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, so 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.

Compliments for 100 Dollars

I walk past a middle school at lunch every day. Most days we all just carry on with our own work (mine: dog walking, theirs: game playing), but today was different.

As I walked by the school yard, one of the kids kicked a ball over the fence and across the street. She asked if I would throw it back over, apologizing a lot as she did. It’s no real burden for me, so I retrieved it and threw it back over.

Another student asked if I could help retrieve a second ball, and then a third (there wasn’t a fourth). Again, not a problem, so I returned those balls as well. And then he said this:

“You’re so generous! Thank you! If I could pay you $100 I would, but I don’t have any money. Your dog is beautiful and healthy. Have a good day!”

Now, I can’t be sure of what drove him to have that little interaction with me. But I would like to imagine it’s a mixture of these things:

  1. Having a very high valuation of time.
  2. Having a very low valuation of a dollar.
  3. Having an innate sense for the existence of reciprocity.

Which then led him to decide that, knowing that he needed to pay for the use of my expensive time, a compliment to my dog was worth $100.

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.

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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.

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