The Art of the “One-on-One”

John O’Reilly reflects on this fundamental organizing tool, and how to do it right

The one-on-one meeting is the quintessential tool of the organizer. The one-on-one meeting is used so frequently in organizing campaigns that it’s usually abbreviated by organizers tired of typing it out (such as myself) simply as the “1on1.” To understand what makes a good 1on1 happen, it’s worth delving into detail about some components which make up the 1on1 and how to understand them.

For the inexperienced organizer, the 1on1 often seems scary. Too scary, in many cases, for them to attempt it seriously. The inexperienced organizer then takes two possible approaches: in one, they under-emphasize 1on1 conversations and rely instead on informal meetings and hang-outs to take their place. In the other, they attempt half-hearted 1on1s that don’t really do the practice justice.

There’s plenty of wisdom about why organizers should avoid informal hang-outs as their primary organizing tool, so I won’t bother repeating that here. But the half-hearted 1on1 is far more pernicious because it’s harder to spot. By identifying the half-hearted 1on1, we can see clues that will push us to see what the good 1on1 looks like instead.

The half-hearted 1on1 looks on the surface like a good 1on1. It takes place in a location comfortable to the worker and the organizer. It has a clear starting time and perhaps a clear established topic: to talk about work. The organizer and the worker are both sober. The organizer has a list of topics that they suspect the worker has grievances around, but is planning on letting the worker lead the way. On its face, it seems like it’s going to go well.

Following the time-tested approach of AEIOU, the organizer leads off the conversation with Agitate, the first piece of the puzzle. They ask the worker about their grievances. They follow up with open-ended, clarifying questions about the grievances to better understand them. They get the worker talking quite openly about all their specific problems and the ways that they play out. The organizer, feeling like they have gotten the issues out in the open, moves to Educate the worker, asking questions about how things could be solved.

Something’s wrong. The worker acts confused by the leading questions the organizer introduces during Educate. “No, I don’t think we can really do anything about it.” “That would never work, here’s why…” “What can we do to change things? Nothing, really.”

What’s happening here? The organizer is losing the thread of the 1on1. The worker is completely negative towards the idea that conditions could improve. It seems like an impossibility to them. What had previously felt like a positive direction switches and starts to feel depressing. The worker walks away from the conversation even more dispirited than before and the organizer is left reeling.

Where did things go awry?

There wasn’t any heart. The 1on1 is not the tactical teasing out of issues and their possible solutions. It is an emotional interplay between two humans which moves them both to a higher level of understanding. It is not developing a laundry list of problems, or a brainstorm of action steps. The 1on1 is a scalpel which slices to the core of a worker’s issues and reveals their significance and intensity. It is the dangerous and vulnerable act of listening to someone’s heart.

Why do we fight?

A good 1on1 starts similarly to our example above, but it quickly steps into murkier waters. It’s never enough to know what someone’s issue is; what matters is why that issue is important to someone. If the problem is healthcare, why does that matter to the worker? Because they’re afraid for their spouse, who has a pre-existing condition? Because they want to have children but are worried about the costs of raising them with the current plan? Because they recently watched a family member or friend spend their life savings on a futile attempt to keep their loved one alive?

Organizing well will lead you into some uncomfortable territory. It’s easier to cosplay with red and black flags and exchange nuggets of trivia with your friends about the heroes of the Left canon than it is to actually sit with the horrors of capitalism in human terms. 1on1s can go very dark, very quickly. Perhaps it won’t be your first one, or your second, but if you want to have real conversations about what motivates people to want a better life and why, you need to expect to see and hear some things you didn’t want to.

That’s why it’s important for organizers to prepare themselves for the long haul. Being honest and caring for the workers that we talk with is important, and so is staying healthy. In order to genuinely care for our coworkrs, we need to care for ourselves. People who work as nurses and social workers frequently struggle with their own mental and emotional health because of the things that they encounter as a part of their jobs. Being an organizer is very similar. Talking about capitalism and work in honest terms requires serious self-care. A good organizer knows the phone numbers for free or low-cost mental health providers, both for their coworkers and for themselves. That’s because asking the questions that bring up real, concrete issues means encountering those real problems.

It also means being able to set boundaries about the nature of the organizer-worker relationship. An organizer needs to know what kinds of questions are beyond their “pay-grade” and when to refer things to a competent outside professional. The organizer-worker relationship is not that of therapist-client, social worker-client, or even best friend. It’s a relationship rooted in the shared conditions of work and the ability to transcend and shatter those conditions through collective action.

By asking these questions about why things matter, and truly cutting to the heart of the matter, we find powerful motivating forces.

A friend once told me something that I hold as a truism today: people won’t fight and die for a dollar more an hour. What they will fight and die for is how a dollar more an hour makes them feel. Think about all the stories of labor’s mighty defeats. Certainly, we have more of them than we have victories. In these stories, we hear of strain, hardships, injuries, and even death. For a few dollars more a day? It sometimes seems preposterous, like these old timers were willing to throw their lives to the winds over something so small. But the truth is that these fights were over nothing trivial at all. They were over the fundamental question of their self-worth. They were over questions of value.

Organizing with a full heart and an open mind

Often, inexperienced organizers are afraid to know too much. They take the route of the half-hearted 1on1 because they fear what a full heart feels like. We need to push ourselves away from this instinct, this classic bourgeois rejection of being too close to someone outside of the nuclear family. What we find out during the 1on1 is not the facts of the matter but the feelings of the matter, which bring us closer to the worker and vice-versa. You cannot do a good 1on1 if you don’t fundamentally care about the fate of the person you’re speaking with. You can fake your way through it, but people are smart and can generally smell fakeness. If you don’t have an open heart, they will know.

You can find yourself asking questions that you would never imagine asking outside the space of a 1on1. Who could be that laughably honest and sincere in this ironic age? But questions that seem “too real” in the abstract can create moments of clarity and transformation:

“What right does he have to treat you like this?”

“How is this acceptable?

“Do you really think this situation is okay?”

“How can you allow yourself to be treated like that?”

“Why are we living like this?”

The answers may be powerful. In my experience, they usually are. They may also require long moments of silence. The inexperienced organizer fears that silence means that they’re failing, and they rack their brains thinking of something to move the conversation forward. But a good question may provoke serious contemplation.

I spoke with a coworker not that long ago and I asked her some of these questions. We were seated in a busy coffee shop on a Saturday afternoon. We were talking about how the conditions of our job made it difficult to care for her young child in the way that she wanted to. We spent several minutes quietly thinking. The bustle of the cafe around us faded away as we struggled to think our way through our problems. Finally, she piped up. “We need to do something to change this,” she said, “it’s not acceptable for things to continue like this.”

When the conversation has achieved serious emotional stakes, the Educate piece becomes much easier. Dealing with issues of deeply-felt grievances opens up conversations to solutions that might previously have been impossible. Anger, it is said, beats fear. The fear of imagining what collective action might look like, usually because it just seems so impossible, can be fought through having the heretofore impossible conversation about what is really holding you down about your job and life. The Educate step works via the trust established with Agitate.

The dialectic

The good 1on1 develops both the worker and the organizer. At the risk of overusing a popular Left phrase, the good 1on1 is dialectical . The organizer provokes, the worker responds, the conversation moves onwards to a higher level: both the organizer and the worker are changed and their perspective on work and the world grows. The organizer asks powerful questions, the worker gives powerful answers. The worker learns what motivates themselves, and learns some of what motivates the organizer.

In general, especially as the conversation moves to the Educate piece, the organizer will learn of tactical and strategic approaches to solving problems that they’d never considered. Many times I have been slowly trying to introduce into a conversation a tactic I thought would be a great way to deal with the grievance when the person I’m speaking with blows me away with a superior idea that had never occurred to me. Most of the organizing tactics I now regularly suggest to groups of workers came to me not from some union training but from the minds of my co-workers at some point. The best 1on1s are these back-and-forths of provocation and response, of thesis and antithesis. As workers we already have a vision of what we’d like to see changed and how it could happen, we just need someone to pull it out of us.

Final thoughts

Creating a space where your coworker can share their heart with you is not something that happens in a day and it’s not something that can be faked. Hanging around with your coworkers is an important way to build trust but the 1on1 is not just hanging around. It’s a targeted attack on the ideology that capitalism makes us wear every day. It utilizes trust between people to pierce the curtain of normalcy.

Here we can see the difference between the good 1on1 and the half-hearted 1on1 with some clarity. As organizers and as people, we need to be able to get uncomfortable in the course of our work, because we’re walking through uncomfortable territory. But although the road is hard, it’s necessary. Organizing campaigns that are motivated by care about coworkers and about their lives are so much more powerful than those where people are just along for the political ride. It makes all the other aspects of union work much less difficult if people know why the task ahead needs to be done: for the sake of people’s real lives.


This piece was written by a former member of the IWW, who quit the organization after being asked to by a member whom he had sexually assaulted.

For journalistic reasons, I don’t believe in either now hiding the authorship, or simply taking the piece down. Why? It doesn’t solve anything. It’s not a real form of accountability, but a form of hiding or ass-covering. Concerns have also been raised that this person could be using this piece to rehabilitate their image or reputation. They have denied this, and this addendum, which is being added with their knowledge, presumably dispels that. 

This episode raises all sorts of difficult questions: does the piece have value in spite of its authorship? The commentary I saw on the web in response indicated so. Does the content of the piece in any way reflect the inappropriate behavior of the author? (Does it hint at manipulation?) Or is the content fine? I have heard no objections to it. 

In light of all of this, I would like to make an open call for submissions on the boundaries between manipulative and non-manipulative behavior in organizing, so that Organizing Work can run a piece on that important topic. –Ed