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Building an Effective Leadership Retreat 101

A disconnect at the leadership level of an organization can result in misaligned goals and decreased productivity that will trickle from the top down. An organization’s leaders have the responsibility to set expectations. Still, since this is a significant undertaking and they often have a busy work schedule, leaders need designated time to discuss these high-level thoughts, work towards a shared understanding, and build their relationships with each other.

That is why leadership retreats are critical to building high-functioning teams.

A leadership retreat is classified as a gathering of members of a team whose work is interrelated. Typically, these are peer colleagues that all report to the same person.

Leadership retreats offer an opportunity to celebrate the organization’s successes over a given period and reflect on what has been achieved by teams, individual contributors, and the organization overall. These retreats can take on various forms, but typically, they are at least one day long and held offsite (not in the company office).

Benefits of a Leadership Retreat

The main purpose of a leadership retreat is to provide the time and space to build a shared understanding of where the organization is heading, define the steps needed to get there, and determine what will be required of the team. As a forum to “think together,” participants in these retreats hear multiple perspectives and create solutions to help achieve strategies and objectives. It also builds the connection between people, purpose, and perspectives and gives your leadership team the space to develop more meaningful relationships and establish trust. You’re nurturing the organization’s culture by learning and growing with one another.

Improving communication within the direct team allows them to cascade a consistent message and direction throughout the company. The result is increased overall effectiveness as a team, which often leads to the achievement of objectives, better results, and higher productivity.

How To Prepare

A retreat starts before it has even begun. The lead-up can often dictate the participants’ experience and mindset. Having pre-work will help set the stage for what the retreat will be about and create momentum leading up to the retreat. One way to do this is by sending out the agenda to participants before the retreat, so they know what’s in store for them and can build their excitement and interest.

You should also head into a leadership retreat with a specific goal. Figure out beforehand what topic(s) you will focus on. A popular subject is strategic planning, which can include things such as:

  • Envisioning the future for the organization.
  • Examining the current state of the business and analyzing internal strengths and weaknesses. Consider the external pressures and competitive threats that your company is or will be navigating.
  • Discussing and determining strategies to achieve company goals.
  • Building a roadmap that identifies key priorities, goals, and objectives; often this is built out using a three-year framework (short, mid, and long-term).
  • Developing or enhancing the company vision, mission, and values.

Another popular subject is team effectiveness and development, which could include doing a team assessment—evaluating strengths, exploring team dynamics, and learning more about each other as individuals and the collective team.

But ultimately, it is up to you to find and focus on a topic that works best for your organization and leadership team.

Executing a Productive Retreat

A key part of an effective retreat is having multiple modalities for learning. This includes individual “think time” and self-reflection, group work, multiple media modes (audio, video), or guest speakers (customer, key partner or stakeholder, or a subject matter expert on a topic that is relevant to the agenda objectives).

If possible, retreats should happen offsite rather than at the office, as a different environment can create space for innovation and creative thinking and minimize disruptions.

Working with a facilitator who is skilled in group facilitation and not directly tied to your company enables you to create a meaningful agenda, discuss key goals, and focus areas. Also, having an outside facilitator allows all team members to actively participate, including your organization’s leader, so they have the space to be vulnerable, share openly what is on their mind, and brainstorm with the group.

But it shouldn’t all be serious; it’s helpful to build in time for a group activity unrelated to the actual agenda—something fun the team can experience together. Often this is done the night before the retreat or, if multiple day retreat, on an evening other than the last day. You want the activity to be something that all can easily participate in, so be cautious about the type of activity you select. It is important to avoid unintentional consequences where someone cannot participate.

You should clarify the next steps during the retreat through good action planning (what, who, when, why, and how). With this clear action plan, you can move forward with actionable steps to improve your organization.

Frequent Mistakes and How to Avoid Them

  • Trying to “boil the ocean.” Often, employers try to accomplish anything and everything. Packing the agenda with unrelated items or topics that are more informational than discussion-based wastes valuable time. Leadership retreats are not meant to address all the problems of an organization; rather, you should have clear objectives of what you want to achieve and why. Focusing on these key objectives will help guide the conversation and keep you from talking about things that participants can otherwise discuss in another setting.

  • Forgetting to build in multiple breaks. Leadership retreats require a lot of mental and social energy. Therefore, breaks are necessary to have a productive discussion and avoid burnout.

  • Not having suitable materials and resources for participants and the facilitator. Prepare for the retreat by having a good room set up with audio and visual capabilities, making sure there’s space for group breakouts, food and drink, and paper and pens for participants to take notes. Ideally, you should avoid having laptops at this meeting to avoid distractions, which include those from back at the office. Unless there’s an emergency, participants should remain focused on the retreat.

  • Underestimating the amount of time that a topic will take or just hitting a topic at the surface level. This typically happens if there are too many topics included in the overall agenda, which limits participants from fully providing their input and brainstorming how the information should be incorporated into their work ahead.

  • Designing an experience that is a “tell” and “present” vs. creating an environment that brings out the voices and perspectives of the participants. You want to engage people in a way that they know their ideas matter; they are comfortable discussing meaty topics and feel safe in discussing past failures in support of strategizing for the future.

  • Assuming that the participants know each other well. Just because you are on the same team as others (maybe even for many years), it doesn’t mean you understand what makes them who they are and what motivates and demotivates them. Taking strides to get to know each other better is critical to a high-functioning team.

  • Having a “one and done” mindset. Retreats often are a launching point towards creating a direction and strategy, and building on what was covered, discussed, and agreed upon at the retreat is integral. Retreats can create momentum and movement and energize the participants, but you still need to continue doing the work afterward. Catalog the information discussed, by assigning a note taker at the beginning of the retreat. After review of the notes, distribute them to the rest of the retreat participants.

Defining Success

The success of a leadership retreat has a lot to do with the leader of the team. Retreats are not simply a “check the box” activity. The leader needs to model what they expect from their team and roll up their sleeves. In other words, the leader needs to be an active participant and not a passive observer. The leader needs to be invested in the topics, hearing from others by encouraging active discussion, leading to overall outcomes. Ultimately, the leader should role model what they expect of others.

Speaking from personal experience as both a participant and a facilitator, I determine success as when the participants walk away with more clarity and a sense of ownership and line of sight to how they will contribute to the success of the overall team and company. If you can create the sense of an “all for one and one for all” mentality and commit to achieving your goals together, you have invested your time well.

Archbright has expert facilitators, including myself, ready to facilitate your next retreat. Contact us at info@archbright.com for more information or to get the planning process started.

Picture of Julie Bogue-Garza

Julie Bogue-Garza

Julie is a seasoned HR leader, coach and business partner with a successful track record of over 20 years partnering with leaders and their teams to build and sustain strong performance and increase individual, team and organizational effectiveness. Julie is passionate about developing people and engaging professionals to leverage their strengths and deliver their best work. Julie has extensive experience in leadership development and coaching, team, leadership and organizational assessment, talent management, change management, recruiting and onboarding strategy and performance evaluation systems. Julie joined Archbright in July of 2016 as an HR Consultant and prior to that has held a variety of HR leadership roles in banking and financial services and health care. Julie has an undergraduate degree in Liberal Arts from University of Puget Sound and is a certified Professional in Human Resources (PHR).