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Some companies see leadership and managerial training as an investment. Others, however, provide very few resources for the transition from individual contributor to leaders. For most of the latter companies, managerial training is a one-off event. Take a seminar or two, and off you go. Sometimes you get a company that offers executive coaching or mentorship to their C-suites. But for many first-time (and even some middle) managers, they’re often left to fend for themselves. This is the problem that leadership coaching startups are trying to solve. The answer, they believe? AI. While founders of these startups acknowledge the limitations, many are adamant that AI can help break the barriers, democratizing a perk that companies often reserve for the very few at the top. In this paid Premium story, you’ll: Learn how AI and human coaching differ in function, and how they can complement each other. Understand how AI can help solve the gaps that are common in today’s leadership development. Identify AI’s limitations as a coach and trainer. Most organizations dont provide managerial training Ian Gover is a trained industrial psychologist with over 25 years of experience in human resources. Initially, he was resistant to the idea of AI having any part in coaching and mentoring. That is, until he started to dig deeper into the dataand realized he was part of a group that he calls the fortunate few. I got amazing training from the companies I worked for, he tells Fast Company, starting from a 30-day, high-immersive sort of leadership programming to having access to coaches and mentors when the company promoted him. He soon learned, however, that those experiences were rare and far between. He quotes a Gartner study that found 85% of new managers receive no formal training. Thats when a switch flipped in Govers brain. He realized that he was asking the wrong question: Its not whether AI can replace humans for this type of learning. Its about how AI can potentially help the majority of managers, who receive very little initial and ongoing support from organizations. Eventually, that led to Gover cofounding Rypple, a platform that aims to help managers by providing them with an AI-driven leadership team. This includes a range of AI assistants that can help managers with tasks like meeting preparation and follow-ups, and point managers to relevant resources that tackle a topic they might be struggling with. There is also a role-play component, where managers can rehearse difficult conversations with an AI assistant and receive feedback on what went well and what they could have done better. All of these interactions build a context-specific and personalized leadership profile, and can analyze patterns and suggest opportunities for growth. Viewing human and AI coaching as two different tools Like Gover, Leon Wever experienced first-hand benefit of one-on-one coaching during his stint as a corporate lawyer. Wever was eager to bring coaching into more working environments, which led him to cofound Coachello. Unlike most AI-coaching startups, Coachello actually provides a hybrid model that incorporates human and AI coaching. Their customers can access coaches that are credentialed through the International Coaching Federation and have access to AI tools. These tools help with role-plays, training sessions, and dashboards that track behavior change progress, competencies, and skill gaps. Wever believes that human and AI coaching are two distinct tool that provide different benefits. Technically, AI cannot resonate from experience, and it cannot care for another human being, he says. What AI can do, he explains, is provide an assessment or a reflection tool, and enrich the human coaching experience. For example, AI can live record your human coaching session. The next time you do something to apply your learning from the coaching session, it can record and suggest feedback. Say youre working on having a difficult conversation with a direct report for the first time. After your human coaching session, you might role-play a potential scenario with an avatar. AI can analyze your performance based on the takeaways and feedback that you receive from your human coach. Your human coach will then have access to that information the next time you meet. In this instance, Wever explains, AI can actually enrich human coaching by making it more accurate. The opportunity to provide on-demand, 24/7 support For James Cross, cofounder of Tenor, going into the AI-leadership space was about solving the lack of time and scalability problem that many companies face when it came to leadership development coaching. When it comes to interpersonal skills that managers need to possess, the former Workday VP explains: We know that humans need to practice and retain those skills . . . Thats what AI is really good at. However, theres only a limited number of qualified coaches in the world, and many are unable to provide 24/7 support. Cross believes that COVID expanded the meaning of what it means to be a manager. Theyre being expected to do more with less headcount, he says, and middle managers and frontline managers are bearing the brunt of it. But with AI, he explains, a manager can tap into an on-demand support, almost like a really good HR business partner and executive coach who knows the business, [and] knows you and your team. He believes this to be especially beneficial for frontline managers in industries like manufacturing and distribution. I think tech company managers are fairly well supported, he observes. In most instances, youre only ever a Slack message away from your HR team. But if youre a manager at a large grocery store chain, youre having to deal with these dynamic situations in the moment. You dont have direct HR support. Cross says many of these managers are working in a fast-paced environment while dealing with issues like lateness, hygiene, and personal problems. They can turn to AI coaches for suggestions on what they might want to do at that specific moment. For example, say an employee has been late several times in a row, managers can ask AI for suggestions on how they might want to approach this conversation in a sensitive way. The more they do that, the more AI picks up on patterns and insights that the managers might not be aware of. Cross finds that once they get over the hurdle of the idea of talking to an AI, managers are often more receptive to AI feedback than they would be to feedback from a human manager. Thats because theres no emotion attached to it, he explains, and they see it as something thats logical and contextual to them. Acknowledging AI’s limitations All three cofounders acknowledge that while AI has its strengths, it also has its limitations. Tenor, for example, has specific guardrails in lace. The moment a manager starts to ask AI for advice on certain topics, it directs them to speak to an actual human. What AI determines as off-limits will be different for every customerCross believes that managers should discuss termination, health concerns, or specific personal problems with another human in the company. Dr. Marais Bester, a Netherlands-based occupational psychologist for software firm SHL, said that it would be a risk for a company to rely on AI as a “one-stop-shop for all learning and leadership growth. After all, human beings are weird, unique, wonderful and unpredictable,” he says. In his opinion, a hybrid model is ideal. This might look like a human coach building a development plan, and using AI to supplement where necessary. For example, say the human coach doesnt have the time to analyze every single persons psychometric testing results. The person that is being coached might use AI to do that, inputting only the information that theyre comfortable with. Kseniia Aksenova, a customer service manager at The Pokémon Company International, observed one downsides of using AI coaching. She found that it didnt provide any surprising or unique insights. It just gave me something that I was thinking of already, she says. It didnt give me much of a new perspective that I was trying to get. At the time Aksenova was using an AI coach, she was going through some personal and professional issues that she wanted to work through. The solutions that she received from the AI coach were ones she already thought of. It was up to her to do a lot of the critical thinking herself. Only then was she able to work with the AI coach and obtain the new insights that she was looking for. AI as a tool to democratize learning Gover is hopeful that in the future, AI can be a tool to democratize learning and coaching. For his team at Rypple, the thing that excites us every single morning is really that idea of what happens if we are able to level that field. Its not about making every manager the worlds best expert in every single leadership topic, he explains. But what if we are able to actually improve the capability and capacity of a material part of that community of managers that are struggling out there right now? What does it mean if we can provide leadership and management opportunities to those who have historically been left out of those discussions and conversations? Gover ponders. The main message, he insists, shouldnt be about AI replacing human coaches. Its about increasing access to all of these leadership trade secrets that only the few and fortunate have had the privilege to access, he explains. Nows the time to open it up and make it available.
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I spent several years of my career in the uncomfortable role of middle manager. On one side, I had executives asking me why my team couldnt do more, and on the other side, my employees told me they were stretched too thin. It was an endless tug-of-war. I was both the enforcer of company expectations and the advocate for my teams needs. At times, my role felt at complete odds with itself. Executives push for efficiency and growth, while employees look for empathy and stability. Middle management, understandably, feels like a pressure cooker. {"blockType":"creator-network-promo","data":{"mediaUrl":"https:\/\/images.fastcompany.com\/image\/upload\/f_webp,q_auto,c_fit\/wp-cms-2\/2025\/04\/workbetter-logo.png","headline":"Work Better","description":"Thoughts on the future of work, career pivots, and why work shouldn't suck, by Anna Burgess Yang. To learn more visit workbetter.media.","substackDomain":"https:\/\/www.workbetter.media","colorTheme":"green","redirectUrl":""}} The shifting role of middle management My role as a middle manager was many years ago. Todays middle managers have the added pressure of potentially becoming obsolete. Big companies like Amazon, Google, and Citigroup have opted to make their management teams leaner. Not to mention the looming threat of AI. With flattening org charts and AI-driven efficiencies, the role of middle management has changed. Theyre no longer the roles that keep things moving. Instead, theyre responsible for people: managing culture and communication across departments and locations. Yet even though the expectations and job descriptions have changed, many of the underlying limitations of middle management havent. Middle managers often have limited authority to implement changes. Yet, somehow, they have unlimited accountability for outcomes. Unlimited accountability that often leads to burnout, especially when managing people. I spoke to one former middle manager who said that she felt like she had to compensate for her employers unsustainable growth practices. I had to choose between screwing people over or shielding my team, she said. It was emotionally draining. Eventually, she quit and took a new job as a non-manager. The reimagined role of middle management To survive in the new world of middle management, you have to acknowledge that youll mostly be a people-manager rather than a task-manager. To succeed in this type of role, youll need to do all of the following: Set the right expectations with upper management, making your teams bandwidth and capabilities clear. Push back strategically and learn to frame conversations around outcomes (If we do X, here is the impact on Y). Protect your teams trust by being transparent, admitting the limitations of your authority, and advocating for fair workloads. Protect your own boundaries by caring for your team without carrying the burden of everyones problems. For many companies, middle management is the only way to get ahead (and earn more money). Yet its an increasingly risky role for companies that see the job only as task-based, not people-based. Those employers are most likely to lay off managers during rough economic times or when AI can replace tasks. Take on a middle manager role with your eyes fully open. If the company doesnt value a people-based role, you might want to find a new job elsewhere. Otherwise, youll find yourself underappreciated, constantly pulled in different directions, and at risk for losing your job. {"blockType":"creator-network-promo","data":{"mediaUrl":"https:\/\/images.fastcompany.com\/image\/upload\/f_webp,q_auto,c_fit\/wp-cms-2\/2025\/04\/workbetter-logo.png","headline":"Work Better","description":"Thoughts on the future of work, career pivots, and why work shouldn't suck, by Anna Burgess Yang. To learn more visit workbetter.media.","substackDomain":"https:\/\/www.workbetter.media","colorTheme":"green","redirectUrl":""}}
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Below, Jodi-Ann Burey shares five key insights from her new book, Authentic: The Myth of Bringing Your Full Self to Work. Jodi-Ann is a writer and critic on race, culture, and health equity. Her essays appear in various arts, business, and literary publications. She created and hosts the prose and poetry salon Lit Lounge: The Peoples Art, as well as the Black Cancer podcast. Whats the big idea? Authentic is more than a critique of the empty promise of being authentic at work. It is an invitation to question the structural realities of what it takes to be a person at work. To begin, we must take seriously the health and wellbeing of workers most impacted by harmful policies, performative practices, and opportunistic rhetoric about representation and inclusion. Listen to the audio version of this Book Biteread by Jodi-Ann herselfbelow, or in the Next Big Idea App. 1. Center the voices of those most impacted. For years, Ive heard the phrase, bring your full, authentic self to work to support diversity, equity, and inclusion initiatives. In public, Ive heard workers of marginalized identities talk about their desire to be more authentic and the barriers preventing us from letting our full self flourish. In private, however, Ive witnessed friends and colleagues scoff at the idea of workplace authenticity, saying something along the lines of, Yeah, right, or They dont want that, or They dont even know what that means. I wrote this book to raise the volume of those conversations. The reality is that the more of ourselves we give, the more institutions take from our careers, health, and well-being, and therefore the more we risk our livelihoods and lives. The stickiness of the bring your full authentic self to work narrative relies on the erasure and silence of those workers who are most harmed by fair-weathered inclusion policies and practices. But we cannot understand how work works without talking to Black people and other people of color, people with disabilities, women, queer people, and especially those of us sitting at the intersections of marginalized identities. These are the identities companies cyclically like to say they value, while targeting us with discrimination, bullying, abuse, and inequities in pay and opportunity. 2. Collective access, not reasonable accommodation. I have a spinal cord injury and must take care of my body in a way that minimizes neuropathic pain flares. Before the global COVID-19 pandemic, my employer made it very difficult for me to meet my access needs. Remote work policies were restricted to two designated days per week. The conference room policy allowed teams to book rooms anywhere on campus, which made my meeting-to-meeting commute chaotic. My co-workers questioned and judged why I took on-campus meetings remotely from my desk or carried a heating pad with me wherever I went, or why I fatigued so quickly walking from building to building. When a colleague tested positive for COVID-19, just one email shut down our whole campus. Around the country and the world, work, school, and life moved onlinefor years. Remote work and other so-called reasonable accommodations previously denied to disabled workers because it was too expensive, too complicated, and bad for productivity and morale, soon became standard procedure. How companies pivoted during the COVID-19 pandemic revealed what had always been possible. Employers restructured jobs, made spatial modifications, and provided personal protective equipment. Relaxed policies allowed workers to reduce their schedules or flex their work hours. This restructuring did not reach everyone. The pandemic affected office workers and frontline service workers unevenly. People who could not work remotely bore the brunt of death and disease because employers and legislators failed to protect them. Still, the COVID-19 pandemic began an experiment of collective access at an unprecedented scale. The support and structure we need as disabled workers are not accommodations, as weve learned to call them. Our access needs must be met to do our jobs. It is unnecessary (and prone to unchecked, unlawful discrimination) for companies to define and determine what is reasonable. Without a doubt, how companies pivoted during the COVID-19 pandemic revealed what had always been possible to ensure disabled workers can have their access needs met. Unfortunately, all those learned lessons seem to have already been lost. Just a few years later, many employers have eliminated access practices, forced compliance through threats of termination, and enacted other punitive measures to constrain an empowered workforce. Ableism hurts us all. 3. No sector is immune to inequity. Its common to make for-profit companies the boogeymen of inequitable, hostile workplaces. Ive spent most of my career working at mission-driven organizations. Early in my career, I worked as a teacher and administrator in charter schools. I spent five years in the global health and development sector. And I worked at a women-focused start-up. Each organization grounded its work in a progressive mission for equity, but that did not exempt these industries from the very same practices of discrimination, bullying, and abuse better known to characterize so-called Corporate America. Institutions that contradict their own missions can corrupt the part of our authenticity fulfilled by mission-driven work. Instead of nurturing possibility, it breeds cynicismnot just toward one institution, but the entire sector. Authenticity isnt just who we are, but what we believe in: our mission and purpose in our careers. We must include practices and policies across sectors to better understand workplace inequities and their impacts on all workers. 4. Being more authentic cannot change company culture. Every workerany personwould want the space and safety to be themselves. We want to express ourselves without contorting who we are. This is especially true for workers subjected to historical and active identity-based discrimination. Institutions often define authenticity by markers of difference. These accoutrements of identity can include hairstyles, clothing, pronouns, assistive objects, religious paraphernalia, or the words we speak. But inclusion takes more than just wheelchair ramps, pronoun pins, or inclusive dress codes. We want to express ourselves without contorting who we are. As workers, we exchange our talent and time for wages. There are much larger institutional levers impacting our professional lives than self-expressionwage theft, pay inequity, workplace fissuring, technological and managerial surveillance, occupationl segregation, racism, sexism, and other forms of structural violence. Redefined as individual acts of self-expression, authenticity narratives abstract unjust and unlawful labor practices that perpetuate workplace discrimination. 5. Community is our greatest resource. Employee resource groups (ERGs) are employee-led identity-based groups that provide formal channels for connection and collaboration. These groups are sponsored by employers, in that they are acknowledged, supported, and sometimes funded. ERGs are a lifeline for marginalized and underrepresented employees. No matter what our rank, department, office location, state, or region, we turn to ERGs for a place to belong. As corporate DEI programs evolve, more than 90 percent of Fortune 500 companies have active ERGs today. I always found the resource part of employee resource groups a bit curious. Who are the resources for? As workers, whatever space weve carved out for ourselves belongs increasingly to the business. Institutions rely on ERGs to support their workforce at large, demonstrate their commitment to diversity, and comply with federal EEO mandates. ERGs help institutions attract and recruit more people of color, women, and other marginalized professionals. Our lived experiences serve critical parts of the business function: sensitivity readers, product innovation, and PR damage control. Do ERGs have the capacity to agitate for the kind of protections we need, as workers, to be our full, authentic selves? Can ERGs provide safety for workers in the form of labor protections? ERGs are projects of representation. By design, their power to ensure material labor protections is limited. ERGs appear union-like but cannot act in ways that are dealing with the organization. They cannot negotiate on the terms and conditions of employment. They cannot hold, act on, or represent collective worker grievances. They cannot engage in any collective bargaining with the employer. No organization-sponsored employee group can be structured to truly empower its workforce. To be more authentic, we need community, protection, and a definition of authenticity that goes beyond projects of representation. Enjoy our full library of Book Bitesread by the authors!in the Next Big Idea App. This article originally appeared in Next Big Idea Club magazine and is reprinted with permission.
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