Conducting successful strategy retreats

Share on facebook
Share on linkedin
Share on twitter
Share on email
Share on print

A strategic retreat offers an opportunity for the team to gain insights into the thinking of the top leadership of the business. Crafting a strategy takes longer – many strategy formulation tasks I have facilitated have lasted three to eight months – depending on company size and top leadership ownership of the strategy process. A great strategy retreat acts as a good consensus forum for the strategy planning process. It helps clarify the strategy planning process, the required support and role distribution. Thereafter, a strategy process launch to all staff becomes natural as key strategy champions know their roles in the journey and the kind of support they need from different staff throughout the company.

As Mr Strategy, my advice to the chief executive and the senior people, is not about documenting a strategic plan. Rather, it is an opportunity for the team to relax, bond and soul search. You go to an offsite to examine the appropriateness of the current business model, the new trends, the emerging competition and how to better position to win. Unfortunately, many leaders expect to have concrete strategic choices after a two- or four-day retreat. It is not possible.  As a strategy expert, it is my responsibility to manage retreat expectations. That is why we usually issue a pre-retreat questionnaire to clarify on key issues. In addition to specific company questions, we ask the top leaders the following questions:

Purpose – Why are we having the retreat? What do we want to achieve? This helps manage offsite retreat expectations. I prefer indoor and outdoor team-building activities that have leadership lessons. For example, the “select your team exercise” deepens team bonding, makes people laugh and teaches people to select people with something they have to offer.

People – Who needs to be there?  Will everyone important be able to make it? Most times leaders think that the top executive team must be part of the retreat. That is true if the budget is unlimited. However, if you must select the top 10 to 15 people out of over 560 staff in the company, you need to take people who demonstrate strategic alertness. Technology has democratized ideas. In this era where the customer is beyond being king, to a dictator, you need folks who have interface with the customers. For example, a financial institution must have at least two branch representatives – one from the best-performing branch and the other from the most improving one. When it comes to strategy, analysis is critical to improving the quality of the decisions including who to be part of the retreat.

Place – Where will it take place? Can we set up the space as we like? As Mr Strategy, I would like to be involved in the venue selection decision. You want a place where people will be relaxed and challenged to think not just outside of the box, but far away from the box. Are snacks and meals sorted? What kind of snacks? Imagine taking your best strategic thinkers to an offsite retreat and the food on the menu is restricted. Someone can only have the fresh juice they want unless they pay out of pocket! Seriously, how do you pay USD 250 per day room rent for your staff, and deny them the flexibility to eat what they want?

Preparation — What equipment do we need? Who’s bringing and managing the tech stuff? Have you checked out the hotel projector? The flip charts. Who will provide the markers? If you have facilitated several strategic retreats, you know how most flip chart holders are defective. You need permanent markers on flipcharts, but most people bring fake ones. It makes the experience poor. No one brings manila paper and masking tape, yet these are essential in group exercises.  

Proceedings — Do we need someone from outside to help run things? How will we capture what’s discussed? When confronted with this issue, I look the top executive in the eye and ask: why is it that cars are not made in such a way to inhale their exhaust? An external person helps bring an outside perspective to the conversation. They may not be your specific industry expert, but they understand the strategic planning process and how to give voice to each of the team members without any biases.

Planning a successful retreat is like creating a menu for an unforgettable experience. It’s a chance for us to step away from the usual hustle, connect, and refocus.

The retreat’s agenda must be carefully designed to not only reflect on the company’s past achievements and lessons learned but also to forge ahead with innovative strategies that align with our core mission and values. Throughout the retreat engage in dynamic discussions, collaborative workshops, and insightful analysis, all aimed at propelling our organization towards a sustainable and prosperous future.

What to Expect:

A review of our current strategic and business plans to understand where we stand and the directions we can take. The retreat is a platform for every voice to be heard, ensuring a collective effort in our strategic planning process. Dive deep into areas crucial for the business’s success, including financial performance, stakeholder engagement strategy, organizational structure, and compliance with relevant laws and acts. Together, we will identify strategic initiatives, set achievable goals, and outline clear action plans with designated responsibilities and timelines.

This retreat is not just about planning; it’s about strengthening the team dynamics, understanding the collective aspirations, and committing to a shared vision. Your active participation is key to the success of this retreat and, ultimately, our organization.

Suggested 3-Day Agenda

Day 1: Getting to Know Each Other

Morning: Ice-breaking activities and setting the retreat goals.

Afternoon: Team-building exercises.

Evening: Casual dinner and informal chats.

Day 2: Diving Deep

Morning: Workshops on key strategic challenges for the business

Afternoon: Group discussions to brainstorm solutions.

Evening: Relaxation time or a fun group activity.

Day 3: Wrapping Up

Morning: Action plans and commitment setting.

Afternoon: Reflection session and feedback sharing.

Closing: Summary of the retreat and next steps.

It is important to keep the retreat agenda light to allow for relaxation and channel the brain to serious thinking, team bonding, and rest making the retreat both productive and enjoyable.

Retreat pre-reads checklist


Document Name



Date Provided


Retreat Agenda

Detailed schedule of events, discussions, and activities for the retreat

Ensures participants are aware of the retreat structure and can prepare accordingly

2 weeks before retreat


Strategic Goals Overview

Summary of current strategic objectives and their status

Provides a baseline understanding of the organization’s strategic focus

2 weeks before retreat


Performance Data Report

Analysis of key performance indicators relative to strategic goals

Facilitates informed discussions on areas of success and improvement

2 weeks before retreat


Industry Trends Analysis

Overview of relevant trends and forecasts in the organization’s sector

Helps contextualize strategic planning within the broader industry landscape

2 weeks before retreat


Pre-Retreat Interview Summaries

Compilation of insights and expectations from participant interviews

Informs agenda setting and focuses discussions on participant concerns

1 week before retreat


Participant List and Bios

List of retreat participants with brief biographies

Enhances networking and collaboration by familiarizing participants with each other

2 weeks before retreat


Logistics Information Packet

Details on venue, transportation, accommodation, and scheduling logistics

Minimizes confusion and ensures a smooth retreat experience

3 weeks before retreat


Background Reading Materials

Selected readings relevant to the retreat’s strategic objectives

Prepares participants for deep dives into strategic discussions

2 weeks before retreat


Action Plan Template

Template for outlining strategic initiatives, responsible parties, and timelines

Streamlines the process of converting discussions into actionable strategies

Provided at the retreat


Current Strategic and Business Plans

A copy of the current strategic plan and business plan for the current year

Analyses achievements in the current strategic plan and lessons learned, as well as current business model and ideas

2 weeks before retreat


Stakeholder Analysis

Stakeholders’ analysis and degree of relationship

Understands the interests and influence of key stakeholders and optimizes them for success

2 weeks before retreat


Organizational Structure

Current organizational structure

Understands the organizational configuration for success – how is the organization configured to win

2 weeks before retreat


Stakeholder Survey Feedback

Stakeholder survey feedback obtained in the last three years

Understands critical stakeholder issues and how to address them moving forward

2 weeks before retreat


Financial Performance Report

Financial performance for the past five years

Understands cash flow and budget estimates for implementing the new strategy

2 weeks before retreat


Vision and NDP Contributions

Key areas in Vision 2040 and NDP III that contribute to

Understands the areas the organization contributes to in Vision 2040 and NDP III

2 weeks before retreat


Key Contact Person Details

Specify the key contact person for this engagement; and their contact details like email, phone, and Skype

All inquiries and reports concerning this assignment shall be addressed to the specified contact person

As soon as possible


Strategy Assessment Report

Current strategy assessment report if any

Analyzes the current strategy’s success, failures, lessons, and recommendations

2 weeks before retreat


Key Laws and Acts

Relevant key laws and acts

Ensures compliance with laws and acts

2 weeks before retreat


Risk Assessment Reports

Risk assessment reports to the Board for the last 4 council sittings

Understands what key risks stagnating growth at the organization are

2 weeks before retreat

Remember, what you do two weeks before the retreat is more important than what you do during the retreat. If you take people to an offsite without preparing them, you will not have the data to inform your strategic problem definition. Failure to define the strategic problem leads to a wrong strategy.

Copyright Summit Consulting Ltd, 2024. All rights reserved.

To book Mr. Strategy to facilitate at your next strategic retreat, email sgodfrey[at]summitcl[dot]com or use the contact us form at

Share this

More To Explore


Motivating your staff

How do you get your staff morale through the roof to deliver value and smiles together to the bank? Many leaders think the primary cause of low energy is poor

Share this
Read Article »

Do you want to transform Business?

get in touch