How to Have Courageous Career Conversations with Vanessa Iloste

We had the privilege of speaking with Vanessa Iloste in 2022. This conversation is adapted from Episode 18 of our Making Sense of Work podcast with Jean Balfour.

Career conversations are an invaluable opportunity for leaders and employees to explore aspirations, map out goals, and build a future path within the organization.

Yet, as Vanessa Iloste, HR VP at Sephora Asia, explains, these conversations are rarely straightforward.

In her discussion with Jean Balfour on the Making Sense of Work podcast, Vanessa shares her unique perspective on what makes career conversations impactful, how they should be approached, and why they are more critical than ever in today’s work landscape.

With over two decades in HR, Vanessa emphasises that career conversations should foster curiosity, expand possibilities, and above all, empower employees to take ownership of their growth.

Here’s what she reveals about the art of meaningful career dialogues and how both leaders and employees can engage in these conversations effectively.

Why Career Conversations Matter

In her discussion with Jean, Vanessa highlights an essential aspect of career growth: employability. She explains that career conversations should help employees not only envision their future within the company but also build skills that make them valuable in the broader job market.

“Employability means understanding where you stand in the market,” she notes, encouraging employees to stay adaptable and continually enhance their skills. Jean expands on this point, reminding us that while many companies support career progression, it’s ultimately the employee’s responsibility to ensure their skills are relevant and market-ready.

This concept of employability reframes career conversations as an ongoing journey, with HR and leaders offering guidance but the employee taking charge of their development.

For leaders, fostering employability means creating a culture where learning is encouraged, and employees feel empowered to pursue growth, whether through training programs, cross-functional projects, or external learning opportunities.

By shifting the focus from job titles to skills and market relevance, career conversations can become a powerful tool for long-term career development.

The Art of Having Career Conversations

For Vanessa, a successful career conversation isn’t about making promises or setting specific goals. Instead, it’s about creating a space where employees feel comfortable exploring their aspirations. “Career conversations aren’t about guaranteeing promotions but exploring possibilities,” she explains.

This openness allows employees to envision career paths that may not be obvious or immediately attainable, making it an essential process for personal and professional growth. Vanessa encourages leaders to use open-ended questions to kickstart these conversations.

Her favourite question, “What if?” allows employees to imagine new roles and responsibilities that align with their interests and strengths, without the pressure of immediate decisions.

By asking “What if you explored a general management role?” or “What if you considered moving into a different department?” leaders can help their team members consider paths that they might not have thought of on their own.

Through her experience, Vanessa has found that this approach also alleviates the pressure for leaders who may fear overcommitting or raising expectations. Instead of feeling obligated to offer specific opportunities, leaders can use career conversations as a way to spark curiosity, plant seeds of possibility, and encourage employees to take ownership of their career journey.

Misconception of Career Conversations

A common misconception about career conversations is that the manager is responsible for outlining a clear career path.

Vanessa, however, views these conversations as a partnership where both parties bring ideas and curiosity to the table. “It’s still my career, and I have to look after it,” Jean notes, emphasising the importance of employee ownership.

For leaders, this means moving away from a directive approach and instead facilitating a space where employees feel encouraged to share their aspirations openly. Vanessa recommends that employees come prepared to career conversations with a clear understanding of their strengths, interests, and potential growth areas.

For instance, employees might start the conversation by saying, “I’d love to discuss my strengths and how I can use them to contribute more.” This level of preparation allows for a more productive dialogue, where both parties can collaboratively explore options for growth, learning, and development.

For leaders, fostering this sense of ownership requires a shift in mindset, from directing employees to guiding them. By positioning themselves as facilitators rather than decision-makers, leaders can empower employees to think critically about their career path and take an active role in shaping their future.

Create a Culture of Aspiration Over Ambition

Vanessa also brings another refreshing approach to career conversations by framing them around “aspiration” rather than “ambition.”

For her, aspiration is a more inclusive and accessible way of talking about career growth, especially for employees who may feel uncomfortable with the idea of ambition or self-promotion.

Aspiration allows people to dream, think creatively, and consider possibilities without the pressure or connotations that often come with ambition.

Using this language, Vanessa helps employees feel more comfortable exploring their dreams. She asks, “What are you most curious about in your career?” or “What new skills excite you?” These questions help employees articulate their aspirations, making the conversation lighter and more enjoyable.

This focus on aspiration also removes the pressure of conforming to a specific career path. By encouraging employees to explore their unique interests, Vanessa fosters a workplace culture where employees feel empowered to shape their own careers in ways that reflect their passions and talents.

Overcome Barriers to Career Conversations

Not all employees have the advantage of a supportive manager like Vanessa.

For those working with leaders who may not prioritize career conversations, Vanessa offers practical advice: be proactive and “politely provoke” the conversation.

She suggests giving the manager a heads-up, such as, “I’d love to discuss my aspirations and strengths in our next one-to-one.”

Vanessa advises employees to approach these conversations with specific examples of their achievements, growth areas, and potential career interests.

This preparation demonstrates both commitment and curiosity, making it easier for the manager to engage.

Vanessa also recommends that employees prepare questions to ask their manager, such as, “What growth opportunities do you see for someone with my skills?” or “How can I contribute more effectively to our team goals?”

If a manager remains unresponsive, Vanessa suggests looping in HR or finding other avenues to express career aspirations, such as networking within the organisation or seeking mentorship.

By consistently sharing their aspirations and achievements, employees create a “little music” within the organization, keeping their career goals visible even if immediate opportunities are not available.

Summary on How to Make Career Conversations Meaningful

Sounds like a lot? We got you covered!

Vanessa’s approach to career conversations offers valuable insights for leaders who want to create a supportive environment for their team’s growth. We broke it down to simple pointers for you.

Here are some practical tips:

1. Start with Curiosity: Open the conversation with questions like, “What are you most excited about?” or “What new challenges would you like to take on?” This approach helps employees feel comfortable sharing their interests without pressure.

2. Discuss Aspirations, Not Just Promotions: Career conversations shouldn’t only focus on immediate job changes. Vanessa encourages leaders to talk about long-term aspirations and skills that employees want to develop, creating a more holistic view of career growth.

3. Emphasise Skills and Employability: Focus on the skills and experiences that will keep employees adaptable in a changing job market. Vanessa highlights employability as a central aspect of career development, which helps employees see their career as an evolving journey.

4. Encourage Ownership: Rather than outlining a rigid path, invite employees to take ownership of their career by exploring their options. This collaborative approach fosters a sense of partnership and mutual investment in the employee’s growth.

5. Reframe Ambition as Aspiration: Using language that feels inclusive and positive, such as “aspiration” instead of “ambition,” can make career conversations more approachable, especially for those who may feel reluctant to discuss their goals.

6. Follow Up Regularly: Career conversations are most effective when they’re part of an ongoing dialogue. Regular follow-ups help both parties stay aligned on goals and progress, reinforcing a commitment to growth and development.

To Sum up…

Vanessa’s insights remind us that a meaningful career conversation is a journey of curiosity, aspiration, and empowerment.

Leaders play a critical role as facilitators, guiding employees to consider paths they may not have envisioned, while employees have the responsibility to take an active role in shaping their career path.

For HR leaders and managers, Vanessa’s approach offers a refreshing perspective – career conversations should not be transactional but transformational, helping employees develop skills that will serve them within and beyond the organisation.

How are you fostering career conversations with your employees?

Be sure to check out the full episode on Apple or Spotify.

Here are more resources on career coaching:

1. How to Become a Career Coach
2. Five Steps to Get Your Job Promotion
3. Choosing the Right Career With the Right Career Values
4. 100 Powerful Coaching Questions Everyone Should Know

Bailey Balfour, we offer an ICF Level 1 coach certification programme designed for coaches and leaders interested in pursuing executive and career coaching. If you’re interested in learning more, you can download our brochure to review our curriculum or reach out to us for further information.

Making Sense of Work Podcast

How’s Work at the Moment? We all work – and yet we often struggle with work. Even very ambitious people find parts of work difficult. This podcast is for you if you’d like to build a new and better relationships with your working life. Join Jean Balfour and guests as they explore everything to do with our working lives, starting with how do we find our purpose, how do make sense of our organisations and what major movements are we seeing in the workplace today?

About the Author

Jean Balfour is Managing Director of Bailey Balfour and Programme Director of our ICF Accredited Coach Training Programmes. Jean is passionate about helping people to have good conversations both at work and at home. She believes that coaching is a life skill and that you never regret learning to coach.

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