to come back to the CEO instead of moving through the team.
Problem solving is inconsistent
Important issues stay unresolved, reappear, or get handled differently across functions.
The annual plan loses momentum
The team plans once, but priorities are not consistently reviewed, learned from, and adjusted as conditions change.
The outcome
Two days should change what happens on Monday.
The goal is not another strategy deck. The goal is a leadership team operating from the same direction, priorities, ownership, measures, and execution rhythm.
Shared long-term direction
A clear three-year view of where the company is going and what the leadership team is building toward.
A focused one-year plan
The few outcomes that matter most this year—not a list of everything the company could do.
90–180 day objectives
Near-term priorities that translate annual direction into coordinated action.
Measurable key results
Clear evidence of whether each objective is moving toward the desired outcome.
Ownership and dependencies
Explicit owners, commitments, and visibility into where teams depend on one another.
An execution rhythm
A practical cadence for reviewing progress, solving problems, learning, and adapting throughout the year.
Professional facilitation
The CEO should be in the session—not running the session.
When a member of the leadership team is responsible for the agenda, process, timing, teaching, difficult conversations, and capturing decisions, that person cannot participate in the same way as everyone else.
A Peak facilitator owns the process so the entire leadership team can stay engaged in the work.
We build the session with you.
We learn how your company plans today, your goals for the session, your stage, team, operating rhythm, and the decisions that matter.
We prepare the leadership team.
The team understands the process, tools, agenda, expectations, and pre-work before the live session begins.
We run the room.
The facilitator teaches, coaches, watches the clock, manages discussion, surfaces issues, and keeps the team moving.
We help turn decisions into execution.
Priorities become objectives, key results, owners, commitments, issues, actions, and a rhythm for follow-through.
The process
We do the work before the room so the room can do the work that matters.
Every engagement begins by understanding how your team already plans and operates. The standard process provides structure without forcing your team into a rigid template.
1
Discover
Annual Planning Discovery Call
Understand what you want the session to accomplish before recommending an agenda.
What we learn
- How you typically plan today
- Your objectives for this year’s planning session
- How goals are set, measured, and tracked
- Your planning, review, and meeting cadence
- Company stage, leadership team, and current pressures
2
Design
Team Lead + Admin Meeting
Translate the desired outcomes into a practical agenda and session plan.
What we do
- Review and customize the agenda
- Confirm team participants
- Schedule dates, timing, and breaks
- Review location, room setup, and logistics
- Identify special topics or decisions requiring attention
3
Prepare
Team Prep Call
Make sure valuable live session time is spent working—not explaining logistics.
What the team receives
- Overview of the agenda and planning process
- Introduction to tools and terminology
- Clear expectations for participation
- Pre-work and information to prepare
- Time for questions before the session
4
Facilitate
Peak Annual Planning Session
Create shared context, make the important decisions, and translate direction into measurable execution.
What your facilitator owns
- Teaching the process and tools
- Facilitating discussion and decision making
- Managing timing and session flow
- Surfacing and triaging important issues
- Capturing priorities, owners, and commitments
5
Activate
Launch the Operating Rhythm
Make the plan useful after everyone leaves the room.
What happens after the session
- Teach the weekly execution and meeting cadence
- Support questions around tools and best practices
- Clarify how objectives and metrics should be reviewed
- Optional quarterly or semiannual sessions
- Optional Peak OS Software for teams that want it
Standard two-day agenda
A proven agenda. Customized to your team.
We begin with a planning framework refined across team sessions and adapt it to your company, stage, planning history, team dynamics, responsibilities, and desired outcomes.
This is the standard starting point—not a rigid script. Topics can be
added, removed, reordered, or expanded based on what your team needs
from the session.
Day One
Direction + Shared Context
Build a common understanding of the business, team, and direction before deciding what matters next.
- 01Team Connect Opening
- 02Opening Message from Team Leader
- 03Share Team Expectations
- 04Review and Discuss Roles & Responsibilities
- 05Review Annual Team Survey / Annual Business Review
- 06Review Prior-Year Metrics & KPIs
- 07Triage Important Topics, Issues & Decisions
- 08Review Mission
- 09Build the Three-Year Vision
- 10Build the One-Year Plan
Day Two
Priorities + Execution
Translate direction into near-term priorities, measures, ownership, and a practical path for execution.
- 01Team Connect Opening
- 02Build 90–180 Day Team Objectives
- 03Build Key Results
- 04Team Review of OKRs
- 05Align Cross-Functional Dependencies
- 06Build and Review the Triage List
- 07Build the To-Do / Commitment List
- 08Review Team Expectations
- 09Confirm Owners and Follow-Through
- 10Close the Meeting
Your planning session should fit your team—not the other way around.
We can change the timing, add deeper strategy work, expand team topics, extend the session, or accommodate how your team prefers to work.
Annual planning best practices
Make the session useful after the session.
The best annual planning work creates decisions and operating habits the team continues using long after the session ends.
Prepare before the room
Move context, surveys, metrics, and basic information into pre-work so live time can focus on discussion and decisions.
Debate what matters
Use team time for issues that genuinely require shared thinking, tradeoffs, and decisions.
Choose fewer priorities
A plan becomes useful when the team knows what matters most—and what is not a priority right now.
Make ownership measurable
Priorities need owners, outcomes, measures, and enough clarity for teams to coordinate without constant intervention from the team leader.
Build the review rhythm
Decide how progress, issues, decisions, and learning will be reviewed before the team leaves the session.
After annual planning
The session ends. The operating rhythm begins.
We do not want your team to leave with a thoughtful plan that slowly disappears under day-to-day work. We help translate the session into a practical cadence for execution and learning.
Learn a practical cadence for priorities, metrics, issues, decisions, actions, and accountability.
Get help applying the planning tools and execution practices as the team begins using them.
Reconnect the team to the plan, review learning, and adjust as the organization and environment change.
Peak OS Software is optional.
Teams that want one shared platform for priorities, metrics, meetings,
decisions, issues, and follow-through can
explore Peak OS Software
,
but software is not required for an Annual Planning Session.
A trusted planning partner
Experienced facilitation. A thoughtful agenda. A flexible system.
Peak Annual Planning Sessions draw from years of work with founders, CEOs, leadership teams, functional teams, cross-functional teams, investors, and growing organizations navigating complexity and execution.
Experienced facilitators
You are not hiring someone to simply moderate a meeting.
Peak facilitators bring operating experience, structured facilitation, coaching, planning tools, and pattern recognition from working through these challenges with teams across different stages of growth.
Hundreds
of team sessions and facilitated conversations across planning,
alignment, execution, funding transitions, and growth.
The thinking behind the process
A proven system without a rigid playbook.
Annual Planning Sessions draw from the Peak OS methodology and the leadership practices behind Peak Teams. Peak OS is designed as a team-of-teams operating system, so each session is tailored to the specific team while helping connected teams operate from shared organizational direction.
Frequently asked questions
Questions about Peak Annual Planning Sessions.
Is the two-day agenda fixed?
No. The two-day agenda is the standard starting point. We customize it based on your company stage, the specific team, planning history, current pressures, and the outcomes you want from the session.
Who should participate in annual planning?
Peak Annual Planning Sessions can be designed for the leadership team or for functional, business-unit, cross-functional, or other teams across the organization.
Peak OS is built as a team-of-teams system, so each planning session is designed around the unique team—its role, priorities, responsibilities, dependencies, planning horizon, and the decisions it needs to make.
For organizations planning across multiple teams, we can begin with the leadership team and then help connected teams translate company direction into their own objectives, key results, commitments, and execution rhythm.
Is a Peak Annual Planning Session the same as an annual planning offsite?
It can be. Some teams hold the session offsite, while others meet onsite at their office. Peak Annual Planning Session describes the facilitated planning process rather than requiring a particular location.
Can the session be onsite, offsite, or hybrid?
Yes. Sessions can be facilitated onsite at your office, at an offsite location, or with hybrid participation.
We highly recommend bringing the team together in person whenever possible. Annual planning benefits from the shared focus, discussion, problem solving, and time together that happens when the team is in the same room.
We also understand that sometimes one or two team members cannot attend in person. Our hybrid process allows those participants to join online seamlessly and take part in the same discussions, tools, decisions, and planning work as the team in the room.
Can we extend annual planning to three days?
Yes. Some teams need additional time for deeper strategic work, team dynamics, organizational design, market discussion, or other company-specific topics. We can expand the agenda when useful.
Do we need to use Peak OS Software?
No. Peak OS Software is optional. The Annual Planning Session is designed to create value as a standalone engagement. Teams that want a shared software platform can explore Peak OS separately.
What if we already use OKRs, EOS, or another planning system?
That is fine. We first learn how your team already plans and operates. The goal is not to replace useful practices simply for the sake of introducing something new. We can adapt the agenda, terminology, and tools around what is already working.
What happens after the Annual Planning Session?
We teach the team a practical weekly meeting and execution rhythm, answer related questions as the team begins applying the tools, and can provide optional quarterly, semiannual, or ongoing support.
Plan the session
Make annual planning the point where the team starts executing differently.
Tell us how you currently plan, what you want the team to accomplish, and where execution gets difficult. We’ll help you think through the right agenda and determine whether a Peak Annual Planning Session is a fit.
Start with a discovery call
Let’s talk about your annual planning session.
We’ll discuss your team, current planning process, desired outcomes, timing, format, and what would make the session genuinely valuable.
Book an Annual Planning Discovery Call No commitment required. Start with a focused conversation.