Throughout my career, I’ve had the privilege of working with incredible mentors, both formally and informally. These relationships have played a significant role in my personal and professional growth, each one shaping me in ways I never expected. In the organizations where I worked, particularly as part of the Human Resources team, we placed a strong emphasis on executive mentorship. It was a standard practice: we paired leaders with mentors based on developmental needs. If someone had a specific gap or challenge, we would match them with a person who excelled in that area. The goal was for the mentee to absorb the skills and insights of the mentor, almost by osmosis. In theory, it made perfect sense. But in reality? If only it were that simple.

Some of the mentoring relationships I experienced were comfortable, almost like slipping into a well-worn pair of shoes that fit just right. These mentors made me feel supported and safe, giving me the confidence to stretch my abilities and take risks in my career. I looked forward to our conversations, knowing I’d leave feeling uplifted and motivated.

Other relationships, however, were the complete opposite. They were rigid, formal, and often made me feel anxious. These meetings felt like obligations, and the discomfort I experienced during them was palpable. The formality of these relationships left me counting the minutes until the end of each session. I would dread going into these meetings, knowing I would leave feeling drained rather than inspired. Yet, even in these difficult relationships, I learned important lessons—though perhaps not the ones I had initially expected.

One of the most valuable things I gained from these mentorships went beyond leadership development, communication skills, or networking opportunities. The true power of mentorship, I discovered, was advocacy. Many of the mentors I worked with were senior leaders in the organization. These were the people who sat in boardrooms and participated in succession planning meetings, where decisions about the future of the organization—and the careers of its leaders—were made. It was during these meetings that names would be written on a whiteboard, with possible future roles attached to them.

Having a mentor who was an advocate for you in those rooms was invaluable. When I reflect on my own career, I realize how fortunate I was to have several Vice Presidents in those rooms speaking up for me, lobbying for my success. They weren’t just giving me feedback in private; they were actively pushing for my advancement in spaces where I wasn’t present. Their belief in me, their willingness to champion my cause, made all the difference in my career trajectory.

But this only worked if you had the right advocates. I was lucky to have several people in my corner, but not every mentor I worked with was a good fit. One mentor, in particular, stands out in my memory for all the wrong reasons. She wasn’t someone I had anything in common with, and frankly, I didn’t find her particularly engaging. She was cold, abrupt, and all business—traits that made our interactions difficult. Her attitude suggested that she didn’t really want to be there, like she was counting down the days until her retirement but still showed up because the paycheck was good enough.

Our sessions were uncomfortable from the start. Each time we met, I felt a knot of dread forming in my stomach. I would agonize over what to bring to the table—what topics or issues I could raise to make the session feel somewhat productive. I’d arrive with a list of three or four items I wanted to discuss, but she would rush through them at lightning speed. It didn’t feel like a conversation, or even a productive exchange of ideas. It felt more like an interrogation.

I often left those meetings feeling worse than I did going in. It wasn’t just the speed of our conversations or the lack of engagement; it was the vibe that she was constantly scrutinizing me. I felt like I needed to come to each session with some kind of emotional armor, ready to protect myself from the sharp critiques that I knew were coming. The blows to my psyche were real, and after each session, I found myself questioning my abilities and my place in the organization.

Despite all this, I pushed through, and there was one session in particular that changed everything for me. On this day, she gave me some feedback that wasn’t directly her own but had come from her peers. They felt that when I did speak up in meetings, I had insightful things to say—but that I didn’t speak up often enough. They wanted to hear more from me.

Hearing this was terrifying. It struck at the very core of one of my biggest insecurities: speaking up in large meetings. I hated it. The thought of having all eyes on me, of being the center of attention while everyone listened and judged every word that came out of my mouth, filled me with dread. I wasn’t just worried about what I was saying; I was hyper-aware of how I might be perceived. Were they judging my appearance? My tone? My choice of words? My accent, or lack thereof? The list of anxieties went on and on.

My fear of judgment was so intense that it far outweighed my desire to be seen as knowledgeable or articulate. I would much rather stay silent and avoid the risk of disapproval than speak up and let my true self come through. I realized that this fear had been with me for most of my life. I remembered my first-grade teacher telling my parents that I always had the right answers but rarely raised my hand in class. When they encouraged me to speak up more, I would—for a little while. But the first time I made a mistake or answered incorrectly, I would berate myself for it and retreat into silence once again. This pattern of avoiding judgment by staying quiet became a safe space for me, one I carried well into my adult life.

That day, in the middle of one of our difficult mentorship sessions, I opened up to my mentor about this fear. I shared how scared I was of being judged, of looking stupid, of being wrong, or worse—being rejected. I explained how these fears kept me from speaking up, from contributing more in meetings and conversations.

What she said next was the most life-changing advice I’ve ever received, especially as someone who struggled with perfectionism. She told me, “Instead of fearing all these what-ifs, why don’t you try prefacing your thoughts with something like, ‘I haven’t put much thought into this, but off the top of my head…’ or ‘I’m not sure if this makes sense, but I’m thinking…’” She also suggested I try something like, “Let me give this some thought and get back to you” when I wasn’t sure how to respond.

It sounded so simple—almost too simple—but it was exactly what I needed. These phrases gave me an “out,” a way to participate without the pressure of having to be perfect. They allowed me to speak up more often without the overwhelming fear of judgment that had always held me back. This advice stuck with me for life, and I’ve passed it on to so many clients who’ve asked how they can advance their careers in subtle yet impactful ways.

In the end, it’s about being seen, being heard, and being valued. Don’t let fear stop you from putting yourself out there. Take it from me, this small shift in how you approach speaking up can open up your world in ways you never thought possible. It’s a lesson I learned the hard way, but one that has changed my life—and it can change yours too.