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Jared Oates is the creator of The Leadership Progress Cycle, a practical framework that helps leaders create lasting impact through better awareness of how paradoxes work. A self-taught software engineer with a background in English rhetoric, Jared has spent over a decade designing learning experiences that go beyond surface-level training. As co-founder of Niche Academy, Jared has helped thousands of leaders in public and nonprofit sectors navigate real-world challenges. Known for blending practical tools and personal insight, he helps leaders find new energy for innovation, trust, and growth. Learn more at leadershipprogresscycle.com.

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.)

Want to Sell a Training Proposal Fast? Don’t Build the Whole Thing First

Training alone isn’t enough to scale great leadership. New managers especially need just-in-time support. That’s where AI comes in.Far from replacing leaders, artificial intelligence is becoming a quiet partner in helping them communicate clearly, make better decisions, and support their teams more consistently. For learning and development professionals, the opportunity isn’t just to teach leaders about AI. It’s to help them use it.Here are four practical ways AI is already transforming leadership development:1. AI as a Communication Assistant Leaders spend much of their day writing—emails, evaluations, strategy documents, team updates, and more. Generative AI tools like ChatGPT and Microsoft Copilot can help draft first versions, suggest more inclusive or motivating language, and adjust tone for different audiences.When I using AI to write, start with a brain dump—what you want to say, who it’s for, tone, length, even your favorite humorists. The more prompt you offer, the better the draft.AI tools are especially helpful for newer managers still finding their leadership voice. They act like training wheels—supporting clarity and consistency until the leader gains more confidence.2. Smarter Meetings With AI Note-Takers AI-powered assistants like Otter.ai or Fireflies.ai can transcribe meetings, generate key takeaways, and highlight action items. These tools let leaders focus on discussion while capturing a searchable, shareable record—reducing confusion and boosting accountability.For L&D professionals, introducing these tools into leadership programs models good meeting hygiene—and provides practical, immediate value.3. Personalized Coaching in the Flow of Work Coaching has impact—but it’s expensive and often limited to executives. AI chatbots and simulators make practice accessible to everyone. Imagine a manager prepping to give difficult feedback. They could prompt an AI coach: “Help me practice a conversation with an employee who’s missing deadlines,” and walk through a simulation with real-time feedback.This kind of practice can dramatically reduce the anxiety that often keeps leaders from having the conversations that matter most.4. Insightful Decision Support AI dashboards and people analytics can help leaders make smarter, faster decisions. Predictive models can flag burnout risk, highlight skills gaps, or recommend peer mentors. Tools like Microsoft Viva Insights and Culture Amp offer dashboards that help managers spot trends and support their teams with data-informed decisions.What L&D Teams Can Do Now Here are a few ways to help leaders benefit from AI:Introduce secure AI tools into programs—like notetakers or roleplay scripts. Teach prompt basics. Show examples that leaders can apply immediately. Encourage experimentation with a 30-day “try one new use” challenge. Emphasize ethics. Reinforce that AI should enhance—not replace—human connection. Leadership isn’t getting simpler. And AI reminds us that most decisions aren’t right vs. wrong—they’re balancing good vs. good. That’s why paradox-aware training is essential. In the Leadership Progress Cycle, we help leaders navigate tensions like these with confidence and clarity. Learn more at:leadershipprogresscycle.com/.

The Leadership Multiplier: How AI Can Elevate Managers and Their Teams

Leadership training needs to clarify that in healthy conflict there is a shared common goal. 

Little Leadership Training Secrets to Avoid Toxic Conflict

The best training to help leaders grapple with AI-related change is soft skills training, not tech training. 

The Best Way to Train Leaders for AI-Related Change

Would you say leaders in your organization tend to be more bold or more cautious when they make important decisions? Not sure? Here are a couple case studies for comparison.Case Study 1:A new CEO took the helm at a technology company and quickly eliminated 70 percent of the product line and announced a partnership with the company’s biggest rival.Case Study 2:At a different technology company, a new CEO was promoted from within, and instead of making bold changes, the CEO began methodically tuning the company culture and carefully analyzing trends and opportunities to refine the directional focus.AnalysisOn the surface, these case studies represent opposite leadership styles, one bold and one cautious. Which would you want to train for in your organization? Is it better to train leaders to measure twice or to teach them that fortune favors the bold?While they appear to be in conflict, caution and courage are both virtues. Knowing the outcomes of each case study adds some useful context.Case Study 1 describes the return of Steve Jobs to Apple in 1997. Jobs made the risky decision to focus on a few products like the iMac and formed a partnership with Microsoft to bring Microsoft Office software to Mac machines. Apple experienced extraordinary growth under Jobs’ second tenure.Case Study 2 describes the promotion of Satya Nadella to the top job at Microsoft. The company was struggling when he took over in 2014 and seemed to be on the fast track to irrelevance. Under his leadership, though, Microsoft has traded places with Apple as the world’s most valuable technology company.Effective Leaders Need Both Caution and CourageThe apparent contrast between courage and caution in these examples reveals a paradox, a tension between two necessary principles that on the surface appear to be contradictory. It’s tempting to dumb down the contrast and talk about different “leadership styles”—one bold, and one cautious, either of which can be effective. This explanation ignores the important reality that every effective leader needs both caution and courage. The traits are like two posts on a suspension bridge pulling in opposite directions. The tension between them is what keeps the bridge in place. For all his caution, Nadela placed big bets on AI, cloud services, mixed reality, and quantum computing. Some of those bets have not yet paid off. For all his boldness, Jobs was intensely data-driven in his obsession with the user experience, not just measuring twice, but hundreds of times and from multiple angles.Both Nadela and Jobs had big aspirational goals that, like a compass, pointed them in the direction they wanted to go. Jobs wanted to fundamentally reshape the way people use technology to create, interact, and find meaning. Nadela has a similar vision for Microsoft that is about empowering every individual and organization to achieve more by leveraging technology. Both leaders also knew they needed short-term achievable goals to measure progress toward those aspirational compass points.The Balance of Courage and CautionTo train effective leaders, you need to help them understand the balance between aspirational goals and achievable goals. They need to understand that all lasting progress is the result of an iterative process of goal setting, barrier analysis, behavior changing, and results evaluation. At Niche Academy, we call this the Progress Cycle.Effective leaders are not born. They are ordinary people who have come to understand and value paradoxes like the tension between courage and caution. Chances are that your team already has people ready to learn and implement the patterns that will move their team forward.

Bold vs. Cautious Leadership—Which Is the Best for Growth?

In today’s world, leadership ideas are shifting, challenging long-standing practices. The traditional “command and control” style, where leaders make all the decisions, is being replaced by trust and collaboration. Leaders are now moving away from micromanagement and embracing team autonomy. If you’re responsible for leadership training, it’s important to understand how adopting these new approaches early can have a big impact.Let’s break it down.A Lesson From Science: Big Ideas That Change EverythingTo understand the impact of big ideas in leadership, consider how major scientific breakthroughs transformed the world. For example:Galileo and Newton described how objects move through space and time.Maxwell and Lorentz built on their work, showing that the speed of light is constant regardless of how an observer moves.Einstein then developed his famous theory of relativity, leading to the discovery that a small amount of mass could be turned into enormous energy—this led to nuclear energy.These ideas didn’t come overnight, but their impact has been profound. Nuclear energy, for example, reshaped international politics and power dynamics, with countries that control nuclear energy gaining major advantages.How This Applies to LeadershipJust like those big scientific ideas, leadership is undergoing a transformation. For years, leaders have managed teams through strict top-down control. Leaders gave orders, and teams followed them. But this old way of leading is giving way to something new.The emerging leadership model is based on:Trust and Interdependence: Instead of controlling everything, leaders are learning to trust their teams to make decisions at the right levels.Clear Goals: Teams and leaders agree on measurable goals, and everyone is accountable for achieving them.Collaboration: Leaders work with their teams to make decisions, rather than just giving orders.A “Speak-Up” Culture: Leaders encourage open communication, knowing the best ideas can come from anywhere.Belonging Over Conformity: Leaders focus on building a sense of belonging within the team, instead of forcing everyone to fit a mold.This shift allows teams to make decisions faster, avoid micromanagement, and reduce internal politics. As a result, teams led by transformational leaders are far more productive.Why Leaders Should Adopt These New IdeasJim Collins, in his book Good to Great, describes transformational leaders as “Level 5” leaders. These leaders drive extraordinary results by empowering their teams through trust and accountability. The benefits of adopting these new leadership approaches are clear:Faster Decision Making: Routine decisions happen quickly because they’re made by the people closest to the situation.Less Bureaucracy: Reducing administrative overhead means less time wasted on politics or approval processes.Increased Productivity: Teams thrive when they have autonomy and a clear vision to guide them.Creating a Transformational Leadership Training ProgramTransformational leadership training involves more than just teaching concepts. It requires a strategic approach that encourages new behaviors and practices. There are four pillars to an effective training program:Set Goals
Teach leaders to understand the big-picture qualitative outcomes they’re after—and the metrics they will use to define progress transparently. Leaders must learn how to set team goals collaboratively and ensure individual goals are deeply aligned.Identify Barriers
Barriers can be external factors like market trends and technological disruption—or internal factors like team dynamics and individual habits. Leaders must learn how to create an environment for honest, sometimes difficult, conversations.Change Behavior 
Teach leaders to treat every change as an experiment and encourage teams to change together—creating an environment that nurtures progress patterns. Lasting team momentum requires individual understanding and consent. It can be inspired, but not coerced.Evaluate Results
Show leaders how to guide their teams in continually comparing performance against metrics, updating goals and experiments based on clear evidence.By implementing these pillars, you can help your leaders transition from traditional command-and-control styles to transformational leadership, significantly enhancing your organization’s productivity.

New Rules in Leadership: Overcoming Toxic Command and Control

Of all the possible training topics that can improve leadership skills and toxic work environments, one might surprise you. Teaching leaders how to communicate and manage conflict makes sense. But what about goal setting?Your leaders may be familiar with setting SMART goals, but do they know how to balance measurable and unmeasurable goals? Many organizations need a better balance between measurable (quantitative) and unmeasurable (qualitative) goals. As a result, leaders—and the people they lead—can’t say for sure where they’re going or work well together to get there. So, what’s the difference between quantitative and qualitative goals, and why is it important? Let’s take a look:Quantitative vs. Qualitative GoalsQuantitative goals are the things you measure, the metrics or the “how.” Usually, these numbers track changes in things like ratings, revenue, expenses, usage, and participation. But if you only set quantitative goals, they can become an end in themselves. It’s easy to lose track of why you do what you do and whether you’re measuring the right things.Qualitative goals are the end product of asking “why” you do what you do. If you ask why you send emails and, ultimately, why the organization exists, you’ll eventually come to important benefits for yourself, your customers, or a community. But if you only set qualitative goals, it’s difficult to organize a team and know whether you’re making progress.4-Step Pattern for Setting How & Why GoalsIf you want to develop high-impact leadership within your organization, teach your leaders the following goal-setting pattern that balances “how” and “why.” The pattern has four steps:1. Find the real “why.”To begin the goal-setting process, have individual team members review what they do during their workday and ask “why?” Why do I send these emails? Why am I creating this graphic? Why am I organizing that project? For each answer, ask why again, and continue until you can’t think of another reason behind an answer. When you get to this point, you’ve likely found your root “why”—your qualitative goal.A good “why” feels inspiring. It gives meaning to work, and meaning is an essential human need. Solid qualitative goals describe a benefit to some specific group. They give people a reason to work together.2. Find the metrics that matter.Once you have your “why,” you need a metric—a way to measure your progress. Some metrics have a direct relationship to the outcome. A city working on public safety can track violent crime statistics. Other metrics are indirectly correlated. A library working on adult literacy might track participation in an ESL program.Next, you need a clear way to track your metric over time. Consistent data collection is key. If leaders don’t understand the information’s value, they may view the process as a distraction from “real” work and not follow through. To help ensure consistency, teach leaders that healthy teams require real accountability—and how metrics show teams when they’re winning. Just be sure each metric ties back to a qualitative goal.3. Choose your experiments.Leaders need to understand that every deliverable, task, and project is an experiment in what will move the metrics that matter. It’s hard to know whether specific actions will make a difference. The question for every healthy team is this:To the best of our knowledge, what’s the best way to [increase/reduce] [metric you care about]? Some leaders are afraid to track metrics because they fear failures will discourage the team. The opposite is true. When teams learn to approach every action as an experiment, the outcome is learning. Every failed experiment gets you one step closer to what will work. 4. Evaluate your results.Metrics give you a way to learn what works and what doesn’t. Well-trained leaders know that with thoughtful experimentation, they will eventually find what works. Then, they can optimize it.They will also realize that some efforts won’t influence the metrics that matter. Paying attention to results helps leaders avoid setting goals to optimize something that shouldn’t be done in the first place.Teaching leaders to balance “how” and “why” goals is key to establishing a thriving workplace culture. 

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