Thoughts on where we go from here

The NExt STep

Tracy Cupper Tracy Cupper

But Did You Learn?

The major task of our growing-up years is learning. Learning how to be a human being, learning how to tie our shoes, learning how to read, to speak a language, to do fractions, and maybe how to bake a cake. It is the work of our childhood, our teen years, and our early adulthood, to learn full-time. No one is paying us to learn, but it’s our job, and we do it.

Then we move into adulthood, and we (hopefully) get a job that entails learning more about how things work and how our skills can benefit the company and the world and we put those learnings to the test, doing our work, and continuing to push and evolve our way of working as we learn more about how to do things more effectively, expanding our impact on the world around us. We add hobbies and families and we learn those new things, and our brain adds those to the database: skills acquired!

The major task of our growing-up years is learning. Learning how to be a human being, learning how to tie our shoes, learning how to read, to speak a language, to do fractions, and maybe how to bake a cake. It is the work of our childhood, our teen years, and our early adulthood, to learn full-time. No one is paying us to learn, but it’s our job, and we do it.

Then we move into adulthood, and we (hopefully) get a job that entails learning more about how things work and how our skills can benefit the company and the world and we put those learnings to the test, doing our work, and continuing to push and evolve our way of working as we learn more about how to do things more effectively, expanding our impact on the world around us. We add hobbies and families and we learn those new things, and our brain adds those to the database: skills acquired!

And then one day, many of us wake up and we think we know everything there is to know, and we don’t need to learn anything else. We have spent our life consuming and adding and processing and we’ve got it, we don’t need to add any more learning to the mix. So we go about our daily work and tasks and we do our things well, because we know them well and we are good at them.

Until something breaks. The client is unhappy. The product stops working. The technology isn’t keeping up. Your skills fall short. You’re bored. And there is a moment that we falter, because it’s supposed to work, it has always worked! And then we keep going, doing the things that we have always done, because those things have always worked and this exception doesn’t need to stop us. We know how this business or this world works, we’ve got this.

But you missed it! The moment of pause. It was important, and you saw it, and you ignored it and kept going. That moment of pause was a signal—there is something to be learned! A flag, planted in the side of the road, waving wildly, if just for a moment.

What you missed was the opportunity for growth and continued success. Because that moment was an indication that doing the same thing you’ve been doing didn’t work for this one moment. And if you take the time to find out why, you can learn more—and you can upgrade your thoughts, your work, and your outcomes to prevent those bumps in the road in the future—and maybe even grow and expand into new possibilities as the world around you changes.

Learning is a challenge for many of us, we want to be seen as competent and capable and coming across as a learner or incompetent in anything hurts our pride and our idea of ourselves. Going from being unconsciously competent in “all the things” to consciously incompetent in something is a step down, in our minds, and we hate it, it makes us uncomfortable in so many ways. But the only way forward is through, as they say, and the only way forward to continued success and growth is through the pause to learn. Ask yourself the hard questions, “Why didn’t this work?” “Why was the customer disappointed?” “How can I do this better next time” “What do I want to be doing instead and what change does that require for me?” and really work to understand the answers—and then apply them to change your processes so it doesn’t happen next time, or you add an additional skill or capacity to your skillset.

In a world that won’t wait for us to keep up, it’s imperative that the learning mindset comes with us, even into old age. Brain health relies on us to keep changing and evolving and growing, but also, our lives and careers and the world would be much more boring if we weren’t constantly learning. Time to put down the pride, and learn something new, even if that thing is intimidating to start. Onward to learning all the things!

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Tracy Cupper Tracy Cupper

The Loyalty Imbalance

Loyalty, according to the fine folks at Merriam-Webster, means “unswerving in allegiance,” such as “faithful to a cause, ideal, custom, institution, or product.” It evokes the concept of strongly attaching to someone or something and devoting your time, life, or skills to it. In the positive, it connotes a commitment to a person, thing, or business that holds steady in the ever-changing winds of life. In the negative, it can evoke the concept of a feudal serf, bound to the land or a person forever in exchange for protection or land.

So which is the more likely outcome—positive or negative—when it comes to business loyalty?

Loyalty, according to the fine folks at Merriam-Webster, means “unswerving in allegiance,” such as “faithful to a cause, ideal, custom, institution, or product.” It evokes the concept of strongly attaching to someone or something and devoting your time, life, or skills to it. In the positive, it connotes a commitment to a person, thing, or business that holds steady in the ever-changing winds of life. In the negative, it can evoke the concept of a feudal serf, bound to the land or a person forever in exchange for protection or land.

So which is the more likely outcome—positive or negative—when it comes to business loyalty? Staying loyal to a brand and product even when the world changes around you (for example, I will not give up my small iPhone SE with a haptic fingerprint button for a giant monster of a phone that uses my face as a sign-in no matter how much you tell me that it’s better) can be both a great thing for the company that makes that product—and that is the end goal of most producers—to get us, as consumers, to stay loyal to their brand, their services, and their products even when other competitors come to play in the same arena, and also a negative thing (as is the case of me and Apple) when they want you to stay loyal to the brand, but upgrade the product over and over again to continue the revenue cycle.

When we translate the concept of loyalty to the internal operational workings of our company, there are also good things (this thing is working—keep going!!) and warning signs to heed. When we apply that concept to our products and services, we can often become entrenched in the ways of “how we’ve always done things” even when the world has changed around us and the product or service could be improved to match those changes. What got us here doesn’t always lead us forward and stagnation often occurs when we stay loyal to ideas over staying curious and in the mindset of continuous improvement.

And further still, when we apply the concept of loyalty to the people side of the business, the scales of positive and negative tip quickly to the negative and stay there. When a CEO says to me: “I expect loyalty from my employees,” the internal business mapping that I’m doing in my brain during the conversation places a flag right on that statement and the inevitable follow up questions are triggered: “How do you understand loyalty? What is your expectation around how your employees show loyalty to you and/or your company? How are you showing them loyalty in exchange? How else can you think about your relationship with your employees?” Because the truth of the matter is, the power imbalance around people-related loyalty is often under-considered by the employer, and ultimately favors the employer, so to expect unwavering loyalty from your employees is ultimately an unfair ask.

Companies ask their employees for time, skills, experience, and attention, and yet, in the matter of minutes or hours, they will cut the same employee’s hours or position to meet a financial metric for shareholders or investors. The loyalty is often completely one-sided, and not to the employee’s favor. Let’s be clear: employees generally believe in the work they are doing, and they want to be loyal to their employers, and reap the benefits from consistent employment and career-advancing opportunities from being known. And generally, employers want to do right by their employees and are not making big decisions about positions and people lightly. But more often than not, employees become pawns in the feudal game, and the promise of protection, thriving, and bounty disappears in a quick minute when the company decides it does.

(Of course, there are good leaders who have to make hard choices in tough economies, like this one, about reductions-in-force and separations and reduced hours, and it can be personally and professionally painful to have to make those decisions out of our own loyalty to our teams and people. But the fact that macro conditions are affecting the business and forcing hard decisions doesn’t negate the fact that the micro impact of those decisions are that the power imbalance remains strongly in the hand of the business, not the employee.)

So loyalty, while often expected unreservedly, should be a cautious ask in every business case, especially when it comes to the employee/employer relationship. It is always in the best interest of the employee to temper their loyalty to the company, and do what is best for them personally, because the business will always do what is best for the business. Even when our business relationships and commitments are personal, and the relationships and the love for your work and your company are real, it’s business, and it’s important to remember that on all sides. Tom Hanks’ character Joe Fox says in the movie “You’ve Got Mail,”: “it’s not personal, it’s business.” Meg Ryan’s character Kathleen Kelly retorts: “All that means is it wasn’t personal to you. It was personal to me. It was personal to a lot of people.” And therein lies the problem. Sometimes, a business relationship and its expectations can be both business and personal, especially as a startup or small business with a small team. But as a company founder, owner, or leader—don’t ask for an outsized expectation of loyalty and personal commitment from your employees or teams when you and your business can’t provide it in return, because if and when the power imbalance around loyalty rears its head, it can become very personal, and very messy, very quickly.

It is always worthwhile for good business owners, founders, and leaders to recognize this fact and understand employee business loyalty for what it can be in its most positive state—a conscious choice for the employee to align themselves, their values, and their skills with this company’s products, offerings, and success—and recognize that may change over time for people and they may choose to move on, and that’s ok, the business can continue to succeed and grow in new directions with new people and ideas on board, and that is often what good businesses need to continue to grow and adapt.

Being a good leader means wanting the best for your people, wherever and whenever that may be—even outside of your company—while also holding your responsibilities to the business as your priority, not theirs. Be careful to hold the concept of people and business loyalty loosely and choose gratitude for those who are in the trenches with you now. Gratitude is a healthier place to start, and it will help you to be in the best place to make better business decisions, while enjoying the shared contributions of all who choose to join you for this moment in time.

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Tracy Cupper Tracy Cupper

Take Out the Garbage: Avoid Leadership Bypassing

If you’re moving toward a leadership position, new to a leadership position, or if you find yourself in a functional dead-space in middle management, here’s a tip: one of your primary responsibilities leading a team is to deal with the hard stuff that your team has bubbling up before it gets to the higher levels of leadership!

This is not a revolutionary concept, but it’s still fairly common in more ineffective leadership environments to see team leaders and managers do a pass-through with difficult issues. An example of what this can look like: my team member has an angry customer due to a mistake on the company’s part, and instead of handling it, I log it, absolve myself of the responsibility to address it, and hand it up directly to my own manager or leader to address or solve. We do this reflexively—most of us are not built for conflict and we don’t enjoy hearing people (either customers or employees) yell at us for a mistake someone else in our company made, so we think to ourselves, “this is above my pay grade, I’m sending this up for them to deal with.”

But the better response in this situation is to pause and remember: one of the primary responsibilities of a team leader is to address issues and prevent them from going up the chain of command to the next leader if at all possible...

If you’re moving toward a leadership position, new to a leadership position, or if you find yourself in a functional dead-space in middle management, here’s a tip: one of your primary responsibilities leading a team is to deal with the hard stuff that your team has bubbling up before it gets to the higher levels of leadership!

This is not a revolutionary concept, but it’s still fairly common in more ineffective leadership environments to see team leaders and managers do a pass-through with difficult issues. An example of what this can look like: my team member has an angry customer due to a mistake on the company’s part, and instead of handling it, I log it, absolve myself of the responsibility to address it, and hand it up directly to my own manager or leader to address or solve. We do this reflexively—most of us are not built for conflict and we don’t enjoy hearing people (either customers or employees) yell at us for a mistake someone else in our company made, so we think to ourselves, “this is above my pay grade, I’m sending this up for them to deal with.”

But the better response in this situation is to pause and remember: one of the primary responsibilities of a team leader is to address issues and prevent them from going up the chain of command to the next leader if at all possible (there are obvious exceptions for legal, HR, and insurance-related issues that need to be escalated immediately to those departments, follow up immediately with your own manager if you have questions about if the issue falls into those categories). When you are a team leader, your responsibility is to lead. And that means dealing with the hard stuff head-on. It’s not fun, and it can be hard work. But it’s important for your team to know that you have their back and can do the hard things when necessary. It’s important for YOU to know that you absolutely have the capability of doing the hard things, and that’s why you’re the team leader! And it’s important for your manager to know that you can handle things, and keep additional work off of their plate so that they can focus on other parts of the business and their own work responsibilities.

Let me be clear: you absolutely should let your own manager know about the issue and what you did to address it—communication is always important to be able to prevent a similar situation in the future—but leading means that you do your best to resolve it in whatever way you have the power to do so, and pass along only what is necessary for process improvement and anything outside of your own ability to solve (and the exceptions listed above).

Flexing the muscles of problem-solving, de-escalation, and advocating for your team are important leadership traits and will only get stronger the more you use them. While it can be tempting to do the quick bypass of sending the harder things uphill, you will be a more effective leader and your career potential will be higher if you implement all these tactics regularly in your leadership role. Remember that you are capable and resourceful and you have the ability to develop, build, and use the skills to effectively handle the hard things in business!

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Tracy Cupper Tracy Cupper

The Curiosity Mindset

We live in a society that thrives on judgment. The explosion of reality television and the social media algorithmic curation have worked together to curate a culture that marinates us all in judgment. Snarky comments about the Housewives of [insert big city name here] is our currency, perusing other people’s fashion choices or vacation choices spawned the very concept of “influencing,” designed to sell lifestyles or products or both leveraging the weight of that currency. None of this is new, of course, the pages of Seventeen magazine told me many moons ago that I needed this look or this product to be beautiful or to fit in or to be considered “normal.” The internet just took this concept and blew it up so that our lives are constantly surrounded by comparisons, and our fears and anxieties around our own societal standing and competence have been weaponized in an effort for others to gain wealth and power and status.

Too often, we turn that judgment inward toward our own behaviors, “I shouldn’t do this,” or “this is the bar others have set, I need to outperform it.” We assign weights in our mind to things, and we need to constantly work to keep the scales even or in our favor, to be caught on the losing end means that all the work that we are doing is all for naught, and that is demoralizing and anxiety-producing.

So it is a monumental task, then, to attempt to stop the runaway train of our judgment and reactions based in fear and anxiety in terms of how we measure up, and instead work to replace those thoughts with the simple concept of curiosity.

We live in a society that thrives on judgment. The explosion of reality television and the social media algorithmic curation have worked together to curate a culture that marinates us all in judgment. Snarky comments about the Housewives of [insert big city name here] is our currency, perusing other people’s fashion choices or vacation choices spawned the very concept of “influencing,” designed to sell lifestyles or products or both leveraging the weight of that currency. None of this is new, of course, the pages of Seventeen magazine told me many moons ago that I needed this look or this product to be beautiful or to fit in or to be considered “normal.” The internet just took this concept and blew it up so that our lives are constantly surrounded by comparisons, and our fears and anxieties around our own societal standing and competence have been weaponized in an effort for others to gain wealth and power and status.

Too often, we turn that judgment inward toward our own behaviors, “I shouldn’t do this,” or “this is the bar others have set, I need to outperform it.” We assign weights in our mind to things, and we need to constantly work to keep the scales even or in our favor, to be caught on the losing end means that all the work that we are doing is all for naught, and that is demoralizing and anxiety-producing.

So it is a monumental task, then, to attempt to stop the runaway train of our judgment and reactions based in fear and anxiety in terms of how we measure up, and instead work to replace those thoughts with the simple concept of curiosity. It is a big ask for my brain to switch from “Ugh, that person got to travel there, I’m so jealous,” or “that person has my dream house, and my little apartment is so small,” or “I can’t believe that person got that promotion, I work so much harder than they do” to observe my own reaction of anxiety and sadness about not having those things and ask instead, “Why do I feel like I should have those things?” “Do I need that to be happy?” “What is this comparison telling me about what I value?” “What would I have to give up to get those things?” “Which life do I want more?” “What do I have to be grateful for that others might be jealous of” “What goals do I have for where I want to go next and does this thing fit?”

The tricky thing about curiosity is it has to sit side-by-side with humility in order to fully engage. If I’m making a judgment call about someone else’s choices and reflecting them against my own, I am inwardly attaching a value to mine and theirs, and this can be both frustrating and a trap (we all know that what we see on TV and on social media has been curated directly to get us to consume more in order to measure up to some standard), and that trap can be carry a certain kind of defensiveness and/or arrogance: “my decisions are better than yours,” “My choices are the right choices.” But to choose curiosity, we have to suppress those desires to justify our own actions and defend our turf, and work to have a genuine interest in how and why others choose things for themselves and their own paths and goals and how they may or may not impact our own decisions and choices.

Asking the right questions, with a curious and open mind, can take us from what we see and the bars that others have set, into a space that is more unlimited—our own potential for change, and tuning in to our own values and goals. This sets our path, personally or professionally, on a direction that will take us to where we want to go. So next time you want to jump to judgment or feel inferior to someone else’s path, stop, observe, and choose openness and curiosity, and you might find the quiet voice inside you leads you forward in your unique path to success.

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Tracy Cupper Tracy Cupper

A Wild Heart and Brass Knuckles

On a recent trip to Washington State, I was at a farmer’s market and stumbled across a stand from The Sherwood Press with embossed postcards and letterpress signs with heartfelt and cheeky sayings. I instantly fell in love with one that said, “Show up with a wild heart and brass knuckles,” and it now lives in a prominent spot in my house. I look at it often, and am reminded about how personal, professional and business growth comes from showing up in the world with both sides of that mantra.

On a recent trip to Washington State, I was at a farmer’s market and stumbled across a stand from The Sherwood Press with embossed postcards and letterpress signs with heartfelt and cheeky sayings. I instantly fell in love with one that said, “Show up with a wild heart and brass knuckles,” and it now lives in a prominent spot in my house. I look at it often, and am reminded about how personal, professional and business growth comes from showing up in the world with both sides of that mantra.

Showing up with a wild and open heart is not easy. Vulnerability in a world that is not great at taking care of delicate things is scary and can be painful, and we learn that lesson early in life. And so we toughen up, and our hearts harden and tame and figure out how to stay in a protective place where we don’t get hurt as often, and where the disappointment can be managed reasonably. But we lose something in the process. A wild heart is open, allowing space for curiosity, for connection, for goals and dreams, for hope and optimism, and for exploration. A wild and open heart allows us to tune in to the heartbeats of our own needs, and for tuning into the needs of and connection with others. There is much risk to be found by having a wild heart, by choosing to consciously open yourself up to feeling the feelings of life. It can be hard to make that choice, and it can be hard to stay there once chosen.

The brass knuckles, on the other hand. We’re better at those, we learn defensive strategies early. Once we learn about the difficulties of life, about inequities, about injustice, and that life isn’t fair, we put those brass knuckles on (figuratively for most of us, but this is a judgment-free zone!) to navigate through the world. Sometimes, admittedly, it can be hard for us to fight for ourselves, and we wonder if it’s worth the effort to stand up for ourselves in the world, but we know that we should fight, so we put on a bravado (sometimes it’s fake, sometimes it’s real) to make our way through a world full of thorns and setbacks—we’re always ready for a good fight. The “brass knuckles” of confidence and toughness give us an edge, a strength, and the ability to swing when we need to swing to protect ourselves and others, to take bigger risks than we would normally.

Success and growth require both mindsets working together. You can’t grow unless you open up the vulnerable parts of you or your business to expose them to the light. Ignoring what you need to do, continuing on the same path, won’t move you forward from where you are today. You’ll continue to make the same choices and the same mistakes without being vulnerable and open to introspection, exploration, and possibilities, and without truly working to understand you and others around you. And once you do the vulnerable work, you will need the toughness to make the changes you need to make, to be ruthless in the pursuit of growth, to be better than you are today. You’ll need to dive in, clearing the thorny parts, to get to the clear place to plant the new things. You will need to believe in yourself and take the uncomfortable risks and swing to protect yourself and your business and your growth.

So this week, show up with a both wild heart and brass knuckles, to become the best version of yourself—holding them both in balance can be a challenge, but you’ve got this!

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Tracy Cupper Tracy Cupper

Mind The Gap

Recently, I was filling out a renewal form and I was updating my employment status as part of the form, as the website had my previous job listed from my previous application. When I put in the dates that I left my last position, and then my current status and when I started this company, the screen flashed up a red flag and a red-lettered banner that said, “There can be no gaps in employment.”

First of all, stop yelling at me, website! Secondly, I literally paused in the moment and contemplated that statement in red: THERE CAN BE NO GAPS IN EMPLOYMENT. What an inadvertent peek into how we as a society think about work.

Recently, I was filling out a renewal form and I was updating my employment status as part of the form, as the website had my previous job listed from my previous application. When I put in the dates that I left my last position, and then my current status and when I started this company, the screen flashed up a red flag and a red-lettered banner that said, “There can be no gaps in employment.”

First of all, stop yelling at me, website! Secondly, I literally paused in the moment and contemplated that statement in red: THERE CAN BE NO GAPS IN EMPLOYMENT. What an inadvertent peek into how we as a society think about work.

As a former VP of People, I am well aware of the recruiter mindset around employment gaps that pervades corporate hiring: “Why is there a gap on your resume?” “Can you explain this gap between jobs?” I’ve always hated those questions and have followed my own rule to never ask them as part of the hiring processes I ran. Because there is a question there, but also maybe an assumption or several. “Did you get fired or laid off and you were unhireable?” “Did you prioritize something outside of work that would make you less committed to this job than we want you to be?” “Are you going to take months off of this job for a family or personal reason, too?” None of these should matter in determining whether the candidate is a fit for the role that you have open and whether they can do the job, and all of the answers to the “gap in resume” questions are irrelevant (and often illegal!) factors to consider in a hiring decision, which is why I don’t ask. So why are so many others asking them? Because we have a hard time, as a society, accounting for the reality of an employment gap for anyone. Our purpose as we understand it is to go from birth to school, from school to work, from work at this job to work at another (hopefully better) job, from work to retirement, and from retirement to the end of our lives. No gaps to mind in there!

But the reality is, there are often gaps in employment, for most/all of us that consider ourselves at a “working” point in our life. Some planned, some unplanned, some emergent, some bucket-list checking. Some are within the larger confines of the dates you are employed at a position (family leave, bereavement, leaves of absence, sabbaticals, PTO, etc.), and some are noted only as a space between dates on a resume (layoffs, terminations, resignations, unemployment, planned time between roles, working on a side hustle, starting your own business, writing your first novel, learning to surf in Australia, learning a craft or skill, going to school, so many reasons!). But whatever the reason, the gap is allowed or encouraged or acceptable—even if a website yells at you sometimes when you fill out your forms.

Because it turns out that there is a secret, that maybe those “gap year” teenagers who postponed college discovered long before some of us did. That being in the gap, for whatever reason you are there, can give us more clarity than being in the everyday grind of employment. Many of us have never had the luxury of taking the time to step back and evaluate if we are spending our time the way we want to be spending it. And, obviously, most of us have to worry about putting food on our table and paying our rent or mortgage or having health insurance and we don’t have the luxury of contemplating the meaning of life while looking frantically for the next role, so, to be clear, I’m not inserting a fairy tale into a crisis here. Your priority is to take care of yourself and your people in the best way you can, and please do that!

But I’m also saying that taking a second to pause and reflect on what is possible and what life looks like doing things differently can be a healthy hesitation, even if taking that time is on a weekend or after work or daydreaming during your lunch break. Our most valuable and limited commodity is time. What do you want to be doing with yours? Sometimes taking a minute or an hour or a month or 6 months or a year (whatever is possible for you) to ask that question can change everything. Mind that gap by being present and observing and evaluating, even if just for a minute, and reset what you can when you can.

There can and will be gaps in employment, no matter what that website says. Use them wisely!

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Tracy Cupper Tracy Cupper

Connect To Level Up Your Leadership

A few years ago, Forbes posted an article titled, “New Research: Women More Effective Than Men in All Leadership Measures.” The article mentions several ways that women score higher on important leadership measures than men do, and then proceeds to discuss the fact that the hiring and promotion pipelines for women leaders are significantly less populated than those of men in leadership, and how companies can build more effective pipelines to foster women in leadership roles all the way up to the C-suite. It’s an interesting read, and will either bear out your confirmation bias or argue against it—feel free to engage as you’d like!

Stepping back from the topic of gender while reading the article, you see one thing standing out—the key advantages of women in leadership that they define are all around one larger topic—connection.

A few years ago, Forbes posted an article titled, “New Research: Women More Effective Than Men in All Leadership Measures.” The article mentions several ways that women score higher on important leadership measures than men do, and then proceeds to discuss the fact that the hiring and promotion pipelines for women leaders are significantly less populated than those of men in leadership, and how companies can build more effective pipelines to foster women in leadership roles all the way up to the C-suite. It’s an interesting read, and will either bear out your confirmation bias or argue against it—feel free to engage as you’d like!

Stepping back from the topic of gender while reading the article, you see one thing standing out—the key advantages of women in leadership that they define are all around one larger topic—connection. The article defines these advantages as including, “Women leaders score significantly higher in their capability to ‘connect and relate to others,’” and “Female leaders more often lead from a ‘playing to win’ orientation—focusing on their natural curiosities about what matters most to the future they are creating and partnering with others to move toward that vision,” and “Women build and cultivate stronger connections.”

S0…women leaders are “good at leadership” by connecting with others—specifically using partnerships, relationships, and emotional intelligence to advance the company and leadership goals by connecting with and engaging people around those goals. That is good data for everyone in leadership, not just women. Because while women might be “better” at these things from an evolutionary, biological, or societal-systems standpoint, leaders from all genders are capable of excelling in these areas. We have (hopefully) all worked with great leaders of various genders who were great at seeing their teams as human beings, connecting with them, motivating them and leading them to shared accomplishments that lifted all the boats in the proverbial harbor.

And, of course, we’ve probably all worked with leaders of various genders that were terrible leaders, incapable of projecting a shared vision, content to never acknowledge anyone else, only concerned about their individual power, performance, and metrics, and unconcerned about others in their sphere, never showing collaboration, connection, or emotional intelligence, yet still finding their way to the leadership chair through some systemic or personal feat.

A takeaway from that Forbes article about women in leadership, then, can be that we should develop more effective pipelines to elevate women into leadership roles (in my personal opinion—yes, we should definitely do this for so many reasons!).

But another takeaway can also be that anyone can be a great leader, if they actively cultivate the tools to become a great leader, and if they genuinely care about and connect with the people they are leading. When we choose to lead from a place of shared vision, humanity, curiosity, humility, and respect, great leadership naturally occurs, and everyone—of all genders—is better for it.

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Tracy Cupper Tracy Cupper

Pop The Bubble on Early-Stage Startup HIring

I was on a business expert panel a few years ago speaking to an MBA class at a local university. The topic was startups and business impact, a topic I am very passionate about, so I was happy to be a participant on the panel and talking to the next generation of business leaders about the potential for businesses to change the world for the better. I was seated on the panel next to two startup chief executives, one of which was asked about hiring for startups, specifically how to hire the founding team, the leaders that will create the business from the ground up. The male executive next to me responded that startups “typically have to hire already very successful experienced tech employees or financially independent young men” to join their founding teams initially, because “those are the only people who can afford to take the market rate pay cut with equity options that early-stage startups provide in terms of compensation.” He went on to explain that women and older men with families and successful established careers were less likely to take the high risk of joining a new startup because they had more at stake in terms of losing family incomes and already established earning paths.

I managed (barely) to keep myself from jumping out of my seat next to him. I responded when he was finished with, “I’d like to challenge that assumption by saying this:…

I was on a business expert panel a few years ago speaking to an MBA class at a local university. The topic was startups and business impact, a topic I am very passionate about, so I was happy to be a participant on the panel and talking to the next generation of business leaders about the potential for businesses to change the world for the better. I was seated on the panel next to two startup chief executives, one of which was asked about hiring for startups, specifically how to hire the founding team, the leaders that will create the business from the ground up. The male executive next to me responded that startups “typically have to hire already very successful experienced tech employees or financially independent young men” to join their founding teams initially, because “those are the only people who can afford to take the market rate pay cut with equity options that early-stage startups provide in terms of compensation.” He went on to explain that women and older men with families and successful established careers were less likely to take the high risk of joining a new startup because they had more at stake in terms of losing family incomes and already established earning paths.

I managed (barely) to keep myself from jumping out of my seat next to him. I responded when he was finished with, “I’d like to challenge that assumption by saying this: there is a wide world of business out there. There are people out there today who are absolute superstars, working in places that you haven’t even considered. They’re working hard running non-profits, retail stores, teaching, providing healthcare, working in social work, doing all sorts of different work. There are people in each of these areas, and many more, that are absolutely brilliant leaders, intelligent strategists, fantastic teammates and individual contributors, and they are working for a salary every day that is much less than your founding team will be making. You haven’t even considered that to take a startup founding salary would be a pay INCREASE for some of them, with huge potential upside..and even if it isn’t, these smart people might want to pivot or take the risk to do something completely new to them, and your business might hugely benefit from the different perspectives that they bring to the table. We have GOT TO START being more creative about who we hire, there is a whole world full of fantastic candidates outside of the tech/startup hiring bubble.”

I was fired up, and the executive, of course, agreed with me, he obviously did not mean to offend or dismiss other types of candidates, but it was a reminder to me that tech/startups can be an insular bubble, used to the way of doing things that they have always done them, and that has typically favored a certain type of founder/early-stage startup hire. It is fairly obvious that we do ourselves a huge disservice when we only open our hiring pool to people who look or act like us, or make assumptions about who will be the right candidate for this job based on where they went to college, which startups they have already worked for, who they know in the VC world, what their financial status is, how old they are, and/or how much risk they’re potentially willing to take based on our own internal calculations. It seems cliché to say that diversity is the key to a successful business (it is, look it up, it’s a business success no-brainer to be as diverse as possible), but whew, sometimes it seems like our implicit biases, bubbles, and staid hiring processes stand in the way of all of that.

I’m biased about this topic, obviously, because I am a social worker who became a successful tech executive. I like to think my way of looking at the world from outside the tech bubble allowed the company that I worked for to thrive in the business we created to serve different types of employees and clients, who also saw the world from outside the tech bubble. I am incredibly grateful to those founders that I was given the opportunity to make that leap from one career to another and become part of a great founding team, and the space to prove that I also belonged there and could thrive and succeed in the startup environment. But deep down, I already knew when I was working every day as a social worker that I could excel in the startup world or any other, I had all the skills, instinct and talents I needed to be a great leader and executive, I just needed the opportunity to show that, and when I was given the opportunity, I did.

So, founders, leadership teams, hiring managers: when you’re building your founding team or your early-stage leadership team, please, please, please widen the aperture of your hiring lens, you’ll get to see things you never thought you could, and your business will be better for it!

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Tracy Cupper Tracy Cupper

This Is All A Lot

When the clock struck 12:01am on January 1 of this year, you likely had an idea about how you wanted the year to go. Whether you were awake and cheering in a New Year, or you were sleeping soundly in a quiet slumber, you had a plan for what you’d like to accomplish. Formally or informally, we often mark the turning of a year (or maybe you use another tracking point—daily, monthly, etc.) with our goals, dreams and wishes for how we’d like to use the time to achieve forward momentum for our life in some way. “I want to eat healthier,” or “I’m going to read more,” or “I want to be a VP by this time next year.” Having defined goals is our way of giving structure to the desires of being “better” in some way. What do you want? How are you going to get there? Start here, start today, start now, and make a plan.

Nothing about that process is a bad thing. In fact, creating a vision and a plan and working your plan is the best way to achieve your set goal, it gives us focus in a world that is extremely distracting, and one of the best parts of my job is helping you create those goals and plans and helping you achieve them, for yourself and your business.

But I’ve been thinking about how we make our plans in a best-case-scenario bubble, not knowing what things will come along to either support us or knock us off course. The old Yiddish proverb, “We make plans and God laughs,” rings true, more often than not. Did we know that the world would look like this today at the beginning of this year? Nope. Waking up today looks different than we expected, in so many ways...

When the clock struck 12:01am on January 1 of this year, you likely had an idea about how you wanted the year to go. Whether you were awake and cheering in a New Year, or you were sleeping soundly in a quiet slumber, you had a plan for what you’d like to accomplish. Formally or informally, we often mark the turning of a year (or maybe you use another tracking point—daily, monthly, etc.) with our goals, dreams and wishes for how we’d like to use the time to achieve forward momentum for our life in some way. “I want to eat healthier,” or “I’m going to read more,” or “I want to be a VP by this time next year.” Having defined goals is our way of giving structure to the desires of being “better” in some way. What do you want? How are you going to get there? Start here, start today, start now, and make a plan.

Nothing about that process is a bad thing. In fact, creating a vision and a plan and working your plan is the best way to achieve your set goal, it gives us focus in a world that is extremely distracting, and one of the best parts of my job is helping you create those goals and plans and helping you achieve them, for yourself and your business.

But I’ve been thinking about how we make our plans in a best-case-scenario bubble, not knowing what things will come along to either support us or knock us off course. The old Yiddish proverb, “We make plans and God laughs,” rings true, more often than not. Did we know that the world would look like this today at the beginning of this year? Nope. Waking up today looks different than we expected, in so many ways.

THIS (::gestures wildly at the city, country, world, internet culture, business culture, economy, etc. we are currently inhabiting::) is all a LOT right now. We are currently at a fever pitch of chaos, of change, of disruption. Some of it will lead to progress forward and new ways of living and working together. Some of it will lead us down a darker path, of conflict, of distraction, of societal shifts, away from connection and humanity.

So—here we are. Trying to exist, move forward, find momentum and our niche in a chaotic world. You didn’t know what today would look like when you created your vision, your goals or your plans for this time, and much of this is out of your control. But don’t underestimate the power of you in this moment—you hold the power for change. You can and should still set goals, decide on a path of action, and move forward. You can choose the path forward for you, your business, your career, your family. Start today. Or tomorrow. But definitely start!

The stories are strong around us for a reason. We turn to myths and heroes and legends because time and circumstance are cyclical, we have been here before in time, and we will be here again, and every time, there have been those who have moved us forward out of chaos and into light, up the spiral staircase into progress, so it looks just a little different the next time we find ourselves in a similar place. We can make those choices, too, and become our own version of a legend or a hero, even if just for ourselves and our lives and our personal and professional communities.

If you want help, I’m here to help—to listen, to support, to encourage, and to strategize how to move forward from here toward your goals and visions. Putting one foot in front of the other can sometimes be easier with others than alone, but you can do it however you’d like, and I believe at my core that even though This Is All A Lot—YOU are powerful and capable and I can’t wait to see how you shine in this moment, and how we move the world forward in our own ways right now. I’ll see you on the spiral staircase!

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Tracy Cupper Tracy Cupper

How a Vacation and a Tiny Pack of Earplugs Changed My WorK Life

I was a on a beach vacation a few years ago, trying to unplug from my very busy work schedule. I was the epitome of the cliché of the early stage startup executive—I was working too hard and too much and not sleeping at all, trying to manage my work responsibilities and the relentlessness of what felt like “being needed all the time by everyone.” I work fast, but the work came in faster, the emails never stopped, and my Type A self was driven to new levels of stress, high blood pressure, and teeth grinding in my sleep, trying to be responsive and helpful to everyone and everything coming at me every day (and trying to keep my email inbox at zero!) and mostly succeeding but sometimes failing miserably, enough to make me keep trying harder.

I was a on a beach vacation a few years ago, trying to unplug from my very busy work schedule. I was the epitome of the cliché of the early stage startup executive—I was working too hard and too much and not sleeping at all, trying to manage my work responsibilities and the relentlessness of what felt like “being needed all the time by everyone.” I work fast, but the work came in faster, the emails never stopped, and my Type A self was driven to new levels of stress, high blood pressure, and teeth grinding in my sleep, trying to be responsive and helpful to everyone and everything coming at me every day (and trying to keep my email inbox at zero!) and mostly succeeding but sometimes failing miserably, enough to make me keep trying harder.

So there I was, on vacation trying to insert some equilibrium back into my life, and I was annoyed and cursing under my breath in my beach chair because I was trying to lay quietly in the sun, trying to listen to the waves crashing on the beach, so I could finally relax, and I kept hearing the conversations of the people walking by my chair instead. I have never been the type of person who can tune out other people well, I have been a people-pleaser all my life, and so I am usually attuned to the wants/needs of others before myself (though now this is something I am very actively working on!). But this particular day, I wanted to rest! And kept getting interrupted! And so I grumbled to my spouse under my breath about how annoyed I was that I couldn’t relax with all these people around me talking. And lo and behold, like the king of self-care, he reached into his bag and held up a new packet of earplugs. “Want these?” he said. “I guess.” I said, begrudgingly putting them in, blocking out both the conversations and the sound of the waves almost instantly. Within 10 minutes, I was asleep on my beach chair, napping peacefully in the sun (with copious amounts of high SPF sunscreen on and under a towel and an umbrella, I am a redhead, after all!).

When I woke up rested, I realized what had happened and said to my spouse, “I need earplugs for work.” What I meant—”I need a way to turn off the noise and the relentlessness of being “needed” all the time.” I needed to stop letting the work control me and start controlling the work.

And so, when I got home from vacation, I stared at my email inbox and my calendar and I made two very big changes. 1) I blocked 3 slots on my daily work calendar for email. 45-60 minutes each. One first thing in the morning, one late morning/ early afternoon, one end of day. I started only checking my email during these time slots, instead of having it on a tab open all day (and then responding all day). It turns out by giving emails certain time blocks, I was more focused on them and able to handle them more effectively, efficiently and more easily, and handled them all within those time blocks every day. It also meant that I was able to tune in to my meetings, calls, and work tasks more fully, and with far less distraction without that email tab dinging upwards all the time and distracting me as I tried to respond and pay attention to the meeting at the same time. 2) I started using the true concepts of inbox-zero to maintain control of my inbox. I would delete emails that were unnecessary/spam immediately, I would delegate emails through forwarding that weren’t my direct responsibility, I would defer it to another day or time frame using the SNOOZE EMAIL feature (the ACTUAL BEST THING for Type-A zero inboxers!), or address it/respond/do the task immediately until they were all cleared out. (For real though, use your snooze email button. It allows you to decide which things you have to do/emails you have to address by the end of today, and which ones can wait to act as a reminder to you until just before that meeting next Tuesday, etc. You’ll start to notice that you have email days that are heavier and redirect some of those less-urgent emails to your lighter email days. It’s a version of kicking the can down the road that is professionally helpful—it actually allows you to focus on the present—what is required TODAY by end of day? Do that thing. The rest can wait! I know this is so hard to believe, but try it with some lower-stakes emails and you’ll see how much it can help clear out your email inbox and get things in order and then you can feel more comfortable expanding to other emails!).

By changing these two ways of interacting with my email inbox, I changed my work patterns, and even I was surprised by how effective it was in giving me back my attention and lowering my stress levels. I essentially put “earplugs” on with regard to my email so I couldn’t be distracted by responding to it all day every day, and could focus/take care of what I needed to take care of today. And ended up taking better care of myself in the process.

Lessons of this story: 1) take your vacations, they allow you to step away and think differently about your work, and 2) putting boundaries around your email (or any other repetitive work tasks) will put you more in charge of your work, instead of your work being in charge of you. Try it!

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Tracy Cupper Tracy Cupper

The Motivation For Change

Change begins with awareness. It is easy to be unaware of our internal thoughts in our very busy world, we are surrounded by constant noise, conflict, and busyness distracting us. But in the quiet moments—right before we fall asleep, when we turn off the podcast, when we’re sitting in the car—we occasionally tune in to ourselves, to the thoughts swirling around in our consciousness. And there it is: the friction that we experience when there is space between where we are and where we want to be.

Change begins with awareness. It is easy to be unaware of our internal thoughts in our very busy world, we are surrounded by constant noise, conflict, and busyness distracting us. But in the quiet moments—right before we fall asleep, when we turn off the podcast, when we’re sitting in the car—we occasionally tune in to ourselves, to the thoughts swirling around in our consciousness. And there it is: the friction that we experience when there is space between where we are and where we want to be.

Sometimes, that awareness is personal—we want a nicer house or a better neighborhood, we want a partner with different qualities (or to be blissfully left alone!), we want our family life to be easier. Sometimes, it’s professional—we want a higher salary, a better position, more responsibility (or less!), recognition. Sometimes, it’s business—we want more clients, more revenue, better processes for our company.

The awareness of these thoughts makes you feel like you can’t settle. Something is out of your reach, and it causes you to become aware of the space in between.

We don’t like feeling that gap, it’s uncomfortable to realize that there is a delta between here and there. But that space is the key to your success! The awareness of that delta is the trigger that motivates us to change. Once we become aware of it, an unconscious process starts to churn—and we become restless. We start thinking about how things could be different if they changed. We start to assess the cost of not changing. We start to hope and to explore our options. And the churn becomes louder and more uncomfortable until it reaches a peak, and then—we decide to make a change.

It’s always a choice to make change, but we often make that choice because the cost of staying the same and being uncomfortable in the gap is too much for us to bear. Deciding to make the change is the “easy” part, the actual process of making change is the hard part, of course. But today, amidst the noise of your busy life, I want to challenge you to just spend some time finding the quiet and your internal thoughts, thinking about where that restlessness is percolating just under the surface. Those thoughts and feelings are worth paying attention to, they are calling you to a change for the better!

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