by Lisa Peers | Peers and Players
Why courageous conversations matter:
Have you ever come away from a conversation with the satisfying feeling that you co-created an experience, that you learned a little more about someone, that your message was received, and you had a clear path forward?
That’s how it should feel, even if you are delivering or receiving a difficult message, learning some unpleasant news, or resolving a difference of opinion.
Poor communication is one of the biggest causes of low engagement and high turnover. How many times have you heard that someone left their job because of frustration with how their manager communicates, or fails to? How many times have you or someone you know waited for their manager, an HR professional or peer to step up and fix the problem?
Whether it’s giving feedback, addressing conflict, or just asking for what you need, challenging conversations can go sideways fast, especially when people feel unappreciated, unprepared, or undervalued. It’s time to step up and learn the skills which will make you an expert communicator!
The goal isn’t to avoid conflict, it’s to make every conversation, even the challenging ones, constructive and productive.
At Peers and Players, we’ve been helping professionals around the world practice the art of workplace challenging conversations through role play, rehearsal, and real-time coaching for over 25 years.
How to have an effective conversation is a learnable skill, made up of simple steps.
Here are 5 practical techniques that can transform your next conversation, from awkward and reactive, to clear, respectful, and productive.
1. Start with a clear outcome
Before the conversation begins, consider your objective:
Don’t wing it, prepare!
- Ask yourself: Why am I having this conversation, what outcome would be good for both of us?
- Share that purpose up front with the other person.
- Keep the focus on working together, not on proving a point.
For example: In this interaction I want to support this person to be more successful, by understanding their behavior, how it impacts others, and how I can help them to be more successful.
A great outcome would be that we work together productively to create a clear path to success.
“I’d like to understand your perspective on the client’s feedback so we can provide the best service together. Is that okay?”
This sets expectations, reduces anxiety, and creates psychological safety.
Tip: Remember to focus on the outcome, before jumping into details.
Include the person you are speaking with in the conversation and respect their perspective, and their objective.
2. Ask revealing questions
First, check in and get permission, ask for cooperation:
Don’t just assume that people are ready to talk.
“Is tomorrow at 2pm a good time to discuss the client expectations?” Once you have a “yes” you have a great foundation for a receptive conversation.
Start with acknowledgement not criticism, to build trust.
Instead of starting by telling someone what you think they did wrong, acknowledge something that is going well first, even if it’s just noting their good intentions, or recognizing a small win or positive behavior.
Ask for their perspective, focus on one point at a time:
Open vs closed questions:
- Closed: “Did you finish the report?” Yes/No.
- Open: “What’s been your biggest challenge with the report?” Invites sharing.
- Closed: Do you like working with this team? Yes/No.
- Open: “What’s been going on for you with the team dynamic lately?” Invites sharing.
Open-ended, neutral questions help you gather the full picture before reacting.
Tip: Tone and body language matter just as much as the words, especially on video calls. Even if your crossed arms cannot be seen, the closed posture can be felt. Make sure you have a grounded posture: feet planted on the ground, open gestures and a measured tone, not too fast or slow.
3. Really listen (and show it)
This sounds simple. But in high-stakes conversations, most of us are already preparing our response while the other person is still talking. If you have prepared your intention before the conversation, keep that in mind while you listen, observe and feel the person you are meeting with. Truly listening creates a space for what’s previously unsaid and provides psychological safety.
Don’t get caught up in thinking about your response while the other person is speaking.
How to listen means:
- Being open to considering another point of view
- Not talking until they have finished a thought
- Evaluating their values and goals
- Seeking to understand their view of the situation
- Making eye contact (or looking into the camera).
- Nodding or smiling so they know you’re with them.
How to show you listened:
Paraphrase back what you heard, in their terms. Consider their preferred style:
Visual people prefer to see information in pictures, diagrams, body language, or seeing the big picture.
“I see your perspective now — your ideas weren’t visible in the decision. Did I capture that?”
Auditory people tune in through sounds, tone of voice, and the exact words used.
“What I’m hearing is that you felt excluded. Did I hear that right?”
Kinesthetic people learn and connect through movement, feelings, and lived experiences.
“I can sense this left you feeling uncomfortable. Is that accurate?”
When we adapt our communication to these styles, we make others feel understood on their terms. The way we communicate is just as important as what we say. This builds trust and keeps the conversation on track.
Checking in paraphrasing what they said, in their preferred language helps people feel seen, heard and felt. As a bonus, understanding their perception of the world opens us up to feel more empathy and understanding of other perspectives.
4. Say the hard thing as soon as possible
Waiting to broach a tricky conversation can breed confusion, assumptions and resentment.
Don’t put it off until people feel confused, unsafe, or are considering leaving.
Agree on a time to discuss the situation, and stick to it:
Own your experience/ perspective without blaming them for theirs.
Use ‘I’ statements to talk about behavior and impact:
- “I noticed that you interrupted twice during the team update.
- “That made it harder for others to get their point across.”
Focus on actual behavior and outcomes, not assumptions. You’re not labelling the person or judging them…you’re inviting a shift in behavior.
Tip: The SBI Model
You could consider using this simple and powerful framework for outlining a situation and/or as a jumping off point for a feedback conversation:
S = Situation: When and where did it happen?
B = Behavior: What did the person specifically do?
I = Impact: What effect did it have on you, the team or the project?
“In yesterday’s team meeting (Situation), you interrupted Julia twice (Behavior), which disrupted the flow of discussion. I noticed she was quiet after that. (Impact).”
Make it as clear, specific and fact based as you can, taking out any bias, reflection or feeling you may have about the scenario.
At Peers and Players, we believe in practice, rehearsing beforehand helps with clarity and confidence in your messaging. We give leaders the space to rehearse these skills with actor/coaches, so they feel confident when it’s time to have the real conversation.
Even if you don’t hire a professional, find an impartial friend or colleague to practice with, and encourage them to be aware of the above guidelines.
5. Agree on what’s next
Certainty builds confidence in you as a leader, you can feel it, and others will appreciate your leadership.
Don’t waste the great place you have come to with this conversation with lack of follow up. Agree on next steps.
Even if next steps are only “Let’s meet again, same time next week. Does that work for you?” This gives a bookend to the conversation and leaves both of you with trust in each other, and certainty about a way forward, something tangible to focus on.
Together, you could define:
- What success looks like going forward
- Who’s doing what, by when
- How and when you’ll check in again
Examples:
- “Let’s both write down our goals before the next meeting, so we’re aligned. Do you have time to do that before Monday?”
- “I’ll update the brief and send it by Friday; can you take a look over the weekend?”
These action steps can turn one revealing conversation into momentum.
Ready to try it?
Great communication isn’t scripted, it’s guided. It takes practice.
Use these 5 steps to guide your next critical conversation.
- Know your objective
- Ask revealing questions
- Listen and respond
- Communicate ASAP
- Agree next steps
And like any skill, your communication will get stronger with practice. You could ask a colleague if you could rehearse with them or run it by your manager. Remember to ask for feedback on your behavior, specific things which you did or said, and some practical suggestions. However, practicing with a professional provides an objective, and unbiased approach to practice and coaching.
If you’d like to:
- Rehearse challenging conversations before they happen
- Get feedback on your communication style
- Learn practical skills to be more effective in future
- Develop effective leadership skills that stick
- Equip your team with confident communication!
Book a free discovery call with a project manager at Peers and Players
Email us at info@peersandplayers.com to get started