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How mentoring an experienced employee works

Mentoring an experienced employee requires a different mindset. Alaina Love shares four key areas to focus on.

5 min read


mentoring an experienced employee Alaina Love

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A multinational manufacturing firm had long neglected investing in talent development for several groups of outstanding employees. It was now beginning to feel the pinch from a competitor that was recruiting away its top diverse employees. 

To address the issue, the newly appointed CEO recently committed to taking bold action to improve the company’s representation of women, Black and Hispanic employees at leadership levels. Among other initiatives, he instituted a mentoring program designed to fast-track participants to management levels and beyond. That meant some people would be mentoring an experienced employee.

mentoring an experienced employee Alaina Love
Allison Shelley/Deeper Learning

Brenda is the longest-tenured participant in the mentoring program, having joined the firm seven years earlier than most of the other mentees. Despite her years of service, she had experienced minimal investment in her professional development from former managers. Brenda was excited about the opportunity to focus on her career and growth but wondered what it might be like interacting with a mentor at this stage of her career. 

When I spoke to her mentor, Jason, I discovered that she wasn’t alone in her concern. “As her mentor, I’m happy to help Brenda in any way that I can,” Jason affirmed. “But what can I teach her about being successful at her job that she doesn’t already know after eight years with the company?” 

Break away from the traditional approach

Jason was viewing his mentor role in a traditional fashion: one in which he envisioned meeting with Brenda periodically to discuss job challenges or examine future roles she might pursue. But they worked in different functional areas, so he felt his ability to add value was limited. 

As we discussed his role, and the objectives of the mentoring program, it became clearer to Jason that mentoring an experienced employee had nuances he hadn’t considered. 

I suggested that while his role was to help Brenda be both present-centered and future-focused, mentoring her was more about gaining insights than discussing how-to’s. We reviewed five major focus areas that he and Brenda might explore together:


Often more tenured employees with greater life experience behind them feel that they’ve developed a high level of self-awareness. “By this stage in life, I know myself,” many will say, and Brenda was no exception. 

I encouraged Jason to dig deeper. Did her level of self-awareness translate into a higher degree of confidence on the job? Was Brenda’s voice being heard in meetings? Were her ideas being implemented? Did her colleagues seek out her opinions? 

Individuals who have truly matured in their level of self-awareness demonstrate a degree of authenticity that engenders respect and trust from others. As a potential future leader of the company, Brenda’s continued attention to developing her understanding of and comfort with her true self is an essential component for success.

Professional growth

Many organizations and mentoring program participants conflate mentoring success with promotion to a job at the next level. While Brenda was hoping for that same outcome, it was more important for Jason to focus on the factors that lead to professional growth. I encouraged him to help Brenda broaden her professional network and connect her with people outside of her functional area, so she can learn from others and develop contacts that might be helpful in the future. 

It was also important to help Brenda strategize about positioning herself for special projects or assignments, ones that could expand her understanding of the company and allow her to build skills. Helping Brenda learn as much as she can beyond her normal role will allow her to demonstrate curiosity and commitment to her own development. That makes her a desirable candidate for promotion. 

Learning is the road that leads to professional growth, and professionals should reinforce that idea when mentoring an experienced employee.


In the early phases of career, many employees spend time defining a path to success by observing individuals in leadership positions. What was their career trajectory? Which assignments helped those leaders make a name for themselves in the organization or the industry? What approach did they develop that can be modeled by others?

Mentoring an experienced employee means helping them move beyond the pursuit of title and power. It’s about encouraging the mentee to seek insights from their experiences that lead to greater wisdom. Wisdom about what matters most in life. Wisdom about how purposeful work contributes to well-being. Wisdom about the limitations of money and power when it comes to achieving fulfillment. 

Jason’s goal is to help Brenda develop and share her wisdom with others so she can become a role model for servant leadership.


It’s never too early to begin helping a mentee think about their legacy. It’s not an exercise that should be reserved for the final years of one’s career; instead, it should be a constant guidepost that marks the way. 

The important questions to ask your mentee are: What are the lasting contributions you want to make to the organization, industry and profession? What memorable impact do you want to have on colleagues and associates, both inside and outside of the organization? How will pursuing your legacy impact your personal life and relationships?  

One of Jason’s most important mentorship objectives is to help Brenda define the legacy she wants to achieve so she can align it with the career and life decisions she makes. 

Mentoring an experienced employee is mentoring at a whole new level. 

Alaina Love is CEO of Purpose Linked Consulting and co-author of The Purpose Linked Organization: How Passionate Leaders Inspire Winning Teams and Great Results. She is a recovering HR executive, a global speaker and leadership expert with Fortune 500 clients. Follow Love on TwitterFacebookYouTube, or read her blog.


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