Jayaraman, now the HR director at JUUL Labs, said the transition from individual contributor to people manager doesn't have to be jarring. In fact, the person making the transition should be pretty confident that they want to assume a leadership role.
One option is to give the person some informal management experience.
"Never make anyone a people manager without making them a mentor for a new hire on your team first," Jayaraman said.
Another option Jayaraman proposed is to organize groups of people who have expressed some desire to be managers and have them go through more formal training. Every few months, a new cohort of would-be managers might review and discuss case studies, or work with coaches and mentors.
And if the person goes through the training and realizes they don't in fact want to be a boss? Jayaraman said, "That is a great outcome."
Markman said that many people transitioning into leadership roles are preoccupied with the decision to be liked or feared.
But "when you actually get into a leadership role," he said, "it really does become much more about what you're trying to accomplish with respect to the organization."
There's work to be done — and spending time worrying what people will think of how you're doing it is generally ineffective.
Take a tip from Tesla CEO Elon Musk, who laid off 9% of the Tesla workforce in 2018, and found that many former employees still believed in Musk and his vision.
Angsuwat is now the vice president of people at Thumbtack. Over the course of his career, he's observed too many interviewers trying to impress the candidate, or flaunt their smarts.
These types of interviewers typically say to themselves, "I can think of some really tough questions. I can trip them up," Angsuwat said. "That's kind of dangerous because you end up with some unfair outcomes, potentially."
Specifically, you don't get a sense of the candidate's abilities so much as their willingness to be cowed by the interviewer smirking and tapping their foot.
Angsuwat said it's near impossible to get a sense of the candidate's potential from asking deliberately tricky questions. What's more, he added, "It's not a great candidate experience."
Across companies and industries, managers have a tendency to hire and promote people who are just like them. It's often a result of unconscious biases.
Greenberg said that anytime someone is considering a new hire or a promotion, they're assessing whether they can trust the person with the job and whether the person is competent. When it comes to trustworthiness in particular, we're often looking — consciously or not — for those who are similar to us.
So, if someone can demonstrate that they'd excel at the job but seem to have nothing in common with you, it's likely you might not believe that they will succeed.
Greenberg emphasized that this type of bias is a fundamentally human tendency, and is typically unintentional. But for the sake of your success and the organization's, it's crucial to learn to stop and reexamine these thoughts.
Scott is a CEO coach and the founder of Radical Candor.
She says most great employees can be divided into two categories: rock stars and superstars. Rock stars are all about stability (hence the "rock" in their name) — so they're the ones who wouldn't especially benefit from a promotion. Superstars are all about upward growth, and promotions may be exactly what they're looking for.
The only way to know whether your employees are on gradual or steep growth trajectories is to get to know them and ask questions. (She emphasized that these trajectories are temporary, so you can be a superstar at one point in your career and a rock star at another.)
Scott said that, if someone's in superstar mode, "what that person needs are new challenges. They need to understand what their path to promotion is. They probably need a mentor because they want to learn new stuff — a mentor beyond you."
If someone's in rock star mode, she added, "you don't want to promote them, either because they're not ready for promotion or because they don't want a promotion at that moment in their lives."
Porter and HBS dean Nitin Nohria conducted a study of how CEOs manage their time.
They asked a total of 27 CEOs, whose companies had an average annual revenue of $13.1 billion during the study period, to keep track of their time in 15-minute increments for three consecutive months.
One of the defining characteristics of the most effective CEOs, when it comes to time management, is that they're agenda-driven. "A CEO needs to have their own personal agenda that they determine is where they want to spend their personal time" for the next three to six months, Porter said. "They can't just react to all the requests" that come in.
Meanwhile, former GE vice chair Beth Comstock has said that the best leaders dedicate 10% of their daily schedule to "discovery."
In an interview with LinkedIn's editor in chief Daniel Roth, Comstock said, "Can I spend 10% of my time a week reading, going to sites like Singularity, TED, talking to people, going to industry events, asking people: What trends are you seeing? What are you nervous about? What are you excited about?"
Goldsmith has worked with top CEOs in a range of fields. And he's able to identify with certainty the most treacherous stumbling block for modern leaders.
"The biggest challenge is not always winning," Goldsmith said. "Not always being right. Not always proving how smart you are."
Goldsmith explained that successful people tend to be highly educated, and have achieved what they've achieved largely by proving over and over again how intelligent they are. "The problem is," he said, "when you move up to the top executive levels, you have to quit doing that."
Instead, leaders must learn to delegate, and to listen to their team. "That's one of the biggest challenges of all the leaders I've coached," Goldsmith said.
Scott knows that most employees are loathe to give their managers candid feedback, for fear of being demoted or even fired.
Her solution? The next time one of your employees gives the standard "Everything's fine" response, silently count to six before saying anything else.
These will probably be an extremely awkward six seconds. But the goal here isn't to give your employee a heart attack — it's to get them to say what's really on their mind. "Almost nobody can endure that much silence," Scott said. "And they'll tell you something."
Wagener is now the chief people officer at DoorDash.
When she works with employees itching to take the next step in their careers, Wagener likes to ask a simple question: "Do you believe you've mastered your current role?"
Typically, the answer is no. In fact, she often hears a curious follow-up comment: "I haven't really ever had a conversation this openly about what I'm not that great at or where I'm not as strong."
To be sure, everyone wants to focus on the stuff they're doing well. But she thinks it's important for managers to create a space "where members of your team feel safe and comfortable talking about what they're not great at just as much as they like talking about the things that they're really good at."
That way, the manager can look out for potential stumbling blocks.
Solomon became the CEO of Goldman Sachs in October 2018, after nearly 20 years with the firm. He previously served as president and chief operating officer.
On an episode of The JJ Redick Podcast, Solomon shared how his leadership style has evolved over time, as well as some advice for managers. "I'd say I'm a much better listener at 57 than I was at 37," Solomon told Redick. "I can be very strident, very opinionated, but I also change my mind. And I'm willing to change my mind and say that I'm wrong, even if I have been forceful about a point of view."
Solomon spoke more generally about leadership: "You will get some things right and you will get some things wrong. You've got to be willing to learn, change your view, be open, and you've got to figure out how to listen."
As Netflix's chief talent officer from 1998 to 2012, McCord and Netflix CEO Reed Hastings created the company's culture deck, which has been viewed millions of times. Now she runs her own consulting business. In 2018, she published "Powerful: Building a Culture of Freedom and Responsibility."
In the book, McCord recommends a strategy you might call the "six-month exercise." You should do it regularly, she writes. Here's how it works:
1. "Write down what the team will be accomplishing six months from now that it's not accomplishing now." It could be a product they're building or money they're making.
2. "Think about how things are being done differently from the way they are currently done." Imagine yourself walking around the office; maybe there's more collaboration or fewer meetings.
3. Think, "In order for those things to be happening, what would people need to know how to do?" It could be technical knowledge or a negotiating skill.
If your current team doesn't have the right skills, knowledge, or experience, you may need to bring in people who do, potentially even replacing some of your current team members.