Grand Rounds Blog

I recently hit my five-year Grandiversary at Grand Rounds. 

This is the longest I’ve ever stayed at a company and when asked why I continue, my answer is always the same. This is the best team I have ever worked with, the impact on our Members is life-changing, and the personal growth opportunities have been invaluable. I feel lucky to have found such a mission-driven company with an awesome team and dedicated leadership. 

I joined the company as a Senior Product Manager and over the past five years, have grown into the Head of Product. Just recently, I was promoted to SVP of Product—an achievement I’m incredibly proud of. These past few years have been some of the most rewarding professional years of my life and I’d like to share my top lessons learned as a lover (and leader) of all things product. 

Invest in Leadership

High performance teams emerge when they have strong leaders at every level. As a product leader, one of the most important things you can do is hire the right leaders for your team, and develop the ones you already have.

Leadership, and in particular strong leadership, is hard to define. From the beginning, Grand Rounds outlined what leadership means to the organization, since it’s a key priority for the business. We’ve selected particular leadership traits that we expect our team to display—managing ambiguity, building effective teams, developing talent, communicating effectively, maintaining customer focus, making quality decisions, and driving results.

This definition gives a tangible framework to use to assess, benchmark, and improve our leaders and teammates (including myself). As an executive there are additional leadership traits we expect: having a strategic mindset, a strong business insight, and the ability to drive vision and purpose, attract top talent, and instill trust.

At minimum, on a quarterly basis, I give feedback to my leaders on how they’re performing against these competencies, in addition to how they’re progressing against their OKRs. This is complemented with regular ongoing feedback and annual reviews. While giving feedback, it’s important to focus on how someone does their work, in addition to what work they do. This focus on development feedback as a company helps us nurture and build strong leaders.

We have a similar focus on leadership during the hiring process. Different members of the interview panel are assigned different competencies so that we can ensure that we’re bringing the right people into the company.

Investing in leadership has given us a lot of returns. We’ve driven results over the years while staying values-driven and keeping our team engaged.

It’s Always Better to Be Kind vs. Nice

Give direct feedback to those around you. It may not always be the nice thing to do but it’s definitely the kind thing to do. If you see someone doing something that you think they can do better, tell them. Do it in a kind way. Do it because you want them to be better. I guarantee you that most of the time, they’ll be thankful you said something and it’ll lead to greater trust in your working relationship with them. I’ve received some of the best feedback from people that cared to share what they observed because they wanted me to become a better version of myself. 

If you’re interested in digging more here, Kim Scott has given a great talk and book about Radical Candor. She gives great advice on caring deeply about people and challenging them directly. It brings to life the notion of being kind vs. being nice in a real way.

Don’t Tolerate Brilliant Jerks 

Never tolerate high ego behavior. Even if an individual is a high performer, don’t tolerate brilliant jerks. They bring down the rest of the team and the net effect is always negative. I love the notion of hiring humble, hungry and smart people—this truly resonates with me. 

If you do happen to have a member of your team with a large ego, be kind and let them know how their behavior is impacting the team. As you give feedback, make sure you have tangible examples, and comment on the behavior you’re seeing and how that behavior is limiting progress. I’ve seen team members completely change the way they operate once they were made aware of how their actions were impacting the team and the team’s desired outcome.

Communicate the Why vs. the What


Even if you think that you’ve explained the end goal or why your team aims to achieve it multiple times, you probably haven’t communicated about it enough. This applies to anyone in the company that’s requesting anyone to do anything. 

Let’s talk about a product scenario to bring this to life. Say I wanted to improve retention in the product and I had an idea on how to do so. I could be prescriptive and tell the team what my idea is, or I could explain to them why retention is important to the business, share my idea as an example, but also explicitly ask them to come up with their own ideas because they may just have a better one. The latter would lead to a much happier employee that has autonomy to figure out the how, all while understanding the why. I’ve seen time and again that the right level of autonomy and empowerment leads to happier teams.

It’s especially important for people in product to explain the why behind the product vision. This allows for the teams to figure out the what and the how and pushes the right level of autonomy and creativity down to various teams. 

Selling is Not a Dirty Word

As a product leader, it’s important to constantly sell. Outside of the actual sales and marketing teams, “sell” can be interpreted as a dirty word but it doesn’t need to be. You’re constantly selling the product vision to the internal team to rally them around the product, to customers to get them excited about the company’s impact to them, and to high-caliber candidates to get them to join the team! 

These are the most important tips I’ve learned on selling, courtesy of our CEO: 

  1. Show your passion and excitement about your organization or product. 
  2. Connect your audience to the problems your company is solving. Get personal and share stories. 
  3. There is no reason to be nervous; no one knows your content better than you!

Selling is not just for the sales team, Product leaders should certainly be selling their vision and passion to all around them. Passion is contagious!

My five years here have been highly rewarding. I’ve learned and grown tremendously as an individual. Hopefully there are lessons here you can apply in your leadership journey, whether it’s defining what good leadership means, practicing kindness, focusing on raising hiring standards, communicating the why to your team, or increasing comfort with selling.  

If you have any questions, reach out to me at I’d love to know if these lessons resonated and if you have any feedback on the same.

Want to grow your career with me? Join the team!

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