Hughes Johnson, who joined Stripe in 2014 as the payments startup's chief operating officer, worked closely with two of Silicon Valley's most iconic entrepreneurs, Patrick and John Collison. And she helped bring her Google management know-how and experience working for Sheryl Sandberg to help organize the growing company.
I invited Hughes Johnson on the Newcomer podcast to talk about her time at Stripe and the management lessons she put down on paper in Scaling People, which she published this year. Towards the end of our conversation, Hughes Johnson turned the tables and gave me some coaching.
Our conversation revolves around two sections of his book in particular. We talked about giving feedback and honesty in a business context. She spoke of her principle that managers should encourage people to "say what they cannot say."
She writes,
How many times have you sat in a meeting and thought, “It really feels like there’s something we’re not talking about right now”? Or have you had a conversation with a report and thought, "I think they're upset by what I'm saying"? Or have you found yourself filtering everything you say? These questions raise a larger one: why don't managers say what they really think?
People often think that good management relies on many filters, and for good reason. There are a lot of things that can feel risky to say or feel like a personal judgment. But beware of over-filtering. By adjusting your filters and pushing yourself to name your observation constructively, you can have a more honest conversation about what's going on. Then you can all start working seriously on a solution.
Hughes Johnson concludes the People Assessment with a chapter titled “You.” It examines the way managers manage themselves.
She writes,
The older you become, the more creative reality becomes in finding ways to fight every day. You'll have days, sometimes several in a row, where your top performer is threatening to quit, an important client has just informed you they're moving to a competitor, you're leading a company-wide meeting the next day and you're out of luck. I haven't had time to prepare and the cross-functional project you launched last week is already going off the rails. Many people lack the psychological strength and resilience to continue. In The Hard Thing About Hard Things, Ben Horowitz calls it “the struggle,” when “nothing is easy and nothing seems right.”
To make everything work, you need to learn to manage your time and energy. First, diagnose what gives and takes your energy. The easiest way to do this is to map out your good and bad days and track activities that add or decrease your energy. A simple tactic is to mark off your calendar for good and bad days. After a month, look at all the good days and bad days, then good weeks and bad weeks, and see what trends emerge. When I did this exercise, I discovered that weeks where I had more than one work event that kept me from eating dinner with my kids and putting them to bed were bad weeks. I then decided to limit my work evenings to once a week – a personal guideline that I don't follow from time to time, but not often. Your goal is to study what combination of time spent on which activities creates your best performance, and then determine where you need to set boundaries to preserve your strongest self.
As a journalist, I have always been resistant to “management” and “leadership” advice. These words made me think of Dale Carnegie's books and for-profit leadership seminars. But as I began to make Newcomer more of a business (I have a full-time chief of staff, three summer interns, and am looking to hire a full-time reporter), I turned my attention to l he idea that being intentional about how you spend your time and how you work with people are essential skills, worthy of serious thought.
I really enjoyed my conversation with Hughes Johnson. Listen to him.
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