LevelUp Leadership | Executive Coaching, AI and Management

LevelUp Leadership

Navigating the complexities of modern leadership in large organisations. An award winning podcast (2026 AVA Digital Media Awards). Join Author and Leadership Coach Lee Whitmore for actionable strategies on leading change, implementing AI, and managing team dynamics. ​Whether you are rewiring workflows or managing burnout, LevelUp provides the toolkit for senior leaders to drive performance without losing their balance.

  1. Suicide Prevention: How Leaders Support At-Risk Employees

    4d ago

    Suicide Prevention: How Leaders Support At-Risk Employees

    Discover how to support at-risk employees through early intervention and better leadership conversations. This episode tackles one of the most difficult leadership realities: how to respond when someone in your team is struggling with their mental health or at risk. Steve Phillip shares practical ways leaders can act earlier, handle difficult conversations, and avoid unintended harm. The conversation challenges the gap between policy and culture, showing why checklists and training alone are not enough. You will hear a clear, usable framework for opening conversations, how to balance performance with care, and what leaders often miss when it matters most. CHAPTERS 00:00:00: Why early intervention matters 00:02:40: The leadership gap in mental health support 00:08:10: Where organisations get it wrong 00:11:00: Culture vs policy in real situations00:15:00: Handling difficult conversations safely 00:18:30: The TED framework in practice 00:21:00: Why men present later 00:23:00: Monthly check-ins that actually work 00:24:30: Connection in hybrid teams 00:27:00: A message of hope for leaders RESOURCES MENTIONED The Jordan Legacy: Suicide prevention resources and training Samaritans (116 123): 24/7 support line Mind UK: Mental health guidance and support KEY TAKEAWAYS FOR LEADERS Intervene earlier: do not wait for visible crisis signals Use simple open questions to create real dialogue Treat every policy through a ‘do no harm’ lens Balance performance conversations with active support Build regular, informal check-ins beyond appraisals KEY TAKEAWAYS FOR COACHES Use the TED framework to model difficult conversations Help leaders rehearse high-risk scenarios safely Challenge ‘tick-box wellbeing’ thinking in organisations Encourage monthly check-in structures in teams GUEST BIOGRAPHY Steve Phillip is the founder of The Jordan Legacy, a community interest company focused on practical suicide prevention. Following the loss of his son in 2019, he now works with organisations to improve early intervention, leadership capability, and mental health awareness. Thank you for watching/ listening. #ad Editing my podcast used to be the most time-consuming part of my week. I now use Descript to edit my audio and video by simply deleting words from a transcript. It allows me to create my YouTube Shorts and TikTok clips in a fraction of the time. If you want to try it for your own projects, you can sign up here: https://get.descript.com/LevelUp Using this link costs you nothing extra, but the small commission I receive helps support the work I do on my podcast and articles. Paid plans start at around £12 / $16 per month (billed annually) for the Hobbyist tier. Music, jingles, and images - attribution. Podcast Background Track: https://pixabay.com/users/poorartistt-45918667/ Guitar Jingle: https://pixabay.com/music/introoutro-guitar-intro-ident-151972/ Images: https://gemini.google/overview/image-generation/ & https://www.perplexity.ai/ Disclaimer. LevelUp and the podcast host do not endorse, verify, or take responsibility for any products, services, views, or claims presented by guests during podcast episodes. Any opinions or statements made by podcast guests are their own and do not necessarily reflect the views or  positions of LevelUp or its representatives. © 2026 LevelUp. This episode is licensed under Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International.  To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/4.0/

    35 min
  2. Theory of Constraints: Why More Effort Points at the Wrong Problem

    Jun 20

    Theory of Constraints: Why More Effort Points at the Wrong Problem

    Learn how to identify the real bottleneck in your organisation and stop wasting resource on activity that looks like progress but compounds the problem. Most organisations under pressure do more of what is visible rather than what is actually constraining performance. In this solo episode, Lee introduces the Theory of Constraints and explains why well-intentioned effort, extra headcount, bigger campaigns, and increased activity, so often makes the underlying problem worse rather than better. Using a practical story about an apple farm and three corporate scenarios spanning software development, recruitment, and retail, Lee walks through the pattern of misdiagnosed bottlenecks and what it costs when leaders optimise the wrong part of the system. The episode closes with one question worth sitting with before the end of the week. CHAPTERS00:00:00: What if your effort is making the problem worse?00:01:30: Introducing the Theory of Constraints00:03:30: The apple farm story00:07:00: Scenario 1: Software development and testing queues00:08:30: Scenario 2: Recruitment pipelines and candidate attrition00:10:00: Scenario 3: Retail conversion and checkout failure00:11:30: Why leaders keep pointing effort at the wrong place00:13:30: What effective leaders do differently00:15:30: The question to ask this week RESOURCES MENTIONED The Goal by Eliyahu Goldratt: The 1984 business novel that introduced the Theory of Constraints. Enhanced Leadership by Lee: Lee's book on leadership under pressure. https://mybook.to/EnhancedLeadership KEY TAKEAWAYS FOR LEADERS Every system has one binding constraint. Improving anything else first is unlikely to improve overall output, and may worsen it. Slowing the pipeline to fix the bottleneck is not retreat; it is precision. Vanity metrics, lines of code written, applications received, footfall generated, measure activity rather than system health. The bottleneck is often where the politically sensitive or technically complex work sits, which is precisely why it gets avoided. The most useful question this week: is your effort aimed at the actual constraint, or at the part of the problem that is most comfortable to address? KEY TAKEAWAYS FOR COACHES Clients under pressure often accelerate the wrong activity. Use the bottleneck framing to help them step back and map the whole system before recommending action. The apple farm story is a useful coaching tool: ask where the rotting pile is, not where the picking is fastest. Watch for vanity metrics as a signal that a client is measuring effort rather than flow. Thank you for watching/ listening.#ad Editing my podcast used to be the most time-consuming part of my week. I now use Descript to edit my audio and video by simply deleting words from a transcript. It allows me to create my YouTube Shorts and TikTok clips in a fraction of the time.If you want to try it for your own projects, you can sign up here: https://get.descript.com/LevelUpUsing this link costs you nothing extra, but the small commission I receive helps support the work I do on my podcast and articles. Paid plans start at around £12 / $16 per month (billed annually) for the Hobbyist tier.Music, jingles, and images - attribution.Podcast Background Track: ⁠https://pixabay.com/users/poorartistt-45918667/⁠Guitar Jingle: ⁠https://pixabay.com/music/introoutro-guitar-intro-ident-151972/⁠Images: ⁠https://gemini.google/overview/image-generation/⁠ & ⁠https://www.perplexity.ai/⁠© 2026 LevelUp.This episode is licensed under Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/4.0/

    14 min
  3. Echo Chamber Leadership: Three Podcasts That Sharpen Your Judgement

    Jun 13

    Echo Chamber Leadership: Three Podcasts That Sharpen Your Judgement

    Learn how to use deliberately contrasting podcast content to sharpen your leadership judgement and challenge the beliefs that are quietly limiting your growth. If every podcast you listen to already agrees with you, your thinking isn't growing, it's just being confirmed. This episode recommends three shows with contrasting styles and philosophies, because the friction between them is where the real development happens. Lee walks through: - Coaching Real Leaders with Muriel Wilkins. - The No BullS*** Leadership Podcast with Marty Moore - The Productivity Show from Asian Efficiency, with Tham Pham. Each brings a different angle on accountability, performance, wellbeing, and how leaders use their time. Together, they create a portable leadership curriculum that challenges you rather than flatters you. The episode also includes a coaching story about a sceptical, involuntary coaching client, and a practical challenge: identify which of the three podcasts feels least aligned with your current views, then commit to three episodes of that one. CHAPTERS 00:00:00: Why your podcast diet matters for leadership growth 00:02:30: Podcasts as an informal leadership curriculum 00:03:00: Recommendation 1: Coaching Real Leaders with Muriel Wilkins 00:06:00: Recommendation 2: No BS Leadership with Marty Moore 00:09:00: Recommendation 3: The Productivity Show from Asian Efficiency 00:11:00: Holding the tension between performance and wellbeing 00:12:30: Coaching story: the involuntary client 00:15:00: Your challenge this week RESOURCES MENTIONED Enhanced Leadership: Lee's book on intentional leadership in an AI-driven world — https://mybook.to/EnhancedLeadership KEY TAKEAWAYS FOR LEADERS Deliberately choosing content that challenges your views builds sharper judgement than content that confirms them. Accountability without wellbeing creates burnout; wellbeing without accountability creates drift. Real coaching conversations, heard in action, demystify what structured thinking partnerships can actually deliver. Small, tested changes to how you manage time and attention can make a disproportionate difference to your sense of control. KEY TAKEAWAYS FOR COACHES Coaching Real Leaders offers rare access to a senior practitioner working in real time, including contracting, probing, silence, and pattern recognition. Recommending it to sceptical clients is an efficient way to shift their assumptions about what coaching is and what it can produce. Thank you for watching/ listening. #ad Editing my podcast used to be the most time-consuming part of my week. I now use Descript to edit my audio and video by simply deleting words from a transcript. It allows me to create my YouTube Shorts and TikTok clips in a fraction of the time. If you want to try it for your own projects, you can sign up here: https://get.descript.com/LevelUp Using this link costs you nothing extra, but the small commission I receive helps support the work I do on my podcast and articles. Paid plans start at around £12 / $16 per month (billed annually) for the Hobbyist tier. © 2026 LevelUp. This episode is licensed under Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International. To view a copy of this license, visit https://creativecommons.org/licenses/...

    17 min
  4. Drivers of Performance: Why Managing Outputs Alone Fails Your Team

    May 30

    Drivers of Performance: Why Managing Outputs Alone Fails Your Team

    Learn how to diagnose the real drivers of underperformance and build the conditions that produce lasting results. When performance is lagging, most leaders jump straight to managing outputs: reviewing numbers, setting tighter expectations, and increasing reporting. This episode challenges that instinct and draws a clear line between performance as an outcome and the conditions that shape it. Lee covers a practical five-part framework, looking at clarity, capability, energy, trust, and feedback, alongside the structural factors that no performance dashboard will ever show you. He also addresses why this distinction becomes even more critical during periods of major change or AI adoption, where the drivers of performance are most volatile and most likely to be ignored. Accountability still matters. This episode makes the case for doing both halves properly: diagnosing the environment first, then holding people to realistic, well-supported standards. CHAPTERS 00:00:00: Introduction: performance vs. its drivers 00:02:00: Why managing outputs alone fails 00:04:00: What overmanaging performance looks like 00:05:00: Accountability without support is just pressure 00:06:00: The five drivers: clarity, capability, energy, trust, feedback 00:09:00: Structural drivers and broken systems 00:09:30: What good diagnostic leadership looks like in practice 00:11:00: Why complex change makes this even more critical 00:13:00: Key takeaway and one action to take this week RESOURCES MENTIONED Enhanced Leadership by Lee Whitmore: referenced in the discussion on trust and psychological safety. Available at https://mybook.to/EnhancedLeadership KEY TAKEAWAYS FOR LEADERS Performance is a lagging indicator. The drivers, clarity, capability, energy, trust, feedback, and systems, are what you can actually influence. Diagnose before you prescribe. Accountability without first examining the environment is pressure, not leadership. During change programmes, the drivers become more volatile, making this discipline more important, not less. KEY TAKEAWAYS FOR COACHES Clients presenting performance challenges in their teams are often describing symptoms. Use the five-driver framework as a diagnostic lens. The trust point is particularly relevant: people need psychological safety before they will be honest about what is really getting in the way. Thank you for watching/ listening. #ad Editing my podcast used to be the most time-consuming part of my week. I now use Descript to edit my audio and video by simply deleting words from a transcript. It allows me to create my YouTube Shorts and TikTok clips in a fraction of the time. If you want to try it for your own projects, you can sign up here: https://get.descript.com/LevelUp Using this link costs you nothing extra, but the small commission I receive helps support the work I do on my podcast and articles. Paid plans start at around £12 / $16 per month (billed annually) for the Hobbyist tier. Music, jingles, and images - attribution. Podcast Background Track: https://pixabay.com/users/poorartistt-45918667/ Guitar Jingle: https://pixabay.com/music/introoutro-guitar-intro-ident-151972/ Images: https://gemini.google/overview/image-generation/ & https://www.perplexity.ai/ Disclaimer. LevelUp and the podcast host do not endorse, verify, or take responsibility for any products, services, views, or claims presented by guests during podcast episodes. Any opinions or statements made by podcast guests are their own and do not necessarily reflect the views or  positions of LevelUp or its representatives. © 2026 LevelUp. This episode is licensed under Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International.  To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/4.0/

    15 min
  5. Outcome Bias: Why Leaders Judge Decisions by Results, Not Reasoning

    May 23

    Outcome Bias: Why Leaders Judge Decisions by Results, Not Reasoning

    Learn how to separate decision quality from outcome quality so you can lead with confidence, build a process you can defend, and stop letting hindsight rewrite your record. A well-reasoned decision can still produce a poor outcome. When it does, two powerful psychological biases, outcome bias and hindsight bias, distort how you and everyone around you evaluate what happened. The result is a narrative where failure feels inevitable, warning signs feel obvious, and the decision maker feels foolish, none of which is usually accurate. This solo episode examines both biases in depth, drawing on original research by Barron and Hershey and Baruch Fischhoff, and brings the theory to life through two landmark real-world cases: Tesco's failed US expansion with Fresh and Easy, and IBM's $5 billion System 360 gamble under Thomas Watson Jr. The episode then makes a critical distinction between a single bad outcome, which may simply reflect the complexity of the world, and a pattern of bad outcomes, which demands genuine scrutiny. The practical focus is on building a decision-making process that is visible, auditable, and defensible, not to avoid accountability, but to protect the integrity of your reasoning when the outcome disappoints. CHAPTERS 00:00:00: Introduction: when good decisions go wrong00:01:30: Outcome bias and hindsight bias explained00:04:00: The research: Barron, Hershey, and Fischhoff00:07:30: Annie Duke and the concept of resulting00:09:00: Case study: Tesco's Fresh and Easy00:12:00: Case study: IBM's System 36000:14:00: Judging decision quality through process, not outcome00:16:00: Making your reasoning visible and auditable00:18:00: Single bad outcome vs pattern of bad outcomes00:19:30: Grounded confidence in your own judgement RESOURCES MENTIONED Thinking in Bets by Annie Duke: framework for separating decision quality from outcome quality using poker as a lens KEY TAKEAWAYS FOR LEADERS Outcome bias and hindsight bias work in tandem: one says a bad result means a bad decision; the other says the result was always obvious. Neither is reliable, and together they make it harder to learn from experience or sustain the confidence to act decisively Decision quality can only be fairly evaluated using the information available at the time the decision was made. Documenting your reasoning before you know the outcome is not defensiveness; it is honest leadership practice. A single bad outcome, even a significant one, is not a verdict on your judgement. A pattern of poor outcomes is. Knowing the difference shapes how you carry failure and how you build from it. The antidote to outcome bias is not caution or over-process; it is a clear, time-efficient decision-making approach that you can stand behind and genuinely learn from. Thank you for watching/ listening. #ad Editing my podcast used to be the most time-consuming part of my week. I now use Descript to edit my audio and video by simply deleting words from a transcript. It allows me to create my YouTube Shorts and TikTok clips in a fraction of the time. If you want to try it for your own projects, you can sign up here: https://get.descript.com/LevelUp Using this link costs you nothing extra, but the small commission I receive helps support the work I do on my podcast and articles. Paid plans start at around £12 / $16 per month (billed annually) for the Hobbyist tier. Music, jingles, and images - attribution. Podcast Background Track: https://pixabay.com/users/poorartistt-45918667/ Guitar Jingle: https://pixabay.com/music/introoutro-guitar-intro-ident-151972/ Images: https://gemini.google/overview/image-generation/ & https://www.perplexity.ai/ © 2026 LevelUp. This episode is licensed under Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International.  To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/4.0/

    19 min
  6. Superpower: How Dyslexia Built the Skills That Define My Leadership

    May 16

    Superpower: How Dyslexia Built the Skills That Define My Leadership

    Discover how to reframe a hidden difficulty as the source of your strongest leadership capability, and what it means for the neurodiverse talent on your team. Every year on the third Thursday of May, Global Accessibility Awareness Day asks a direct question: who is being left out by the way we design things? This episode takes that question into the workplace and makes it personal. Lee shares the story of Theo Paphitis, the Dragon's Den entrepreneur who credits his dyslexia as the foundation of his business instinct: the ability to problem-solve verbally, make fast decisions, and trust pattern recognition over text. Then Lee reflects on his own journey, from the panic of the workshop flip chart to consistently volunteering to present, and how a strategy built entirely around avoiding writing ended up shaping a career in communication and leadership coaching. The episode closes with a direct challenge to leaders: when you mandate the method, you design out the people whose thinking doesn't move in straight lines. Ask for the outcome. Define it clearly. Then get out of the way. CHAPTERS 00:00:00: What is Global Accessibility Awareness Day and why it matters00:01:30: Theo Paphitis: building a business empire while navigating dyslexia00:03:30: Lee's story: struggling to write and what that quietly built00:06:00: The workshop pattern: always volunteering to present00:08:00: The leadership challenge: method vs outcome00:09:30: How to unlock the superpowers in a neurodiverse team KEY TAKEAWAYS FOR LEADERS The workarounds people build to navigate difficulty often become their most transferable skills. When you mandate the method, report, slide deck, written update, you frequently design out the people whose thinking works differently but whose output could meet or exceed your standard. Separating outcome from method is one of the most practical inclusion moves a leader can make, and it costs nothing. KEY TAKEAWAYS FOR COACHES Clients who have spent years managing a hidden difficulty may not have connected their strongest capabilities to that difficulty. Exploring the 'workarounds' they built, rather than the difficulty itself, can surface a more accurate and energising account of how their skills actually developed. This episode is a useful prompt for that conversation. Thank you for watching/ listening. #ad Editing my podcast used to be the most time-consuming part of my week. I now use Descript to edit my audio and video by simply deleting words from a transcript. It allows me to create my YouTube Shorts and TikTok clips in a fraction of the time. If you want to try it for your own projects, you can sign up here: https://get.descript.com/LevelUp Using this link costs you nothing extra, but the small commission I receive helps support the work I do on my podcast and articles. Paid plans start at around £12 / $16 per month (billed annually) for the Hobbyist tier. Music, jingles, and images - attribution. Podcast Background Track: https://pixabay.com/users/poorartistt-45918667/ Guitar Jingle: https://pixabay.com/music/introoutro-guitar-intro-ident-151972/ Images: https://gemini.google/overview/image-generation/ & https://www.perplexity.ai/ Disclaimer. LevelUp and the podcast host do not endorse, verify, or take responsibility for any products, services, views, or claims presented by guests during podcast episodes. Any opinions or statements made by podcast guests are their own and do not necessarily reflect the views or  positions of LevelUp or its representatives. © 2026 LevelUp. This episode is licensed under Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International.  To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/4.0/

    12 min
  7. Vanity Productivity: Why Your Culture Rewards the Wrong Work

    May 9

    Vanity Productivity: Why Your Culture Rewards the Wrong Work

    Find out how to identify vanity productivity in your organisation and build a culture that rewards genuine collective value over quick, visible wins. The 'work smarter, not harder' image is a leadership fixture. But the person rolling a stone ball didn't find a smarter method; they destroyed a useful block, generated waste, and left the consequences for others. That pattern, prioritising the visible quick win over genuine value, is what this episode calls vanity productivity. Lee examines why organisations inadvertently reward the wrong behaviours, where the incentive to look clever overrides the obligation to deliver collective value. He offers three diagnostic questions to help you audit your team's culture, reconnect recognition with real outcomes, and create the conditions where genuine smart working can thrive. CHAPTERS 00:00:00: The ball roller story and what is wrong with it00:05:00: Vanity productivity and how it corrupts culture00:07:00: What genuine smarter working actually looks like00:10:00: Three questions to audit your team culture00:12:00: Closing challenge for leaders RESOURCES MENTIONED Enhanced Leadership by Lee Whitmore: Lee's book on purpose and authentic leadership, available on Amazon https://mybook.to/EnhancedLeadership KEY TAKEAWAYS FOR LEADERS The visible quick win that ignores project context can cost far more than it saves. Prevention, planning, and coordination rarely generate applause, but that is where genuine smart working lives. Ask three questions: what do you celebrate when someone goes above and beyond; how clearly is success defined at system level, not just task level; and is your culture safe enough for people to raise downstream concerns without being seen as a blocker. The person voicing a slow, systematic worry is often your most strategically astute voice. KEY TAKEAWAYS FOR COACHES Use the ball roller metaphor as a coaching prompt to surface the tension between local optimisation and system-level thinking. Explore with clients where recognition structures may be quietly misaligned with actual organisational value, and what it would take to shift that. Thank you for watching/ listening.#ad Editing my podcast used to be the most time-consuming part of my week. I now use Descript to edit my audio and video by simply deleting words from a transcript. It allows me to create my YouTube Shorts and TikTok clips in a fraction of the time.If you want to try it for your own projects, you can sign up here: https://get.descript.com/LevelUpUsing this link costs you nothing extra, but the small commission I receive helps support the work I do on my podcast and articles. Its a great way to support the channel!Music, jingles, and images - attribution.Podcast Background Track: ⁠https://pixabay.com/users/poorartistt-45918667/⁠Guitar Jingle: ⁠https://pixabay.com/music/introoutro-guitar-intro-ident-151972/⁠Images: ⁠https://gemini.google/overview/image-generation/⁠ & ⁠https://www.perplexity.ai/⁠© 2026 LevelUp.This episode is licensed under Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc-nd/4.0/

    14 min

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Navigating the complexities of modern leadership in large organisations. An award winning podcast (2026 AVA Digital Media Awards). Join Author and Leadership Coach Lee Whitmore for actionable strategies on leading change, implementing AI, and managing team dynamics. ​Whether you are rewiring workflows or managing burnout, LevelUp provides the toolkit for senior leaders to drive performance without losing their balance.