What Do I Know: Why the Best Leaders Obsess About Getting Better

One of my colleagues, Meghan Keaney Anderson, is a top-notch leader. She’s championed some of the most important efforts at our company over the past few years, and is regularly recognized as one of the organization’s top managers, marketers, and mentors. And yet, one of my favorite things about Meghan is a necklace she wears regularly around the office. On it is a quote from Michel de Montaigne in French that translates roughly to, “What do I know?” In addition to being an artifact from one of her favorite writers, it’s a daily reminder to stay humble and continue learning and growing.

To me, Meghan embodies a trait of the best leaders I know: she constantly obsesses over getting better, and in doing so sets high expectations of herself, her team, and anyone who works with her on a daily basis. The result? You elevate your game when you meet with her, you check your ego at the door because you know she does the same, and you actively want to keep up with what she’s reading, the events she’s attending, and the people she’s connecting with because you know she’s focused on how she and the organization can get better.

How can all of us follow Meghan’s example and obsess about getting better?

1) Always Be Learning: Between emails, calls, meetings, and management, it’s hard to maintain a personal life, let alone find time to read. Yet, the best ideas often come from external input and experience. Setting the tone that reading regularly, meeting with people you want to learn from, and attending events and talks in your industry is not only encouraged, but required, is imperative.

At HubSpot, we make this as easy as possible through our Free Books Program, whereby any HubSpotter, at any time, can request a free book that helps them improve at their job. There’s no formal approval process or requirement beyond the caveat that the book helps individual or professional growth. So there’s no excuse not to read. Don’t have a free book program? No sweat—use The Skimm to stay current on news and trends or make it a weekly practice to share articles that inspire the whole team. Doing so keeps everyone honest about prioritizing external inspiration and education if only for twenty minutes each day.

2) Sharpen Your Skills: It’s really easy to get rusty at even your sharpest skills, so identify the top five skills you need to maintain or improve to grow your career and block time on your calendar each week to revisit them. Smarterer offers two-minute tests on hundreds of skills from Web Design to Word and Blogging to Business Grammar. Invest the time to test your current skill levels at the top skills important to you and then create a plan to tackle the ones that have accumulated dust over time.

To use a personal example, throughout my career I have historically created a lot of content, but last year during a particularly demanding period of work, I found my writing was lackluster and I was no longer as efficient or effective at creating content. I took advice from my masterful writing colleague Beth Dunn and started writing every day. By facing my skill gap head on and taking some actionable advice from a colleague, I was able to get back on track. Use your network and your knowledge to de-rust even your sharpest skills—the results will speak for themselves.

3) Take a Breather: Every few months, Brian Balfour, who leads HubSpot’s Sidekick team, takes a day with his team to reflect on how the team is working together and receive input from everyone on how they can collectively make their collaboration better. Doing this ensures that the team isn’t comfortable with the status quo, and that everyone feels ownership for fixing areas that can be better versus being complacent. Some of the questions they ask themselves include identifying the lowest ROI tasks they have done, why they did them, and identify ways in which they can avoid doing more low-return projects. I love that lens as a function to prioritize time, energy, and investments. Simply put, hubris has a funny way of seeping into every organization and every team if you’re not vigilant.

Meghan’s necklace is a great reminder that what we know pales in comparison to what we don’t. Rather than be defeated by that perspective, learning more and getting better fuels the best leaders in the world. I just happen to be lucky enough to work with some of those leaders, and they remind me daily just how much I have to learn.