Managing up is one of the most important leadership skills and one of the least taught.

In this episode of Leading Ain’t Easy, Ryan Calkins and Erny Epley talk about what it really looks like to lead when you don’t have authority over the people who influence your success: your boss, senior leaders, and cross-functional departments that control the data, budget, timelines, and decisions you’re expected to execute.

If you’ve ever been told “figure it out” without support… if you’ve been burned by a surprise that climbed the chain… or if you’ve struggled to communicate your vision clearly under pressure... then this episode is for you.

In this episode, we cover:

• Why leadership hates surprises (and how to avoid blindsiding your boss)
• How to tailor your communication to how your boss receives information
• How to challenge leadership without being seen as “difficult”
• Why documentation matters (and how to protect yourself with clarity)
• The mindset shift: clarity beats competence

Question for listeners:
Where do you struggle most with managing up; clarity, timing, politics, or trust?

Key takeaways

• Don’t let your boss get blindsided; give heads up early.
• Communicate to be understood, not just heard.
• Lead with the solution, then support with context.
• Use data to paint a clear picture fast.
• Document agreements and decisions (protects everyone).

Leading Ain’t Easy is hosted by Ryan Calkins and Erny Epley.

• Ryan is the founder of Reframe & Rise, a career and leadership coaching practice helping veterans and other professionals realign their work and lead with purpose.
• Erny runs Bus Pro Network, supporting school transportation leaders across California with training and development.

Subscribe to the show on Apple, Spotify, or wherever you listen.

Follow us on LinkedIn and Instagram for clips, prompts, and behind-the-scenes updates.

If this episode resonated, please leave a review, as it helps more leaders find us.