Skip to content
Let's Meet
Let's Meet
    September 17, 2023

    The Future of Performance Management: Insights from HR Tech Investor William Tincup

    William Tincup has delved into the HR and tech space from various vantage points for over two decades. As the founder of HCM Technology Report and Recruiting Daily, Tincup runs a media company that studies both HR tech and talent acquisition (TA) tech, gaining insights from practitioners and vendors alike. With experience as an investor and advisor known to be a thought provocateur, Tincup thrives on engaging in thought-provoking conversations to comprehend the challenges different industry stakeholders face.



    William Tincup, HR Tech Investor, Advisor, and Founder of


    I recently sat down to chat with Tincup about future of work trends as part of my research to produce Season 1 of The Lever with Drew Fortin. This show highlights how the rise of artificial intelligence (AI), robotics, and Web3 will shift the paradigm of humans at work for the better. I wrote this article based on my notes and transcripts from the interview. You can also watch a video of my interview with William Tincup, HR Tech Investor, Advisor, and Founder of, below.


    Navigating the Inherent Employer-Employee Relationship Divide

    Reflecting upon the employer-employee relationship, Tincup dismisses any notion of a harmonious bond, asserting that its broken nature has persisted throughout history. He likens this dynamic to the historical struggles between unions and management. Even during pre-pandemic times, when things may have appeared amicable, the underlying tensions were only unveiled by the upheavals of the Covid-19 pandemic. This global crisis, accompanied by the rapid shift towards remote, flexible, and hybrid work arrangements, exposed the fragility of the employer-employee relationship.

    Tincup uses the term "pitted" to describe the conflicting interests at play. Management aims to maximize output while minimizing resources, perpetually seeking more with less. On the other hand, employees strive for a better work-life balance and equitable compensation, desiring less work for more benefits. These divergent objectives create an inherent tension that challenges the establishment of a perfect equilibrium. While finding a middle ground where both parties agree on what they receive may appear as a solution, Tincup acknowledged the complexities of human nature that make this challenging to achieve.

    It is essential to recognize that the broken employer-employee relationship is deeply ingrained in the fabric of work itself. From time immemorial, the dynamic between those in leadership positions and the workforce has been characterized by conflicting interests. As Tincup aptly observes, management seeks more from employees than they provide in return. This reality underscores the perpetual nature of the strained employer-employee relationship.

    Humans and Robots: Finding Value in Collaboration

    In a world increasingly dominated by robots and automation, the role of humans may seem uncertain. However, industry expert Tincup believes that humans still have a crucial place in the workforce, albeit in different capacities. As technology advances and tasks that were once manual are automated, humans can focus on higher-level analysis, critical thinking, and decision-making processes that require human judgment and intuition. This shift optimizes efficiency and allows individuals to develop new skills and embrace opportunities for growth.

    Tincup highlights the importance of leveraging technology to streamline routine tasks. For instance, algorithms can now perform data-intensive tasks like scrutinizing actuarial tables, freeing human employees from mundane and error-prone work. However, humans still retain their essential role in providing contextual understanding, assessing the accuracy and relevance of data, and making informed decisions based on the outcomes. By embracing automation and focusing on tasks that leverage their unique cognitive abilities, humans can continue to make valuable contributions to the workforce.

    "A human being should never be going through an actuarial table and looking for errors. That's just dumb. We've done it up till now is because we didn't have a better way." - William Tincup, HR Tech Investor, Advisor, and Founder of

    The changing landscape of work also necessitates a shift in mindset regarding job roles. Rather than resisting change, individuals should view it as an opportunity for growth and retraining. Tincup encourages employees to explore new avenues and acquire skills that align with emerging technologies and business needs. Employers play a crucial role in supporting this transition by providing training and development opportunities that empower their workforce to adapt to evolving demands. By embracing continuous learning and upskilling, individuals can position themselves for success in a world where collaboration between humans and robots is key.

    Navigating Work's Changing Landscape: Embracing Growth and Relatability

    Tincup emphasized that work is constantly in flux, shaped by evolving technology. Work is dynamic - new elements are added as others are phased out. Tincup acknowledges that technological advancements such as fax machines, email, and the internet have displaced jobs in the past but that these advancements will ultimately create more job opportunities than they eliminate. The choice to adapt and learn new skills rests with individuals. Tincup suggests that the timeframe for acquiring new skills has accelerated, now standing at around nine months rather than the previously estimated five years. He notes that this choice to learn is subjective, and not everyone may be willing to embrace technological changes. However, Tincup emphasizes the importance of choosing growth and actively pursuing new knowledge.

    Employers also play a crucial role in the changing work landscape. Tincup asserts that companies should invest heavily in training their employees, providing ample opportunities for those who are motivated to learn and acquire new skills. By nurturing a culture of continuous learning, businesses can empower their workforce and ensure they remain adaptable in the face of technological advancements.

    With the rise of remote and hybrid work, the development of soft skills poses a challenge. Tincup highlighted the significance of teaching relatability, a highly valued soft skill, particularly among millennials and Gen Z. Traditionally, soft skills were often learned through in-person interactions, such as hallway conversations and client visits. However, as the work environment shifts, teaching these skills through platforms like teaching these skills through platforms like Zoom becomes necessary as the work environment shifts become necessary. Employers will covet employees who can effectively relate to others in a digital context.

    The conflict between employer expectations and employee preferences arises naturally in this changing landscape. Tincup recognizes that employers desire specific outcomes from their workforce, while employees, especially digital natives, seek the flexibility to work in ways that align with their preferences. This natural conflict calls for a balance that respects both perspectives.

    The Gig Economy is the Future of Work

    Tincup envisions a future where companies are built entirely around freelance workers, aligning with the preferences of digital natives. He notes that traditional terms like jobs, careers, and internal mobility are becoming outdated among the younger generation. Instead, they view work as a series of "gigs," embracing transactional and flexible opportunities. Tincup believes that companies must adapt to thrive in this changing landscape.

    Tincup emphasizes that individuals are empowered to work on their own terms in this candidate-driven market. The availability of systems and platforms enables them to cobble together multiple revenue streams or choose from a variety of freelance jobs. For companies to succeed, Tincup suggests gig-thinking and promoting employees based on their gig performance. This approach involves continually presenting employees with new opportunities and creating a dynamic and engaging work environment.

    "Companies that thrive into the future are the ones that think in terms of gigs, but also promote people in terms of gigs." - William Tincup, HR Tech Investor, Advisor, and Founder of

    While Tincup acknowledged the viability of running a business entirely on fractional work, he also recognizes the importance of a cohesive team and company culture. He suggests finding a middle ground by starting with fractional or gig workers and gradually transitioning to full-time roles as the business grows and demands increase.

    The future of work lies in embracing the gig economy, providing flexibility, and adapting to the preferences of digital natives. Companies that can effectively navigate these changes will thrive in the evolving landscape.

    Rethinking the Concept of Companies: Embracing Flexibility and Transparent Communication

    Tincup believes it is essential to reconstitute our perception of a company in the modern era. He emphasizes that the landscape has transformed since 2019, and companies need to adapt to the changing dynamics, particularly when it comes to flexible work arrangements. Tincup commends platforms like Upwork for recognizing the growing trend of flexible work and creating mechanisms to support it. However, he also acknowledges that this adaptation should have occurred earlier.

    When asked about the increase in union activity in the US, Tincup holds an interesting perspective. He considers them to be outdated, as the availability of information and transparency through the Internet has diminished the need for unions in most cases. Tincup argues that strong management and leadership, combined with transparent communication and fair compensation, create an environment where unions are unnecessary. He suggests that when employees are treated well, and their needs are met, unions struggle to gain traction.

    "We have to reconstitute the idea of what a company is in our mind. A company in 2019 was one thing and a company that made it through COVID and on the other side - one that transformed into thinking about flexible work for everyone all the time - is no longer the same company." -William Tincup, HR Tech Investor, Advisor, and Founder of

    Tincup's viewpoint highlights the importance of effective leadership and management in preventing the emergence of unions. By fostering positive employee experiences, transparent communication, and fair treatment, companies can mitigate the need for external representation.

    Performance Management Focus Shifts to Values

    Tincup challenges the traditional notion of performance management and measurement. According to him, performance measurement serves as a tool for management and leadership to understand the value they receive for what they pay. Tincup argues that it is not intended to help employees improve or thrive.

    Instead, he advocates for a personalized approach that involves constant communication, active listening, and understanding employees' unique needs. Tincup emphasizes that every employee requires different support to thrive, and leaders and managers are responsible for identifying and providing those resources. This individualized approach removes barriers and creates an environment where employees can excel.

    "I think in terms of how you help employees thrive, it isn't with performance management. It isn't with performance measurement. It's literally asking them how they thrive and being constant in their life, listening to them, being aware of what's going on in their life." -William Tincup, HR Tech Investor, Advisor, and Founder of

    Furthermore, Tincup addressed the limitations of performance management in today's ecosystem, where relying solely on LinkedIn profiles and resumes does not validate actual performance. He suggests shifting focus to skills, experience, potentiality, and outputs as the true indicators of value. By evaluating these factors and aligning them with organizational goals, companies can make more informed decisions about compensation and ensure pay equity.

    Tincup urges leaders and managers to adopt a value-driven mindset in their decision-making processes, similar to how consumers consider return on investment (ROI) when making purchases. He challenges traditional HR and recruiting practices that fail to apply this concept to talent acquisition and development.

    Taking Ownership of Your Career: The Individual's Role in Career Management

    Tincup emphasized the importance of individuals owning their careers. In discussing the evolution of career management, Tincup highlights the shift from companies managing employees' careers to individuals proactively managing their own paths. He attributes this change to factors such as the rise of free agency in both sports and professional life, which led to a breakdown in loyalty between employers and employees.

    According to Tincup, the responsibility for managing one's career lies with the individual. He believes that if individuals truly care about their careers, they should actively take charge of managing them. However, Tincup also acknowledges that companies still play a vital role in providing opportunities that align with employees' career goals.

    "The idea is you need to be thinking about what you want out of life and work, and so that you have a framework for when things are put in front of you." -William Tincup, HR Tech Investor, Advisor, and Founder of


    Tincup argues that companies should not shy away from career management but should view it as an opportunity to attract and retain talent. Companies can create an environment where employees are motivated to thrive by putting forward opportunities that align with their aspirations and demonstrating their potential for success.

    However, Tincup emphasizes that employees must also have a clear vision of what they want to achieve in their careers. He encourages individuals to think about their desired outcomes, how they want to interact with work, and what they want to accomplish within a specific timeframe. This proactive approach allows individuals to evaluate opportunities based on their alignment with personal goals.

    "If you care about your career, you should be managing your career. If the company just so happens to put things in front of you that align with how you see your career playing out, great." -William Tincup, HR Tech Investor, Advisor, and Founder of

    Navigating the AI Hype

    In closing our conversation, Tincup provided sage advice for those feeling pressured to jump aboard the AI rocketship for fear of becoming obsolete. It's important to keep a realistic perspective when it comes to chatbots and AI, according to Tincup. Although he recognizes their value and potential, he warns against overhyping them as the ultimate solution to global challenges. While AI can provide valuable insights, it's not a cure-all for the world's problems.

    "AI is not going to solve all the world's problems. Neither will any other thing being over-marketed out there. So just beware of that. Beware as a consumer. Beware that these things are just being over-marketed and the reality is not near what the marketing shtick is." - William Tincup, HR Tech Investor, Advisor, and Founder of

    Tincup advises consumers to be cautious of exaggerated claims made by marketers and to look beyond flashy advertising. We will all benefit from approaching AI and other emerging technologies with a critical mindset. While they have their merits, they should be seen as tools rather than miracle solutions. He suggests considering practical limitations and acknowledging that the reality may not operate as advertised.

    Want to hear more from William Tincup, HR Tech Investor, Advisor, and Founder of Recruiter Daily?


    Drew Fortin

    Drew is a people-first, values-driven leader with nearly 20 years of growth strategy and team-building experience across retail, marketing technology, local media, and HR tech. He spent 7 years at The Predictive Index, where he was Chief Growth Officer responsible for the company's strategy to build the world's first...

    More from the blog

    View All Posts