Losing (and Finding) My Voice as a Leader

Photo by Panos Sakalakis on Unsplash

I’ve heard many female (and some male) leaders tell me that they struggle to speak honestly in their roles. Sometimes it’s in conversations that involve a power dynamic, like with a manager, the CEO, or an investor. They are afraid to state their beliefs. They don’t think they have enough experience or worry that they might destroy their credibility or relationships.

I’ve spent years struggling with reclaiming my voice, and I’m coming to some breakthroughs. I’m eight years into running and scaling Chewse, a startup based in SF with 200+ employees and $30M in venture financing. And yes, I still struggle with speaking my truth. Growing your team size and raising more money is no guarantee that you find your voice. So best to start early and deliberately.

I’m starting to believe that truth is the highest leadership virtue. Leadership isn’t about making other people happy or even fulfilled (although these are both byproducts of speaking truthfully). It’s about inspiration, alignment, and service. These are all feelings and states of being that leaders stir up when they risk putting their opinion fully out there. And I call it a risk because there is the risk of judgment. Without the risk, it wouldn’t be worth writing a blog post on since everyone would do it.

To be clear, speaking truth is not blurting out everything you are thinking. As leaders, we aren’t here to process everything in our heads with the people we serve. Truth can look like an invitation to have a conversation about something that feels difficult in addition to it feeling true. Truth is not just stating the facts, but also about stating how you feel about the facts. This is the next layer of truth beyond the factual, into those realms that seem taboo in business: the emotional.

Speaking truthfully has unlocked for me the most profound leadership moments. Being truthful — paired with its requisite pairing of being vulnerable — has inspired and rallied my team in the darkest of times. When we were looking at the end of our cash runway coming six months away, I told my team I was scared and that I would be sad not to work with them. That I was motivated for us to grow. And we pushed through and raised a Series A without losing anyone.

Speaking truthfully has authentically connected me to others when I felt ashamed and feared losing connection. It could be the single most powerful leadership value I hold. At Chewse, we call this value “speak directly with kindness.” It’s candor with care.

I’ve seen two consistent beliefs crop up that squash my voice.

1. “I don’t want to hurt others.” This is the belief that speaking candidly will harm my relationship with others or demotivate them.

I once had a leader who wasn’t scaling with the company. It was evident in the results he wasn’t bringing in. And while I could discuss him missing targets, I shied away from the larger conversation. I was scared that if I shared my concerns about his ability to scale, I would have only demotivated him. So I focused in, more safely, on the results and I avoided the larger and harder conversation. He ended up leaving the company, and I still wonder what would’ve come of a more honest conversation earlier.

It came up recently when I had to give someone feedback, and I was afraid they would get demotivated. The voice in my head even said they might leave! But this time, I put my new tools to work and decided to share the feedback AND fear. And the person gently laughed and said they agreed with my feedback and they had no intention of leaving anytime soon. Which made me laugh at myself a bit, too :)

2. “I don’t trust my opinion.” As a first-time founder, I don’t have deep expertise in most topics. Hell, that’s why I hire experienced executives to take on their functions and go deep. But the problem crops up when I have an opinion on something they know well, and we disagree. Then I defer. I stop trusting my own intuition and gut — which, if I end up holding it back, has the double whammy of not moving the conversation forward and makes me berate myself for not speaking up.

So then I hold back, which is me deferring and giving away the power of my intuition and opinion.

1. Reframe truth as a way of helping others.
At Chewse, we believe you can’t care for someone without holding them to the highest standard and helping them grow along the way. One technique for embodying this belief is to visualize a difficult conversation in its best possible light. I walk into a feedback conversation visualizing the other person excited to hear the feedback and grow from it. I imagine them thanking me for the feedback. And given that I’ve hired people who have a mindset of continual growth and improvement, this is the most probable outcome.

2. Use the language of “stories” to invite conversation.
Sometimes feedback isn’t entirely feedback. It’s a hunch, an intuition. It needs a partner to develop and understand. In situations where I have high trust, I invite the other person into the feedback conversation. This is pretty nuanced, but if both people are open to reaching truth and growing, then it’s the most powerful way of having a feedback conversation that you co-create.

For example, I was hiring for a role, and I’d found an incredible candidate. He had gone through the whole interview process: meeting the team, talking to our investors, learning about each other’s families and work dreams. We both were eager to work together. At the time of the offer, he brought up a big deal breaker that surprised me. After I hung up the phone, I toyed with ending the process: not just because of his request, but also because I feared he had been dishonest. That’s when I realized that I had created a story that he withheld information so he could get to the offer stage and see his options.

Instead of walking away from it, I decided to lean into the candor and tell him about my story. It was risky, and I was nervous to extend such trust so early in the relationship. But that’s when he told me that he had shared this deal breaker with our recruiter, which I didn’t know. And he went a step further and took ownership over not having the conversation more clearly directly with me. Not only did I learn about a break in our interview process, but I also learned that he took ownership and was willing to be real with me. It also made space for us to open up about any other things that we might not have been sharing it kicked off our relationship in a powerful way. We ended up being able to honor his request and hire him.

3. Be candid that you struggle with being candid.
This is the single biggest lesson that’s helped me. I like to explain to people I work with what my weaknesses are, where they come from, and then invite them to support me on it. This is, by the way, super scary. It opens you up to judgment, which is a risk. But in every interaction where I’ve shared this, I’ve only been met with empathy (I’m not the only one who feels this way!) and deep support.

For those who you invite into the fold, one great way to give others guidance on supporting you is to have them ask you “What are you saying that I’m not hearing?” This question gives me the space to explore what hasn’t been said and say it, in an environment where an honest dialogue can happen. For a manager, investor, romantic partner, or even a peer that wants an authentic relationship with you, they shouldn’t have a problem having this question in their back pocket. You shouldn’t always rely on someone else to start truthful conversations, but it should be a tool available to you both.

Showing up as authentically as possible and speaking up is challenging for everyone, but it’s mission-critical if you’re a leader to find your voice. I’m still on a lifelong journey towards finding my full voice, but managing these reframes and practicing with people I’m close to has helped me move forward quickly. And it’s created way more richness and connection in both my work and personal life — which makes this entire journey of leadership and personal development worth it.

Executive & Psychedelic Coach for tech founders. Founder, Love Engine. Former founder @Chewse, surfer, #fighton