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Actionable best practices for a strategic planning retreat

By Julian Canlas

Companies thrive when they’re guided by clear, mutually agreed-upon strategies. But it can sometimes be difficult to fit high-level strategic planning around day-to-day activities.

Strategic planning retreats bring company leaders and employees together for a few days to discuss core company themes, identify opportunities, and develop a clear roadmap for the future. They allow everyone to take a step back and think about the bigger picture.

In this article, Basejam will share some of the best practices in planning a strategic retreat that will ensure your event is a success.

What is a Strategic Planning Retreat?

A strategic planning retreat is an off-site event that gives an organisation’s decision-makers a chance to build new strategies and concoct plans for the future. It's meant to bring together key members of the organisation and have comprehensive discussions on how to drive company growth and success.

In addition to this main goal, strategic planning retreats also aim to strengthen team dynamics while meeting a set of desired outcomes. This way, you’ll have a cohesive team equipped with the right tactics that can benefit the organisation long-term.

How Can Actionable Strategic Planning Retreat Benefit Your Team?

Opportunity to assess team value contribution to the business

During a strategic planning retreat, team members can take a break from their daily grind and redirect their focus toward the overall performance and direction of the team or company. They can evaluate how well they’re functioning as a unit, determine which areas they’re excelling, and identify areas for improvement.

It’s also a great opportunity to make sure everyone is aligned toward accomplishing individual and administrative goals.

Fostering team cohesion

Strategic retreats are like family reunions.

They allow your team to get together in a relaxed and open environment to reconnect and ground themselves. It’s a chance for team members to loosen up and get to know each other better. Spending time together in a team offsite and engaging in team-building activities during the retreat strengthens your bond, allowing you to trust each other more and communicate openly.

Teams and organisations who have harmonious relationships perform better and are more likely to succeed.

Develop leadership skills

Strategic retreats do not only focus on improving team cohesion; it’s also designed to help team members become people leaders.

Through various activities and training, individuals can improve their decision-making capabilities and develop their leadership skills. This helps create a competent team that can handle their responsibilities well.

Things To Consider When Planning Strategic Planning Retreat

  • Date: It should be set on a mutually agreeable date when everyone could attend, including key stakeholders, managers, and directors

  • Objective(s): Aside from fostering team cohesion and developing leadership skills, objectives should also include organisational matters, such as developing a new strategic plan and reviewing current company performance

  • Duration: Give your team enough time to achieve your objectives, plus extra time for team bonding and activities

  • Budget: Take into account cost per attendee, venue, transportation, food and beverages, and activity-related expenses

  • Responsibility: Assign specific individuals with tasks, such as organising bookings, finding venues, preparing presentation materials, etc.

  • Attendees: Determine who should be included in the retreat;

  • Facilitator: Assign a facilitator to ensure that the agenda is met and that all attendees can participate

  • Location:

  • Meeting facilities: Think about what facilities are needed as well as the size of the room (there should be enough space to accommodate all attendees and activities)

  • Accommodation

  • Catering

  • Recreational activities

  • Data: Decide on what information is required from managers and directors for the group discussions and presentations

Actionable Strategic Planning Retreat Best Practices

Pick a location that aligns with your goals

To concentrate and keep distractions at bay, leaving the office is essential. But not any venue will do—it needs to align with your goals for the retreat.

Start with baseline requirements like your headcount and required facilities. These are great ways to narrow down your search by eliminating venues that don’t fit the bill. Then add in those important ‘nice-to-haves’ like:

  • Climate (i.e., hot, warm, or cold)

  • Nature (i.e., beach, forest, lake, etc.)

  • Available recreational activities

  • Catering options

With Basejam, you have access to a curated list of retreat-ready venues along with information about each one. You can filter your search results based on your location, accommodation style, amenities, number of people, and even reason for retreat. This way, you’ll surely discover a venue that is perfect for your specific needs.

Establish specific deliverables

What do you want to achieve by the end of your strategic planning retreat? Be specific—a clear deliverable (or multiple) will give your team direction and purpose.

Be extremely clear about the goals you have for the occasion. Consider the ideal result and the criteria you will use to evaluate its success. When you have a clear objective in mind, work backwards to create a strategy that will get you there.

Identify who should participate

After defining the objectives and scope for your strategic planning, it's time to identify who should attend the meeting and their roles throughout the event.

Include those who will lead and implement the strategy. Their active engagement before, during, and after the meeting increases the likelihood of a successful retreat. Employee participation is essential at every stage of the planning process, but strategic planning retreats often involve leadership and key decision-makers.

Set an agenda

Make an agenda that addresses all the critical problems identified in your pre-retreat evaluation. Make sure the agenda is open to unexpected debates or new topics. Consider holding break-out seminars to address departmental challenges.

The schedule should also include adequate time to discuss the tasks that emerged from the retreat. Set aside time to create a follow-up strategy to guarantee that the plans discussed during the retreat are effectively implemented.

Design a structured process

It’s time to develop a structured process for the retreat once you have a clear grasp of the objectives, scope, and participants. Plan with specific goals in mind, and decide who will lead each discussion.

While you may be eager to see results, keep in mind that the quality of the dialogue is critical. Aim for genuine participation from all those involved. Create a safe environment in which team members feel comfortable sharing their ideas without fear of repercussions from workplace politics. Also, make sure that no individual dominates the discourse.

Move from the macro to the micro (and then back to the purpose)

Begin your retreat by talking about the broad picture—external forces and your organisation's mission. After that, address your objectives and challenges.

Use cue cards to have a private talk about the challenges. Solve these problems together.

Review goals and actions to ensure they are in line with the mission of your organisation. This method results in a productive and aligned retreat.

Use data-driven insights

When making strategic planning decisions, rely on facts and relevant insights.

To ensure a strong SWOT analysis, conduct interviews and surveys wherever possible. This analysis will give the necessary context for strategic decisions.

Create and use pre-work templates after gathering enough feedback to ensure that all meeting participants begin with an idea of the present situation, difficulties, implications, and objectives. This baseline allows everyone to get started on the same page.

Encourage diverse perspectives

In both small and big group conversations, encourage everyone to speak up. When the loudest voice dominates the discourse, valuable viewpoints might be lost, resulting in bruised feelings and dissatisfaction.

Allowing everyone to contribute allows you to realise your team's full potential. It results in a strategy plan that is not only visually appealing but also effective in attaining your objectives.

Prioritise actionable items

Make a targeted strategy plan by identifying essential initiatives and ranking them in terms of impact and feasibility. Keep objectives manageable to avoid being overwhelmed. To turn goals into actionable tasks, create a detailed action plan with specific phases, responsibilities, and dates.

Document everything

Keep complete notes of all retreat conversations, decisions, and action plans. These records will be useful references in the future. By documenting everything, you can quickly track progress, revisit ideas, and verify that the retreat's conclusions are applied properly over time.

Ready to plan your strategic planning retreat?

Don't pass up the advantages of a strategic planning retreat. Form a cohesive team, hone your leadership abilities, and set actionable goals. By taking a break from your daily work routine and dedicating time to a strategic planning retreat, you can form stronger collaborations, well-defined strategies, and a clear roadmap to your business’ success.

Explore a curated list of inspiring company retreat venues with Basejam and start planning your transformational retreat now!

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