Introduction
This resource is based on a session from the Democracy Resource Hub Learning Series, a series of practitioner-focused learning experiences focused on building civic capacity and local leadership.
This resource introduces one-to-one relational conversations as a practical leadership tool for people working to build civic life in their communities. It comes from the Democracy Resource Hub Learning Series, which brings together organizing, bridge-building, and participatory democracy practitioners to share skills for strengthening democracy and civic life.
In this session, experienced organizers Ben Fink and Roshan Bliss teach how to use one-to-one conversations not just to connect with people, but to understand what they care about and how they might become part of shared civic work. This is one of a three-part series especially designed for place-based civic hub builders and nonpartisan local leaders who are not starting with a defined outcome, but are trying to discover what is possible and needed by building relationships first.
When would I use this?
Use this resource when you want to build civic relationships through intentional one-to-one conversations.
It can help when you are:
- starting a local civic initiative and trying to understand what people care about
- growing participation without simply recruiting people into a pre-set plan
- building relationships across difference, uncertainty, or mistrust
- trying to discover shared self-interest before deciding what work to pursue
- preparing to invite people into deeper civic involvement
- strengthening relationships within a team, network, or community group
This resource is not a script for persuasion or recruitment. It is a practical guide to listening for what motivates people and whether there is a real basis for working together.
What Makes This Approach Different
Many organizing resources teach one-to-one conversations as a way to recruit people into a campaign or move them to take action on a specific issue.
This approach is different.
Here, one-to-ones are used to:
- understand what motivates people before defining the work
- uncover shared self-interest rather than persuade or convince
- build public relationships that can support future collaboration
You are not trying to pitch your project, win an argument, or secure a commitment on the spot.
Instead, the goal is to:
- learn what motivates another
- discover where your interests overlap, if at all
- decide whether it makes sense to keep building a relationship
A successful one-to-one does not require agreement. Even discovering that there is no meaningful shared interest is valuable, because it brings clarity about where to invest your time and energy.
This makes one-to-one conversations especially powerful in nonpartisan civic work, where the goal is not to activate people around a predetermined issue, but to build the relationships that make collective action possible in the first place.
Key concepts
A One-to-One Relational Meeting
A structured conversation designed to build a public relationship rooted in shared self-interest.
An uncommon conversation where we can learn brand new things about people we’ve known for years.
Video: Watch this section of the Webinar
Handout: “One-to-One Relational Meetings” (Ben Fink)
Public & Private Relationships
- Private relationships are based on care, loyalty, and personal connection.
- Public relationships are based on working together to achieve shared goals.
One-to-ones are a tool for building public relationships. Public relationships are not less human. They are simply more intentional about purpose, boundaries, and accountability.
Handout: Public and Private Relationships (Ben Fink)
Self-Interest
Self-interest refers to the values, experiences, and motivations that shape what someone cares about and what they are willing to act on.
Power
This work is also grounded in a practical definition of power. Power is the ability to act together to make things happen. It grows from organized people, shared understanding, and aligned effort.
The Purpose of a One-to-One
A one-to-one conversation has three core purposes:
- To understand the other person’s self-interest
- To discover any shared self-interest
- To determine whether it makes sense to continue building a relationship
These conversations are not open-ended or purely social. They are intentional and focused, even when they feel informal.
Just as important is what a one-to-one is not. A one-to-one is not:
- a pitch for your project
- a recruitment conversation
- a debate or attempt to persuade
- a casual check-in or networking chat
The goal is not to get someone to say yes. The goal is to learn what actually matters to them, and to see whether there is a real basis for working together. In many cases, the most valuable outcome is clarity. If there is no meaningful shared interest, that is useful information. It allows you to focus your time and energy where alignment actually exists.
People may need to experience a one-to-one before they believe it is worth the time.
Video: What is a One-to-One?
How to Run a One-to-One Meeting
A one-to-one conversation follows a simple five-step structure. The steps are straightforward, but the quality of attention and listening is what makes them effective.
1. Introduce yourself
Be clear about who you are, what you are part of, and why you wanted to meet. This sets expectations and establishes the purpose of the conversation.
2. Warm up
Start with what you already know or have in common. Ask a few easy questions and share a bit about yourself in return. The goal is to establish comfort and find initial points of connection.
A simple opening is: “Tell me a bit about yourself. How did you get into this work?”
Don’t jump too fast into depth. Build rhythm, then deepen.
3. Go deeper
Once there is some flow, begin asking questions that explore the person’s story, values, and motivations. Focus on personal stories, not positions or opinions.
You are listening for:
- what matters most to them
- what experiences shaped their views
- what excites or frustrates them
- how they respond to challenges
Use your own brief stories to build connection and to invite deeper reflection, but keep the focus on them.
4. Make a small ask (if appropriate)
If you discover shared self-interest and want to continue the relationship, end with a small, specific next step.
This might include:
- meeting again
- attending an event
- making an introduction
If there is no clear alignment, you do not need to force an ask.
You might discover that there is no meaningful shared self-interest… and that is a successful one-to-one.
5. Evaluate afterward
After the conversation, take a few minutes to reflect.
Ask yourself:
- What did I learn about this person?
- What do they care about and why?
- Is there shared self-interest?
- Should we continue building this relationship?
Do not take notes during the conversation. Capture what you learned afterward.
Tips for strong one-to-ones
- Aim to listen about 70% of the time
- Ask questions that go beyond surface facts into experiences and motivations
- Share your own story briefly to build trust and connection
- Do not pitch your work unless it clearly fits the moment
- Ask who else you should be talking to. Ask for an introduction.
- Focus on the person, not their role or organization
- Practice with your own team before reaching out. Doing one-to-ones with each other builds confidence, clarity and relationships.
Video: 70/30 Rule for One-on-One Conversations with Ben Fink
What You Are Listening for
In a one-to-one, you are not just listening for facts or opinions. Strong one-to-ones depend less on asking the “right” questions and more on how you listen.
At a basic level, you are listening for self-interest: What matters to this person, and why?
This includes:
- what they care about deeply
- what experiences shaped those priorities
- what excites or frustrates them
- what they are already choosing to spend time and energy on
Listening for the story behind the story
People often start with surface-level information about their role or background. Your role is to move gently from the “what” to the “why.”
This might sound like:
- “How did you get into that?”
- “What made that important to you?”
- “Was there a moment when that really clicked for you?”
- “How did that feel?”
These questions help uncover the experiences and values underneath the facts.
Listening for energy and patterns
Pay attention to where the conversation comes alive.
Notice:
- when someone becomes more animated
- when their tone shifts
- when they linger on a topic
- when something clearly matters more than everything else
Over time, patterns begin to emerge:
- recurring themes
- consistent frustrations
- repeated values or experiences
You are not formally analyzing this. You are noticing when something starts to stand out: “There’s something here.”
Listening for shared self-interest
As you listen, you are also tracking alignment:
- Where does what they care about overlap with what I care about?
- Where might we want to work on something together?
You do not need to name this immediately. It is something you track internally as the conversation unfolds.
Being willing to find no alignment
Not every conversation will reveal shared self-interest. That is not a failure.
Discovering that there is no meaningful shared interest is still a successful one-to-one. It brings clarity about where to invest your time and energy.
Letting the other person set the depth
Strong listening means respecting boundaries.
- Follow the other person’s level of openness
- Ask deeper questions when invited
- Do not force vulnerability
A useful guideline is to probe, but not pry:
- go deeper when it helps you understand
- stop when it becomes intrusive
The goal is not to extract information. The goal is to understand the person well enough to build a real relationship.
People do not get the opportunity to be listened to in a deep way very often at all.
Video: Understanding Self-Interest in One-to-One Meetings – Video
What makes one-to-ones hard?
One-to-one conversations are simple in structure, but not always easy in practice. Many of the challenges come from real tensions that leaders are navigating in their work.
These are not problems to solve. They are tensions you will keep navigating as you practice one-to-ones.
Listening vs. recruiting
The tension
You want people involved in your work, but one-to-ones stop working when they feel like a pitch.
The shift
The goal of a one-to-one is not to recruit. It is to understand what matters to someone and whether there is a real basis for working together.
What to do
- Keep your introduction brief and clear, then shift focus to them
- Ask questions about their experiences, values, and motivations
- Pay attention to where energy and interest show up
- Only make a small ask if real alignment emerges
One of the best ways to recruit is don’t try to recruit.
Self-interest vs. selfishness
The tension
The language of “self-interest” can feel transactional or at odds with values like care, service, or community.
The shift
Self-interest is not about being selfish. Self-interest is about understanding what motivates people to take action.
Everyone cares about more things than they have the time or energy to act on. Self-interest helps clarify what actually moves someone to show up.
What to do
- Listen for what someone chooses to spend time and energy on
- Ask about the experiences that shaped what they care about
- Treat self-interest as a source of clarity, not a problem to fix
- Be honest about what motivates you to do this work
A one-to-one relational meeting is a meeting where there is one and only one goal, which is to understand the other person’s self-interest.
Open-ended invitation vs. concrete ask
The tension
You may be building a civic effort without a clear focus, issue or direction yet, which makes it harder to explain what you are inviting people into.
The shift
You do not need to have a fully defined project to start building relationships. One-to-ones are how you discover what work is possible, not just how you advance a pre-set plan.
What to do
- Be honest about where things are: “We’re trying to understand what matters in this community”
- Focus the invitation on learning and connection, not outcomes
- Ask what they care about before describing what you are doing
- Let shared direction emerge over time rather than forcing it early
If you spend 20 minutes explaining what your project is, that is not a one-to-one relational meeting.
Relationship-building vs. getting to action
The tension
It can feel like one-to-ones are slow, especially when there is pressure to move toward visible outcomes.
The shift
One-to-ones are not just how you advance a plan. They are how you discover what the work should be. Without understanding people’s motivations, efforts to activate often stall or fail.
What to do
- Treat one-to-ones as foundational work, not a delay
- Focus on depth of understanding, not volume of conversations
- Use what you learn to identify where real alignment exists
- Follow up with people where shared interest is clear
No two human beings have ever built a relationship based on what they don’t have in common.
Inclusion vs. strategic focus
The tension
Civic renewal work aims to be inclusive, but leaders still have to decide where to invest time and which relationships to prioritize.
The shift
Not every relationship will lead to shared work. One-to-ones help you understand where alignment exists so you can focus your energy where it matters most.
Inclusion does not mean treating every connection the same. It means engaging broadly while making intentional choices about where to build.
What to do
- Have one-to-ones with a wide range of people, especially early on
- Notice who shows energy, commitment, or alignment
- Pay attention to who is connected to others in the community
- Prioritize follow-up with people where shared interest is strongest
Love is stronger than fear, but fear is faster than love.
Download Resources
Videos
Handouts
Download the handouts used in this session:
Session Guide
- One-to-One Relational Meetings GUIDE (PDF) One page introduction and guide for relational 1-1 meetings.
Handouts
- 1–1 Conversation Basic Guide (Ben Fink) (PDF)
Step-by-step guide through the structure of a 1 to 1 Meeting - Nine Principles for Building Broad-Based Community Organizations (PDF)
Broader organizing philosophy behind this approach - Public and Private Relationships (PDF)
Clarifies the difference between relational modes and how they function in civic work - Propositions (PDF)
How to invite others to build power together in pursuit of mutual self-interest.
About the Facilitators
This is part of the Learning Series produced by the Democracy Resource Hub, a project of the Shift Action Lab.
This was the second session of a three-part mini-series, Who, What & How: Foundations for Civic Leadership, designed for people building place-based civic renewal projects.
Ben Fink
Ben Fink led this session as a community organizer and trainer. He has organized in rural and urban communities across the eastern United States, including the Kentucky coalfields, Minnesota, Wisconsin, Baltimore, and Alabama. In this session, Ben brought a broad-based community organizing perspective to the practical skills of building public relationships, identifying self-interest, and using one-to-one relational meetings. Download Ben’s resources here.
Roshan Bliss
Roshan Bliss co-facilitated this session and contributed an organizing and civic engagement lens. He is based in Denver and serves as Director of Democracy Innovations for the National Coalition for Dialogue and Deliberation, though he noted that he joined this session primarily in his role as a longtime community organizer and trainer. His organizing experience includes student debt organizing, criminal justice advocacy, youth organizing, leadership development, and training others to become more effective organizers. Bliss Collaborations
Explore Further
- Identifying Strategic Local Partners: How to Map Relationships and Focus Your Outreach
- Orienting Around Shared Purpose in Diverse Communities
- Related Commons Library resources –