Stephen Shortt is a dynamic and visionary speaker dedicated to helping entrepreneurs, family businesses, and leaders thrive in today’s fast-changing world.

As CEO of CareerFit which helps people discover their ideal careers, Talent Select which helps companies hire the right people every time, and founder of the HAPPY People Project which helps people and organisations build happier lives and workplaces by design, Stephen brings a unique blend of experience in entrepreneurship, leadership, and human potential.

Having grown up in two family businesses and later founding Successful Succession, Stephen has first-hand insight into the opportunities and challenges that come with building, leading, and passing on family enterprises. A former EO Global Chair of the Global Student Entrepreneur Awards (GSEA), he has inspired entrepreneurs and their families on five continents.

Drawing on decades of experience leading businesses, building global networks, and developing innovative frameworks for leadership, hiring, and career strategy, his talks are practical, transformative, and inspiring – with a dash of humour that EO audiences love.

​Having been an EO member for over 13 years and a founding member of EO Ireland, Stephen knows first-hand the different elements that matter most to both chapters and their members.

Each chapter has unique priorities, and he has designed a set of keynotes and workshops that can flex to those needs – whether it’s a single keynote, a family-focused evening, or a multi-day programme combining leadership, hiring, and family business.

The options below are crafted to be appealing individually, but they also work brilliantly as part of a combined experience spread over one or two days.

The future of work is changing faster than ever – AI, automation, and shifting global markets mean the jobs of tomorrow may not even exist today. Parents want the best for their children, but pushing them into “safe” careers often backfires.

This talk equips EO members and their families with the tools to help the next generation discover careers aligned with their unique talents, interests, and aspirations – building not just successful futures, but fulfilling ones.

Key Takeaways:

• How to guide children toward careers that fit their personality, abilities, and interests.
• Why traditional “safe” jobs may not be future-proof – and what to focus on instead.
• A practical framework for helping the next generation thrive in the age of AI and automation.

Family businesses are both a blessing and a challenge. The potential for legacy, wealth, and impact is enormous – but so are the risks of conflict, resentment, and burnout.

Drawing from his own experience growing up in two family businesses – and nearly walking away from it all, Stephen shares his Successful Succession Framework to help families thrive across generations without losing relationships in the process.

Key Takeaways:

• How to separate family dynamics from business decisions.
• Practical tools for managing succession expectations across generations.
• Building harmony, legacy, and profitability at the same time.

Leadership is not one-size-fits-all. Understanding your leadership style – and how it interacts with others – is the difference between leading effectively and unintentionally sabotaging your team.

This interactive session includes a personalised LeadershipProfile.com Dashboard for every participant, giving EO members and their executives tailored insights into their leadership strengths and blind spots.

Key Takeaways:

• Identify your personal leadership style and how it impacts your team.
• Discover potential blind spots and how to overcome them.
• Learn how to adapt your style to get the best results from others.

Hiring mistakes cost companies time, money, and energy – and they’re often the result of relying on gut instinct instead of a structured approach. In this session, Stephen shares a proven, end-to-end hiring process that helps leaders consistently attract, evaluate, and select the right people for their teams.

Using a blend of SPEC the Role to define what success looks like before you hire, Calibrating TALENT to assess the traits, aptitudes, enthusiasm, and team fit of potential candidates, and finally Competency-Based Interviews to be able to extract real evidence of ability, Stephen gives EO members and their key executives a practical system they can apply immediately to make better hiring decisions.

Key Takeaways:

• How to SPEC the Role clearly so you know exactly who you’re looking for before starting the search.
• Why the Calibrating TALENT Framework provides deeper insights than CVs, references, or gut feel.
• How to conduct Competency-Based Interviews that reveal genuine ability and fit.
• A repeatable framework to avoid costly mis-hires and build stronger, more aligned teams.

As artificial intelligence reshapes the workplace, the real competitive edge won’t come from technology alone but from leaders who embed meaning, purpose, and happiness into their organisations.

This session explores how members and their teams can navigate the collision of rapid change and rising pressure while creating cultures where people feel fulfilled, trusted, and inspired.

By combining human-centred leadership with future-focused strategy, participants will discover how to align business growth with personal well-being – unlocking innovation, engagement, and long-term success.

Audience Takeaways:

• A fresh perspective on how aligning business success with personal fulfilment drives stronger teams and sustained growth.
• Practical frameworks, including the HAPPY Work Life MAP, to help leaders foster adaptability, trust, and well-being.
• Clear steps to build intentional, future-ready organisations where people and business flourish together.