Five Ways to Hone Your Mentoring Skills
There’s no better way to give back in the business world than to help someone else succeed. Here’s some expert advice to help you be a better mentor.
Samantha Wong felt lost when she finished school and embarked on a marketing career, starting out as an intern at Microsoft. “I didn’t have a clear idea of what I wanted to do next,” she says. “I wasn’t sure what I was truly good at or what I was passionate about.” But then other women stepped up to support her — 14 years later, she is now a senior account executive at Microsoft.
With the help of her mentors, Wong developed long-term goals and learned to be strategic about the roles she chose in the company, an early career move that helped her trajectory through increasingly senior sales and marketing roles. One mentor, in particular, saw potential in her that she didn’t see herself, supporting her in taking the lead on a high-stakes project that Wong says redefined how she saw her own capabilities. “That experience taught me the importance of taking calculated risks and trusting in my ability to grow through challenges.”
Not long into her career, other women began asking Wong for professional advice. “A lot of people are kind of lost when they enter the corporate world,” she says. “I wanted to find a way to give back.”
To become better at mentoring, Wong participated in formal mentorship programs at Microsoft, honing her active listening skills and learning how to be more vulnerable with others to become a more empathetic guide for her mentees.
Wong has been mentoring within Microsoft for almost nine years and has also enrolled in the Rosie Mentorship Program, an initiative affiliated with The Prosperity Project that offers a free six-month mentorship program for women seeking career advancement. The program allowed her to broaden the reach of her mentorship so she could also support people outside the corporate world.
One of the most rewarding aspects of being a mentor, she says, is the opportunity to help others navigate their career journeys with confidence and clarity. “It feels incredibly fulfilling to share insights, lessons and even mistakes from my own experiences — things I wish I had known sooner in my career. Knowing that my guidance can help someone avoid unnecessary challenges or accelerate their growth is deeply satisfying.”
Wong sat down with ROOM to share her top five tips to help you build your mentoring skills and make the most of your mentor-mentee relationship.
1. Set clear goals in a kickoff meeting
It can be tempting to jump straight into advisor mode, Wong says, but she encourages mentors to take a step back and determine what the mentee’s goals are. “In the very beginning of every mentee-mentor conversation, ask: ‘What is it that you want to get out of this?’” she says. “This provides context for future conversations.” Establishing clear objectives with mentees, both in terms of their professional development and the mentor-mentee relationship itself, can help you build a roadmap for their progress and set measurable goals.
2. Adapt your approach to fit different personalities and career goals
“Different mentees have different needs and learning styles,” Wong says. While some mentees might appreciate a more “prescriptive” teaching style with lots of notes and homework, others may prefer to listen and learn. In addition to modifying her mentorship style to her mentee’s learning style, Wong will also adapt her approach based on their personality and current career level. “If they’re shy, I want to find opportunities for them to speak a little bit more versus me talking all the time,” she says.
When adapting her approach to suit a mentee’s seniority, Wong will focus more on building foundational skills for those just starting out, like setting clear career goals. For mid-career mentees, she’ll emphasize leadership development skills and strategic thinking.
3. Be vulnerable and authentic to build trust in your mentor-mentee relationship
Wong isn’t afraid to tell a mentee about her own failures. She says that sharing the lessons you’ve learned when you’ve been in a similar situation makes you relatable and helps build trust and understanding. She recalls telling a former mentee she felt nervous about pivoting from a marketing role to a client-facing one. “By discussing my fears and how I navigated the shift, I was able to reassure her that feeling uncertain is natural and that embracing change can lead to growth,” she says. “Being vulnerable and authentic is key to building trust.”
Wong also encourages mentors to admit the limitations of their own abilities and networks. For example, when a mentee asked what it’s like to be an engineer at Microsoft, she couldn’t answer that question first-hand, but committed to helping connect the mentee with someone else at her organization who could provide that advice.
4. Develop reflective listening skills
Because meetings so often take place virtually, Wong says it’s crucial to reduce distractions. “Sometimes, when we’re on a virtual call, we feel the need to multitask,” she says. “An email might come in, or a phone message, but we really need to minimize those distractions.” Giving your mentee your undivided attention will allow you to fully understand their challenges and provide meaningful guidance. She adds that practicing “reflective listening” is a good way to become a more active listener. “Summarize and paraphrase what the mentee said to confirm your understanding of it.”
She also recommends letting go of the natural impulse to fill in the gaps in a conversation. “You run the risk of interrupting or jumping in too quickly with a solution,” she explains. “Be okay with the pauses and silences to make sure that the individual has gotten their full thought out.”
5. Ask for — and incorporate — feedback to continue honing your mentoring skills
“I always ask for feedback at the end of sessions with my mentees,” Wong says. “I’ll ask them, ‘How did you find our conversation today? Was it good? Was it effective?’ I want to know if they got what they needed out of it. For instance, if they tell me that I ran through something too quickly, it allows me to go back to adjust my delivery style.”
Ultimately, Wong says the best way for mentors to continue supporting their mentees is to regularly update their own skills and knowledge. “Relying solely on past experiences might not address the new challenges and opportunities that mentees face today,” Wong says. “By actively refreshing our own knowledge and skills, mentors demonstrate a commitment to lifelong learning. This not only enhances our credibility but also serves as a powerful example for mentees.”
