Speaking Up and Connecting

How to open doors by reaching out authentically

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.