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Hey Reader,
Happy Saturday!
Hit reply and tell me the hardest problem you're dealing with in your business right now. I'd love to chat about it (it'll also fuel new ideas for mini-essays in the weeks to come).
Let's get to it...
A quote to make you think from a book podcast worth listening to
“When you get to certain levels of responsibility with management and leadership… you could technically be the smartest person in the room, but if you have no emotional intelligence or dimensionality in contemplating emotional states, you are going to struggle to lead.”
- Claire Hughes Johnson on The Tim Ferriss Show #724
From the outside Stripe appears to be one of the all-time great talent magnets of this generation. Claire was the COO of that business and remains an advisor to the founders.
I continue to be inspired by Stripe’s level of operational excellence and the thoughtfulness with which their founders and execs lead. This interview with Claire Hughes Johnson is a perfect example of why. If you’ve run a company, then you’ll recognize Johnson as a world class operator, not just from the topics she covers, but the way she covers them.
I’ve yet to read it, but I just ordered her book, Scaling People, which was published by Stripe press. This interview (and I assume her book) are the kinds of resources that will make you a better operator prepared for making impact at scale.
Three links to encourage deep thought and breakthrough growth
1 Managing People by Andreas Klinger | Read time: 10min
“Always assume people you hired are motivated, and have the best intentions in mind… And fire the ones that don’t.”
This article is hilarious in that it’s a list of bullet points, which is the most engineering-leader-way to communicate ideas in the absence of code. That said, if you’ll excuse the format you’ll find that it yields a very high density of wisdom per word.
Question to consider as you read: Which of these ideas could I immediately implement with my team? Which of these ideas do I disagree with and what proof do I have that my way of managing is better?
2 You Don’t Need to Work on Hard Problems by Ben Kuhn | Read time: 5min
“In fact, [easy problems] turned out to be even more interesting! Why? Because “hard technical problems” wasn’t my root goal—my root goal was to use my skills to get the most possible leverage on improving the world.”
I use these words often: “use your career to solve hard problems that make the world a better place.” And that’s for a reason — many problems that will make the world a better place if solved are indeed hard. BUT that does not equate to the idea that hard problems are valuable because they’re hard. Instead, choose problems based on the impact of the solution. A helpful reframe by Ben Kuhn.
Questions to consider as you read: Are you working to solve a hard problem or an easy problem? Did you pick that problem because it’s hard or because the solution will make a positive impact? If you’re working on a problem whose solution really doesn’t matter that much, what would it take to shift to an important problem, perhaps even an easy but important problem?
3 Don’t Trade Your Autonomy for Stability by Henry Oliver | Read time: 1min
“A large recent study of artists’, film directors’, and scientists’ careers found that before they start a hot-streak of high-impact work, they take influences from a wide range of sources, which they then use to produce their breakthrough. They don’t work on the most popular topic they find or their most recent discovery. They choose what they are most interested in, where they see the most potential. Self-directed discovery is what sets-up the hot streak. ”
If you start a career in a big business with the intent to one day to become an entrepreneur, it’s surprisingly hard to make good on that commitment to yourself. Oliver makes a case for why you should start on the entrepreneurial path instead.
I include it here because while I write for founders, I also know there are many people here who might one day be founders. Consider this the reminder that there will never be a good time to get started, but the key to making the most impact is often maximizing your autonomy. The best way to do that is to become a founder.
Questions to consider as you read: What would it take for you to become a founder? How could you engineer circumstances that expose you to as wide a range of ideas as possible in order to spark the idea that you work on for the next decade?
An idea sparked by my work with founders
One of the things I love about working with founders is seeing the things that are unique about each person. I also love seeing the commonalities between founders (and execs).
One of those commonalities is the tendency to avoid hard conversations. Examples of what I mean when I say “hard conversations” are:
- We should be pursuing different strategy
- We shouldn’t be making that acquisition
- We need to fire that person
- This other person isn’t meeting our performance expectations
- We don’t have enough money to execute on our plan
- One of us might need to leave the business for the good of the team
- I don’t want this anymore
- Your behavior negatively affected the team
The list could go on.
Not everyone avoids these conversations. Some folks wade right in and bulldoze anyone who stands in their way. But far more often I see founders shy away by focusing on other areas of the business.
Why? Well, hard conversations are hard. Having them in a way that is generative and increases momentum is difficult.
But the choice to lead well is the choice to embrace hard conversations.
Before we go further, I want to validate why we find hard conversations difficult and I want to do that through the lens of the big 5 personality traits. At least four of them affect our desire to lean into hard conversations:
- If you’re high in agreeableness, then you care deeply for others, empathize with their experience, and don’t want to make them feel bad
- If you’re high in conscientiousness, then you likely try your best to get things right, spend time preparing, are conscious of how your actions affect others, and assume the same of others
- If you’re high in openness, then you want to hear new ideas and are willing to explore possibilities, which means you might be hesitant to assert your own ideas or direction
- If you’re low in extraversion, then challenging conversations with others might zap your energy and take a lot of effort to lean into
- Even neuroticism could affect this if it’s high, in that if you’re moody, get stressed easily, and worry too much, then it might prevent you from proactively engaging in conversations that you perceive as adding stress
It takes a rare person to have none of the personality traits that would make them hesitant to engage in hard conversations, and even then it’s a skill you have to build through experience.
Adam Grant had an excellent Tweet this week in which he shared the combined results of seven studies on hard conversations. Those studies revealed that we overestimate how bad those conversations will be and we underestimate the positive effects.
This is exactly what I see in teams. It’s the avoidance of hard conversations that leads to more conflict, more frustration, and less progress towards business goals. If you asked me for my top predictors of whether a culture is healthy, a commitment to having hard conversations well would be at the top of the list.
So, what hard conversation are you shying away from right now? What aspects of your personality might be feeding your hesitation to have the conversation? What are the assumptions you’re making about the costs of having the conversation? What are the potential benefits that you haven’t yet acnknowledged?
If this sparks a willingness to lean into the hard conversation, I’d highly recommend using the nonviolent communication framework as a starting point. There are four basic steps:
- Describe the facts of the situation without opinion, blame, or emotion
- Share the impact of the situation on your emotions, without assigning blame for those emotions
- Name the unmet need or needs that your emotional reaction reveals
- Make a request of the other person or people to meet the need or make changes going forward
Your ability to have hard conversations in a generative way is one of the most important predictors of the size of the impact you’ll make with your company. The sooner you build the skill, the better.
Much love and respect,
PS: Things you can do to support me...
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