Coaching Up: How to Have Better Dialogue with Senior Leaders

In this issue…

• Coaching Up: How to Have Better Dialogue with Senior Leaders - by Audra Stevenson

• Extra Insights: Traits of a Good Leader: The Four Needs of Followers - Dr. Brian Brim

• Weekly Motivation Boost: How to Create Change - Simon Sinek (YouTube)

• Action for the Week: Amplify Your Listening for Better Engagement

• Together with The Rundown AI

🎯 EXPERT OF THE WEEK

📰 Coaching Up: How to Have Better Dialogue with Senior Leaders

By Audra Stevenson

Strong working relationships don’t just happen—they’re built. Often, they’re built by people in the middle of the organization who choose to lean in, get curious and create clarity where there’s ambiguity. Many mid-level professionals assume influence flows only from the top down—but the reality is that some of the most meaningful change happens from the middle out. This is where coaching up comes in.

Whether you’re in operations, HR, marketing, finance, or project management, chances are you’ve experienced challenges when trying to align with senior leadership. Maybe you’ve struggled to get timely feedback, seen your priorities bypassed or delayed, or felt the sting of decisions made in a silo without your insight. Coaching up is not about challenging authority—it’s about creating stronger partnerships, solving problems together, and helping the entire organization move forward.

Here are five practical strategies to help you navigate tough dynamics and lead more effectively from wherever you sit.

#1 - Lead with Curiosity, Not Correction

When something’s not working—whether it’s a broken process, mixed signals, or a lack of direction—it’s easy to become frustrated. Effective coaching up starts with curiosity.

Ask thoughtful, open-ended questions to uncover what’s really going on. It helps you build trust with your leader, rather than inadvertently putting them on the defensive.

Try this: “I’d love to get your perspective on what’s working well and where we might have an opportunity to collaborate more effectively. I want to make sure I’m aligned with your expectations.”

This shows emotional intelligence, humility and a genuine interest in improving the partnership. You're not criticizing—you’re inviting collaboration.

Why it matters: Curiosity softens resistance. It communicates that you’re open to learning and not just looking to fix “their” problem.

#2 - Connect the Dots to Shared Goals

Senior leaders have a lot on their plates. They’re often focused on big-picture strategy, board reporting, financial targets and customer satisfaction. If they resist feedback, delay decisions, or seem disinterested in a process, it may be because they don’t immediately see how it supports their goals.

This is your opportunity to draw the connection.

Try this: “I know you’re focused on hitting our Q3 targets, and I think this approach can help us get there more efficiently. Can I walk you through how it ties into your priorities?”

You’re showing that you understand their world and that what you’re advocating for is a tool, not a task.

Why it matters: Leaders don’t ignore things out of spite. But if you can’t frame your message in a way that resonates with their goals, it likely won’t get prioritized.

#3 - Make It Easy to Engage

We’ve all experienced the last-minute meeting cancellation, the email that goes unanswered, or the leader who simply doesn’t have time for a touch base. Instead of feeling defeated or chasing them down, shift your strategy.

Offer flexible ways to keep them engaged, while still getting what you need to keep momentum.

Try this: “If a standing meeting doesn’t work well right now, I can send a weekly update with where things stand and highlight any decisions or input needed from you. Would that be helpful?”

Or—if they’re unavailable long-term: “Is there someone on your team who I can connect with to keep things moving when you’re unavailable?”

Why it matters: You’re removing friction while still driving progress. You’re also showing respect for their time without sacrificing your own ability to deliver.

#4 - Use Real Examples to Build Awareness

Sometimes leaders aren’t aware of how their actions—or inactions—impact the team. They may not see the delays, the disengaged employees, or the missed opportunities happening downstream.

Your job isn’t to blame—it’s to help them see the bigger picture.

Try this: “We had a strong candidate excited about the opportunity, but after a few days without feedback, they moved on. Quick input can make all the difference in keeping momentum.”

Or: “Last week, we hit a bottleneck because we didn’t have clarity on direction. If we can tighten up that loop, I think we can move faster and avoid confusion next time.”

Why it matters: Leaders often operate at 30,000 feet. You’re giving them the ground-level view—and offering a solution, not just a problem.

#5 - Follow Up with Clarity and Gratitude

Coaching up doesn’t stop when the meeting ends. Consistent follow-up reinforces trust and accountability. It also demonstrates that you're organized, professional and serious about collaboration.

Try this: “Thanks again for the time today—I appreciated the open conversation. I’ll follow up with a summary and next steps so we can stay aligned moving forward.”

Include a brief email with key points, decisions made and any pending items. This keeps expectations clear and removes the need to revisit the same issues later.

Why it matters: It’s not just polite—it’s strategic. Leaders often juggle competing priorities. You’re helping them stay focused and building a reputation for reliability.

Bonus Tip: Assume Positive Intent (Even When It’s Difficult)

Not every leader communicates well. Not every leader gives timely feedback. But most of them are trying to do the right thing with the information and resources they have. When you approach situations assuming positive intent, it changes the tone of the conversation—and often the outcome.

It doesn’t mean you ignore bad behavior or stay silent when something is broken. It means you start from a place of empathy, not assumption. That mindset often opens the door for a more honest and productive exchange.

Final Thoughts

You don’t need a leadership title to lead. You don’t need permission to communicate clearly, to ask thoughtful questions, or to offer better ways of working together. Some of the most impactful shifts inside an organization begin when someone takes the initiative to coach up—with respect, intention and a desire to build something better.

When you focus on trust over territory, collaboration over control, and progress over perfection, you’re not just building stronger relationships—you’re modeling leadership in action.

In today’s professional climate, that matters more than ever.

💡EXTRA INSIGHTS

The Four Needs of Followers: Traits of a Good Leader

From Dr. Brian Brim, Gallup courtesy Clifton Strengths

5-Minute Watch

🏅WEEKLY MOTIVATION BOOST

How to Create Change - Simon Sinek

8-Minute Watch

🏃🏽‍♀️Action for the Week

Amplify Your Listening for Better Engagement

1. Set aside distractions.

Yes, this is obvious. But also most still struggle with this. Put your phone away, close the laptop lid and silence notifications. Remove as many distractions as you can to keep your focus on the conversation.

If it’s a virtual meeting, minimize or close all other tabs to stay focused on the conversation.

2. Uncross your arms. Take a deep breath.

This opens up your body language to subconsciously remind yourself to keep your mind open as well. Even if you’re on camera in a virtual meeting, others will notice your crossed arms.

3. Repeat back what was said.

Clarify your understanding to make sure there were no misinterpretations.

4. Don’t interrupt.

Interrupting shows the other person you’re not fully listening since you’re more focused on interjecting your own voice. There will be a time for that.

5. Pay attention to non-verbal cues.

If they step back, they aren’t as engaged. If they cross their arms, they’re likely feeling defensive. If they fidget a lot, they’re possibly nervous, anxious or uncomfortable. If they use their hands a lot when they speak, they’re likely confident in the topic. Understand these cues and know when to adjust.

6. Ask and thank them for their feedback.

Asking for feedback shows you’re engaged and willing to hear perspectives. Thank them for their time and feedback, both which you should treat as a gift.

💎 TOGETHER WITH LEADERSHIP UNPLUGGED

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