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How to Run a Great Annual Leadership Team Offsite Meeting

Editor's Note: Take a look at our featured best practice, Strategic Planning: Process, Key Frameworks, and Tools (79-slide PowerPoint presentation). This document provides a holistic approach for undertaking strategic planning. While covering the traditional strategic planning approach, the document touches on adaptations that may be used in an unpredictable environment. Contents: 1. Strategic Planning Overview - Key questions and [read more]

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Editor’s Note:  Peter DiGiammarino is a professional CEO and founder of growth strategy consulting firm, IntelliVen.  IntelliVen is also an author on Flevy, producing a series of frameworks covering a variety of management and leadership topics.  View all this Flevy materials here.

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111129-F-WS541-004Most 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.

Trade Perfection for Completion

  • Do not try to build the perfect plan.
  • The plan will get better every year.
  • Pull together this year’s plan knowing that next year’s will be better.
  • The key is to pull the plan together and get it done.

Financials Matter but so does Everything Else

Plan more than financials. There are many dimensions to a plan. For example:

  • A Financial plan
  • A Market plan
  • A Product plan
  • A labor plan

Many think primarily in terms of a financial plan and never get around to the others but all are important.

Preparing each requires the team to think through how to make the financial plan believable.

Aggressive, but Achievable

  • For the board to approve the plan it has to be judged doable.
  • That said the board does not want a plan that is too easy.
  • Strive for a plan to have a specific, say 75%, probability of being achieved.

Plan of Attack

  • Assign each management team member a page of the plan.
  • Assign every important part of the organization (e.g., every function – such as marketing, sales, delivery, development, etc.; every major client; every offering; etc.) to a member of the management team to develop its plan.
  • The result serves as the foundation for personal performance goals. The sum forms the entire plan.

Strategy Is How You Plan to Win the Game You Are Playing

  • Separate Strategy from Operations.
  • The Strategic Plan and the Operating Plan are two distinct outcomes of a well-conceived annual planning process.
  • Ask each leader to work with her/his team to prepare a Strategic Plan for their assigned area of responsibility.
  • Review their Strategic Plan to ask questions to gain clarity and also to push up thinking, give guidance, and add to the evolving overall Strategy for the entire organization.

Ask each leader to work with her/his team to prepare an Operating Plan for similar review, questioning, and guiding.

The Strategic Plan is short, high-level, and prepared from the top-down. It covers:

  • What the organization is trying to accomplish.
  • How the organization is going about doing it.
  • Current year strategic initiatives focused on what has to be done differently going forward.

Except for the current year initiatives, the Strategic Plan does not change much from year to year.

It is best to work on strategy and then reconvene to discuss operations after a separate effort working out how to implement the strategy.

Formulate and review strategic plans separate and apart from operations. Once conversation moves from strategy to operations it is difficult to then lift up and get back to discussing strategy.

The Operating Plan is more detailed and is prepared from the bottom-up.

It covers:

  • How the organization will do what it does.
  • How the organization will create demand for what it does.
  • How the organization will grow.
  • How well the organization is doing relative to its past, plan, and peers.
  • How current year strategic initiatives are to be implemented.
The sum total of what each leader plans to do must at least equal, and ideally exceed, the overall plan.

Each leader drafts their Page-of-the-Plan to show how s/he will do what the organization is counting on from her/him to achieve the planned financial results, accomplish the strategic initiatives, and lay the foundation for future years.

Evolve Top-down and Bottom-up

  • Iterate
  • Strategy and Operations impact, constrain, and push each other iteratively as they develop during the planning process, and continuously as things play out over the performance period.
  • Work with the Strategic Plan and the Operating Plan to bring the top-down strategic view into harmony with the bottom-up operating view to meet somewhere in the middle that makes good sense to the team and, ultimately, also to the entire organization and to the board.

Involve the Board

  • Seek board input throughout.
  • Share top-down, big picture strategy, draft initiatives, and prospects to get their best thinking and guidance before going offsite.
  • It may seem easier to not involve the board until the plan is done but involving the board sooner heads off surprises and almost always adds value to management thinking.

Tell the Story

Bring the past, present, and future into focus.

The board, management team, and employees all count on the organization leader to help them understand “Who we are, where we have come from, where we are now, where we are headed, and what we must do next”.

The strong leader opens a board discussion and kicks off management planning sessions, and All Hands sessions with an inspiring description of the following to bring their leadership to life:

  • Where the organization has recently been and how it is today in terms of whose problem the organization solves and why customers buy.
  • How the organization does what it does, creates demand for what it does, and how it grows.
  • How well the organization performs relative to: how it has performed in the past, how it had planned to perform, and how its peers perform.
  • How the organization has progressed with Strategic Initiatives over the past performance period.
  • What is most important to do differently next.

Go Offsite

Break away from the press of the day-to-day.

Get the best out of  leadership by convening a facilitated offsite session. Outside help maximizes the chance to advance team skills, relations, and results.

  • Learn how to orchestrate an Annual Planning Offsite.
  • Learn how to settle on what you sell to whom and why customers buy it.
  • Learn how to set the context for change and strategic initiatives.
  • Learn how to assess and develop the ideal leadership skill set.
23-slide PowerPoint presentation
Strategic Planning is an essential tool for organizations aiming to thrive in today's dynamic business environment. It's not just about setting goals--it's also about crafting a roadmap for sustainable success. For executives, understanding and effectively implementing Strategic Planning is crucial [read more]

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About Peter DiGiammarino

Peter DiGiammarino is a senior executive with over 30 years of success leading businesses that target tight public and private markets around the world. In addition to running companies, he serves public, private, private-equity-owned, and venture-capital-backed software and services firms as an adviser and/or board member and has consistently helped them to achieve their full potential to perform and grow. Peter currently serves on boards and advises leaders as CEO of IntelliVen. IntelliVen is also an author on Flevy (view materials here).

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