how to have a difficult conversation with a young person (or colleague) (or anyone)

Mar 5

OkaySo Co-Founder

Most people don’t see “have a difficult conversation” on their calendar and feel excited about it. Whether it’s with a young person, a coworker, or someone you supervise, these conversations can feel heavy—and easy to avoid.

But when we skip them, problems usually grow. Relationships strain, expectations get fuzzy, and young people don’t get the clear support they need.

This post offers a simple, high‑level way to think about difficult conversations so they feel a little more doable.

what makes a conversation “difficult”?

A conversation usually feels difficult when there’s a mix of:

Strong emotions: Fear, embarrassment, frustration, or anger—for them, for you, or both.
Fear of conflict: Worry that it will turn into an argument or damage the relationship.
Uncertainty: Not knowing how they’ll react, or what will happen afterwards.
Unhelpful self‑talk: Stories like, “I’m terrible at this,” or “They’re going to blow up,” which make it feel even harder to start.

It makes sense that you’d hesitate. One small reframe that helps:
instead of seeing the conversation as a punishment, see it as a way to support someone’s growth because you’re on their team.

doing a little prep first

You don’t need a full script, but a few minutes of preparation can make a big difference:

Clarify your purpose: What do you hope will be different after this conversation—for them, for the team, for the young people you serve?
Check your story about them: Notice if you’ve started assuming the worst (“they’re lazy,” “they don’t care”). Those assumptions often leak into your tone.
Consider their perspective: How might they be seeing the situation? Even a rough guess can make you more open and less judgmental.
Choose time and place thoughtfully: Aim for a relatively private, low‑distraction space, with enough time that neither of you has to rush out.

These small steps communicate respect before you’ve even said a word about the issue.

a simple structure for what to say

There are many models for difficult conversations. One straightforward approach we teach uses three ingredients. All you have to do is remember FBI:

Feelings – briefly naming how their behavior affects you or the work
Behavior – describing what you’ve actually seen or heard, as concretely as you can
Impact – sharing what happens (or could happen) if nothing changes

Keeping each piece specific (“when you arrived late to yesterday’s meeting…”) instead of global (“you’re always late…”) makes it easier for the other person to hear you without shutting down.

You might:

give a short heads‑up (“I need to have an uncomfortable conversation with you”),
name that you care about them and their success, and then
share those three elements in one clear, simple statement.

After that, try to pause and let them respond, instead of filling the silence.

staying grounded during their reaction

People might respond with anger, tears, relief, appreciation, or defensiveness. Underneath, there are almost always real feelings, needs, or worries—like wanting to feel respected, safe, or competent.

A few things that help:

Create a brief pause: Suggest taking a minute, or offer water or tissues, to give them space to settle.
Keep your tone and body language calm: A steady voice, open posture, and conscious breathing can lower the temperature of the whole conversation.
Thank them for sharing: If they tell you how they feel or how they see it, acknowledge that it took something to say it out loud—even if you don’t agree with every detail.

If they stay very stuck in their reaction, you can gently restate your concern and, when it feels right, start shifting toward, “So what could we do next?” rather than re‑arguing the past.

helping your team feel more confident with this

This post only skims the surface of what we explore in our “How to have a difficult conversation” training.

In the full training, we support staff to:

unpack what makes these conversations so stressful
prepare in ways that fit their roles and context
practice a clear, caring structure for what to say
work with real‑life reactions from youth and colleagues

OkaySo is a national nonprofit offering online, on‑demand trainings that help staff become safe, honest, supportive adults for the young people they work with.

If you’d like your team to feel steadier and more skilled in hard conversations, please reach out about partnering with us so we can explore what would be most useful for your organization.

Elise Schuster