Sam Zun, the Legal Director for Payments and Commerce at Facebook, set up a one-on-one meeting with me one day. We had worked together for a while, but he had never once asked to meet individually. I saw him in broad group meetings, and we were polite — but largely distant — colleagues.
We started our meeting with the typical chitchat, and eventually, I said to him, “Sam, how long have we been working together?”
He replied, “Three years.”
I asked, “Why did you only ask to meet with me now?”
Sam looked at me and said, “I didn’t want to waste your time.”
I was taken aback. “For three years?! You didn’t think I had time to talk to you for three years?” I had always prided myself in running an inclusive organization, so I felt terrible that I had missed out on getting to know him. I had taken his excellent work for granted; there were rarely escalations or issues thanks to how on top of things he was.
We spent the next twenty minutes talking about some of the upcoming challenges with our product, discussing some support he needed in an escalation, and reflecting on his insights into our strategy. But I was still reeling from his earlier confession. I had to ask him, one manager to another, “If someone on your team was afraid to reach out to a senior leader to set up a time to connect, what would you say to them?”
“I would tell them to get over it and reach out,” Sam replied, laughing. “I see what you did there, throwing it back at me.”
After that, I made it a point to include Sam and his team in our product reviews, our mid-cycle team-wide check-ins, and our planning discussions. I also met with him regularly to reconnect and hear his thoughts on key issues.
I asked Sam if I could share our story because this kind of thing happens more often than you might think. We hold back from speaking up, asking questions, and reaching out because we worry about what others will think of us. But what if instead we looked at all the new possibilities available to us when we do speak up?
Believing in Possibilities
How many times have you missed out on an opportunity because you were afraid to ask? How many times have you held back from pursuing something because your fears outweighed your hope?
I am extremely shy. I remember when I first became a product manager, I realized that most of my job involved talking to other people. This was incredibly difficult for me. I would actually spend time physically working up the courage to send an email, make a phone call, or reach out to someone.
Many of you — those who are introverts, in particular — understand the dread of having to reach out and ask for something. The question runs through your head: What if they say no?
The other day, I suggested to the Ancestry mobile team that they make a minor change to the app. It was a pretty small adjustment to how the app worked, but I sensed some hesitation. Eventually someone asked, “What if users don’t like this change? What if our star ratings go down?”
I replied, “What if they love it and use the app more?”
The point is that any change, whether in your product or your career, brings some inherent risk. The result can go either way. If you only look at the potential downside, however, you are not opening yourself up to the possibility of the upside.
Speaking Up Authentically
When Intuit was looking for a new board member, Sheryl Sandberg introduced me to then-CEO Brad Smith (who is now the Executive Chairman). Intuit was a company I had long admired, and I remember how nervous I was walking into his office to meet with him. I had no idea what he was looking for, but I was pretty sure that I wasn’t it. So I decided to go for broke. I went into the meeting with everything I wanted to say about Intuit’s products, products I had faithfully used and passionately evangelized for more than 15 years. I decided to put it all on the table because as a user, I had so many things I wished they could build and so many questions about why they chose to do certain things. I figured this was my one chance to share my point of view both as a long time customer and a product leader, and I went for it. At the end of the conversation, Brad asked me if I wanted to join the board. I was shocked.
Rather than giving polite answers and surface-level insights, I spoke honestly and authentically from my perspective and expertise, precisely because I felt I had nothing to lose. Sometimes we say what we think others want to hear, but what they really want is to connect and learn especially from our experiences, not hear platitudes or the easy answer.
Truth told with love is part of how we all grow as individuals. When given the chance, rather than giving the easy, superficial answers, what if we tried sharing authentically and with compassion? What if we were willing to ask the harder questions to foster growth and deeper connection?
Seeking Alignment, Not Likeability
We have an innate need to be liked, but in my experience, those seeking likeability tend to do so at the risk of a deeper relationship.
I remember a PM I once worked with. We had a good relationship, but I always felt like he was holding something back. Each time we talked, it seemed like he was trying to gauge what I was looking for and preemptively fill that need.
One day he asked me why I didn’t support him more. I spent a few days thinking about it and realized that I didn’t feel like we were truly aligned. Yes, I liked him, but I couldn’t quite understand him and connect with him. We spent several hours talking it through, and I shared how I felt. And he confirmed he was hesitant to be too open.
Alignment is not superficial. It often takes hard work and requires pushing on areas where there is friction. It can be painful, but it is also how you bottom out and reach a state of true understanding. This process requires trust, candidness, and the willingness to listen to all points of view before true alignment is reached.
Sam and I could have had the polite conversation in our one-on-one and not thought twice about it. Instead, we had the difficult and uncomfortable discussion about why he had taken so long to reach out. I in turn acknowledged that I had taken him, and his team’s work, for granted. We reached a level of truth and authenticity on which to keep building our relationship, and it made us so much closer as a result.
Sometimes it is easier to let these things go, to stay silent, but think of what you are missing when you do that. Imagine the relationships you could cultivate and the opportunities you could discover if you spoke up and reached out. Digging deeper in your interactions, even when it’s uncomfortable, opens up a wealth of new possibilities.
Make a list of people you should reach out to or situations you know you need to resolve. Then pick one to make progress on each week. Speak up and continue to push forward, even if you just take baby steps at first. Each time, note what happens when you work to untangle a situation that you previously ignored. You will be surprised by how much you can accomplish by speaking up.
Coda: I shared this post with Sam, and he agreed to let me share his response.
“Thanks for sharing. Brings back memories of the relief I felt after that conversation and the meaningful difference it made on how we worked together after that.”
I'm forever grateful for that conversation, and for you caring enough to push me to rethink my approach. It was a game changer for our relationship, but also for how I've approached connecting with people at work. I might be the biggest fan of this substack, so I'm also pretty stoked to be included in this post. Thank you and looking forward to talking again soon :)
Thanks for sharing these concepts Deb. I feel so often we shoot for harmony rather than alignment and find later that it's not the same thing!