AMA: Square Product Lead, Carrie Zhang on Influencing the C-Suite

Can relate to this question! I definitely struggled with similar situations earlier in my career. Interestingly I got the solution from the executives I was working with at the time. He suggested “get us together, tell us the team is struggling with completely different directions, and ask us ‘where should the team go’”. I think any seasoned executive, or team leader for that matter, knows they need to provide clear guidance to their teams. Sometimes the executives are just not aware their difference in opinions are causing confusion and blocking progress. This is not the only way to solve it, but I found just being transparent about the issue, and bringing your own opinions on the topic can help drive alignment.

This likely depends on the size of the company and the different rituals you may have. Obviously the bigger the org, the harder it is to get direct exposure to the c-suite. If your company happens to have the following opportunities, take advantage. * Product reviews. Does your company run regular product review meetings with the executives? If so, that’s a great forum. I’ve always found it helpful in these meetings to 1/ bring them up to speed on your team’s work, 2/ raise difficult questions and get their input. Just remember they are most likely not as close to the problem as you are so don’t follow their input blindly. * Regular updates. On important initiatives, I’ve found it helpful to send regular updates to your executives and other stakeholders. When I worked on a 0-to-1 product, I sent bi-weekly updates on product performance, customer insights, and roadmap priorities. Got incredible comments and suggestions from senior leaders. It’s a lot of work to write a good update, but it’s worth the time. * Executive office/ couch hours. At my company, the senior leaders have office/ couch hours where you can book and discuss any topic with them. It’s an awesome mechanism to interact with them in a 1:1 or small group setting. Bring high quality topics/ questions though. Don’t waste their time.

I don’t think we should try and align with certain people. Product development is about solving customer problems. So fundamentally I think we should deeply understand our customers’ struggles and figure out how we can use technology to help them. Additionally, we need to put that in the context of company level strategy and priorities. You don’t want to work on something that the company doesn’t care about. If you can clearly articulate how you are aligned with customer needs and company priorities, you are more likely to gain momentum.

Not sure these can be called “best” habits. Just some principles I try to follow myself. * Take a top management perspective. This means elevating your thinking to that level, and thinking beyond the tunnel view of your product. To do that well, you have to be curious and keep tabs of what’s going on across the company (products). You will also need to have a good understanding of the business. Practice thinking “what would I do if I were running this product/ business unit/ company?” * Clear and concise communication. Whether it’s written documents, or in meeting discussions, go “answer first” for less controversial topics, and follow the “situation -> complication -> resolution” structure if you need to convince others. Skip unnecessary details, especially around your process to get there. * Obligation to dissent. We bring the front line perspective to executives that are not always immersed in the details. It’s our obligation to dissent if we disagree based on facts and our knowledge. That said, voice your opinion but disagree and commit to move everyone forward.

We can be more tactful and realize we don’t need to rely on logical reasoning alone! To this date, I am still amazed at how one of my colleagues got an executive to change their opinion. We were working on a new product launch at the time and had proposed a pricing bundle that included a feature from another product. Our executive was adamant that we should keep them separate and not bundle. Several meetings went nowhere and we were stuck. At our company the product teams provide weekly updates in a consolidated deck for senior leaders. For several weeks, my colleague purposely included direct customer quotes in the weekly updates. These quotes showed that for our target segment, this feature is a must-have and that our new product will be hugely disappointing without bundling it. Guess what? This slow drip of customer insights worked! When we then met with the executive, our pricing proposal went through.

Ultimately c-suite needs to allocate resources that generate business value. So I think the best way to influence that is to make sure what you are working on produces the desired customer/ business outcome, and/ or financial value. Based on my own experience, we can do a few things that help influence the decisions our way. * Good writing to clearly articulate your product vision/ strategy. When we tried to convince leadership to invest in a new 0-to-1 product, we wrote a short proposal that focused on: * What is the customer problem that we are trying to solve? * Why is that worthwhile solving for? Why should we get into this space? * Why is now the right time to get into this space? * How are we going to get started? * Demonstrate execution velocity. In general, high velocity teams that release more and faster are more likely to earn executive trust. Yes, it’s output based but you cannot really achieve outcome without the output. I have not seen executives willing to allocate more to teams that are slow and don’t produce as much. * Get a network of advocates. Goes without saying that before reaching the c-suite, you will want to gain the support from your BU/ functional leaders first. Having sponsor(s) for your idea/ work can help back-channel when necessary and help you get the support.

I think first of all, we need to have our own opinions of relative priorities. There are so many frameworks out there on prioritization. For me, it always comes down to alignment with strategy, alignment with customer problems, and relative effort level. When communicating with executives, it’s important to bring our tradeoff decisions and rationale to them. Resources are not infinite so there is only so much a team can do. It’s pretty straightforward to force a conversation like: based on team capacity, we can work on A, B, and C. This is why we prioritized A, B, and C. We can re-prioritize D above them, but that means we are going to lose blah blah. Are we ok with that tradeoff?