Outlier’s Path

Having spent more than a decade as an operator at LinkExchange, Tellme Networks, and Zappos, and then the last decade representing Sequoia on the boards of some exceptional and legendary companies, I have learned much from outlier founders.

Our expectations of ourselves affect our performance, and the expectations of those around us also affect our performance. Our outlook and visions of the future matter, as they can often become self-fulfilling prophecies. Let’s have high expectations of ourselves and those around us.

Situational awareness is critical to leading teams through complex challenges. Once we understand the situation, we want to pick the most effective tools for our circumstances. Perhaps we should spar with the team during “ecstatic highs” to see around corners to reduce future setbacks and be a shock absorber during “suicidal lows” by helping our team remove bottlenecks.

Let’s reflect on what we, individually and collectively, want to accomplish before the end of 2024. When we have the right strategy and are executing well, pushing forward with minor course corrections is likely all that is needed. If not, we must take more extreme measures and plot a new course to reach our desired outputs.

At a recent offsite, we traveled to Second City in Brooklyn, NY, for an Improv Workshop. It highlighted the power of “yes and” thinking, leading us to ideas we didn’t conceive of before. However, it also illustrated, stretched to the extreme, that some of the ideas generated are so far out there that it is hard to see them leading to fruitful options.

Sometimes, the path to greater efficiency is figuring out ways to complete tasks in parallel rather than serial. The next time we face a large-scale complex problem, we should be wary of defaulting to serial processing.

When you can see people clearly, you are better at appreciating them, helping them grow, and putting them in a position to succeed.

This past week, Pat Grady hosted an invite-only event to meet Frank Slootman, an iconic CEO, who led Data Domain, ServiceNow, and Snowflake to massive success. Founder Tanay Tandon returned from this trip and sent the following email to his board and his employees. Thank you Tanay for being this week’s guest post.

As we settle back into our game of choice, let’s try to make every point better than our previous points, every decision better than our earlier decisions, and every day better than our prior days. While we know that won’t happen every time, we do so to pursue the extraordinary and make every decade better than the last. It is our path to be legendary.

We had the pleasure of having Angela Duckworth speak at our 2019 Global Offsite. Angela shared four psychological assets that contribute to grit. Grit is about holding the same top-level goal for a long time. Gritty effort is the constant application of force over long durations.

Don’t let the summer happen to you. Be deliberate and proactive. Determine what you want to accomplish this and every summer. The days will now get shorter and shorter until the Winter Solstice. Use the daylight wisely and let’s go!