Jen is a highly sought-after leadership coach, entrepreneur, brain tumor survivor, mom, podcast host, writer, and founder of Plucky, where she guides CEOs, entrepreneurs, and leaders across various levels to foster healthy dynamics and improve work-life balance for everyone. Jen has empowered professionals at over 200 companies, including industry giants like Google, Facebook, Slack, The New York Times, and many more. Her insights have been featured in The Wall Street Journal, and she has appeared on multiple podcasts, such as Harvard Business Review’s Women at Work.
Listen on Spotify
Listen on Apple Podcasts
Watch the video:
Key Insights with links to jump ahead are below
About Guest
Name: Jen Dary
What she does: Jen is the Founder of Plucky, a leadership coaching firm.
Company: Plucky
Where to find Mona: LinkedIn | Website
Key Insights
⚡Act like a leader before you become one. Start demonstrating leadership qualities before you’re in a leadership role. This approach is how you’ll be top of mind for decision-makers in your company when they’re selecting the next manager. Jen explains, “If people are talking in a boardroom about ‘Who should be our next manager? Who could we promote?’ you want to be on their mind. You want to be an idea that comes to them. So now we step back, and we say, how do you get on people’s minds? Well, I don’t know the neuroscience here, but in my observation, they’re going to almost look through their mind of who has demonstrated some kind of leadership before. So you want people to think of you as a leader or a potential leader.”
⚡Good leaders are mindful of their environment. While leaders may have a personal style, the ability to read the room and respond appropriately is a critical skill for success. Jen explains, “I think that asking yourself the question, ‘What does the company need from me right now? What does the team need from me right now?’ puts you in a mindset where you realize that some version of your leadership is responsive to the climate that you’re in. […] So, in that sense, the type of leader that you are really does come out of where are you and what’s the environment and how’s the economy and how’s everybody’s morale and those sorts of things. And it doesn’t mean that you can’t have some things that are definitely personally your style, but the ability to read a room is a huge skill that leaders should use.”
⚡Honesty and transparency often outweigh field expertise in managerial roles. Good leaders don’t always have to be experts in every technical detail. While it’s essential to have a solid understanding of the field, what truly matters is honesty and a willingness to learn.
Jen explains, “My instinct is that you don’t have to always be fluent in everything you’re going to be working on, so you’re suggesting a very technical team, which is a great example, but you should have some reasonable understanding of the arena you’re stepping into. So if all of your developers are going to be well versed in one language and you don’t necessarily know that, I would say that doesn’t take you out of the game, but you might speak to that in the interview to say, ‘Just to be upfront about this I’m a very technical person. I’m not super fluent in go, but I’m a great learner, and I’m very willing to sort of pick up the ball and run with that. Here’s another example of a time in my career when I stepped into a role, and I didn’t know all the skills I really enjoyed learning, and blah, blah, blah.’”
Episode Highlights
What is the ideal career path for managers?
The workplace landscape has significantly evolved over the last decade, offering managers a variety of possible paths to pursue. The ideal career trajectory is very individual. Jen says, “I think an ideal career path for any role would be something you’re interested in, something you find fulfillment from, and then specific to managers I guess I will say that you don’t get too much responsibility too soon. So, ideally, you are given, I can imagine, like a volume knob. It’s like first you’re in charge of something, and then you’re in charge of a little more and a little more versus a very common story, which was so-and-so went out sick or so-and-so got poached, and now I’m in charge of the company.”
It’s not about you; it’s about your people.
In difficult situations, it’s vital to remember that it’s not about you as the manager but about your people. This mindset ensures that your actions are constructive, which ultimately helps create a positive and respectful environment.
Jen shares an example, “In this class I teach, we talk about how to fire someone, and everyone gets very quiet and nervous as I demonstrate these things. And I always say, when you go into that room, you want to keep it very simple. So you want to say, ‘All right, we’re here today because today is going to be your last day at the company. We appreciate the contributions you’ve made, but it probably is no surprise. We’ve been having a lot of conversations about performance, and so today is the last day. So we have some forms for you to sign.’ And then, etc., etc, you say whatever else you need to say. But do not go have a slideshow of memories. This is not the time. This is a hard day. ‘But you were amazing at that karaoke party.’ No, no, you keep it simple, and I’m leaving aside all the legal implications, all that. But this is not about you, the manager. This is a life moment for that person.”
Adaptability is the secret sauce of leadership.
A great leader understands the importance of adaptability and responsiveness to the needs of the team and organization. Jen explains, “I think that asking yourself the question, ‘What does the company need from me right now? What does the team need from me right now?’ puts you in a mindset where you realize that some version of your leadership is responsive to the climate that you’re in. So when you were giving those examples, I could imagine if everything is gangbusters and you have a million billion dollars and you could R&D your face off, then you might need to be an innovative leader. ‘I have ideas’. And if you just had a riff and you laid off half the company, that might not be the kind of leader they need.”