Making Hard Decisions Easier

Over the course of my career, especially as I was learning to lead, I made a lot of mistakes. Most turned out fine in the end, but basically all of them required me to go and find an adult. And as I became more proficient as a leader, there were two truths that used to shock me a lot:

  1. I am the adult now. If I need help, I have to find adultier adults.
  2. At some point my mentors were also shocked to find that they were the adults.

All of my leadership skills were earned not learned, and I am here to debunk this myth for you: leaders don’t always know the answers and they aren’t always fearless. My mentors—the people who have taught me how to do this—what they had that I didn’t have was a network of advisors, and a few excellent tactics to work through inaction.

A Few Excellent Tactics

I use these tactics routinely, not as a way to hack my productivity, but as a way to ground myself in where my autonomy lies. As an added bonus, they can also help you address specific, short-term fears in a way that I have found to be truly empowering.

For When You’re Afraid
Use the 10-10-10 Rule. This can help you to identify if the thing you’re afraid of is a short-term problem. You pretend you made the decision right now, and ask yourself how you would feel 10 minutes from now, 10 weeks/months from now, and 10 months/years from now. If you’re afraid to contradict someone (10 minutes), and you know that the change will be complex (10 weeks), but you’re certain that the long-term benefits balance it all out (10 months), then you know that you can stand the discomfort of the decision.

Next Level: Check for the area of effect – are you using single use potions or spells that help all surrounding allies. If challenging a path forward will inconvenience two people, but save multiple hours of work for seven, that might be a fair trade.

For When You’re Overwhelmed
Use the Eisenhower Matrix. This can help you identify where your time is best spent. For every task that is on your plate you determine if it’s urgent or not, and whether it’s important or not. Where each tasks lands in those quadrants will tell you how you should handle them. If it’s Urgent + Important, then you should focus on completing the tasks. It’s it’s Not Urgent + Important, then you can plan for a time to do that. So on and so forth.

Next Level: The practice of identifying the differences between urgent/emergent/routine tasks can help us to find more autonomy in the decisions we make. This decision matrix can help define what you can affect change on, you can have a more proactive pattern of approaching your work (also known as circles of concern and influence).

For When There Are No Good Options
Use the Maximin Strategy. This can help you identify how to minimize the potential negative impact. When faced with nothing but bad choices, you think through who is impacted and how. Thinking through how big the negative impacts can be, can give you some way of ranking options that originally all felt less than optimal. At the very least, it will quickly clarify which options are not possible.

Next Level: If you can state clearly why you decided against any option, then it can help identify why you would say yes. It’s so often the case that there are many possible “yes”es and far fewer “no”s. Discovering one will help reveal the others.

Still stuck?

It happens. Your advisors might have some insights, but they aren’t perfect either. If you don’t know how to proceed, but you must choose something, then remember these things.

  1. Limit information gathering to what’s immediately relevant.
  2. A mistake is only as dire as the outcome that follows it.
  3. And when you do make a mistake, think of it as a lesson learned.

You can do it! Good luck!

Leadership Basics: Ethics in Communication

It’s often said that if all you have is a hammer, then everything looks like a nail. It is meant to suggest that people are always seeking confirmation for the things they already believe. And it turns out that I really believe in the use and application of good communication.

@chanthaboune once said that all problems are really communication problems. I think that is the case here.

Communication is something all living creatures do whether through written word, spoken language, sign language, or any other means. No matter how you manage to share information with others, the best leaders I’ve had are aware of a few universal basics.

The Basics of Ethical Communication*

One of the skills I share with any leader I mentor, is the need for ethics in our everyday communication. The National Communication Association has adopted a credo for ethical communication. Their credo states that “ethical communication enhances human worth and dignity by fostering truthfulness, fairness, responsibility, personal integrity, and respect for self and other.”

I hope you take the time to read it, but if you haven’t decided if it’s for you or not, I’ll give you the highlights below.

  • Be truthful and begin with understanding, then engage in civil discourse. Don’t intentionally deceive anyone, and before you disagree with someone else’s point of view, make sure you’ve made the effort to understand what they mean. If you disagree, discuss your differences in a way that doesn’t negate the inherent value of the person you’re speaking with.
  • Speak bravely in the pursuit of fairness and justice, and be clear about where you stand. If you see a way that a solution could be more equitable, speak up about it. When you have a point of view, respectfully make it clear so that others know so that we can all strive to know each other better.
  • Be aware that all communication has an effect, and strive to make that effect positive (but admit when it’s harmful). Anyone who calls communication a soft skill hasn’t experienced having to work through the difficult process of communicating harmful things with care. We have all caused people to feel and act a certain way with what we’ve expressed to them, and knowing that we have that kind of impact from the start can help us make better choices.
  • Share information around significant choices, while being respectful of privacy and confidentiality. As leaders, we should always try to inform those who are most impacted by something first. It can be a lengthy process depending on the size of your organization, and certainly takes effort to get used to. But it is a necessary part of creating psychological safety in your organization as well a fundamental responsibility you accept when you agree to lead.

tl;dr for the tl;dr

And if even that was too long, it boils down to this: Communicate with care (for your words and your people) and embrace your responsibility (for the processes and the outcomes).

*It’s important to note, as always, that no one gets these things perfect every time. It’s not about perfection over all else, it’s about being mindful and committing to trying your hardest.

The Power of Vulnerability

In 2010, Brené Brown delivered a TED talk that changed the way I understood leadership. She talked about the importance of sharing our failures, and the power of vulnerability in leadership. It’s an exceptional talk, and worth a listen if you’ve never given yourself the time.

Three of the most remarkable concepts she shared are about shame and fear of disconnection; vulnerability and courageous imperfection; and certainty in the absence of vulnerability.

So let me give you the tiniest rundown, in case you didn’t watch her talk.

  • Fear of Disconnection: Brown’s research found that the heart of shame (and hiding parts of who you are) is a fear of disconnection. You don’t want to be left out of a group, so you don’t mention the things that might make that happen. The less you talk about those things, the more you are sure they will cause people to leave you, and the more shameful you feel about them.
  • Courageous Imperfection: Her research also found that people who did not struggle with a fear of disconnection didn’t have an abundance of perfect alignment with people around them. They mostly just felt that, imperfect though they were, they were still worthy of being included. They didn’t feel comfortable or uncomfortable in the embrace of their own vulnerabilities, they had the courage to move forward anyway.
  • Absence of Vulnerability: The final life-changing concept she shared was that those who refuse to embrace imperfection strive to make everything certain. They have one way, one version of what’s right, and everyone else is just wrong and dumb. And as my mentor once said “As long as you know you’re right, you will never be able to grow.”

Being vulnerable can make us terribly sad, but it can also open us up to the possibility of being terribly happy. Because once you know that we’re all a little bit imperfect, it’s easier to let yourself be imperfect, too.

Imperfection in Leadership

Being imperfect in leadership* is one of those things that you never quite finish learning. It’s hard to commit to being able to say “I don’t know, but let’s find out” when you see people looking to you for guidance. And, to bring it completely out of hypotheticals, it’s terrifying to be an imperfect leader as a woman because some people are just waiting for you to be wrong.

In my experience, it’s best when approached as a balance. A large part of my leadership philosophy hinges on the idea that being wrong doesn’t mean you are bad, it means you are trying something new. Being wrong is the sore muscle of personal and professional growth.

For anyone who is new to this concept, it feels unsettling. And I think that’s good. If you want to try to do this anyway, I have a few pointers for you!

  1. Meet people where they are. No one ever changed their perspective by spending time with only people who are exactly like them. If you are a leader, you may find that you’re coming out ahead in power imbalances, so do what you can to seek out others.
  2. Share the foundations first. When offering plans for next steps, always come prepared to share how you got there. Letting others know that you have done some thinking, gives them the courage to ask you to think about other things as well.
  3. Don’t rush the unknown. No one likes being unsure of what to do next, but when we rush through uncertainty it can lead us to solutions that are limited in their effect on the problem. Get comfortable with growth mindsets and fearless exploration.
  4. Listen twice as much as you speak. One of the characteristics that all my favorite leaders have in common is their thirst for information. They ask questions from everyone, they comment last, and they do their best to disagree constructively.

Never Stop Learning

And for myself, I always remember that there was a time when I knew nothing — knew nothing about WordPress, or leadership, or cooking, or life — and that if I had been surrounded by conversations that stifled my curiosity I would never have become the person I am today.

I want everyone to have the chance to be their best self, and when we commit to the shared human experience of learning we can change ourselves (and others) in immeasurable ways.

* In case you’ve never heard my definition of leadership, it is pretty broad. I don’t think it’s about titles or hierarchy, I think it’s about anyone who has engaged in mentorship, anyone who is someone’s role model, and anyone whose duty of care reaches beyond themselves.

Fostering Collaboration Across Cultures

Diversity doesn’t come without tension. The key is to know how to make it into jazz and not discordant noise.

Stereotypes are shortcuts our brains use to make fast decisions (especially when there is too much information or potential unknowns). We tend to infer a lot about others based on our past experiences, whether it’s accurate to do so or not. As the world becomes more connected and our interactions more immediate, we interact with people unlike us every day without even realizing it.

Our brains, being the prediction machines that they are, take these stereotypes and form an idea of how interactions will go.

Illustration: Design vs Development

As a quick example let’s look at the work-centric, cross-cultural environment between Design and Development.

A stereotypical concept of a Designer might be that they are:

  • untidy
  • unencumbered by deadlines
  • value form over function
  • generally “right-brained”

A stereotypical concept of a Developer might be that they are:

  • fastidious
  • unencumbered by manners
  • value function over form
  • generally “left-brained”

Objections over these questionable stereotypes aside, these two groups objectively look like completely different cultures. Each have their own language or jargon that sets them apart. The etiquette of how to interact with their work is different. Humor among these two groups can be impossibly nuanced, but it ties them together.

These things act as communication barriers and can hinder a process called the Negotiation of Meaning.

Read More

Empathy vs Altruism in Modern Leadership

The concept of empathy is one that has become popular as a leadership ideal. We expect empathy from CEOs, ask designers to join empathy challenges, and tell people to put themselves in someone else’s shoes. Empathy is, at its simplest, knowing what someone else is going through. It’s often identified as a counterpart to sympathy and is seen as an important quality of modern leadership.

But setting empathy as a gold standard in leadership has its downfalls [1]. Empathetic leadership relies on personal experiences with situations that are atypical for you and assumes similar tolerance levels for discomfort. More importantly though, it assumes that experiencing something is the same as understanding.

Read More

Building a Culture of Safety

When I think back over the many communities I’ve been part of over the years — whether at work, as a volunteer, or in a church — those that were most vibrant had many things in common. They had leadership that was engaging, they had regular gatherings, and they were clear about who they served. As I’ve grown into my own concepts of leadership, I have come to recognize that one of the largest (and most hidden) things they had in common was a dedication to cultural safety. Letting people come as they are, and honoring that, was foundational to how they operated.

Safety can mean different things to different people, though, so here’s a quick overview of how I see it.

Types of Safety

  • Physical Safety – The ability to remain free from bodily harm. For my current work in the WordPress project, this mostly comes up in relation to in-person events.
  • Psychological Safety – The ability to express yourself freely. This comes up in all of the community’s communication channels, from Slack and team blogs to twitter and events.
  • Social Safety – The ability be your whole self among others. This, naturally, comes up in all of our spaces both in-person and on-line.
  • Moral Safety – The ability to reconcile your work with your morals. This comes up mostly with volunteers in WordPress.

Though I’m sure this isn’t a comprehensive list, I do feel that these four kinds of safety line right up with some basic needs of healthy modern communities: personal safety, open communication, inclusivity, and aligned values.

Read More

My Leadership Philosophy

For no fewer than three years, my twitter bio has included the statement “I’m bad at writing recipes, great at cooking the food.” When I set out to define my leadership philosophy, I didn’t realize how true that statement would be.

I’ve been guiding and advising future leaders for many years, as a mentor and overall advocate, and my advice hasn’t changed much in that time. My concept of good leadership is informed by being a woman in a male-dominated field, a person of color in a primarily white-dominated world, and a general faith in the power of a good-hearted group of people.

Read More

To All Women in Tech*

There are many “right ways” to be a woman in tech, and I hope that people have learned to welcome you with open arms. But at the same time, I worry that some women may not feel brave enough to ask if they are welcome.

I have something subversive to share with you.

I once felt that to be a woman in a male-dominated field (that’s just existing, not even excelling) you had to be as un-female as possible. I had this suspicion in the back of my mind that not allowing women to express themselves as women (but then also claiming them as part of your diverse workforce) — I had this suspicion that it was a lie.

Then I had two great chats with two great women, and I’m going to share their wisdom forever. And I’m writing it here so that you can, too.

  1. Helen 侯-Sandí and I were at a WordCamp afterparty and wearing very fancy dresses. I told her I felt self-conscious because “it was too feminine” (it wasn’t) and her response was “Women have boobs. If we want women in technology, men will have to learn that boobs** aren’t what keep people from being developers.”
  2. I told my sister I was having a heckuva time choosing the color of my laptop. I was stuck on “If I get a pink one, will anyone take me seriously?” and also “Should I be working to dignify WordPress overall” (by getting a dark grey laptop? idk). And she said to me “Anyone who will choose not to take you seriously because your laptop is pink was already not going to take you seriously. Get a pink laptop and remind them that women are leaders, too.”

That is when I saw through some distracting self-perpetuating nonsense:

  • Women, do not shame other women for being too feminine.
  • Women, do not shame other women for being too masculine.
  • Women, do not shame others for not fitting your idea of who they should be.

It’s hard enough out here trying to smash this towering patriarchy. Don’t hamstring everyone from within. Get your sister-phoenixes and get the heck ready to rise.

*Tech and medicine and any other male-dominated field out there.
**The use of the word “boobs” isn’t a vocabulary choice that you would associate with my blog, and especially not in a post labeled “leadership”. However, I felt that given Helen’s notoriety, no one would believe me if I pretended that the word choice was anything but that.

The Trouble With Following Your Passion 

As a high school student, I was regularly told to follow my passion. It’s the advice many teens are given specifically related to career aspirations, elective selection, and future college applications. Find what you’re passionate about and focus on that. It’s a trope that lines up beautifully with “love what you do and you’ll never work a day in your life”.

As I’ve progressed in my career, and taken on mentorship of those who will come after me, I’ve learned how perilous that advice can be.

Unknown Unknowns

When you receive the advice to follow your passion early in your life or your career, you have so many things you haven’t encountered yet. In my case, I was passionate about music. In part, I was passionate about it because I naturally excelled at music and I greatly disliked doing things I was bad at.

I focused intently on music with the ultimate end goal of “being famous*” since that’s what most musicians we know of are: famous. I didn’t realize that there were other parts of music that we going to be more appealing to me. Things like learning how to work in an ensemble, and how to guide an ensemble. Or the semantic language of music and its deep ties to math.

Passion Paradox

And while we’re on the subject of things we’re naturally good at, let’s talk about what makes you passionate. In order to enjoy a task, it’s important to have some level of mastery. So few people find joy in being bad at stuff (which is separate from enjoying new experiences). When we tell inexperienced people to follow their passions, we run the risk of cutting off the opportunity to grow their skills.

Consider lexicography.

This is one of those jobs that would make absolute sense for someone with a voracious love of reading, writing, and the ever-evolving nature of language. You might not suggest to any teen who loved reading that they “pursue professional reading” since there just aren’t that many job opportunities. Exposure to related work and fields is paramount to discovering those nuanced parts of what drives a passion.

Network Disadvantage

Not that this suggestion is perfect. I am aware that exposing your student to a broad spectrum of vocations isn’t possible for everyone. Take Your Child to Work Day gives them insight into your work world, which is of course helpful. Having a network that helps or encourages internships or job-shadowing is definitely a matter of privilege.

My best suggestion for broadening your knowledge without a network is to get a mentor. In my limited experience, it’s not been hard to get someone who is willing to mentor you. What is hard is being easy to mentor (and making the best use of everyone’s time).

Examined Pursuits

As with so many things, my recommendations boil down to “going in with your eyes open”. If you want to be famous, and you’ve learned all the many ways you can be in an industry without being the improbable star, yet still want to strive toward stardom then great. You have every right and you’re probably going to be amazing!

Just make sure that you take the time to know more about the entire landscape before you start.

* I have not, in case you missed it, gone on to be a famous musician. I work in technology.

Ex Officio: The Best Title You’ll Ever Take

From time to time I have the pleasure of introducing the concept of ex officio to groups I work with. It’s normally a concept reserved for non-profit boards, but I’ve found that its value goes far beyond that.

In the most basic terms, it refers to a position that participates in research, discussions, and overall analysis but has no voting power. In my experience, it’s held by former voting board members or close advisors.

“What’s this,” you say? “A board member who fights but never gets any power of voice?”

Not exactly.

As I said to my incomparable friend Helen today, I have infinite empathy, trust, and use for this type of voice in organizations.

The Strength to Move Forward

Good leaders know that one of their key responsibilities is to future-proof their organization. That means making sure you know who should take up the reigns after you, and who could take them up after that person. It means knowing that new ideas are how you stay relevant. It means knowing that having institutional knowledge isn’t the same as having visionary excellence.

There’s power in the ability to look the future of your cause (or company, or church) in the eye and say “I’ll help you remember what got us here, but it’s up to you to get us there.”

The Wisdom to Look Back

I’ve served in an ex officio capacity on a number of occasions. I bring over a decade of knowledge in non-profit service, leadership, and marketing to the table (among some other skills) and I have seen a lot of teams through growth and change. I am always delighted to offer that knowledge as a resource, without limits. A group mentor for learning leaders.

And that is the thing that always charms me most.

These learning leaders (regardless of their age) have asked you to do this so they can learn from the mistakes of others. Or so they can always have a concept of their roadmap by deciding where to go while also connecting to where they came from. Or so they don’t suffer through a solved problem.

Probably a little bit of each, if we’re honest.

The Space for Lasting Change

When you have a clear-eyed group of leaders and a selfless set of advisors, you can make more confident plans for future visions. You can forecast how a program will be received. You can gauge how long it takes your organization to embrace a new direction.

Most importantly, though, you set everything up for success and get to help train a new generation of powerful, life-changing voices.

Tips for the First-Time Ex Officio

  • Set aside the notion of “Only One Right Way” – Consider the possibility of “A Few Clearly Wrong Ways” and many ways that are basically right.
  • Present facts both positive and negative – A good resource tries to be balanced and this is no exception.
  • Don’t lobby – This isn’t the time to make carbon copies, it’s the time to uncover shared foundations. See item one.
  • Offer perspective proactively – There are so many unknowns. That’s why you’re there, to shine lights on mysterious spaces.
  • Refrain from “I told you so” – We all get it wrong sometimes. Shaming people forces inaction, not correction.
  • Practice tender discipline – Challenge people to do more than they are comfortable with, but work with what they have.