Six LION members share the secrets to a great staff retreat

LION members who operate mostly remotely (but also in person) are increasingly using team retreats to strengthen work culture and align on strategic decisions. Based on the experiences of six LION members, we offer a brief guide for those who want to invest in this strategy. Bonus: Some of these recommendations can also work in an online environment. 

This post is part of a series of articles that will offer in-depth overviews of actions LION members are taking to strengthen their internal operations.

Does your organization need a team retreat?

After two and a half years of years of rapid growth, CivicLex hosted several staff retreats to reorient their organization’s operations, revenue, and impact strategy to their new scope. “We’ve grown quickly,” said Richard Young, executive director of CivicLex, “and we needed to pause to improve our work culture and operations.”

The organization stepped back and assessed how they could better support their staff and increase efficiency. “Through a series of three all-staff retreats – including a four-day operations retreat – we covered pain points related to burnout, goal setting, professional development processes, communication styles, job descriptions, and more,” Richard said.

In-person retreats serve several purposes: they help improve work culture, reduce barriers created by the nature of remote work, foster trust among colleagues, and advance strategic conversations that can happen more quickly in person. They also provide an excellent opportunity for professional development and to create a shared language across the team.

However, a team retreat isn’t always the answer. If not done properly, it can result in wasted time and resources. If your team simply needs more in-person time to have fun and get to know each other, consider planning a short social hour.

Before moving into the planning process:

• Assess team dynamics: If your team operates mostly remotely and is experiencing communication challenges or a lack of cohesive culture, a retreat might be beneficial. It can provide a space for open dialogue, improve transparency, and address misunderstandings. Additionally, if there’s a noticeable disconnect among team members, a retreat can help build stronger relationships and foster unity. 

• Check on strategic needs: If your organization is undergoing significant changes or needs to align on major decisions, a retreat can provide the necessary environment for deep discussions and planning. If there are discrepancies in understanding or alignment around the organization’s goals and objectives, a retreat can help ensure everyone is on the same page.

• Assess leadership readiness: Ensure your leadership is committed to the retreat process and is open to self-reflection and growth. Leadership’s readiness and willingness to engage in meaningful dialogue and development are crucial for the retreat’s success.

“At 2Puntos, we work completely remotely,” said Emma Restrepo, founder of 2PuntosPlatform, “and we have team members located in Colombia and Philadelphia.” Last year, they added new employees and were experiencing communication problems. On top of that, “leadership thought that everything was urgent and important,” Emma recognized, which added a new layer of stress to the team. So they organized a one-day team retreat in Colombia focused on planning strategically to execute the goals for this year, taking into account bandwidth across the team. They also incorporated some training on prioritization skills.

Planning and setting the agenda

Now that you’ve decided that a retreat is the right choice for you, the next step will be carefully planning the agenda. 

Start with your goals: What do you want to accomplish during the retreat and what does success look like for the organization? 

One of the most common mistakes we often see at LION is a jam-packed agenda coming from a scarcity mindset. I get it: organizations feel they need to fill every second of the time they’re spending in person to make the investment worthy. But remember, an in-person retreat is not a luxury, and if done right, this exercise can save you time and money down the road.

For Santa Cruz Local, their first retreat was all about strategic planning. They ran surveys, interviews, and focus groups with their members, partners, major donors, staff, and board to understand what kind of impact they wanted and how aligned their products were with the community’s needs. “We ended up doing two retreats,” said Kara Guzman, executive director of Santa Cruz Local, “to set a clear vision for the future grounded on feedback from our staff and the board.” 

Although Santa Cruz Local started in 2019 as a bootstrapped organization, they doubled their staff in 2023 from three to six full-time employees. “We grew our major and mid-level donor programs, became a non-profit organization, launched our Spanish service, and started conversations with foundations that would ask us: What would you do with $1 million?,” Kara said. They were paired with LION analyst and coach Bene Cipolla as part of the Sustainability Audit program, and they started to think about what the next five to 10 years would look like.

Broadband Breakfast underwent a similar journey. “We cover infrastructure and the impact of access to broadband on people’s lives,” said Drew Clerk, CEO of Broadband Breakfast.  After receiving a Sustainability Audit facilitated by CalMatters CEO and LION board member Neil Chase in November last year, the four-person team did a one-day online team retreat with the goal of refining their product to focus on their most profitable targets and rework their audience development strategy, both recommendations they received as part of their Audit.

What we’re learning from members like Broadband Breakfast and Santa Cruz Local is that it is beneficial to break down your goals into an actionable agenda and outline the main activities related to those goals each day. You may also want to include a mix of work sessions, team-building activities, and free time. But also, be aware that you’ll need to build some time to allow for spontaneous discussions and adjustments based on new insights that emerge at your retreat.

If you’re having trouble finding specific activities, here are five from our members that you can steal and adapt:

1. Speed discussion on projects for next year: CivicLex used 10 consecutive minutes to briefly discuss their project focuses for next year. The goal was not to plan anything, but to have the lead for each project explain their goals and give staff a chance to add, subtract, and ask questions.

2. Organizational health check-in: A simple transparency action like sharing the current stage of organizational finances can go a long way in building trust. “We are beginning to share ‘State of the State’ quarterly meetings where we check in as a team to review financial data and community impact, alongside priorities for achieving our top three organizational goals,” said Sonya Wierzowiecki, director of development at Fort Worth Report. 

3. Hear from leaders from other news organizations: “As the CEO, a big part of my job is looking at industry best practices,” Kara Guzman said, “including forming relationships and partnering with others.” They decided to host a Q&A with Bene Cipolla and Nicolas Rios, audience and community director at Documented, to talk about impact and audience development. “The retreat was a great time to show our board and staff what is happening with the rest of the industry,” she said.

4. Mission and values alignment across the team: At their first all-staff retreat in June 2023, the MLK50: Justice Through Journalism team created their organizational values. “We brainstormed together, talked through what came up, and then narrowed them down together,” said Lupita Parra, development director at MLK50. They broke into teams, and each team worked on one value. Then, each team presented their work in front of everyone, and they workshopped it together. “This activity really kept giving because it helped to put a framework around a lot of our work from that point forward,” Lupita said.

5. Kiss and Kick: 2PuntosPlatform’s team put the names of every team member on a flipchart and made two columns: Kick and Kiss. Kick was for things that weren’t working, and Kiss was for things that were working. “When the activity was finished, we reflected on the solutions and what we could do to make our work culture better,” Emma Restrepo said.

Remember that a good agenda should have a mix of:

• Welcome and orientation activities: Start with a fun icebreaker or team-building activity followed by an overview of the retreat’s purpose. “We split up into teams to decorate and build gingerbread houses,” Sonya said, “then displayed them in the newsroom with the top three receiving recognition.”
• Work sessions: Schedule focused discussions on strategic topics. Those could include solo reflection time, time in pairs, whole group discussion, and collaborative work.
• Team-building activities: Include exercises to strengthen relationships and trust.
• Breaks and free time: Allow for downtime to recharge and make space for informal interactions.
• Reflection and wrap-up: Conclude with a session to summarize key takeaways and action items.

Budgeting your team retreat

When calculating the cost of your retreat, take into account:

• Venue: Rental fees, equipment, and any additional costs. Consider local universities and their event spaces for hosting the retreat.
• Travel: Transportation for all participants.
• Accommodation: Lodging expenses.
• Food and beverage: Meals and refreshments. Consider budgeting enough for a nice lunch, snacks, and beverages. 
• Materials and supplies: Any needed items for activities and sessions. Newsroom swag is always a perk, and there could be co-branded sponsor opportunities.
• Facilitation: Costs for hiring a professional facilitator, if needed. LION will launch an Expert Network soon where you can find and hire some amazing facilitators.

If you decide an in-person retreat is the right choice for your organization but would like to cut costs, you might explore partnering with universities in your area. They could offer free or discounted rates for co-working spaces. If most of your team is based in a particular city, consider holding the retreat there to minimize travel and lodging expenses. “Last year, some friends allowed us to use a university room to hold our work sessions,” said Emma. To reduce costs, they also stayed in an Airbnb.

Another way to cut costs is to explore potential revenue strategies. “Including newsroom swag is always a perk,” said Sonya, and “there could be co-branded sponsor opportunities there.” Fort Worth Report’s team also recommends exploring with the board or single donors who might wish to sponsor one specific activity like a lunch.

But if this is totally out of your budget, you can also adapt some of the dynamics of an in-person retreat to an online environment. Broadband Breakfast hosted a remote-accessible team retreat for little to no cost via Zoom. “I worked on the agenda,” said Drew, “shared our Sustainability Audit report along with other materials for reference, and we used half a day to discuss online.” They recorded the meeting and distributed it to team members who could not attend.

Take a heads-down (meeting-free) day or week and get some of the same work done via an online tool like Zoom or Google Meet. If digital is the best route for you, explore including fun activities, maybe hiring a company to host an online celebration to infuse fun and build camaraderie.

When to use an outside facilitator

Some organizations prefer to hire an outside facilitator to help with challenging conversations, and it’s no surprise that most of those sessions address work culture. After auditing 314 organizations since 2022, we have found that almost 80 percent of news leaders feel they often or always have an unreasonable workload. Only five news leaders said they never have an unreasonable workload. Take a second to digest that number. Five.

As for staff, 31 percent of news leaders mentioned that their staff always or often has an unreasonable workload.

“An outside facilitator naturally brings an outside perspective,” said Bene. They can help introduce new approaches for a retreat as well as introduce new directions for staff. “Sometimes even hearing the same tune from a new voice can feel revelatory!” she said.

Consider an outside facilitator if:

• You need an unbiased viewpoint to mediate discussions and navigate sensitive topics.
• You’re addressing complex or contentious issues that require specialized knowledge or experience.
• You need to boost participation and ensure that all voices are heard.
• Your organization lacks the internal skills or experience to effectively facilitate a retreat.

When looking for a facilitator, Bene recommends considering someone “with a strong sense of empathy and compassion, who can bring people into conversations in myriad ways.” She also suggests taking into consideration that “this person will need to work to build trust with the team at the outset, while staying aware of healthy skepticism and productive conflict.”

As part of their BUILD grant program from the Ford Foundation, the team from MLK50 hired Marlo Barrera Consulting to assess internal culture and host their staff retreat. The consultant conducted internal empathy interviews and identified all-staff training and ways to improve internal communication. “I do feel it was important and a huge help for us to have this kind of support,” Lupita said. Marlo ensured that all staff input and voices were included in the planning process. “Marlo’s conversations with staff ahead of the retreat seemed essential to setting goals and parameters on what we would be discussing,” Lupita said.

How to measure success and implement next steps

It’s time to go back home. Every retreat should be followed by a carefully planned evaluation and follow-up strategy to ensure that what happens at the retreat doesn’t actually stay at the retreat. “This is the hardest part,” said Richard. They have implemented 70 percent of what they surfaced at the retreats, including setting up some systems and processes responsive to staff needs. “But we need to acknowledge that this is a work in progress,” he said.

After their first all-staff retreat in June, MLK50’s leadership team worked with their facilitator to define next steps. “The facilitator gave staff the option to have a coaching call on the topic of their choice,” Lupita said. They could select any topic they felt they needed to work through or get more guidance on, and they implemented an all-staff weekly meeting.

Consider some of these actions:

• Survey your staff to assess how well (or not) you achieved your initial goals.
• Host a debrief session with your outside facilitator to identify common trends and recommended actions. 
• Create a working document and a plan to move forward.
• Establish regular check-ins individually and in team meetings to track progress toward retreat goals.

No matter how small or big you want to go, consider a retreat. 

MLK50 has a shared language to talk about their work and mission. 

Santa Cruz Local reports they are aligned on impact, what it means for their organization, and how they will measure it. 

Broadband Breakfast took a series of tactical steps that streamlined their editorial process, including adopting a new content management system. 

2PuntosPlatform initiated a ruthless prioritization strategy that improved their work culture considerably. 

And Fort Worth Report has a shared understanding of the company’s growth plan and a clear vision that has united and inspired team members who feel empowered and included.

What could your organization uncover and address?

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If your team has done a retreat in the past and you want to be featured in a LION post, please reach out to Elaine Diaz at [email protected]. If you’ve taken other steps to strengthen your internal operations, I’d like to hear from you.