Leadership Off-Site 101: Part I — Benefits, objectives, design choices

This blog post is a part of a larger Facilitation collection that explores the various aspects of crafting and leading successful corporate events. This blog post is a good start and offers a basic background on the anatomy of leadership off-site design.

So, you’ve been asked to organize the next leadership off-site/on-site/workshop/meeting/retreat?

Congratulations! You are climbing up the ladder — and convening a leadership event is a corporate right of passage. If you want to hit the ground running, here are some basics.

Why are leadership off-sites so popular?

Leadership workshops (or whatever name is used for the gatherings) are frequently and effectively used to develop and agree on shared plans of action.

Benefits come from 3 sources:

  1. Preparation process — a forcing mechanism to put down on paper current thinking, as well as structure and advance analyses and plans

  2. Face-to-face discussion of issues — a process to expedite decision-making, reveal areas of disagreement or ambiguity, and get everyone on the same page

  3. Follow-up actions — activities to maintain off-site momentum, including further off-sites

How do you conjure corporate magic?

What makes (corporate) magic happen is

having the relevant people

in the same place,

at the same time,

with an open mind,

and with sustained cognitive energy level to:

focus on the right issues,

draw on a common set of facts and insights,

and make decisions that lead to action.

And if this is magic, I am a sorceress — for that’s what I do. And right at this moment, you are my apprentice, for you are reading my post.

What are the typical design choices?

Magic, sorceress, apprentice — isn’t this a bit over the top?

Well, crafting and leading successful leadership off-sites takes a lot of diverse skills and thinking through many design choices. Here is a list (in no particular order) to get you started:

  • Objectives

  • Participants

  • Issues to discuss

  • Session content

  • Definition of success

  • Format of sessions

  • External participants (speakers)

  • Degree of facilitation

  • Degree of preparation

  • Preparation activities

  • Meeting materials

  • Format of output

  • Mix of social vs. “work”

  • Follow-up mechanism

  • Location

  • Duration and timing

What are typical off-site objectives?

Let’s start with the most essential design choice: off-site objectives. Any leadership event would have a blend of objectives — and it is up to you to clarify these ahead of time.

The 3 main types of objectives are:

  1. Get work done — for example, decision-making, problem solving, planning

  2. Get on the same page — for example, inform team on developments, align team on decisions, enable team to consistently communicate company story

  3. Build team/capability — for example, increase team cohesion and excitement, establish effective leadership practices, develop/transfer skills

Explore more blog posts from this Facilitation collection to prepare for, and lead, a fantastic event.

Written by Aneta Key. Last edited March 2019.