Tag Archives: financial planning

How to Run a Great Annual Leadership Team Offsite Meeting.

Most leaders find it difficult to adequately prepare— assuming they even know how — to facilitate a high-powered, executive offsite. The truth is that it is nearly impossible for a leader to facilitate and participate in, let alone also lead, their own offsite. A better strategy is to hire experts who use proven approaches, tools, and methods to prepare and facilitate a great annual leadership team offsite meeting.

The ten tips and resource links below will help the thoughtful leader to get out in-front of the planning process and make clear to the board, top team, and employees that the organization is in good hands and well-led.

Plan the Plan

  • Inform the board and the management team that it is time to work on plans for the coming year.
  • The management team can be as small as three to five members or as many as 15 to 20.
  • If there are more than seven, pick three to five to serve as an executive committee.
  • Prepare a time-line of steps, outputs, and review points.
  • Assign a process leader who will manage planning as a project.
  • Schedule offsite session and line up facilities and facilitation support.

  See details on leadership team strategy and planning sessions. 

Continue reading How to Run a Great Annual Leadership Team Offsite Meeting.

Plan Evolution

The following sequence leads to a fully developed financial plan that the CEO, Executive Leadership Team, Senior Leadership Team, board, and employees all buy-in to achieving:

  • Executive Leadership Team (ELT) takes the Senior Leadership Team (SLT) offsite to review where we were, where we are, and where we’re headed, what we’re proud of and what we need to work on next following the script laid out here.

    While it is important to have both a high-level top-down and a preliminary sense for a bottom-up view of the financial plan, the offsite is not mostly about the numbers … it is about strategy.

    Specifically, what is working, what is not working, what is possible, what do we want to do, and what are we going to do. The objective is to set the context for the top down aspirational view of the future to iterate and come together with the bottom-up view during the detail planning.
  • The ELT briefs the board in the fall meeting to share how the current year is turning out, status on key initiatives, and to proffer/review/tweak planning guidance for next year.
  • Then All Hands meeting communicates the where we were, where we are, and where we’re headed with the full backing and support of the SLT, broader leadership team, and the board. Note how it all cascades down from CEO to ELT to Broader Leadership Team to Board to Company as a Whole, building an ever broadening base of support for what the CEO carries as a vision and direction.
  • Then, the bottom-up planning begins in earnest with each unit of major responsibility preparing and reviewing with the CEO how they have done, what they are working on next, and how things will be going forward.
  • The sum of the unit plans needs to be greater than the plan because it is unreasonable to plan on absolutely everything going according to unit plans.
  • The CEO and ELT strive to construct a top-down plan that is rational relative to the bottom up plans. They iterate until the top-down and bottom-up plans are in sync and judged to be aggressive but achievable…for example Planned Revenue ~= Firm Revenue (i.e., Booked & Highly Probably) + 1/3 (Highly Qualified Pipeline).
  • The spring All Hands is to inform everyone how things are going and to engage the whole company in moving forward on the top one, two, or three Strategic Initiatives.
  • The spring ELT offsite is for the top team to bond, assess, refresh, and get a common sense for each other, how things are going, and where things are headed.


Annual Process
Annual Planning Offsite POAD
How to Run a Great Annual Planning Offsite