🏆 One Trait All Successful People Share, ⚖️ Accountability Deep Dive, and 📉 Intentional Underperformance
PROGRESSION: 2025, Volume 4
About a year into my time at DoorDash, I had an exit conversation with Chris, a highly-regarded engineer. Chris was leaving because DoorDash had changed. He told me, “When I first joined, I could just build whatever I wanted. Now we have this new head of engineering telling me what I can and can’t work on. I need more freedom. I’m done having someone tell me what to do.”
I fought back a smile. The engineering org had been struggling to keep the website up for months. The exec team was working hard to close a round of funding. We were all hands on deck trying to build a great business. And here we had an engineer leaving the company because his new boss was stealing his perceived freedom and holding him accountable.
The Need for Accountability
All leaders sit somewhere on an accountability spectrum. On one side, we have the absentee manager who abdicates responsibility and is too hands-off. On the other side, there's the micromanager who has their hands in everything, living in unnecessary details. Both extremes are ineffective. Micromanagers may get more negative attention, but absentee managers are equally ineffective.
Many well-intended leaders fall more on the absentee side of the spectrum. They don’t want to be too pushy. They want to promote freedom and autonomy. Basically, they don’t want to be a jerk. I’ve seen too many leaders fall into this trap. I’ll share one example.
One of my CEO clients, Randy, faced this challenge. A project that should have taken his company several months was still unfinished a year later. The primary reason: Randy rarely set deadlines. And if people missed a deadline he had set, there was no accountability. Team members would drop the ball, and he'd let it slide. He didn’t want to rock the boat. Randy's team intended to complete projects on time, but deep down they knew there were no repercussions for missing deadlines.
Randy was frustrated. He had unintentionally created a culture of low expectations and slow execution. To help him change, I shared three approaches to improve team accountability.
Three Ways to Hold Your Team Accountable
The first is publicly praising team members who hit their targets. Reinforcing existing good behavior is an easy first step for leaders who worry about coming down too hard. We all want praise. Praising those who hit deadlines reinforces the standard.
The second approach is to ask your team to tell you immediately if they can't meet a deadline. Setting the expectation that it’s on them to proactively communicate updates will remove the burden of constant follow ups.
The third approach is to shift how you react when a deadline is going to be missed. Rather than yelling at a team member, or giving them the silent treatment, you can ask, “How can I help you get that done?” or “What do you need to hit the deadline?” This will reveal blockers that stand in the way while reinforcing that you take deadlines seriously.
Tony Xu, CEO of DoorDash, was excellent at this third approach. Expectations were insanely high and people often told him that project timelines were impossible. He’d push back but do so by asking a question. He'd ask them what they needed from him or from other teams to hit the deadline. This created a conversation and together they’d be able to remove barriers or re-prioritize other initiatives.
Tony didn’t take “that’s impossible” at face value. He went deeper to understand key assumptions. He knew that performance falls to the lowest acceptable standard, and it was his job as CEO to demand excellence.
Holding Yourself Accountable
We’ve tackled how to hold your team accountable. But it’s equally important to hold yourself accountable. Elon Musk is notorious for asking the question, "What did you do last week?" Your boss likely doesn’t demand that you answer this question, but it’s a great habit to build.
Shortly after I joined LinkedIn, a mentor gave me this advice . He encouraged me to write a short email to my boss answering the "what did you do last week" question. Why? Three reasons:
Your boss can't keep track of everything you do.
It signals you have high ownership and want to be held accountable.
It forces you to identify how your work actually moves the needle.
Don't wait until someone demands "what did you do last week." Be proactive and provide updates without being asked. This is how you become indispensable.
Finally, one other technique I’ve found helpful is finding an accountability partner who is not your boss. As a self-employed executive coach, I don’t have a boss, but I meet regularly with a coach to review my personal and business progress. In triathlon, I have ambitious goals, including drop 10+ minutes off my Ironman 70.3 personal best. So I’ve built a trusted system that keeps me accountable.
If you have aspirations outside of work and want support (finding a new job, strengthening a key relationship, getting in shape, etc.), you need to find someone who will hold you accountable. Thomas Monson said, “When performance is measured, performance improves. When performance is measured and reported, the rate of improvement accelerates.”
Meaningful progress comes when you hold yourself and your team accountable.
What I’m Learning
I’m reading Sahil Bloom’s new book, The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life. He shares that the common trait of the world's most successful people is a tolerance for uncertainty.
There is no such thing as the clear, linear path to success. It's a fairy tale that doesn't exist.
The reality: Long periods of stagnation, where the rewards will feel anything but certain. Those who can continue to show up every single day will eventually find a way to win.
I’ve learned through experience that how you do anything is NOT how you do everything. Some activities demand your best. Others can be done with little energy or not done at all.
I recently was a guest on Jim Harshaw Jr.’s podcast, Success for the Athletic-Minded Man. We covered a variety of topics including strategic underperformance, the idea that you can intentionally underperform in non-core areas of your life.
I invite you to answer this question: What is an area in your life you can intentionally deprioritize so you have more energy/time to prioritize what’s most important?
Gratitudes
I’ve found power in regularly expressing gratitude so I’ll continue the habit. I’m grateful for healthy kids. Our family was rocked by sicknesses the second half of February. Health is one of those things that I don’t fully appreciate until it’s gone. Everyone’s finally healthy again. The kids are back to school and sports. I’m grateful for good health.
If I can do anything to help you, please reach out. As always, thank you for reading.
All the best,
Nathan
Read my book, The Unconquerable Leader | Learn about coaching
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