LevelUp Leadership | Executive Coaching, AI and Management

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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.

  1. 3d ago

    AI ROI for Business Leaders: Start with Outcomes

    Learn how to achieve AI ROI by tying adoption to measurable commercial outcomes, choosing use cases around real business problems, and setting practical measures before scaling. Ashley Gross explains why chasing quick wins across disconnected tools can create technical debt and amplify broken workflows. Start with the technology your organisation already has, align business stakeholders and IT on ownership and risk, and plan for what happens when tools fail. The conversation also examines how leaders can reduce constant status checks and give teams room to learn and experiment.#AIROI #AIAdoption #BusinessLeadership #AITransformationCHAPTERS00:00 AI adoption and measurable commercial value01:30 Ashley Gross’s journey from marketing to AI consulting05:44 AI tool overload, quick wins and ROI08:14 Technical debt and IT ownership bottlenecks11:30 Start with existing tools and business problems14:24 Fix workflows before automating with AI16:00 Agree ownership, risk and contingency plans18:23 Apply change management to AI adoption20:00 Leadership habits that support experimentation22:44 Career development and practical AI learning24:00 Accountability in AI leadership25:49 Key lessons for AI implementation and ROIRESOURCES MENTIONED- Jasper: AI tool Ashley used to automate marketing work.- Claude and ChatGPT: Standalone AI tools mentioned as examples.- Google Docs: Used to coordinate privacy, security and contingency planning.KEY TAKEAWAYS FOR LEADERS- Define the commercial and workforce outcomes you want before choosing AI tools.- Set long-term goals and short-term indicators before measuring progress.- Audit workflows and existing tools to find process gaps and unused capabilities.- Agree who owns tool administration, access, risk and contingency plans across business and IT.- Reduce constant status checks and give teams room to learn and experiment.KEY TAKEAWAYS FOR COACHES- Ask clients what personal or business outcome they want AI to help them reach.- Map the current workflow and its friction before discussing tools.- Help leaders clarify ownership, risk and contingency plans across stakeholders.- Explore how a leader’s check-in habits affect team safety and willingness to experiment.GUEST BIOGRAPHYAshley Gross is the founder and CEO of The Alliance, an AI boutique consulting firm. She has more than a decade of marketing experience and describes entering AI without a STEM background.https://www.linkedin.com/in/theashleygross/ https://www.aiworkforcealliance.comThank 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.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/

    AI ROI for Business Leaders: Start with Outcomes

  2. Oct 25 ·  Bonus

    "Rogue AI" Is Clickbait

    When an AI system behaves dangerously, leaders need specifics: which system, what permissions it had, and why its safeguards failed. This short calls for clear reporting and human accountability in AI governance.#AIGovernance #AutonomousAI #Leadership #AI Risk

  3. Oct 24

    Managing Rogue Stars: Why Top Performers Ruin Team Alignment

    Learn how to manage disruptive high performers and build structural team alignment without sacrificing collective capacity. When a brilliant individual refuses to follow shared processes, their personal velocity creates massive operational drag for everyone else. We often misdiagnose this as a personality clash, but it is a structural failure of leadership accountability. This episode breaks down why rewarding solo achievements destroys team alignment, especially when artificial intelligence accelerates isolated output. You will understand how to redefine the finish line for rogue top performers, protect your reliable staff from burnout, and decide when to isolate a star in a standalone role. Stop sacrificing the stability of your entire operation for the ego of one person. CHAPTERS 00:00 The myth of the solo saviour01:34 Why reward systems destroy team alignment02:49 The rowing crew test for synchronisation04:22 Sales and engineering bottlenecks explained06:22 Autonomy versus strategic clarity07:29 How AI accelerates the rogue star problem08:18 Restructuring roles to protect reliable staff RESOURCES MENTIONED Enhanced Leadership: A book by the host exploring the tension between autonomy and strategic clarity. LevelUpLeadership.uk: The official website for more articles, episodes, and resources. whitmorelee.com KEY TAKEAWAYS FOR LEADERS Redefine success metrics to include process adherence and collaborative delivery, not just individual output. Identify where an individual's excessive speed is causing operational drag for the wider delivery team. Remove rogue performers from the critical path by placing them in standalone projects or unstructured markets. Protect your reliable staff by translating a star performer's natural talent into repeatable institutional systems. Stop confusing unrestricted autonomy with strategic clarity; ensure execution happens within the constraints of the team's operating rhythm. KEY TAKEAWAYS FOR COACHES Ask your clients to map the specific cognitive load their top performer places on the rest of the business. Challenge leaders to identify if their current reward systems incentivise rogue behaviour and institutionalise dysfunction. Use the rowing crew analogy to help clients visualise the difference between individual power and systemic speed. ATTRIBUTIONS AND END NOTES 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. Music & Image: attribution. Podcast Background Track: https://pixabay.com/users/poorartistt-45918667/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/

    Managing Rogue Stars: Why Top Performers Ruin Team Alignment

  4. Oct 17

    Career Plateaus: Why Leaders Feel Stuck & How to Navigate Them

    Discover how to navigate career plateaus and protect your team from burnout by understanding the difference between a lack of purpose and a need for operational recovery. Leaders often misdiagnose their own career frustration as a lack of purpose. Instead of forcing growth during unstable periods, high-performing executives must learn to read their environment and adjust their expectations. Suneet Bhatt explains why treating Maslow’s hierarchy as a dynamic sailboat rather than a static pyramid changes how we approach professional development and risk. You will understand how to categorise different types of career plateaus, deploy self-forgiveness to build resilience, and know when doing the right thing means coaching an employee out of your business. CHAPTERS 00:00 The reality of career plateaus 02:51 Why leaders get bored at work 07:15 Stop searching for purpose when stressed 11:32 Maslow's sailboat and contextual leadership 15:45 Rethinking what it means to be stuck 18:25 Self-forgiveness for leadership resilience 24:55 Coaching employees out of the business RESOURCES MENTIONED Making Sense of Purpose: Suneet Bhatt's book on understanding and applying personal purpose. https://www.linkedin.com/in/suneetbhatt/ If you want to learn more about Suneet's framework and explore the resources mentioned in this episode, you can visit his book's official website at makingsenseofpurpose.com Scott Barry Kaufman: Cited for his work on human potential and redefining Maslow's hierarchy of needs. KEY TAKEAWAYS FOR LEADERS * Diagnose your plateau before acting; determine if you are resting, healing, or genuinely stuck. * Stop attempting to find your ultimate purpose during a period of professional turbulence or crisis. * Shrink your work down to a proportionate size if your current role pays the bills but lacks deep meaning. * Use self-forgiveness as a primary mechanism to clear guilt and refocus on operational execution. * Make objective decisions based on what is right for the individual, even if it means coaching a good employee out of the business. KEY TAKEAWAYS FOR COACHES * Ask clients to define the specific nature of their current plateau: is it initiation, recovery, or a true ceiling? * Use the sailboat analogy to help clients assess if their current environment can support the risk of new growth. * Challenge clients who constantly switch roles to identify the internal work they are avoiding. * Prompt clients to practise self-forgiveness when they dwell on past operational mistakes. GUEST BIOGRAPHY Suneet Bhatt is an executive coach, workshop facilitator, and lecturer at Rutgers University where he teaches the concept of purpose. He is the author of the recent book, Making Sense of Purpose. 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. 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/

    Career Plateaus: Why Leaders Feel Stuck & How to Navigate Them

  5. Oct 10

    Who Do Top Leaders Actually Admire?

    Learn how to overcome organisational change resistance and build high-performance teams that execute under pressure.Driving major organisational change often fails because executives ignore the daily frictions their teams face. In this episode, 14 experts break down the exact operational choices that separate high-performance cultures from dysfunctional ones. You will understand how to replace outdated performance appraisals with daily accountability, why you must study the worldview of those resisting change, and how to position your team for structural success. Stop forcing transformation through hierarchy and start building systems based on rigorous listening, clear boundaries, and decisive action.CHAPTERS00:00 How to overcome organisational change resistance01:52 Leading through radical business disruption03:19 Fixing culture to drive commercial performance04:19 Human-centred approaches to transformation06:33 Why annual performance appraisals fail07:44 Accountability and strategic implementation08:32 Studying the worldview of those resisting change10:04 Conflict resolution over grievance policies11:18 Investing in team potential and capability12:00 Influencing strategy through careful listening12:38 Structuring teams for collective success14:18 The operational value of measured leadership15:53 Building camaraderie during execution risk16:58 Everyday interactions that shape careers18:48 Creating one percent daily improvements20:13 Finding the space between stimulus and responseRESOURCES MENTIONEDNo Rules Rules: A framework for challenging traditional organisational policies and adapting culture.The TCM Group: An organisation focused on deploying resolution frameworks over standard grievance policies.Start With Why: Simon Sinek's foundational concept on purpose-driven strategic alignment.Man's Search for Meaning: Viktor Frankl's work on finding purpose and the space between stimulus and response.KEY TAKEAWAYS FOR LEADERSDemand insight over hierarchy; instruct your team that their primary job is to prevent catastrophic failure, not to appease you.Audit your change management strategy by first studying the exact words and values of those resisting the transition.Replace delayed annual performance reviews with immediate, daily accountability loops.Position talent based on strict operational strengths rather than forcing individuals to fit outdated structural archetypes.Implement a resolution framework to handle team conflict instead of defaulting to bureaucratic grievance policies.KEY TAKEAWAYS FOR COACHESAsk clients to identify where their current hierarchy is actively silencing better operational thinking.Challenge leaders to map out the exact cultural bottlenecks standing in the way of their team's performance.Use the space between stimulus and response framework to help executives manage decision fatigue and reactivity.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.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/

    Who Do Top Leaders Actually Admire?

  6. Sep 26

    Burnout Prevention for Leaders: Fixing Workload Design

    Discover how to stop burnout culture by treating human capacity as a finite strategic resource rather than an elastic buffer. Burnout is rising across sectors, yet many organisations still treat it as an individual wellbeing issue. Providing resilience workshops will not fix a system where demand consistently exceeds capacity. This episode unpacks why burnout is fundamentally a structural leadership problem driven by poor workload design and decision bottlenecks. You will understand why managing human capacity requires the same discipline as managing a budget. We examine how to push decision-making to the edges to give teams autonomy, and how to use AI to identify workload risks before they cause team collapse. CHAPTERS00:00 Why burnout is a leadership problem01:46 The failure of wellbeing programmes05:00 Treating capacity as a strategic resource06:36 Fixing decision bottlenecks07:54 Using AI to manage workload risk09:23 Spotting the early warning signals RESOURCES MENTIONED Glassdoor: Employee experience and burnout data patterns Enhanced Leadership: Host's writing on how environment shapes performance whitmorelee.com KEY TAKEAWAYS FOR LEADERS Treat human capacity as a finite resource rather than expecting teams to absorb endless demand. Stop offering wellbeing apps as a solution for structural workload problems. Push decision-making to the edges to give your team greater autonomy and reduce cognitive load. Model sustainable boundaries by protecting your own recovery time and logging off visibly. Evaluate AI tools for their ability to remove low-value work and highlight capacity risks. KEY TAKEAWAYS FOR COACHES Audit the client's decision load to identify where they are acting as a bottleneck. Ask: "Where is your organisation creating pressure by design rather than demand?" Help leaders map the informal signals they send to their teams about availability and constant connectivity. ATTRIBUTIONS AND END NOTES 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. Music & Image: attribution. Podcast Background Track: https://pixabay.com/users/poorartistt-45918667/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/

    Burnout Prevention for Leaders: Fixing Workload Design

  7. Sep 12

    How to Give Difficult Feedback & Lead Like A Coach

    Learn how to frame difficult feedback so it stops feeling like a conflict and starts driving high performance.Are you tired of feeling "stuck in motion" - busy all week but with nothing to show for it? Executive coach Nikki Goldman unpacks the hidden cost of avoiding hard conversations and how "conflict debt" drains team performance. She shares practical frameworks for reframing feedback, bridging generational communication gaps, and defining what "winning" actually looks like for busy leaders.We also explore why maintaining your calm is a leader's ultimate superpower, especially when guiding teams through AI adoption and rapid organisational change. Discover how to step out of the weeds, stop dropping the glass balls, and start leading with intention.CHAPTERS00:00 Description01:54 Nikki Goldman's Journey to Coaching06:05 Bridging Generational Communication Gaps08:52 The "Spinach in Your Teeth" Feedback Rule13:30 Why Coaching Needs 360-Degree Feedback16:47 The Danger of Being "Stuck in Motion"18:58 Defining Your Personal Win Conditions20:00 Preparing Teams for AI-Driven Change22:15 Why Calm is a Leader's Superpower24:39 Real-World Example: Employee-First LeadershipRESOURCES MENTIONEDRadical Candor by Kim Scott: A framework for delivering feedback that challenges directly while caring personally.IO Coaching: https://www.iocoaching.co/Nikki Goldman's newsletter with weekly insights on leadership and performance: https://www.iocoaching.co/KEY TAKEAWAYS FOR LEADERSTreat negative feedback like telling someone they have spinach in their teeth: do it quickly, directly, and kindly.Stop relying on external validation; define your own clear "win conditions" for the week.Map out the communication styles of your team to reduce friction and misalignment.Treat your composure as a tool: if you cannot regulate your own emotions, you cannot lead your team effectively.View AI adoption as a capability to build into your team's development path, not just a tool to use.KEY TAKEAWAYS FOR COACHESConduct interview-style 360 reviews to pull the thread on complex stakeholder dynamics.Push clients to track the difficult conversations they are having—or avoiding.Help clients distinguish between "glass balls" (critical tasks) and "plastic balls" (tasks that can bounce).Recognise that your role is a temporary thought partner, not a permanent fixture; prepare clients to eventually fly solo.GUEST BIOGRAPHYNikki Goldman is the founder of IO Coaching, a Miami-based executive coaching firm specialising in leadership development, communication, and high-performance team dynamics.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.Music & Image: attribution.Podcast Background Track: https://pixabay.com/users/poorartistt-45918667/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/

    How to Give Difficult Feedback & Lead Like A Coach

  8. Aug 29

    Structured Problem Solving for Senior Leaders - The Toyota Way

    Discover how to use Toyota problem solving to identify root causes and build team capability, not just fix symptoms.Many leadership teams move quickly but solve the wrong problem. This episode breaks down how the Toyota Way helps you slow down just enough to improve decisions, reduce duplication, and focus on what actually drives performance. You will learn how ‘go and see’ changes judgement, why A3 thinking sharpens conversations, and how continuous improvement builds capability over time. The episode also explores the tension between pressure and clarity, and why better questions outperform faster answers in complex environments. If you are dealing with overloaded meetings, unclear priorities, or teams stuck in reactive cycles, this gives you a practical structure to reset how work gets done. CHAPTERS00:00 Why leaders solve the wrong problem01:05 The two pillars: improvement and respect03:00 Go and see: understanding real work04:05 Duplication vs capacity: a case example05:00 A3 thinking for decision clarity06:10 Respect for people in practice07:00 Kaizen and daily improvement habits08:00 Using tension to drive learning09:00 Applying Toyota thinking to leadership KEY TAKEAWAYS FOR LEADERS Go and see the work before deciding what the problem is Separate symptoms from root causes; map the current state clearly Use A3 thinking to force clarity and shared understanding Build capability by asking better questions, not giving faster answers Improve processes incrementally; do not wait for large transformations KEY TAKEAWAYS FOR COACHES Use ‘what is the actual problem?’ as a recurring intervention Introduce A3 as a structure for 1:1 and group reflection Challenge clients to validate assumptions through direct observation Help leaders calibrate stretch without overwhelming teams 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/⁠Images: ⁠⁠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/

    Structured Problem Solving for Senior Leaders - The Toyota Way
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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.

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