Jared Oates 2025

Jared Oates

Good things are not mutually exclusive. Paradox isn’t a barrier to progress. It’s the path to it. 

Peacemaking in a Polarized Time: 40 Men, a Crisis, and a Lesson in Leadership

Have you ever rolled out a leadership training program only to watch the very people who need it most tune it out with crossed arms or glazed eyes? If you have, you’re not alone.The leaders most in need of growth are often the first to resist, because the training doesn’t validate their focus.The accountability-focused leader tunes out empathy training, because they won’t risk results. The empathy-focused leader tunes out accountability training, because they won’t risk relationships. So, they dismiss the content—even when it’s exactly what they need.When Strengths Become Stumbling BlocksMost problem leaders were promoted for their real strengths. But taken too far, every strength becomes a liability. Consider these negative patterns:The Ghoster avoids hard feedback in the name of kindness.The Bulldozer charges ahead, determined to win—even if the team is flattened.The Rescuer micromanages out of helpfulness, disempowering the very people they want to support.In each case, a strength—warmth, persistence, helpfulness—has become polarized. One virtue has been elevated, and a counterbalancing strength—accountability, buy-in, empowerment—has been neglected. L&D professionals can best help address the breakdowns that follow polarized behavior by framing them as unbalanced strengths.Training for Paradox-AwarenessPolarized leaders fall into either/or thinking—the assumption that for one side to win, another must lose. Paradox awareness turns the friction of opposing values into fuel.A paradox is the tension between two truths that seem contradictory but actually need each other. Confidence and humility may seem like opposites, yet together, they create credibility. Structure and flexibility, far from rivals, are both essential for resilient teams.Paradox-aware leaders look for innovative solutions that honor both sides of a paradox.Why This Works for Resistant LeadersTraining that just focuses on a neglected skill often feels like an accusation: Leaders hear “You’re the problem,” and respond defensively.Paradox-aware training begins by validating an existing strength, establishing common ground. It presents the counterbalancing strength as an addition, not a replacement, that improves real results. For training professionals, this shift turns the task from “fixing a broken leader” to “helping a capable leader find balance.”Yes, But What About Constraints?“Both / And” thinking can sound like having your cake and eating it too until you acknowledge resource constraints. Time, money, and attention are finite. But the options inside those limits are often far more abundant than leaders assume.A manager, for instance, may believe they must either hit a deadline or protect employee well-being. Paradox awareness helps them find options that honor both—perhaps through re-scoping, delegation, or staged milestones. Leaders stop asking, “Which do I choose?” and start asking, “How do we honor both needs?”The Leadership Progress CycleThe Leadership Progress Cycle is a practical system for helping polarized leaders who feel stuck or blocked. The cycle has four steps:Set Goals – Clarify what you’re trying to achieve and how you’ll measure progress.Identify Barriers – Look for neglected strengths that may be blocking progress.Experiment – Design a SAFE: a Small, Affordable, Fast, Experiment. SAFEs lower the risk of trying new behavior. Instead of sweeping change, leaders test small adjustments. For example, a conflict-avoidant leader might offer one piece of constructive feedback.Evaluate Results – Did the experiment move you closer to your goal? If yes, build on it. If not, refine and try again.This cycle turns paradox awareness into practice. Leaders don’t just talk about balance; they run real experiments that create evidence, insight, and momentum.A Simple First StepIf you’re an L&D or HR professional, the best entry point is simply helping leaders see how strengths can tip into liabilities. To help with that, I created a free Leadership Habits Self-Assessment. It highlights common paradox patterns as a conversation starter. You can find it here.Your OpportunityParadox isn’t a problem to solve; it’s a reality to embrace. The best leaders don’t choose either empathy or accountability, confidence or humility, structure or flexibility. They create “Both / And” solutions that fit the messy reality of human work. Paradox-aware training turns problem leaders into your partners in progress.

Why the Leaders Who Need Training Most Resist It—And How to Reach Them

If you’re an L&D professional trying to get internal buy-in for a new training initiative, you’ve likely felt the pressure to create a full-blown, highly detailed proposal before bringing it to leadership.But what if the fastest way to a “yes” isn’t about completeness, but about confidence?Here’s a powerful, time-saving idea: Pilot your idea before proposing the full program.Instead of writing a 20-page proposal and waiting weeks for feedback (or silence), run a small version of the training with a test group. Think of it as building a prototype instead of a polished product.Why Pilots WorkExecutives aren’t just evaluating your proposal—they’re evaluating you. A pilot says:“I’ve already tested this idea.”“I’m not asking for a leap of faith.”“Here’s real-world data and feedback.”Even better, it gives you the chance to:Gather quotes and results that strengthen your case.Adjust based on early feedback (before you go wide).Demonstrate initiative, ownership, and results-orientation.Real-World Example: A Pilot That Opened the DoorIn 2020, the U.S. Air Force recognized a growing need to strengthen data governance across its departments. Instead of pitching a massive training overhaul, they started with a three-day pilot course for just two staff members. The results were so promising that leadership approved a three-year agreement to expand the program across the entire agency.How to Pilot FastHere’s the streamlined version:Start small. Pick one team or department where the training will have a noticeable impact.Keep it light. Think microlearning, a one-hour workshop, or even a facilitated team meeting with a training component.Measure something. Track one or two outcome indicators—engagement, confidence, behavior change, feedback ratings.Share the story. When you pitch the larger initiative, lead with a real story: “Here’s what happened when we ran this with the support team last month…”Suddenly, your proposal isn’t just an idea—it’s a proven improvement.Especially Helpful If You’re NewIf you’re new to your organization, a pilot can be your secret weapon. You’re still learning the culture and building credibility. A lightweight prototype lets you earn trust, start conversations, and show results fast—all without needing immediate executive buy-in for a massive rollout.The TakeawayYou don’t need perfection to get approval. You need proof. A well-executed pilot gives you that proof—without burning time or political capital.Ready to Try a Pilot? Start Here.Find a friendly team. Choose a department with a known need and a manager who’s open to experimentation.Pick a slice. What’s one lesson, tool, or concept from your bigger idea that you can test in 30–60 minutes?Measure one thing. Ask participants one question before and after. Even a small shift can signal impact.Want to Increase Your Chances Even More?Download the LPC Winning Training Proposal Checklist—a one-page guide you can use to quickly evaluate your proposal (or pilot!) before you send it up the chain.Covers the top elements executives look forBased on research-backed insightsWorks at any stage: idea, draft, or ready-to-sendGrab the checklist here → leadershipprogresscycle.com/winning-training-proposal-checklist.(And if you want a second pair of eyes, reply to the download email—we write a lot of proposals and we’re always interested in sharing, gathering new insight, and building relationships.)