The ‘Adaptable Leader’ is the New Holy Grail — Become One, Hire One

The ‘Adaptable Leader’ is the New Holy Grail — Become One, Hire One

Anne Dwane, CBO at Chegg, has had to adapt a lot in her career as she's started and sold companies. Here's what she learned.

When Anne Dwane became CEO of Zinch, the college matching service, it felt like “diving into a pool needing to figure out how to be a synchronized swimmer.”

“It was a tricky dynamic because there was an existing team,” she says. “I had to insert myself, establish our priorities, and hash out how we were going to operate as a team but there was a lot of missing context.” It was the Olympic Games of adapting to a new job.

Throughout the process, and again when Chegg acquired Zinch in 2011 and Dwane became Chief Business Officer, she learned how to transform herself into a constant learner — the best way to adjust to any new environment or role quickly and effectively.

“Most folks would agree that learning is good,” she says. “The catch is that modern life hones skills — like pattern recognition and selective attention — that are at odds with learning. With hectic personal and professional schedules, we live much of life sensing and responding, only engaging in creative or critical thinking occasionally.”

In this exclusive interview, Dwane explains how to adopt the most important learner mindsets — Gamer, Beginner, and Growth. “The implications of these changes are far-reaching,” she says. “But the changes themselves cost nothing and don’t take much time. You can make these changes while reading this post.”

When you boil it down, learning is about changing your mind.

The Mind of the Constant Learner

There are three distinct mindsets that allow new employees and leaders to become constant learners: the Gamer Mindset, the Beginner Mindset, and the Growth Mindset. Knowing all three can provide a framework that throws your personal switch to “LEARN” when you need to rapidly adapt and get to work.

Adaptability is all about being fixed on a goal but flexible on the details.

Here, Dwane talks about each mindset in depth and the ways to apply them for best results.

Take Risks like a Gamer

The Gamer Mindset, popularized by Jane McGonigal, Director of Games and Research at the Institute for the Future, challenges us to apply the courage and willpower — and also optimism and creativity — we have when playing fictional games to real world problems.

“When you play games you feel like your best self. You’re hopeful, empowered, and strategic in your ability to turn anyone into an ally,” Dwane says. Gamers are determined to win. She believes games build three psychological strengths:

  • The ability to control your attention, and therefore your thoughts and feelings.
  • The power to turn anyone into a potential ally and strengthen your existing relationships.
  • The natural capacity to motivate yourself and super-charge your heroic qualities, like willpower, compassion, and determination.

However, when you ask a gamer why he or she doesn’t bring those disciplines offline, they say ‘Oh, I can’t get things done,’ or ‘I’m not that confident.’

According to Dwane, we have more control than we think. Clarity of objectives, (you focus on a single goal when playing a game), empowers individuals to be resourceful.

She relates the influence of self-efficacy in the classroom to the way we operate in our careers. “There’s a lot of hope when you feel like you can do something, but the moment a child feels like they can’t, it’s a downward spiral.”

Even at our earliest ages, our mindset serves as a frame of reference for the way we respond to our circumstances. When you feel empowered — whether artificially or authentically — you’re more likely to be tactical and take risks.

Dwane suggests bringing a gameful approach to a project. Start by asking: How would we approach this if it were a game?

Next define the rules of engagement and determine how you’re going to work together to win.

“At work, good leaders create a context that embraces the joy of figuring things out,” she says. “Naturally, the joy of figuring things out often requires enduring the struggle of working things through. In gaming, the whole process is expected, and the mental rewards of figuring things out sustain gamers through hours of practice and failed attempts.”

The gameful leader expects adversity, but remains excited about solving the puzzle.

Play Like a Rookie

The Beginner’s Mindset is rooted in openness, being childlike and curious. You don’t have preconceptions about the way things are and are eager to explore new possibilities. It’s about asking “what if” and “why not”, and not being dismissive. It’s popular today to talk about reasoning from first principles versus reasoning from analogy. This is a facet of Beginner’s Mind.

The key to being adaptable is taking yourself out of autopilot to shift into awe, curiosity, and wonder.

“Consider comedians. Comedians don’t live in a different world everyone else; they just see the humor in it,” says Dwane. “Likewise, entrepreneurs see opportunity where the majority sees mature, intractable markets. Entrepreneurial epiphanies come from a beginners mind, not a jaded one.”

A sense of optimism is inherent in a beginners mind. If you believe things will work out, you’ll see opportunity. If you think things won’t work out, you’ll see obstacles.

To switch out of autopilot (which is no easy feat for most of us), ask yourself: What would I think about this if I had no biases, or if I had never seen a situation like this before?

This frame of reference is essential for excelling in a new role, particularly if you are a senior leader. Rely on active listening and asking questions to ground yourself in the present circumstance and ensure that your past experiences don’t act as blindspots.

Dwane provides three tactics to achieve this:

  • Ask yourself, “What do I believe that the rest of the world doesn’t?”
  • Spend time with a child and observe how they see and feel things for the first time
  • Create an inner alarm to sound the moment you have the thought: ‘Of course, this the way to do it!’ Silence it by stepping back and reassessing the situation.

She also cites Joelle Emerson, Founder and CEO of Paradigm, who gives seminars to teams on fighting unconscious bias. She notes that folks who believe themselves to be the most unbiased, open-minded and meritocratic are actually the most at risk for unconscious bias — precisely because they let their guard down. They don’t actively engage their conscious mind to avoid the pitfalls of going on autopilot. The only way to avoid bias and to stay open to the possibilities of learning, is vigilance.

For example, when interviewing candidates for a job, review the objective hiring criteria before sitting down, and plan your questions ahead of time. If you don’t, you’re liable to do what many of us fall victim to — you’ll ask softball questions of candidates you’re biased toward, and you’ll hit the other candidates with zingers.

Value asking questions and people who ask questions. This was a big a-ha for Dwane. Early in her career, she’d never consider asking her boss a question. It would show ignorance and weakness. She’d toil away to research things — even things that the boss already knew, rather than ask. It was like that struggle was some kind of rite of passage.

It’s clearly much wiser (and respected) to ask questions. This includes clarifying questions of your manager, customers, experts online, even services like Quora or Wonder.

In interviewing folks or in performance-related conversations, Dwane recommends paying particular attention to the questions posed by the candidate or team member. No questions? Canned questions? Big red flags.

She also always asks, “What have you learned in this conversation?” Learners will have been processing the conversation and cues, and will be able to share observations and takeaways.

Finally, in an interview where a case study is used or project is assigned, she’s listening intently to see whether the candidate asks clarifying questions along the way, not just at the end. Asking such questions is a telltale sign of an avid learner.

Grow, Don’t Judge

The Growth Mindset empowers you to take risks by freeing you from associating failure with your self-worth. Carol Dweck of Stanford University pioneered this type of thinking, which posits that brains and talent aren’t fixed, but starting points. Abilities can be developed through dedication, hard work and confronting challenges.

This is important because it implies that your performance, positive or negative, is a reflection of your current skills, which can always be improved. Folks with a growth mindset relish taking on challenges, because mistakes and setbacks aren’t reflection on themselves — just on their preparation and current ability, which are adaptable.

“Those that embrace the growth mindset possess a self-motivated passion for learning. They’re quick to come up with a new strategy, acquire a new skill, and have a new outcome,” Dwane says. “They’re actively in self-improvement and self-actualization mode; Constantly life-hacking.”

Dwane compares the mentality to exceptional athletes who compete to win but don’t turn in their uniform if they lose. They examine their performance and question how they can get better

Doing the right thing is more important than doing things right.

This is extremely relevant as you make your first contributions to your new team. The less anxious you are about ‘getting it right,’ the more you’ll focus on finding a solution for the problem at hand. You won’t get tripped up by unnecessary perfectionism. Instead you’ll get closer to perfect faster by getting the feedback you need immediately.

“Most worthwhile tasks are not easy,” Dwane says. “The struggle for mastery is something we should enjoy. It’s the journey and the destination.”

It’s vital to remember that there’s no direct correlation with past and current success. “Bad things happen. How you react to good and bad situations determines who you are, how you are, and how you live your life. It’s what you make of it.”

Between stimulus and response, there’s always choice.

“Too often when something goes wrong, it leads people down the wrong path,” Dwane suggests stopping yourself at this point and asking: What does this really mean? Can I apply a new strategy?

“In the dark days of 2011 at Zinch, we were at a point with very low cash and bad prospects,” Dwane says. “It could’ve been game over but thanks to a great team it was a resolution to rebound and find a new strategy… Not every day was good, but looking back, the team was the rewarding part. That’s the part about enjoying the challenge. Your greatest strengths come out of these moments.”

As a new team member, rely on the three constant learner mindsets to internally emphasize your progress, not your setbacks. They’ll help you get situated and find new answers to your team’s most pressing problems.

If these mindsets feel foreign to you, rest assured, you can rewire your brain to adopt them. Start slow, testing each of the tactics and questions Dwane provided, and celebrate the moments when you notice a shift in your frame of reference. Awareness is going to be your most important tool here. If you can be intentional about adopting a particular mindset and remaining cognizant about how it’s changing or informing your decisions, you’ll have a much easier time changing your everyday behavior.

Assemble a Team of Constant Learners

The most defining attribute of adaptable leaders are the individuals that they surround themselves with. They are often on teams with other flexible, resources, innovative people. Whether now or in the future, Dwane provides the hiring framework she uses at Chegg to help you identify self-motivated individuals who will enrich your team’s aptitude for learning.

“The most powerful way to construct a job description is to clearly communicate that unyielding, consistent learning is a core part of the job.”

Confront candidates with these questions and projects to find the right individuals for your team:

During the Interview

After making introductions, Dwane begins with a pointed two-part question: What motivates you and what do you want to do next?

Most candidates deflect the question by repeating their resume. “They try to add to it but it doesn’t demonstrate what I’m looking for which is: active listening, the ability to answer the question, and self-awareness,” Dwane says.

These are the questions she uses to identify if a candidate is an adaptable learner:

  • What have you started?
  • How would you describe yourself in your own words?
  • How would a colleague describe you in three adjectives?
  • What current trends are you seeing in your profession?
  • What new things have you tried recently?

The last two questions are strong indicators that your candidate is self-motivated to explore and embrace new trends, routines, and technology. Take note of this as a critical demonstration of self-learning in your interview. Dwane advises probing more about the new process he or she introduced, why it intrigued them, and the results of implementing it.


“I love to give people an opportunity to give a compelling presentation on a topic they care about,” Dwane says. “That’s the game. If they look pained while they are doing it or don’t enjoy the assignment, then you know someone isn’t going to have a gameful approach. You want someone who is going to enjoy talking about the topic and putting the presentation together.” Chegg uses this strategy for their business and data science hires.

When You Check Their References

The last part of Dwane’s process, before evaluating candidates with her existing team, is consulting their references. Reputation matters — a lot.

“The best reference check tip I’ve ever received is to leave voicemails for the references provided by your candidate. If you get a voicemail, which you almost always do, say: ‘Please call me back if this is an outstanding candidate for a job that requires learning.’”

If the candidate is outstanding, you’ll get a call back immediately. The reference might even apologize for missing your call. If you don’t hear back, leave one more message, but take note that you didn’t get an enthusiastic call back. If you still never hear from the person, take that as a very telling sign, and revel in the time you saved.

“References can be instrumental if you’re asking thoughtful questions and really listening to what someone has to say. People will go the extra mile for the people they recommend,” Dwane says. If a candidate can’t provide you with two or three strong references, that’s a big red flag.

If you only follow one hiring mantra let it be this: Hire people for the way they approach problems. It follows, if you can only ask a reference one question about a candidate, this should be it.

It’s challenging not to be seduced by impressive resumes, however, Dwane advises leaders to hire for an approach that you like versus a demonstrated track record.

“We all want to hire people who have successfully done what we need,” she says. “That’s really rare, though. Just because someone has done something before doesn’t mean they can do it again. It’s not a self-fulfilling prophecy. This is where you can say that experience can be overrated.”

Cultivate Constant Learners on Your Team

While your goal is to hire individuals who are already self-motivated, it’s wise to dedicate parts of your onboarding process to demonstrate what active learning means at your company.

When you encourage people to think differently, you bring out their very best.

From the moment a new hire walks into the office, make it clear that you’re excited they joined and that you really believe he or she is going to make a difference. This puts them in a growth mindset calling them to contribute on their first day.

Simple, but powerful ways to quickly engage new team members are adding them to a Slack channel, subscribing them to a newsfeed or a series of blogs, and inviting them to a company offsite where they can interact with the rest of the team. Each of these situations will enable them to gain direct insight into how your values fuel your approach.

Dwane defines these lessons as “cultural literacy.” New hires at Chegg also spend time with Dan Rosensweig, the company’s CEO, who makes it a point to very clearly demonstrate that self-learning happens on all levels of the organization.

As a leader, your most critical responsibility is to help new team members set goals so they can experience wins during their early days in their role. Encourage them to be “explicit about what they want to learn personally or professionally this quarter and within the next year. New hires should feel empowered, respected, and ready to play the game.”

Goal-directed learning provides clarity and stability enabling individuals to answer the question: How am I working smarter, not harder, and raising the bar?

Adaptable people aim to do the right thing at the right time for what they want to accomplish.

The insatiable quest to learn is no longer a unique trait of self-motivated leaders. It’s a requirement to remain relevant as every field accelerates ahead.

“Knowing has become obsolete,” Dwane says. “Learning has become our true currency. We’re not knowledge workers. We’re learning workers. If you aren’t actively trying to learn, no one can help you. If you make it central to your professional life, no one can stop you.”