Notes

If I had to choose, I'd prefer to succeed in achieving the wrong outcome for a client than to fail in achieving the right outcome.

Wrong outcome success: Designing a landing page focused on the wrong target audience.

Ideal client response: "We appreciate all the thinking that went into this but it's not exactly what we're looking for. Maybe we weren't clear on that, let's make sure we re-calibrate so we're on the same page going forward. Once we're aligned, we're excited to see what you come back with."

Right outcome success: Designing a landing page that poorly represents the brand for the right audience.

Ideal client response: "We're beginning to worry about your ability to do this work for us. While you clearly understand our goals, you really missed the mark. We'll need to discuss feedback and get back to you on next steps."

Wrong outcome success can be turned around with a simple conversation.

With right outcome failure, we have to regain the client's trust while figuring out how to improve the work. Even with feedback, this can be a challenge, especially if we thought we hit it out of the park.

Of course, neither are desirable but we can't always count on right outcome success. We can, however, choose to put our best foot forward. If it doesn't work out, look for the lesson and apply it next time.

Every day, we instinctively brush our teeth, get dressed, eat, use the bathroom, and sleep.

These are our non-negotiables. Our training began at birth, and now every day, we make sure our practice continues. It's essential.

Then, there are the activities that align with our goals: exercise, meditation, reading, eating healthy. We try to build the habit, but when it doesn't stick, we get discouraged. We forget that every habit takes practice.

Imagine who we'd be if we treated our non-negotiables this way. Actually, don't. It's scary.

Instead, imagine who we'd be if our non-negotiables included the habits we know would do us good.

Much better.

In January, I established a new habit around my social media consumption with my iPhone's Downtime setting. Downtime allows you to "restrict" access to specific apps by time limit or time window. While it is easy to bypass the restriction, all notifications get hidden, and the app icons fade on the home screen.

I attempted using Downtime once a couple of years ago. The first time, I restricted access by a time limit. I was unsuccessful. As my time on social media varied each day, the restriction became unpredictable, making it hard to build behavior around.

Drawing on my success with intermittent fasting, I wondered if I'd have more luck setting up a daily "social media fast." Using Downtime, I applied a restriction to any social app from 8 pm to 9:30 am.

I was deliberate about the time window I selected. For one, I knew that I might want to browse Twitter after work at 6 pm. Between working out and getting dinner ready, 2 hours seemed like plenty of time to take a look. I didn't want any distractions in the morning, so I only made room for 15 minutes before the workday gets going around 9:45 am. These days, I wake up, journal, read, get dressed, make coffee, and by the time I sit down to begin my work, I haven't even thought of scrolling through social.

Today marks 99 days of practicing this new habit. It's made me see just how much social used to fill my time. I don't miss it at all, but I do enjoy the balance. It's nice to remain connected without being consumed. When I started on this pursuit, I had a slight fear that I'd miss out on something important. Months later, I've learned that if it's important enough, it finds its way to me.

I recently incorporated a series of questions in my weekly one-on-ones to generate conversation when there's not much on the agenda. A couple of weeks ago, two senior designers chose to answer the question: What is your favorite part of your role? Why is that?

Both designers gave answers along the lines of:

“Autonomy. I love having control over my work and day while also having your support. I know that if I need help, you’ll be there, but otherwise, I can hold my own. I feel like I’ve earned it, and that feels good.”

It felt great to hear this. This sense of autonomy is not a result of me suddenly handing over the keys. It is the culmination of continually working toward a culture where the team has space to make their own decisions while also having the support of their manager or mentor when they need it.

Reflecting on this topic reminded of an excerpt from one of my favorite books, Turn the Ship Around:

"SHORT, EARLY CONVERSATIONS is a mechanism for CONTROL. It is a mechanism for control because the conversations did not consist of me telling them what to do. They were opportunities for the crew to get early feedback on how they were tackling problems. This allowed them to retain control of the solution. These early, quick discussions also provided clarity to the crew about what we wanted to accomplish. Many lasted only thirty seconds, but they saved hours of time."

Autonomy

Confidence = Control

As managers, sometimes we think we create space for "autonomy" by assigning tasks to our team and expecting them to tackle the work independently. This approach does not give the team control if they are merely taking orders. The issue is that the minute they hit a roadblock, they'll return to receive new orders rather than actively working toward a solution on their own.

People feel good working autonomously when they feel in control, and they believe in and understand the work as much as their manager. What contributes to feeling in control? Control is a product of confidence in decision-making.

Knowledge + Feedback = Confidence

We're most confident when we have the knowledge we need and can count on consistent feedback along the way. Without feedback, there's no sure way to know if what we're doing is working or not. When there's a void in feedback, we tend to create narratives about our performance and start to doubt our decisions. That doubt chips away at our confidence, and eventually, the thought of working autonomously can be pretty intimidating.

I always try to give feedback in real-time. For example, I'll make sure to take a few minutes to review feedback right after a big presentation, regardless if it went well or not. Positive feedback reinforces good decisions. Critical feedback teaches us how to make better decisions next time. When feedback about a situation comes after too much time has passed, details get lost, and we may forget why the feedback was even important.

Trust

I know my team will never feel like they have control unless we trust each other. I have to trust that they'll make thoughtful decisions; they have to trust that I'll be there to support them, no matter what happens. Support means giving them constructive feedback, helping them see a situation from different perspectives, and coaching them in their craft.

Below are three methods I've found effective in building a foundation for trust with my team.

1. Continuous coaching. Ongoing one-on-ones are helpful in checking in how on each team member is feeling and maintain a clear line of communication. It's important to go beyond "things are good" and dig deeper to uncover more insights, especially early on. Over time, trust builds and these insights will likely come through more freely. One-on-ones do not replace real-time feedback; they exist to eliminate blind spots and make sure there's always an open channel for support.
2. Responsibilities alignment. I've learned that simply clarifying and re-clarifying responsibilities with team members can go a long way. What are they responsible for, and how do you expect to work with them? Who is in charge of presenting the work? Alignment can even get into more micro-level tasks. Who will be making the final decision on the website's animation? Once there's alignment, it's important not to change course without a conversation. Jumping in to take over a task can quickly erode trust.
3. Vision-setting. Establishing a vision for every project (this does not need to be a formal, lofty statement) helps give the team a guiding light and understand what they're trying to accomplish together. Not only does a vision help make feedback more productive, but it also allows for more thoughtful decision-making and helps everyone feel more in control.

Here are a few posts related to the topics covered in this note:

• Weekly One-on-Ones
• Building Teams with TLC
• BL&T No. 011: Creating a Culture of Leadership
  

Through my experience mentoring designers, I've noticed a tendency to oversimplify a meeting's purpose. We stop at "present website concepts" then focus our preparation on explaining what we've designed as clearly and confidently as we can.

Some meetings go well; others don't. When they don’t, we feel bad. When we don’t know how to improve for next time, we feel even worse. It can be challenging to surface these insights when our only focus was what we were planning to say, missing who we were saying it to or why.

A simple practice I enjoy is taking a few minutes to collect my thoughts on what I expect from a meeting before it takes place. After the meeting, I can revisit my notes, reflecting on how it went and what I’ve learned.

This habit is a powerful tool for not only leading meetings more effectively but feeling better doing so. Below are ten questions to use as a guide:

Pre-Meeting

1. How do I feel heading into the meeting? Do I have the energy to participate fully?
2. What information do I hope to gain today?
3. What questions might the client (or my peers) ask? How will I respond?
4. How do I want the client (or my peers) to feel by the end of our meeting? Me?
5. How will I know this meeting was a success?

Post-Meeting

1. How do I feel right now?
2. What did not go as planned? Why?
3. What went well? Why?
4. Do I have what I need to move forward? If not, how will I capture what I need?
5. On a scale from 1 to 5, rate the success of this meeting. Why this rating?

In Playing With Movement, author Todd Hargrove shares how worry can lead to the exact outcome we're trying to avoid:

"In many situations, worrying about a bad outcome will make it more likely. Fear is the enemy, and playing with risk is a way to learn to master it."

In Stillness is the Key, author Ryan Holiday explores a similar idea:

"Whatever you face, whatever you’re doing will require, first and foremost, that you don’t defeat yourself. That you don’t make it harder by overthinking, by needless doubts, or by second-guessing."

When I was actively performing music, I could relate with this concept when playing new songs or revisiting old ones. I'd get anxious about forgetting the lyrics, so I'd do everything I could to embed them in my mind. I refused to stand on stage with my own lyrics written on a piece of paper as a guide. It felt inauthentic as a songwriter and performer. I wanted the audience to feel my relationship with the words I sang, and I thought this would get in the way.

Once I got on stage, the show would go in one of two ways:

• If I let myself become immersed in the music, I'd enter a flow state. The words would come to me, almost unconsciously, like I'd been singing them for years.
• If while singing, I let my mind wander to my doubt for even a second, I'd forget the words almost immediately. It was as if my determination to remember the lyrics was what made me forget them.

It didn't matter how I prepared or how much time I put in; mindset was everything.

Beyond Music

I've come to apply this concept to so many aspects of life; building new habits, acquiring skills, presenting my ideas, and truthfully, experiencing life. I remember feeling nervous when going to get my motorcycle license until realizing that there was nothing more I could do to prepare. When it came time to take the test, I took a deep breath and drove like I would any other day. I passed.

I believe that when we overthink what we're doing, it's hard to give it our best shot. We can't get in the flow because we're too focused on getting it "right." As a result, we get it wrong.

While it's unrealistic for me to think that I'll never get nervous about anything again, I've decided to trade my doubts and concerns for commitment to myself and my growth. Once I decide to go after something, I've learned it's best to go all in.

I was excited to catch up with one of my former professors today, Christine; it had been over a decade since we last spoke. Once we got on Zoom, it felt like no time had passed.

We got to talking about the books we've found valuable over the years and how we're often inspired by stories from outside our field. As we ended the discussion, Christine added: "We're all just people after all."

Regardless of our profession or industry, we're all just people working with other people. Framed this way, we're acknowledging our nature and inherent commonalities as humans. We're opening the door to learning from one another.

We all have times where we think our experience is unique and that no one else has ever dealt with the same problems in this way. Not only have countless others experienced the same problems but many are experiencing them right now and many others have overcome them.

We resist help because we can't imagine our friend who works in finance could ever understand what it's like to work in a creative agency. They may not be designing for a living but they have clients relying on them. They also have to earn their trust. They have deadlines. They want their manager to let them know how they're doing. They want to be recognized for doing good work. You get the idea.

We're much more alike than we think. When we remember that, the world suddenly becomes an open book and if we dive in, we just might learn a thing or two.

How do you describe an agency?

A group of people with unique perspectives and backgrounds working with other groups of people with unique perspectives and backgrounds toward a common goal.

What could go wrong?

I'm actually encouraged by this definition. It's the reason why misunderstandings and challenges are inevitable, but it's also the reason that I enjoy coming to work each day.

In moments of conflict, I like to remind my team of this reality. Like most things in life, collaboration takes patience and practice. When a situation gets tense, it can be easy to let our emotions take the wheel and quickly lead us off track. We forget that we all want the same thing.

We all want the same thing. Time and time again, I'm amazed at how powerful this statement can be. Even when we don't see eye-to-eye, it's a reminder that we have the same intent.

When we accept this statement as fact, conversations immediately become more productive, and resolution soon feels within reach. If we discover a disconnect in what we want, we can take appropriate action, but we're not acting on assumptions.

I was a resilient little kid and sometimes, a little reckless. I once "escaped" home, just after learning to walk, and was promptly found meandering far down the street in my diaper. As a kindergartener, I pulled the fire alarm on the school bus, and all the kids had to evacuate. When asked why I did it, I responded: "I just wanted to see what would happen."

I look back on my childhood and admire my curiosity and determination. When I wanted to achieve something, there wasn't much I would let get in my way.

One day, I decided I was ready to ride my bike without training wheels. My Dad wasn't home so, I got help from a neighbor after unsuccessfully trying to remove the training wheels myself. I then proceeded to go full speed down the hill next to our house off a skate ramp. Luckily, I landed. From then on, I was confident I could ride on two wheels. Little did I know, the momentum of riding down a hill is non-existent on flat ground.

Not long after the training wheel operation, I distinctly remember falling on the sidewalk right outside my house. I didn't cry until I looked at my elbow and saw the blood. By this point, my older brother, Nick, had already run inside to get help from my parents.

I'm not sure why this memory of falling off my bike comes to mind now and again, but it does. It's fascinating to me that while the impact of falling didn't bother me much, the sight of blood was alarming.

As an adult, I may not be as reckless as I once was, but I still relate to my perseverance as a child. I've come to embrace the fall and take the long game when it comes to success. That said, what does the blood represent in my life today?

I began writing this note to find an answer to this question. I think the blood represents a truth we tell ourselves about how failure looks. Even when the fall doesn't hurt us; we feel hurt when we see the blood. It makes our failure feel real and can be discouraging.

Similar to the saying, if a tree falls in a forest and no one is around to hear it, does it make a sound? I wonder if I fell off my bike and my elbow didn't bleed, would I have immediately stood up and returned to riding, not a tear in my eye? Would I have acknowledged the fall?

When we fail an exam, what if we never saw the grade? When we lose a race, what if no one was declared a winner?

I'm not suggesting that we stop giving grades or declaring winners. I'm more interested in what would happen if we didn't.

This trip down memory lane has taught me is that it's not worth crying over the blood. Whether it's there or not doesn't change the situation; it only serves as a distraction. All that's important is we pick up, move on, and keep trying.

I'm currently reading The Millionaire Real Estate Agent, and in it, the author, Gary Keller, shares his thoughts on failure. I'll leave you with a relevant excerpt from my reading today:

"You can’t know what you’re really capable of doing until you try and never give up. In fact, many people have said that they believe that failure is not the worst thing in the world. They believe the very worst is not to try at all. It’s been observed that many of life’s failures are people who did not realize how close they were to success when they gave up."

Back in September, I wrote my first-ever newsletter about adopting Webflow at Barrel. At the time, I had recently learned the platform through the design and launch of this website. I thoroughly enjoyed the simplicity and control of the experience. I ended up doing the bulk of the design work right in Webflow after some initial light concept work in Figma.

Less than a year later, Barrel has launched 16 websites on Webflow, including our own, with a few currently in the works. The previous iteration of the Barrel website was on WordPress. One of the constant challenges we faced was making design updates and adding new pages on the fly. Now, I can wake up with an idea for the website and have it done by the time I finish my morning coffee. Yes, this has happened, and it's a beautiful thing.

There's a lot to love about Webflow. We're excited to continue our work exploring all it has to offer. Personally, it's been a pleasure to see our team embrace it and push what's possible.

I recently "sat down" with the folks at Webflow and shared more insight into how we use the platform and why we find it valuable for our process and clients.

Read the case study here: https://webflow.com/customers/barrel

In team workshops centered around sharing personal experiences and challenges, we've been experimenting with establishing norms. I introduced the idea in a team-wide coaching workshop weeks ago, and it seemed to open the group up to more honest conversation.

For many, speaking openly in front of a room or Zoom full of people is not easy. Even if there's trust among the group, it's hard to be vulnerable.

Establishing norms means that the group accepts each norm as fact. It means that the space they occupy is safe and free of judgment.

Here are the norms we've experimented with so far:

• We all can be better collaborators.
• We believe feedback is information.
• We trade all judgment for curiosity.
• We communicate openly and honestly.

The times we've done this, I've displayed them at the start of the meeting and asked for volunteers to read each one. To me, this is a special moment. It's inspiring to hear your peers commit to these statements out loud. In our first workshop, I asked everyone to follow up in the chat with "yes" or "agreed." I love seeing the responses flow in as each norm is read.

I'm looking forward to evolving this idea further in future workshops. The hope is that, down the line, these will become commonplace. Even if we continue to recite them together, they'll be an integral part of our team's DNA.

Even with the best intentions, we are not always aware of how others interpret what we say or do. In last Tuesday's note, I wrote about how a simple question made an employee feel that a co-worker was dismissing them.

Since then, I've been interested in uncovering what other responses may inadvertently elicit a similar feeling. Through my interactions over the week, I've compiled a list.

1. Acknowledgment of what was said followed by "but..."
2. Abruptly moving the conversation to a new topic
3. Revisiting an earlier point without acknowledging the one just stated
4. Sighing or laughing in response to an idea or question
5. Telling someone they are wrong without explanation
6. Saying "don't worry" when someone is expressing worry
7. Explaining how the "new" idea has been done before and didn't work out 
8. Belittling impact with phrases like "oh, that's not a big deal" when someone is stating concern
9. Jumping to feedback when someone asks to talk through a tense situation
10. Suggesting a solution without digging into the problem first
    

This list does not mean that we should walk on eggshells whenever we communicate with others. For me, it's simply about awareness. When I have a better idea of how I might come off, I can more proactively share context and ask questions to ensure what I'm saying is not misinterpreted.

When someone feels dismissed, they eventually feel afraid or insignificant. When someone feels this way, they either become scared to share their ideas or don't think anyone wants to hear them, so they stop providing input. When they shut down in this way, they get by on taking orders. When this happens, their heart isn't it, and that's the beginning of the end.

This morning, I re-discovered this excerpt from Tell to Win by Peter Guber (via Readwise):

“The best stories lead from the heart, not the mind.”

Initially, it resonated with me because it's an idea I revisit constantly when I write. But as I sat with the statement longer, it began to take on new meaning.

Look at what happens when you omit the best stories:

"Lead from the heart, not the mind."

Notice the word lead. It is not about acting emotionally. It is about pursuing our instincts, not second-guessing ourselves or overthinking what we feel.

Our mind is what holds us back. It worries about what others will think. It fears the discomfort of telling the truth. It sidesteps momentary pain for short-term pleasure. All along, our heart knows we are making the wrong choice, but when we lead with our mind, our heart takes a back seat.

When it comes to communication, collaboration, and just purely interacting with other humans, I cannot think of a better mantra. At home, at work, in life.

Last Friday, I shared a new essay, Building Teams with TLC. I can't tell you how good it felt to hit the publish button! The framework has been a work-in-progress throughout my time building out the design team at Barrel. Until last year, these concepts only existed in my head. While the team was living them every day, it became challenging to chart the future without visualizing the current reality.

In October 2020, I wrote about visualizing project staffing models and how powerful it was to align with the team. This exercise was the beginning of the framework.

From there, I continued my work codifying other core concepts as I planned for the next stage of my team. Through the process, I found that their application was universal, which led me to document and share them with you.

Since publishing the framework, it has been fun to get feedback from within the team and peers beyond Barrel. Just yesterday, I enjoyed hearing how one of our team members used the Best Fit Activities Diagram to help delineate roles when conducting a website audit at the start of a project. See below.

Whether you’re in the process of building a team, scaling an existing one, or even an individual contributor on a team today, I hope the TLC framework brings you new insights on the power of creating a clear team structure.

If you decide to give TLC a try or have questions/feedback, I'd love to hear! Feel free to shoot me an email.

Interested in a TLC template? I'm planning to create templates for each of the framework's components. Sign up here and you'll be the first to receive them when they're ready.

Sometimes, we miss the mark. It happens.

Unfortunately, we missed the mark with one of our clients this week. While I'm not intimately involved with the project or on calls, talking it through with the designer reminded me of a powerful lesson.

Let's take a look at the situation.

The Situation

Round 1

We present the designs via Zoom. We're super excited about what we've done. Luckily, the client loves the look and interactivity of the work. Check. The issue? They feel like we failed to capture the unique selling points of the product. They admit that they have some work to do in gathering the content, but at the same time, we know it's our job to guide them.

The client does not provide additional feedback. They say, "we provided all we have to say during the call."

We regroup and make revisions, focused on creating a page that clearly outlines what the product offers and why it's unique.

Round 2

We present the revised designs, once again via Zoom. Within minutes of the call, the client lets us know this is not what they're looking for; it's feeling very sales-y and off-brand. We finish walking through the designs and end the call.

The internal team does not feel great, and we assume the client does not either. The team sleeps on it (some lose sleep over it) then regroup the next day.

Round 3

In round 1, we nailed the visual but missed the why. In round 2, we nailed the why but missed the visual. In round 3, all we have to do is find the perfect combination of both. Right? We take a step back and revisit the structure with a wireframe. We send it to the client and ask for feedback.

As I write this note, we're still waiting to hear what they have to say before we take it back into design.

So, besides the client being unhappy, what's the issue here?

The Challenge

The client's feedback was reactive on our calls because that's what we asked of them. We did make room for follow-up but from their perspective, they said all they needed to say. Our process did not create space for the client to spend time with the work. Caught up in finding a way forward, we did not re-align with the client on exactly what they're hoping to see. Outcome? We're shooting in the dark.

As demonstrated in this situation, clients often see our work for the first time on calls. When they love it, this can work out fine. When they have feedback, which is inevitable, it's hard for them to give meaningful insights after spending just ~30 minutes with the work.

Many times, this means they regroup offline and send written feedback a couple of days later. In situations like this, we may not get anything more. From there, we have to jump on a second call to make sure we understand the feedback or share revised designs.

Have the Second Meeting, First

If we could do this all over again, I'd suggest we have the second meeting, first. A topic I wrote about in my newsletter in February.

Send the designs the day before the first call, outline the key ideas, and ask for initial thoughts. Give the client time to sit with it and gather their thoughts.

When they provide feedback, we may even have time to address it before the first call. Now we're that much further along. If the client is unhappy with the direction, we can cancel the meeting to revisit the work or get on a call to talk it through.

Either way, the meeting we'd typically have second is the one we have first. Not only do we save everyone's time, but we also invite more thoughtful feedback, and in the end, we're more likely to hit the mark by the first meeting.

I'm confident we'll get this project back on track. In the meantime, I'm excited to apply this thinking more actively across all current and upcoming projects.