When Leading Feels Like Walking a Tightrope: A Leadership CHEW for Difficult Decisions

The Daily CHEW™

CHEW on God’s Love. Live Transformed. Multiply Hope

This morning I sat in my car for five minutes before walking into the office, knowing I needed to have a conversation that could change everything for our team. One of our most talented consultants had been consistently missing deadlines and deflecting responsibility, and despite multiple attempts at coaching, the pattern was only getting worse. As the leader, I knew I had to address it directly—but the stakes felt enormous. Handle it wrong, and I could lose a valuable team member and damage team morale. Handle it right, and there might be a path to real breakthrough and growth.

Maybe you know this weight. Maybe it’s the decision about restructuring your team, or the conversation with a high-performer who’s become toxic to company culture, or the choice between short-term profits and long-term values. Maybe you’ve felt that crushing responsibility of knowing your decisions will significantly impact real people’s lives, careers, and families—and wondering if you have the wisdom, courage, and character to lead well.

Here’s what I’ve learned from years of coaching executives and walking through my own leadership challenges: leading well isn’t primarily about having the right strategies or perfect emotional intelligence. It’s about making decisions and having difficult conversations from the overflow of God’s love and wisdom rather than from fear, people-pleasing, or self-protective control. When we lead from our own need to be liked, avoid conflict, or manage outcomes, even our best leadership intentions become another form of self-reliant performance. But God’s love offers something fundamentally different—the ability to lead with both grace and truth, strength and gentleness, because we’re secure in His love regardless of how others respond.

Finding God’s Heart Before the Difficult Conversation

Join me for a deeper CHEW right now—designed specifically for those moments when leadership requires courage, wisdom, and love that you don’t feel equipped to give.

CHEW in 5-10 Minutes:

  1. Take several deep breaths—remembering that God’s love for you doesn’t depend on your leadership performance or how well people receive your difficult decisions.
  2. Adore (1-2 minutes): “Father, You are the perfect leader—full of grace and truth, patient yet decisive, loving yet just.”
  3. Confess (2-3 minutes): What fears are driving my approach to this leadership challenge? Am I avoiding this conversation because I want to be liked? Am I approaching it harshly because I’m frustrated? Where am I trying to control outcomes instead of trusting God with the results? What’s the deeper fear—fear of conflict, fear of failure, fear of being seen as incompetent?
  4. Hear (3-4 minutes): What truth about God’s love do I most need as a leader right now?
    • “The Lord will guide you continually and satisfy your desire in scorched places” – Isaiah 58:11
    • “If any of you lacks wisdom, let him ask God, who gives generously to all without reproach” – James 1:5
    • “Speaking the truth in love, we are to grow up in every way into him who is the head, into Christ” – Ephesians 4:15
    • “Let your speech always be gracious, seasoned with salt, so that you may know how you ought to answer each person” – Colossians 4:6
    • “Be strong and courageous! Do not be afraid or discouraged. For the Lord your God is with you wherever you go” – Joshua 1:9
  5. Exchange (1-2 minutes): If God’s love truly secures me, I would exchange my fear of difficult conversations for confidence in His wisdom working through me. I would exchange my need to be liked by everyone for commitment to loving people well through truth. I would exchange my anxiety about outcomes for trust in His sovereignty over results.
  6. Walk (1-2 minutes): What’s one specific way I can approach this leadership challenge from God’s love rather than my own fear or control? Maybe it’s beginning the conversation with genuine care for the person’s growth. Maybe it’s being honest about my own mistakes while addressing theirs. Maybe it’s choosing to speak truth wrapped in genuine love rather than frustrated criticism.
  7. Thanksgiving & Worship (1 minute): Thank God that He leads you perfectly even when your leadership feels imperfect. Thank Him for the privilege of leading others and for His wisdom that’s available in every decision. Rest in His sovereignty over the outcomes of your leadership.

Additional Guidance for Complex Leadership Decisions

Before the conversation: Pray specifically for the person you need to address. Ask God to help you see them as He sees them—someone He loves and wants to grow, not just a problem to solve.

During the conversation: Remember that your security comes from God’s love, not from their response. This freedom enables you to speak truth with genuine love rather than defensiveness or people-pleasing.

After the conversation: Trust God with the results. Your job is faithful leadership; His job is hearts and outcomes.

Remember This

Gospel-centered leadership isn’t about being perfect or having every conversation go smoothly. It’s about returning—again and again—to the love that holds you whether your team thrives or struggles, whether difficult conversations bring breakthrough or require more patience. God delights in your dependence on His wisdom, not your ability to manage every leadership challenge flawlessly.

CHEW On This™:

If I really believed God’s love gives me perfect security and His wisdom is always available, how would that change the way I approach difficult decisions, challenging team members, and conversations I’ve been avoiding?

The CHEW system works best when practiced in community. Consider finding other leaders who can pray for your decisions and hold you accountable to leading from God’s love rather than fear. Explore what changes when you create consistent rhythms for seeking God’s heart before making leadership decisions—not just in crisis moments, but as a daily foundation that prepares you for whatever leadership challenges arise.

Want More?

Get God’s love from your head to your heart—subscribe to The Daily CHEW™ and experience real change, peace, and hope every day.

Ready for lasting transformation?
Learn how to make CHEWing a daily rhythm. Our hope is that everyone can learn to CHEW without ever needing to pay us for help.
If you have a question about the CHEW practice or hit a roadblock you can’t solve, we’re happy to help with quick guidance.
Reach out anytime at [email protected] and we’ll do our best to help you keep growing!

CHEW on God’s Love. Live Transformed. Multiply Hope


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Ryan Bailey

Ryan C. Bailey helps Christian professionals live from the reality of God’s love in the middle of real leadership, work, and family pressures. For over 30 years, he has walked with leaders, families, and teams through key decisions and seasons of change, bringing together Gospel‑centered counseling, coaching, and consulting with practical tools like CHEW through Ryan C Bailey & Associates.