Small Actions. Steady Pace. Lasting Impact.

Having hard conversations is, well, hard.

We overthink them, underprepare for them, and sometimes spend more time worrying about how they might go than actually having them. Depending on the situation, our natural response might be to freeze, flee, or occasionally feel like fighting (not physically, of course…although I suppose that depends on the day).

After more than 26 years in education and 20 years in leadership, I can honestly say I’ve never walked into a difficult conversation thinking, Well, this should be fun!

But here’s what I’ve learned: Some of my greatest leadership lessons have come from conversations I would have much rather avoided.

Early in my leadership career, I thought getting better at hard conversations meant becoming more confident, finding the perfect words, or learning how to manage someone’s reaction. Experience has taught me something different. It’s less about having the perfect response and more about being intentional with how we prepare, how we listen, and how we follow through.

And let’s be honest, even after two decades, I’m still learning.

In The Drip Effect, Jimmy Casas and I explore how small, intentional actions, repeated over time, create lasting impact. While we often think about these actions in the context of school improvement, personal growth, or building relationships, I’ve found that our four rhythms—Pause, Clarify, Act, and Refine—are just as valuable when we’re navigating conversations we’d prefer not to have.

Here’s how I’ve been thinking about putting those rhythms into practice.

Pause: Not Every Conversation Needs to Happen Right Now

Why is it that difficult conversations always seem to find us at the least convenient times?

Maybe it’s the email that arrives at 4:45 on a Friday afternoon, just as you’re getting ready to leave. Maybe someone catches you in the hallway between meetings, or perhaps it’s the familiar knock on your office door followed by, “Got a minute?”

(For the record, it’s rarely just a minute.)

As leaders, we’ve been conditioned to believe that being available means being effective. We respond quickly, solve problems immediately, and sometimes wear our accessibility like a badge of honor. I’ve certainly been guilty of this, especially when I think handling something right away will make someone else’s life easier.

But I’ve learned that being available and being prepared to engage in a meaningful conversation aren’t always the same thing.

In our rush to be efficient, we can lose the opportunity for effective communication.

Sometimes I’ve entered conversations distracted, frustrated, or simply not in the right mindset to listen well. While my intentions may have been good, the timing wasn’t, and I didn’t always show up as the leader I wanted to be.

Pausing doesn’t mean ignoring an issue or avoiding accountability. Sometimes it means recognizing that a conversation deserves more attention than we can give it in that moment. A simple response like, “I want to make sure I give this the time it deserves. Can we connect tomorrow?” can create space for both people to come to the table prepared.

Other times, the pause is just for us. Save the email as a draft, take a walk, or step away long enough to separate the moment’s emotion from the issue that needs to be addressed.

I’ve never regretted taking a little extra time to prepare for an important conversation. I have, however, regretted a few conversations I jumped into too quickly.

Clarify: Root Cause Over Quick Fixes

At our school, we’ve spent considerable time looking more closely at attendance and student engagement across both campuses. One phrase that continues to guide our work is root cause over quick fixes.

It’s easy to look at a student’s attendance record, identify a concern, and immediately start developing a solution. But the more we learn, the more we recognize that what’s happening on the surface doesn’t always tell the whole story.

The same is true when we’re working with adults.

Think about the last time you had to address a concern with a colleague, family member, or someone you supervise. How much of the conversation had you already played out in your head before you walked into the room?

I know I’ve been guilty of creating an entire narrative based on an email, a comment in a meeting, or something someone else shared with me. By the time the actual conversation happens, I’ve sometimes already decided what the issue is, why it happened, and what needs to change.

The problem? I might only have part of the story.

Clarifying requires us to slow down and ask better questions before jumping to conclusions. What do I actually know? What has already been communicated? Where might there be a misunderstanding? And perhaps most importantly, what am I assuming that I haven’t taken the time to verify?

This doesn’t mean we ignore facts, dismiss concerns, or avoid holding people accountable. It simply means we do the work to understand the situation before deciding how to respond.

One lesson I’ve had to learn is that listening to understand doesn’t mean I have to agree. I can acknowledge someone’s perspective while still being clear about expectations, responsibilities, and next steps.

When we approach hard conversations with curiosity instead of conclusions, we create a much better opportunity for productive dialogue.

And sometimes we discover that the problem we thought we needed to solve wasn’t actually the problem at all.

Act: Have the Conversation

Okay, buckle up. This is where things get real.

I wish I could tell you that after 20 years in leadership, I’ve developed some magical formula that makes difficult conversations comfortable. I haven’t. I still think through what I want to say, consider how someone might respond, and occasionally rehearse the opening line more times than I’d like to admit.

One habit I’ve had to work on is volunteering to be the person who delivers the difficult message. If we’re meeting with a family or addressing a challenging situation with a colleague, I’ve often been the first to say, “I’ll take care of it.”

My intentions were good. I wanted to protect relationships, support my team, and make things easier for someone else. But here’s what I’ve learned the hard way: Just because I’m willing to have the conversation doesn’t always mean I’m the right person to have it.

Sometimes, in my effort to take something off someone else’s plate, I’ve stepped into a conversation that would have been more effective coming from the person closest to the situation. Other times, I’ve unintentionally become the “bad cop,” leaving someone else to maintain the relationship while I delivered the difficult message.

That’s not always helpful, and it certainly isn’t sustainable.

Part of acting with intention is identifying who needs to be involved, what needs to be communicated, and how to approach the conversation in a way that supports both accountability and relationships.

A few practices have helped me over the years:

• Set the stage. Whenever possible, schedule time for the conversation and provide some context about what you’ll be discussing. Nobody likes walking into a meeting wondering what they’ve done wrong.
• Practice your message. Find a trusted colleague or coach who will help you think through your approach. And make sure it’s someone willing to challenge your thinking, not simply tell you you’re right.
• Write down your key points. I still bring notes into difficult conversations. They help me stay focused, particularly when emotions are running high or the conversation takes an unexpected turn.
• Make room for dialogue. This one can be tough, especially when you’ve spent considerable time preparing what you want to say. But hard conversations shouldn’t become one-sided presentations. We need to leave room for questions, silence, and perspectives we may not have considered.

I’ve also learned that avoiding a difficult conversation rarely makes the problem disappear. More often, it creates confusion, frustration, or resentment that could have been addressed much earlier.

We can be direct without being disrespectful. We can hold people accountable while still treating them with dignity, and we can disagree without damaging the relationship.

Clarity and compassion aren’t competing leadership skills. We need both.

Refine: The Conversation Doesn’t End When the Meeting Does

One practice I’ve developed over the years is checking back in after a difficult conversation, often within the next day or two.

I’ll be honest, there was a time when I thought getting through the conversation was the accomplishment. If we addressed the issue, clarified expectations, and everyone left the room, I could check that task off my list and move on.

But relationships don’t work that way, and neither does leadership.

Sometimes a difficult conversation leaves people with questions they didn’t think to ask in the moment. Other times, someone needs a little space to process what was shared. And occasionally, despite our best intentions, we walk away believing we communicated clearly only to discover that we weren’t on the same page at all.

That’s where refining becomes important.

A follow-up doesn’t need to be another formal meeting or a lengthy email. Sometimes it’s a quick check-in: “How are we doing?” or “I’ve been thinking about our conversation and wanted to make sure we’re clear on next steps.”

Other times, it’s about asking for feedback on our own leadership. Was I clear? Is there something I could have communicated differently? What do we need from each other moving forward?

Those questions aren’t always comfortable to ask, especially when we’re the ones responsible for making a difficult decision. But they can create opportunities to strengthen trust and demonstrate that we value the relationship beyond the disagreement.

I also think it’s important to recognize that refining doesn’t mean reopening every decision or second-guessing ourselves. There will be times when someone disagrees with the outcome, and that’s okay. Our responsibility isn’t to make everyone happy. It’s to communicate clearly, follow through on commitments, and continue treating people with respect.

And sometimes, the refining happens within us. We reflect on what went well, what we would do differently, and what we want to remember the next time a difficult conversation comes our way.

Because trust isn’t built through one perfect conversation. It’s built through how consistently we show up before, during, and after the difficult ones.

Small Actions. Stronger Conversations. Lasting Impact.

After two decades of leadership, here’s what I know for sure: Hard conversations don’t necessarily get easier, but we can get better at having them.

I still don’t enjoy them, and I suspect I never will. But I’ve come to appreciate the growth that can happen when we’re willing to lean into discomfort instead of finding ways around it.

The four rhythms of The Drip Effect remind me that we don’t need a perfect script or a flawless outcome to lead well. We need to be willing to pause before reacting, clarify before assuming, act instead of avoiding, and refine rather than simply moving on to the next thing.

And let’s remember, even when we do all four, the conversation might not go the way we hoped. Someone may still disagree with our decision. Feelings may still be hurt. We may even leave wondering if we handled it the right way.

That doesn’t automatically mean we failed.

Leadership isn’t about eliminating discomfort or ensuring everyone agrees with us. It’s about having the courage to address what matters while maintaining the care and respect that people deserve.

We can’t always control the outcome of a hard conversation, but we can control the intention, preparation, and care we bring to it.

That’s the Drip Effect. Small actions, repeated with intention, that strengthen how we lead and how we connect with others over time.

Your Next Drip

Think about a conversation you’ve been putting off. Maybe it’s one you’ve been rehearsing in your head, hoping the situation will resolve itself, or waiting for just the right moment to address.

Which rhythm do you need most right now—Pause, Clarify, Act, or Refine?

You don’t have to figure out the entire conversation today. Just identify one small step that will help you move forward.

Because sometimes the conversations we least look forward to are the ones that help us grow the most.

Small Actions. Steady Pace. Lasting Impact.