The most counterintuitive leadership tip? Leaders, stop doing what you’re good at.

Playing to your strengths as a leader doesn’t make you a good boss – in fact, it can make you a bad boss. Here’s why.

Of all the tips to be a good manager, “leaning into your strengths” has got to be one of the most frequently cited.

“Do what you’re good at. Focus on your strengths.” That’s the conventional advice we all receive. There’s no shortage of StrengthsFinders assessments and personality tests urging us to triangulate which strengths we should zoom in on.

However, I recently had a conversation with Peldi Guilizzoni, CEO of Balsamiq. His insight on this topic turned my head sideways… in a good way. Peldi asserted:

“Doing what you’re good at hurts the team.”

Huh? Let me explain.

Peldi admitted to me that he’s good at getting stuff done. He makes things happen. He thinks he’s killing it. But as a CEO, 10 years in, should he really the one doing all the doing?

After a decade running his business, Peldi noticed he’d created an environment where his coworkers were depending on him to get things done. If he takes a vacation – he leaves them hanging. If he has to be out for a week – they’re stuck.

Peldi conceded:

“What I realized is that I should stop myself from doing things I’m good at  —  which is so counterintuitive  —  and instead, focus on delegating training and making sure that everybody gets good at doing those things.”

Doing what he was good at was hurting his team, not helping.

I could relate.

I’m good at communicating. So I do it internally. A lot. I write-up about what we’re doing, why we’re doing it, a new approach I’m thinking about, a new concept we should try… But, when I take a step back, it’s a bit too much. We’re a tiny, two-person company. For our size, all that communicating is overkill. I could easily spend some of that same time somewhere else in the business and have it be more meaningful.

For both Peldi and I, our predisposition became a preoccupation. We’re good at it, so we automatically assumed it was good for our team.

Whenever you’re good at something, you don’t objectively assess its effectiveness as you should. You apply less of a discerning eye. You know you’re good at it, so you figure the more you do of it, the better.

But as with anything, repeated actions without rigorous judgment become lazy and reckless. And naturally, they have unintended consequences.

Now avoiding this pitfall is hard.

No one is going to stop you. Rarely do others have the temerity to stay, “What you’re good at is bad for the team.” Plus, doing what you’re good at is fun. It’s inherently satisfying to flex your strengths. Who wants to not feel that way?

So, you have to ask yourself: Are your actions feeding your team, or your ego?

Focus on what you’re good at, and the team never becomes good at it themselves. Focus on what you’re good at, and you never see things for what they really are.

Resist viewing your strengths as the only way to make the team strong. Resist falling in love with the short-term results of doing what feels good to be doing.

Pause. Don’t be so busy. Take stock. Why are you doing those things? Because you like doing them? Because you’re good at them? Or because it’s the best way to move the team forward?

Find someone who will tell you the truth. Your co-founder, your coworkers. Ask them if what you’re doing that you’re good at is really helping move the team forward.

This truth-seeking takes 10 minutes to do. Start today. And stop doing what you’re good at, all the time.

P.S.: If you did indeed enjoy this piece, please feel free to share Thanks 😊 (And you can always say hi at @clairejlew.)

Big news: Know Your Company is now Know Your Team 🎉

After four years, we’re launching a new product, business model, and company name. Here’s why.

We’ve always been a bit weird.

We’re a two-person company serving 15,000+ people who use our product in over 25 countries. We’ve generated almost $2MM in revenue to date, have been profitable since Month 1, and every year since. We’ve never raised money from investors, or taken out a bank loan. (And, we started out as a tiny prototype that Basecamp spun-off.)

Today, we’re doing something weird, again.

We’re launching a new product, business model, and company name.

We’re now Know Your Team software that helps managers become better leaders. We give you educational guides, tools, and a community of support to help you avoid becoming a bad boss.

Know Your Team costs $65/month per manager (or $600/year).

You can check out the new Know Your Team here.

Here’s why we decided to make this change.

Quick background, first.

If we’ve never met before, hello! I’m Claire, CEO of Know Your Team. It’s nice to meet you, albeit virtually.

Our original software, Know Your Company, used to be focused on helping business owners with 25 to 75 employees get to know their company better. We charged $100 per person, one-time, for life.

We generated $1MM in cumulative revenue in a little over two years. We helped tens of thousands of people at companies like Airbnb, Medium, Kickstarter. And not just at tech companies, but law firms, marketing agencies, retail stores, and even a few churches.

When we surveyed customers, 94% of employees said Know Your Company helped them feel more connected to their coworkers, and 85% of CEOs said Know Your Company positively impacted their company culture.

Yet as 2017 was winding down, we noticed our sales becoming flat.

“What’s wrong?”

I remember thinking this around this same time, last year, in December.

As I reflected on 2017, I noticed three things:

  1. Our online community for leaders took off. We’d launched our Watercooler community in October 2017, to help managers learn from each other. More than 200 people signed up for it in the first month. (Today we have almost 1,000 members.)
  2. Our writing about leadership took off. The writing I’d been doing on our blog increased our organic traffic by 3X in a month’s time. It would go on to increase by 20X over the next six months.
  3. Our software sales went down. Our sales, however, did not increase. Not 20X. Not 3X. In fact, sales were fairly flat in 2017, if not dropping during some months.

Seeing the discrepancy between our audience and our sales, we scratched our heads.

Yes, Know Your Company was helpful as a piece of software. But for who?

When we got started back in 2014, we focused on selling to business owners. But by the end of 2017, our audience had evolved. After some digging, we learned that our 20X increase in traffic were mainly managers at companies of all sizes.

We had a mismatch. Our audience was managers, but our software was for business owners.

Our audience was asking the question, “How do I become a better leader?” But our software, Know Your Company, wasn’t answering that question.

In fact, no one was doing a good job of answering that question, “How do I become a better leader?”

Sure, you can read books, but they lack practical application. Trainings are expensive and one-time. And man, making mistakes and learning trial by fire is awfully painful.

I searched high and low for a good answer to, “How do I become a better leader?” I couldn’t find one. So we decided to build our own.

The result is Know Your Team.

Introducing Know Your Team: The new product.

To answer this question, “How do you become a better leader?” we re-imagined our product.

We pulled together research from working with 15,000+ people over the past four years, and discovered that the best leaders do three things exceptionally well:

  • Trust: If you don’t build rapport as a leader, nothing moves forward.
  • Honesty: If you don’t speak the truth to your team, problems fester.
  • Context: If you don’t get everyone on the same page, confusion sets in.

Because of this, we designed Know Your Team to help a leader develop these three skills of Trust, Honesty, and Context.

You can read more about our methodology here.

The best way to learn anything is to go do it. The second best way is to practice doing it. So with Know Your Team, we combined theory with practice. You can’t become a better manager by just reading books, or just by using software tools, alone. We built Know Your Team to include 3 complementary resources, to be used together:

  • Guides — Written guides on leadership, based on data, with 50+ chapters on topics such as one-on-one meetings, giving honest feedback, building trust, and more.
  • Toolbox — Dead simple software tools to help you run effective one-on-one meetings, ask for feedback, get high-level team updates, foster rapport, and more.
  • Community — Online support from 1,000 other managers from all over the world, where you can discuss tough situations like firing, hiring, and more.

You can read more about our resources here.

And, we’re not done! We’ve got loads of ideas for more guides, more tools, and more resources that we’ve already started working on creating. There’s so much to be done to help people become the leaders they’ve always wanted to work for.

Changing our business model.

For new customers who sign up for Know Your Team, we chose a new business model. Know Your Team costs $65/month per manager to purchase. As a monthly subscription, this makes it easier for managers to swipe their credit card without having to ask for permission from their boss.

Previously, our one-time pricing model had been useful to get us to profitability quickly. For example if you had 19 employees, we charged $1,900 one-time. We were essentially collecting the lifetime value of the product upfront.

But over time, we noticed our one-time pricing model becoming a big barrier to sales. A business owner had to justify a $2,000 or more expense to their finance department, to their investors, and to their leadership team.

Now that we’re selling to managers, there was no way a $2,000 product was going to feel accessible to them, even if the cost was only one-time. We wanted Know Your Team to feel like a “no-brainer” purchase for folks who might not have access to the company’s budget. So we moved to a monthly subscription model.

Building Know Your Team with two people.

We spent six months building Know Your Team. This meant designing and coding new features, writing 50+ chapters on leadership for our guides, and constructing a new billing system, new onboarding system, and new marketing site… All with just two people.

Every piece of copy, code, and illustration you see is something our CTO Daniel Lopes or myself created. (We did this while maintaining our current product, doing customer support, writing blog posts and pursuing other marketing projects.)

This is a big move for us. As a bootstrapped company, we don’t have piles of cash stacked up, in case it doesn’t work. We don’t have investors to run to if we get stuck in a bind. (In fact, we have $140,000 in the bank, to be precise.)

But, the change feels right. Since I’ve been running the company in 2014, this launch, today, is the most energized I’ve felt.

Why the weirdness?

Admittedly, our approach is weird.

You might be wondering, “Why are you making things so hard on yourself, Claire? Why not raise some money to make this change? Take out a bank loan or open a line of credit? Hire more people? Buy yourself more time?”

Those are not bad ideas. We considered them. And who knows, maybe we’ll pursue them in the future.

But for right now, the short answer is: I don’t want to.

When you run your own business, you have to remember why you wanted to run it in the first place. What you want. Not what others want.

In business (and in life), we’re addicted to pattern-matching. We snuggle into where the grooves are carved, where the tracks have been laid — not necessarily because we want to — but because they’re just there.

For me, I got into this whole starting-a-business thing because I wanted to do it on my own terms: Small in headcount, big in impact, independent, profitable. Life is short. Why build a business any different from your vision for it?

Of course, you shouldn’t mindlessly listen to your own din, in isolation. You should carefully choose who to listen to. The only people I want to listen to are our customers, current and prospective: Employees, managers, leaders, CEOs.

The minute you take on investors, accept money from a bank, put people on your board — you change the people who you’re listening to.

I don’t even want to listen to Jason and David, the founders of Basecamp (and Know Your Team board members) 🙂 We’re lucky that Jason and David want us to do things our way, too. We disagreed on some of the strategy of the roll-out of Know Your Team, but they were very supportive of us choosing to ignore their advice. (I’ll write more on this perhaps another time…)

If you have the luxury to choose who to listen to, choose intentionally.

Is Know Your Team for you?

You might be one of those people I want to listen to.

If you’ve spent late nights googling things like, “how to be a good manager” or “how to run a team meeting” or “how to delegate well”…

If you’ve bought carts of leadership books on Amazon, desperate to avoid beginner manager mistakes…

If you’ve ever thought to yourself, “I have no idea what I’m doing as a manager”….

Know Your Team is for you.

I’d be honored if you gave Know Your Team a shot.

If there is anything else — truly anything — I can do to help you become the leader you always wished you worked for, I’m here. Feel free to email me at claire@knowyourteam.com or ping me on Twitter at @clairejlew.

I look forward to hearing what you think. I’ll be listening to you.

On the journey with you,
-Claire


P.S.: If you did indeed enjoy this piece, please feel free to share so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)

From The Heart(beat) ❤️: Leadership lessons I wished I’d learned earlier

Here are a few of my favorite leadership tips from CEOs, founders and executives featured recently in our Heartbeat interviews.

Every two weeks, I ask one question to a founder, CEO, or business owner I respect and share it on The Heartbeat ❤️, our bi-weekly newsletter on how to become a better leader. The question I always ask is, “What’s one thing you wish you’d learned earlier as a leader?” Here’s what some of our recent interviewees had to say…

Leaders don’t need to know it all.

Rob Walling is the co-founder of Drip, an email marketing automation software company that we in fact use a Know Your Company. What does Rob wish he’d learned sooner? That it’s okay for leaders to ask questions. He says:

“I wish that I had learned that I didn’t need all the answers as a leader. [I hire] people that are better than I am at something, and then when a problem comes up I can look around the room and say, ‘I don’t know. What do you think?’” — Rob Walling, co-founder of Drip

Embrace failure.

Aynn Collins is the Director of Talent Strategy at MailChimp, the world’s largest marketing automation platform with more than 900 employees. Aynn’s advice to her younger self is to understand that failure is part of growing as a leader.

“Embracing failure and understanding how you learn and grow from those failures is what I would tell people to learn early in their career. They can own failures, talk about them, debrief with your team on…and not try to just make everything shiny and pretty. Because we know business and leadership is not always perfect, and shiny and pretty.” — Aynn Collins, Director of Talent Strategy at Mailchimp

Forget the org chart.

Dan Mall is the founder of SuperFriendly (a design collaborative that’s worked with clients such as Apple, Time Magazine and ESPN) and CEO of SuperBooked (a software application that helps people find creative work). For Dan, he wishes he’d known that an organizational chart isn’t the end-all, be-all of business.

“The leaders aren’t the ones at the top. They should be the ones at the bottom. They should be the one supporting everyone else…They need to be able to see everything. They need to be able to support people. So, I wish I would have learned the idea of servant leadership, which is becoming more and more popular now.” — Dan Mall, founder of SuperFriendly and CEO of SuperBooked

 


 

P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)

14 questions to ask an underperforming employee during a one-on-one meeting

When an employee is struggling, here’s what the best managers do.

Someone’s slipping. You see it. You feel it. You’re not on the same page. You desperately want to pull the person up, but you’re not sure exactly how. Do you encourage them? Switch them off the project? Change how you’re leading them?

You’re now facing one of the toughest tasks as a leader: How do you manage underperformance at work? And more specifically, how do you sit down and talk about their underperformance with them, during a one-on-one meeting with her or him?

It’s tempting to look outward first. To blame the person herself or extenuating circumstances. “They don’t pay attention to detail.” Or, “The client is being unreasonable with them.”

While those may very well be the case, you should also turn inward. As leaders, when an employee is underperforming, we must self-reflect. What are you doing that is stopping this person from doing their best work?

The hard part about managing an underperforming employee is choosing to look both inward and outward for the sources of underperformance at work: What are you doing to hold an underperforming employee back? And what is the underperforming employee doing to hold herself back?

Oftentimes, we think we know the answer to those questions. We have hunches about what’s causing the underperformance: “It’s their perfectionist tendency getting in the way, obviously…” or “It’s my lack of context I shared about the project, clearly…”

So, we just create a performance improvement plan based on those hunches, and move forward.

That path is instinctual — but that path is flawed. Assuming what’s wrong doesn’t help you get any closer to finding out what actually is wrong. While your hunches may end up being spot-on, in my experience, I discover the truth of what’s really holding an employee back when I ask, not when I assume. Coaching a struggling employee to success begins with asking the right questions, not simply arriving with the supposed answers.

Given this, when you sit down in a one-on-one with an underperforming employee, what should you ask? What questions will help you look both inward and outward to get to the underlying source of underperformance?

Here are 14 questions to try. They are by no means the only questions you ask during a one-on-one (here are other ones to consider). But, they provide a good starting place to delve into how to better manage an underperforming employee.

Ask these questions to look inward.

You’re trying to figure out: “How have I been letting this person down? How have I been getting in the way?”

  • Is it clear what needs to get done? How can I make the goals or expectations clearer?
  • Is the level of quality that’s required for this work clear? What examples or details can I provide to clarify the level of quality that’s needed?
  • Am I being respectful of the amount of time you have to accomplish something? Can I be doing a better job of protecting your time?
  • Do you feel you’re being set up to fail in any way? Are my expectations realistic? What am I asking that we should adjust so it’s more reasonable?
  • Do you have the tools and resources to do your job well?
  • Have I given you enough context about why this work is important, who the work is for, or any other information that is crucial to do your job well?
  • What’s irked you or rubbed you the wrong way about my management style? Does my tone come off the wrong way? Do I follow-up too frequently with you, not giving you space to breathe?

Ask these questions to look outward.

You’re trying to figure out: “What on the employee’s end is limiting them? What choices or capabilities of their own are keeping them from the results you want to see?”

  • How have you been feeling about your own performance lately? Where do you see opportunities to improve, if any?
  • What are you most enjoying about the work you’re doing? What part of the work is inspiring, motivating, and energizing, if any?
  • What part of the work do you feel stuck? What have you been trying the “crack the nut” on, but it feels like you’re banging your head?
  • What part of the work is “meh”? What tasks have you feeling bored or ambivalent about?
  • When’s the last time you got to talk to or connect with a customer who benefited from the work you did? Would you like more opportunities to do that, and should make that happen?
  • Do you feel you’re playing to your strengths in your role? Where do you feel like there is a steep learning curve for you?
  • Would you say you’re feeling optimistic, pessimistic or somewhere in the middle about the company’s future?

You’ll notice that none of these questions ask, “What do you think you’re doing wrong?” or “What do you think I’m doing wrong?” The point of these questions is not to end up in an accusatory place, either way. Your goal is to reach a place of better understanding.

By approaching the conversation with an underperforming employee with questions to ask, rather than answers or directives to insert, you create space for that employee to want to do something different. To actually change and improve.

That change, that improvement, is the goal, after all.


 

Watch our lessons for leaders: The Heartbeat Interview ❤️ with Elena Valentine, CEO of Skill Scout…

With a focus on diversity and inclusion, the CEO of a Chicago-based media company focused keeps it real about the myths and struggles of leadership.

Every two weeks as part of The Heartbeat ❤️, I asks one question to a founder, CEO, or business owner I respect. This week, I interviewed Elena Valentine, CEO of Skill Scout, a media company that helps transform hiring with video. Watch & read what she has to say here…

Claire: Hi everyone, I’m Claire Lew and I’m the CEO of Know Your Company and it is my honor today to introduce a very good friend of mine who is on the heartbeat, the one and only Elena Valentine. She is the CEO and founder of Skill Scout, and she’s actually based here in Chicago but we couldn’t get together in person unfortunately, but her company is amazing if you don’t already know about it. They’re on a mission to bring storytelling into the workplace and have just worked with some amazing brands and companies as this media company to help folks better recruit for the jobs that they have.

And so, the other reason for why I love Elena other than just being this badass CEO is that she is incredibly intentional about creating a more diverse and inclusive workforce, first and foremost starting with Skill Scout. They have primarily hired women and people of color and the way she looks at it is, if you care about diversity you’ve got to walk the walk and so her company in many ways is a shining example of that.

Just so excited to have you here today Elena.

Elena: Yes woo hoo!

Claire: So Elena as you may know, I’ve been asking this one question to all sorts of leaders over the past few months, and it is … You ready? It is: What’s something you wish you would have learned earlier as a leader? It can also be more than one thing, if you want.

Elena: Yeah this is hilarious but literally I have been thinking about this, it’s your receivables.

Claire: Oh.

Elena: You don’t realize that when it comes to your cash flow, you have to keep really good track of your receivables to make sure you don’t lose money. So that was certainly a big thing and one that we constantly go through even now to make sure that we can continue to do what we do, which I think, then gets me to the other one, which is the not so glamorous side of being an entrepreneur and leader.

That it’s about staying alive like a cockroach. And that’s not glamorous and sexy whatsoever. But I think it’s really all about, especially in the beginning, it’s being able to survive another day and doing whatever, by any means possible to make that happen and sometimes that means that your business plans look really messy and it doesn’t necessarily fit with the original intention.

And it’s being okay with the fact that things will not go as planned and that, at the end of the day, it’s about continuing to move forward to survive, to build your business.

Claire: This is why I love you Elena. Keeping it real because I think there is this grand illusion around running your own company that oh, it’s growth, you’re killing it and I’m not saying that you’re not but you’re bringing us back down to reality of building a business though is in many ways just about making it to the next day. It’s about making sure you are making more money than you spend. It is about making sure you have enough receivables and in some mythology that we’ve created, whether it’s the media, whether it’s all these ridiculous articles and books that we read around entrepreneurship or leadership, that gets lost.

Claire: Do you feel like before you became an entrepreneur and before you started your own company, you had bought into myth or did you know going into this journey as a leader that, all right, this is about surviving, this is gonna be part of the struggle? Were you aware?

Elena: Yes and no. I’ll be honest. And this is so hilarious and naïve of me to think this way but when I got into this, I kinda came in thinking that there was only one way to build a business and that was to raise a lot of money and grow it to a point that you sow or you IPO, which is so stupid and naïve to think considering that the majority of businesses in the world are boot strapped.

Claire: Yep.

Elena: And are small businesses.

Claire: Yep.

Elena: And are privately owned. But I think that was probably the most naïve thing was I only really saw, kind of, one facet to building a business. I think for a long time I compared and contrasted what I saw out there to what our experience should be.

It took a really long time to realize that I was comparing myself to elephants when I was really a giraffe and I needed to find other dope giraffes. And that took me probably up until the end of last year to really follow my true north and see that I’m a giraffe, I’m proud to be a giraffe and there are businesses that are incredible, that are run by giraffes.

Claire: Absolutely. There are so many dope giraffes and I love that you’ve embraced the fact that you are a giraffe but here’s the thing Elena, I really want to dig into this because I think you have hit on something that so many leaders struggle with, which is our desire to fulfill some sort of story arc that sometimes isn’t even our own. Like you said, you used to only see one potential path to being a successful leader and running a successful business. And I think as leaders, we often think, oh yeah, there is only one type of successful leader and it looks like Steve Jobs or it looks like Elon Musk, or whoever that person in our minds is.

Claire: For you, speaking to other managers and leaders and CEO’s who are watching this, what would you recommend to leaders who struggle with trying to fulfill that story or sort of please other people in that way? What’s your advice? How have you copped with it? Especially at the end of last year like you said, you sort of came into your own on this..

Elena: It’s not gonna make your payroll in two weeks.

Claire: Yeah.

Elena: Yeah. Honestly. It’s not gonna make your payroll in two weeks. And I think that’s what ended up coming down to it was I have to follow the path and I have to find leaders, kind of, building a similar business or type of business, really again, focused on kind of making it to that next month, those next two years. I think inevitably I am here to build a business to last, not to sell and once I realized and kind of knew that, that was my true north, it was circumventing everything else. Then I knew that there was a different story and that there were different leaders that I could aspire to be who were thriving, who were extremely successful in doing that.

Claire: Absolutely. Man, I’m taking it all in because it’s really refreshing to hear that clarity. I think a lot of leaders, myself included, have always wrestled with what is my true north?

For example, especially when it comes to leadership style… You read that maybe leaders should be decisive and that leaders should be strong and have all the answers, but if that’s not sort of your style, then how do you know what your true north is? Or here’s the other thing, I work with some CEO’s Elena and they go, “Claire I’ve been reading about all this stuff about being open hearted and listening and really emotionally in touch. I’m just not really like that though as a leader. Do I change my personality?”

So talk to me about how do you find your true north and what advice might you have for leaders who are trying to do that? Should a leader sort of conform to what the books are saying, what they’ve been reading and … I mean, how did you find that truth north for yourself? And your own sort of leadership style?

Elena: Yeah. So truth is, there’s no one right way to be a leader, that’s why there’s thousands of books on it. And thousands of Brené Browns and Simon Sineks of the world, because there’s not one right way to do it. I mean, I think that’s the uniqueness of the human experience is that it’s extremely multi-faceted. So that’s one thing I would say. Now certainly there are narratives that are more popular than others .

But I think when it’s about finding your own true north as a leader, it’s the idea that you are continuously learning and exposing yourself to all different kinds of styles. Even if you inherently know that, that’s not the right one for you, to the very least know that it exists.

Because part of my business is service and building relationships, which means that on the other side of the table, if that’s a client, if that’s a potential employee, I’m dealing with that specific kind of personality.

And I in turn have to understand how I adjust and how I can elevate that relationship regardless if it’s not exactly like my own, so that’s one. But I will say I was very lucky, and I’m sure in many ways like yourself, we’ve all had our mentors and the kind of leaders that we aspire to be and I was super lucky to be professionally raised in the kind of innovation design, design thinking space. So my professional parents are Chris and Cira Conley who are the founders of gravitytank now Salesforce, and they were kind of a main stay innovation design firm here in the city and that’s the main exposure that Abby and I had of leaders, which were leaders who ate last, leaders who were empathetic first. And leaders who saw their biggest role as being servants to their organization and to the people who they worked with.

And so, as a result of that, I was working there and having these visions of the kind of leader I wanted to be. I wanted to be the female version of Chris Conley. And the way that he had taken me under his wing and allowed me to grow and allowed me thrive. It wasn’t a lot of dictation, it was a lot of how would you solve this problem Elena? And giving me the space to fail, and to also present new ways to actually do it. There is a gift to being able to identify strengths of someone and helping them to leverage that.

The other thing I really learned from him inherently as a result, again of being a design researcher, being someone who’s always trying to put themselves in someone else’s shoes, was always that, if someone fails, if one of my colleagues fails, if I failed under Chris Conley, the question always was, what did I do as a leader that set you up for failure? And what can I do as a leader to set you up for success? What barriers do I have to remove for you? What kind of structures of guidance do I need to put in place to make you successful?

And when you do that, when you realize that, you start to open yourself up to actually having a true feedback conversation. So it doesn’t just become around, hey Abby, Nicole, Colette, this is what you did wrong. It’s to say, so I’ve been able to reflect on this, and here’s what I know I did wrong. Here’s my CEO failure bow, of why I know this didn’t look how it should have. And here’s what I’m going do to improve that. And so I open up all of those conversations when it comes to success and failures, of also making sure that I’m opening myself up to reflect on what I could have done better, but also making comfortable for them to let me know what I could have been working on, in addition to their own reflections of what could have gone better in terms of them being able to bring something to the table.

Claire: Absolutely. No, I think you’ve touched so much that’s helpful for folks in terms of making sure … I love what you were saying first of all, of the awareness piece, right. Being aware of how you’re coming across, right? Even it’s not necessarily your style but what effect does that have on the client or the employee you’re working with? I love your mention of mentors and how much that shapes where you draw inspiration from. I think all of us, hopefully, haven’t just had the bad boss experience where we’re like, “Okay we don’t wanna be that.” Hopefully many of us have had the good leader experience and gotten to work with someone who we really admired, I know that’s shaped some of my views as well. And then this last idea of wanting that feedback and being very open and saying, “Okay, here’s where I messed up. Here’s where I just fell flat on my face. Tell me how I can be better,” and how in those ways that can help shape your true north, your personal style of leadership, those three different pieces.

That’s brilliant Elena. I guess for new leaders and managers, we have a lot of folks who watch this who are newly promoted or a leader of a team for the very first time. What would you recommend for them to internalize … I mean, going back to the very first thing you talked about of surviving another day, what would you tell them to sort of internalize that ethos? Or is there anything more tactically or on a day to day basis for them to not get overwhelmed also by the process of feeling like leadership is … Yeah, it can be a grind and it can feel like you’re just trying to survive and just get to the next day.

Elena: I mean, I think it’s a reframe. I mean, obviously not everyday should feel like survival.

Claire: Yeah.

Elena: But I will kind of harken back to another one of my great professional uncles, who we both mutually know, Josh Braun and whether it be a sale or whether it be leveraging your own team, your role as a manager or sales in general, is what can I do to help make you more awesome? And that could be about removing barriers, that could be about putting processes in place but I think that there’s something really poignant about reframing to understand it on a personal level, be it for an external facing problem or an internal problem, what is it as a manger that I could do to help make you more awesome? So that I would say, is kind of … It’s more of a key question and it’s seeing that as a manager these are people and you have to look at them holistically and sometimes it isn’t just a work tactical problem.

There’s something deeper than that and so I think part of it is not being afraid to go there because I think some of the best leaders who can go there can help to understand what are some of other just general and inherent motivations of that employee, to help support them or to know that they can feel comfortable saying, “Hey this is my kind of personal problem that I’m facing.”

And even to have that kind of cathartic experience with that hopefully, and knowing that you’re listening, can dramatically help shift their work day that day, or what they’re looking to accomplish. So I think that definitely reframing the how can I make you more awesome? Thinking about it more holistically. And a very simple question that I’m always asking is, what can I do to make you successful in X?

Can I be doing anything better? And it may not necessarily be personal, it literally will be … They’ll just tell you, yes I’d like to be able to carve from 11 to 11:30 every day to do this. And so, asking that simple question gets you very far.

Claire: That’s amazing Elena, thank you so much. I’m sure folks watching this are writing that question down, keeping it in mind. And in general, thank you so much for sharing all your wisdom on the things you wish you would have learned, on the things that have been helpful to you. This has been so fun.

Elena: Yes! Thank you Miss Claire Lew.

Claire: All right. See ya, thanks Elena.


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