Group Leadership Development Roundtable

Host guide

Group Leadership Development Roundtable

Thank you for hosting a Group Leadership Development Roundtable to strengthen your grassroots group for the future!

As the saying goes, we want to stay ready so we don’t have to get ready. By investing in our teams early and during odd years, we can have the biggest impact possible. Organizing this year might not only look like making calls or knocking on doors to get out the vote; you might focus on establishing or growing your core team, filling a leadership role you realized you needed, gaining and retaining group members, and/or teaching your volunteers new organizing skills. Then when the next election cycle rolls around, we’ll be ready to mobilize quickly and effectively to win those critical elections.

At any point in the planning process, we encourage you to schedule a meeting with your Swing Left regional staff contact. For quick questions and tech help, email our support team at host@swingleft.org.

Start with a reflection

Think back on your work in the last election cycle. What went well for your group, and why was it successful? What were some challenging moments, and why do you think they didn’t work out as well?

Now imagine yourself on September 1 of the next election year. There are 65 days until the general election. You are feeling prepared. You’re meeting your goals for events and recruitment. You have a plan and people in place for GOTV. How did you spend this year so that you’d be ready for this moment? What did you continue, add, or change when you had more breathing room to strategize? What lessons from previous years did you act on?

Consider where you’ve been and where you want to go. Investing in your team now can help you get there. Organizing to win elections is challenging, urgent, fast-paced work, and it can be tempting to skip over foundational steps and go straight into execution mode. But when we take time to step back, strategize together, reconnect with our purpose, and get the right people in place, we’ll cultivate effective teams that last.

Event logistics

Select a date, time, and location. Whether you’re doing virtual or in-person will impact your invitation and agenda, so consider your options while you’re planning out the event details. We recommend hosting in-person if that’s feasible for your group!
Invite current and/or prospective leaders. Once you have a general idea of what your event will entail, you might invite active volunteers you want to move into leadership roles, along with members of your current leadership team if you have one.
- Tip: If you’re focused on getting certain volunteers to take on more/new responsibility, send them a personalized invitation including why you’re asking them to join the conversation.

Plan your roundtable

With your reflections in mind, map out the agenda for your event. Every group’s roundtable will be different, so be sure to set aside enough time to take in the resources and suggestions below to create your own unique plan.

We’ve put together three examples; we know you might not fit neatly into one of these categories, but we are confident that you can pick and choose to build an effective event:

You’re a solo group leader looking to build out a core leadership team

Roundtable purpose: Establish a leadership team for your group moving forward, with roles that will help achieve your group’s long-term vision.

Articulate team purpose
Identify your team’s strengths
Draft initial team structure, roles, and next steps

Why spend time building a core leadership team? No matter how talented, passionate, and committed you are, no one can do this work alone year after year. Putting together a strong team can enable you to scale sustainably and increase your impact.

Consider in advance:‍ ‍

What is the purpose of your Swing Left group? In general, what are you working toward? What does your ideal group look like in a few years?
Based on that, think about who might be a good fit for your leadership team. Who has the skills you need to contribute to the team’s purpose? Who would bring a unique perspective to the table? Who has been a reliable, collaborative teammate in your previous work together?
If you do add members to your leadership team, what next steps might you take together in the short term?

Suggested activities:

Here are a few ideas for you to work from! This is not meant to be a strict agenda or set script; please take it in whatever direction you think will be best for your group. See the sample slide presentation for corresponding slides that you can customize. If you want to facilitate your roundtable without slides, that is perfectly fine!

‍ ‍

Opening

Welcome: Introduce yourself, go over the agenda for the event, and most important, share why we’re here today. Review Swing Left Community Agreements.
Icebreaker: Choose a prompt or activity based on what makes sense for your group. If everyone is already close friends this will look different from if folks haven’t gotten to know each other yet.
Swing Left strategy: Give your attendees a high-level overview of what Swing Left is all about so we’re all on the same page before we begin.

Ground the conversation in your team’s purpose

Your purpose should feel consequential, challenging, and clear. Consider using the format “Our team exists to…by doing [key pieces of work you do]...so that [your impact!].”
If you already know some of your group’s plan for the year, you can include a preview of that as well.

Asset mapping: Find out what strengths and superpowers are in the room

Individual reflection: Have each person write down what knowledge, skills, mindsets, and behaviors they possess that might be an asset to the team’s purpose. Hard skills (such as Excel, photography, event planning, Mobilize, etc.) might come to mind first, but remind the group to think outside the box: being a fast learner, outgoing, or an eternal optimist, and having a lot of free time, connections to local community groups, access to a free event space, etc. are all valuable assets to share.
Share out: Have each person verbally share what they wrote. If you’re meeting in person, you could have everyone write their name/asset on individual post-it notes and put them up in different categories on walls throughout the room, and then do a “gallery walk” where everyone gets up to look around.
Discussion: Acknowledge the amazing wealth of knowledge and skills that already exists in your potential team. Share what you’ve been thinking about in terms of how you might structure a leadership team, and why, drawing on lessons learned from past election cycles. Lead a conversation on how we can take the group’s assets and transform them into team roles that are (a) critical to the success of the team, and (b) leverage each person’s strengths. Help attendees think creatively about their own potential: someone who doesn’t use social media, but has said they’re a good writer and tech savvy, could be interested in becoming a digital organizing lead, even though they don’t have the exact experience yet.

Put it all together

Recap the discussion and determine if you can make any decisions regarding team roles (what a role entails, and who will fill it). What decisions are you able to make today? What information is needed to decide on anything outstanding? Remember to read the room! Make sure anyone committing to a new role doesn’t feel like they’re being put on the spot. Consider doing a pulse check and encouraging each person to share how they’re feeling about any decisions.
Share how you plan to communicate as a team moving forward, if applicable, and seek input from your new team on communication processes (email vs. text chains, meeting cadence, etc).
Outline how you’d apply your new (or potential) team structure to your group’s next action. For example, if you are planning an upcoming event or action, give each person a preview of what their role might look like for that initiative.
Close with gratitude! Thank your attendees for going through this process with you; consider inviting each person to share their closing reflection.

Resources: This content is, in part, adapted from outside sources. Dive deeper into each subject by visiting their websites.

PowerLabs: Designing powerful teams with Ruth Wageman

You’re leading a well established group with a solid core leadership team in place

Roundtable purpose: Set goals for the year that ladder up to Swing Left’s long-term strategy of building democratic power and electing Democrats at the state and federal level.

Revisit your team’s purpose
Practice strategic goal setting
Begin drafting this year's plans

Why spend time setting goals as a team? Goals drive results. Aligning on goals with your team gives you a way to define success and make decisions that will get you there. Setting—and meeting—goals also helps you show off your impact and inspire volunteers to join or continue engaging with your group.

Consider in advance:‍ ‍

What is the purpose of your Swing Left group? In general, what are you working toward? What does your ideal group look like in a few years?
What do you already know about your group’s goals? If you’ve done strategic planning or goal setting in the past, locate those and determine if they’re still relevant or need updating.
What has helped you meet your goals (formal or informal) in the past? What has prevented you from meeting your goals? Did you have the right people in place? If you fell short of a goal last year because you did not have volunteers or leaders skilled in a certain area, consider who from your group you could invite to contribute.
Suggested activities:
Here are a few ideas for you to work from! This is not meant to be a strict agenda or set script; please take it in whatever direction you think will be best for your group. See the sample slide presentation for corresponding slides that you can customize. If you want to facilitate your roundtable without slides, that is perfectly fine!

Opening
- Welcome: Introduce yourself, go over the agenda for the event, and most important, share why we’re here today. Review Swing Left Community Agreements; if your group has its own agreements or norms, highlight those as well.
- Icebreaker: Choose a prompt or activity based on what makes sense for your group. If most of your attendees already know each other well, use this time to make sure any prospective leaders feel comfortable and included.
- Review existing strategic plans: Give your attendees a high-level overview of what Swing Left is all about—and how your group has contributed to the work in years past—so we’re all on the same page before we begin.
Visioning exercise
- Ground the conversation in your team’s purpose. Your purpose should feel consequential, challenging, and clear. Consider using the format “Our team exists to…..by doing [key pieces of work you do].....so that [your impact!].
- Individual reflection: Ask the group to imagine themselves in September of the next election year. The primaries are over, the conventions have finished. How do they want to be feeling? What do they want to be doing? Encourage everyone to write a few bullet points, focusing on what’s within their control. Give an example that is true to you; for example, “I feel heartened that our group is part of a local coalition this year working with 3-5 other chapters/organizations on many of our voter contact events; I feel proud that two of the new volunteers I recruited through tabling and trained on phone banking in the last year are now hosting their own weekly phone banks for GOTV.”
- Share out: Ask everyone to share what they wrote. Set a norm for how you’ll respond (snaps, claps, emojis, etc). If you’re in person, you could get creative and have attendees write on post-it notes or butcher paper so that all of your reflections are displayed together. As the facilitator, note common themes (and tensions, if there are any!).
Setting strong goals for this year
- Taking into account Swing Left’s mission, your team’s purpose (and previously set goals, if applicable), and the themes you’ve heard from your team, transition the conversation toward goal setting. What do you want to accomplish this year to set your group up for success in the next election cycle? First you’ll spend time setting goals, and then you’ll begin determining how you’ll work toward those, including responsibilities and next steps.
- Explain what makes a good goal. We recommend using the SMARTIE acronym: Strategic, Measurable, Ambitious, Realistic, Time-bound, Inclusive, and Equitable (sometimes listed as Specific, Measurable, Achievable, Relevant, Time-bound, Inclusive, Equitable). Many organizations have recently changed SMART to SMARTIE to add "Inclusive" and "Equitable" as criteria for effective goals. Give examples of a vague goal vs. a SMARTIE goal (available in the sample slides).
- Brainstorm: Getting suggestions from the group, start a short list of general goals you want your group to accomplish this year.
- Drafting: Either in pairs or individually, depending on the size of your roundtable, assign people (or let them choose) to transform each goal idea into a SMARTIE goal to the best of their ability. For now, focus on the high-level goal statement; we’ll get into the specific plans for how we’ll achieve each goal in the next section. Option: See examples in the slide deck, and print this worksheet (one per goal) or have your attendees make a digital copy.
- Discussion: Have each person/pair share what they drafted. Workshop each goal as a group. Keep the conversation moving so you can touch on each goal; it’s OK to leave some placeholders for the owner of the goal to figure out later. If possible, try to create a way for everyone to visually see what’s being discussed and recorded, whether that’s a google doc you’re sharing on the screen, or butcher paper on the wall.
Next steps: Planning for this year
- Discuss how your new goals line up with your existing team structure and actions. Who will be responsible for what, and what activities will help you achieve each goal? Depending on your team’s existing structure, this could be immediately obvious. But it might warrant some discussion to clarify and get everyone on the same page about next steps.
- Start to come up with a realistic plan to achieve each goal (tactics and activities, based on your team’s personnel, time, resources, and capacity). Use these plans to come up with a loose timeline for your group overall.
- Recap the decisions you made and ensure everyone knows what to expect—and what’s expected of them—based on today’s session. Attendees might have immediate next steps, or items to follow up on with others in the group.
- Close with gratitude! Thank your attendees for going through this process with you; consider inviting each person to share their closing reflection.
Resources: This content is, in part, adapted from outside sources. Dive deeper into each subject by visiting their websites.

You’re leading a group with newer leadership, or one that experiences turnover

Facilitating your roundtable

Prepare your materials:

Fill out this blank agenda template (make a copy) with your planned “run of show” for the roundtable and any talking points or notes you’ll need to facilitate. Ensure your planned activities (and breaks!) can be completed within the timeframe of the event.
If you’re using slides, make a copy of this sample slide presentation. Carefully read the instructions on the first slide; then customize, delete slides that don’t apply to you, and add additional slides as needed.
If your event is in person, determine if you need to print any worksheets or other materials. If you need attendees to bring their laptops to access activities digitally instead, remind them to do so; consider accessible alternatives for anyone who does not have their own device.
Facilitation tips:
- Make it fun! You’ll be covering serious topics that you all care deeply about, so it’s important to remember to set a joyful tone. Build in an ice breaker or two, encourage mingling during breaks, and keep the environment energetic and upbeat.
- Share the “why” behind what you're asking the group to do. If your attendees understand the purpose of each exercise, they’ll be more likely to stay engaged.
- Set clear meeting norms—even if it’s a very small group—and stick to them. As the facilitator, you can model the norms and call back to them whenever you need to so you’re able to keep the meeting on track.
  - See examples of norms for both in-person and virtual meetings in the sample slide presentation.
- Create an inclusive and respectful environment. Do your best to make sure everyone’s voice is being heard, opinions are being interpreted accurately, and different learning styles are being taken into account. Consider these techniques:
  - Repeat back: When someone gives their input, summarize what they’ve said before moving on. When you recap by saying something like, “What I’m hearing is _____. Is that right?” that both helps the group understand the speaker’s point and also gives the speaker a chance to correct anything that might have been misinterpreted.
  - One-minute reactions: Some people can hear new information and react immediately; others need more processing time before speaking up. If you want to give everyone a chance to react to a big idea or decision, set a few minutes of individual reflection/writing time, and then go around to give each person 60 seconds to speak uninterrupted (if they wish) to share their thoughts.
  - “Fist to five”: Whether you’re sharing a new concept or recapping a decision, getting a pulse check on the group is a good way to know if everyone is ready to move forward. Ask the group to indicate their comfort level on a scale of zero (fist) to five. If anyone ranks themselves a 0-3 let them speak to their concerns and ask what might get them to a 4-5 on the scale.
  - Call out the speaking order: If you ask for input and three people raise their hands, call out “we’ll go to Jennifer, then Robert, then Jamie.” That way attendees aren’t anxious about being heard, and they can focus on fully listening to one another.
- You don’t have to be perfect! These roundtables will include lots of live discussion that can’t be perfectly mapped out in advance. Mentally prepare for having to adjust on the fly. You might not get through the exact agenda you planned, and that’s OK! Your attendees should be a small group of current or prospective volunteer leaders, just like you—this should feel like a supportive environment to try new things together.

After your event

Send a follow-up email to your attendees to thank them for joining. If applicable, synthesize notes from roundtable discussion. Reiterate new commitments and priorities the group decided on, plus any next steps the team or individuals should take.
Consider individual followup to any attendees who agreed to take on a certain leadership role, plan an upcoming event, etc. to ensure they're set up for success in the near future. In addition to getting support from you, they can always reach the Swing Left team at host@swingleft.org.
If you need to schedule a follow-up meeting to finish your discussions, get that on the calendar as soon as possible and collect RSVPs.
Debrief with us! Let your Swing Left staff organizer know how your roundtable went, and any support you need for next steps. Schedule a meeting through this link.

Next steps

Whatever decisions or changes your group makes during or following the roundtable, there might be next steps you’ll want to take soon after. Some action items to think about:

Did you determine new goals and priorities? Update your Group Builder page and customized welcome email (found under the “Email members” link in the Leader tools section on your group admin page) so current and prospective group members can know what you’re all about this year.
Did you add new volunteers to your core leadership team? Visit the “Manage Members” tool on your Group Builder page and click “Add leader” to add their photo/name/contact to your group’s homepage. And remember to change their role from “basic member” to “core member” under the “Manage Members” tool in Group Builder so that any events they create on Mobilize will appear on your group’s page; if they’ll need admin access to Group Builder (to send emails, manage volunteer data, etc.), make them an “admin” instead.
Communicate relevant news to your full group: Share the news of any new team leaders, refreshed strategy focuses for the year, opportunities for them to connect with you, upcoming ways they can start working toward your group’s goals, and beyond.
Keep in touch with any team members who agreed to take on new responsibilities. Work with them to make sure they feel set up for success.