👋 Hey Reader, you're receiving this email because you signed up at Second Wave Dive or CDO School. Inside, we tackle questions and challenges about leading design teams and orgs, driving impact, and accelerating your career.

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I expected things to be different.

It's Ryan. Today’s newsletter is going to be a bit different. I want to talk as me, not as a small business owner, teacher, coach, etc. I’m struggling to balance everything right now, and I’d rather talk about that because it’s all I can put my mind to.

I’m four years into this experiment of being a small business owner. I expected things to be different.

I’m struggling to know how Second Wave Dive and CDO School fit with you and me. I've taught 700+ people like you through various courses, cohorts, and programs. While the materials and programs are finally where I hoped they would be, you’ve changed, I’ve changed, and everything seems to have changed.

We’re 3+ years into a global pandemic. The climate crisis is stomping all over us. Wars continue to do the terrible things that wars do. Fascists and racists continue to terrorize. The tech industry isn’t so human after all. So many people are out of work at no fault of their own. I mean, adulting is always hard, but everything everywhere seems to be happening at once right now.

In the middle of it all, I'm supposed to be running this little company. Today, I have little confidence that I’m doing this right. I have zero idea how I’m supposed to write newsletters like this. I'm supposed to tease you, highlight your pain, share a bunch of CTAs, tell you how this is going to be the answer you're looking for, more CTAs, and tell you if you don't act now, you'll miss out. It all feels too deceptive for my likes. It's robotic, like the 100s of dudes with VP titles I worked with over the years.

As a result, I have been asking myself a lot of questions as I try to write this. Is this how I should be showing up? Am I actually helping you? Am I just making you feel worse? Have I become the soulless blue shirt in khaki pants sales guy? If I leave the CTAs out, am I screwing myself and my family from financial security?

I feel this way today because I’m so tired of being constantly bombarded with rhetoric reminding me I'm doing it wrong. Daily, I'm told I should buckle down, push through, do better, learn more, be clear, and show something different than I already am. It’s in every aspect of my life, not just work. It’s pervasive in every digital space I go to.

I get emails in my inbox reminding me I could be a better business owner. I read posts on LinkedIn letting me know I could be a better leader. I see videos on TikTok about being a better parent. I hear podcasts about being a better spouse. The content is good, not great, fine, terrible, consistent, and filled with contradictions.

• Charge your worth, but also make it affordable!
• Allow your kids to express themselves, and also keep good boundaries!
• Lead people by stepping back, but make sure you make the right decisions!
• Actively listen to your spouse, and here are 8 ways to spice up your sex life
• Measure with quant to show your true impact, but focus on qual because it’s the only thing that truly matters

It’s all a bit too much.

Despite being surrounded by all these posts, ads, or videos offering courses, best practices, downloads, communities, and coaching, I still don't know how to talk to you. None of them are helping me talk about what I do in a way that feels meaningful to you and me. I have little confidence that I’m doing this right.

It's not an enjoyable feeling, so I'm writing this instead.

This is a familiar feeling

Everything I’m going through now reminds me of how I felt as a manager, director, and executive. While doing that work, I spent most of my time helping others grow their skills and confidence, but I didn’t know if I was helping or hurting. I didn’t know if I was doing it right or if the way I was showing up was the right way.

While I now know I was doing a pretty ok-to-decent job, at the time, I had very few signals I was doing anything well because it was entirely up to me to figure out. Each time I made more progress, I faced new challenges and felt more alone in figuring them out.

The wonderful mentors and bosses I had before I became a manager seemed to vanish as soon as I moved into management. Did good managers stop because they were tired? Were executives never good at management at all? Where with the types of leaders that Fast Company, Adaptive Path, and HBR were talking about?

I had so many questions that I didn’t get any answers for. I faced so many challenges that I didn’t get the specific help I needed. As I gained more responsibility for developing people and teams, I had fewer and fewer people helping me develop. I had every expectation that I would get better, more adult-y help as I progressed through my career.

I sometimes have to laugh about it because it’s so utterly backward! It simply didn't expect it to be like this.

That feeling is similar to what I’m experiencing today. The more progress I make running my own tiny company, the less I feel like I know what I'm doing and the more alone I get while doing it.

It's not just the feelings, either. As I, and others, became managers, directors, and executives, we were all surrounded by similar advice I see today:

• Be a servant leader, but also have a bias for action
• Garner credibility with metrics but also build relationships
• Don’t treat work like a family but also find a best friend at work
• Empower the team but definitely don’t use Waterfall
• Set expectations and prepare to change expectations the next day
• Establish clear performance guidelines for the team and treat everyone like the individuals they are

It was all very fine, but also quite generic. I tried a lot of specific techniques, but they didn’t really help me get unstuck. Getting good at one thing just seemed like it pushed me further away from getting better at seeing the big picture.

Both the feelings and rhetoric around improving are similar for me right now.

As a small business owner, I want to learn new things that help me make hard things a little easier. I want to have more confidence in my decisions while running this company. I want to maintain a pace that I can handle. I want to do good work that makes a difference for you, and it’s enough to help me keep going financially and emotionally.

I imagine you want some of the same stuff from your work.

My promise to you

​When you lead Design teams, practices, and orgs, Design is the product. CDO School is built to help you mature that product.

Here's our working argument:

• Anyone can be a design leader, but not everyone is a design manager
• There are specific challenges in scaling, growing, and developing good design teams, practices, and organizations
• There is no one way to drive, show, or feel impact for customers, products, teams, and businesses
• Management work can feel very reactive, and prioritizing work so it fits together is challenging
• Many companies treat management as a "learn on the job" kind of role
• Design Managers and Executives would like to see what's working (or not) for others
• You want to know your time and effort is worth it

Whether you’re a first-time Design Manager, a Director, or a Chief Design Officer, it's my job to help you define what good design is where you are. We teach very learnable, practical skills you can apply right now. I teach because I like it, have a lot of hands-on experience with the subject matter, and am good at it.

While there are times when I show up as a teacher or coach, there are lots of times when I show up as me. You'll get this version of me too. I'll share my POV when asked. No hesitation. I'll share when I haven't had a particular experience or am good at a specific skill. I'll be clear about my own confidence level in what I'm sharing as I share it.

As a result, you'll get better at predicting what's most important to address as a manager. You'll learn new ways to take on the various challenges you face so you make more confident decisions to deal with them. You deserve to get the help you need to manage design teams and orgs well.

I hate everything about marketing and selling the value of this work, though, so while I’m figuring out what to write these damn newsletters, my more important job is to make sure you're not figuring out management on your own. It feels good when people like you feel more confident as a manager. Not just because you get relief but because I know you'll be better at spreading confidence to others, thus giving them relief too. We'll all benefit from it as professionals, colleagues, customers, and inhabitants of the planet.

The courses I’ve created are damn good. The cohorts I lead are better. The people who do well in our cohorts show up in two ways:

• They are ready to do the work
• They do the work when they’re ready

If/When you're ready to do the work, we just announced our September cohorts. Current CDO School students have begun enrolling, and I'd like to do this work with you too.

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CDO School: September Cohorts and schedule

In our cohorts, you'll be creating real-world things you can use at work. You'll be learning with others too who are facing similar challenges. Choose from 6 programs led by me, designed to elevate your management skills. Each cohort requires 3-5 hours per week of your time to get the most out of them.

Our cohorts start the week of September 18, 2023. Here's the lineup:

Cohort 1: Position Design to Win; Design a Winning Org Strategy

In this cohort, you’ll create your team or org strategy. When you leave this cohort, you’ll have a clear vision, priorities, measured outcomes, and a game plan for your team.

Who is this best suited for?

• Managers, Directors, Operators, and Executives

When will we meet?

• Tuesdays, 11a-12p ET, September 19 - October 17

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Cohort 2: Connect What Matters to Metrics; Map Design Drivers to Business Outcomes with North Star Maps

In this cohort, you’ll make a North Star Map. You’ll connect long-term ambitions to your prioritized, short-term tactics all through the POKR (Perspectives, Objectives, and Key Results) structure. Our goal is that you clearly understand how your objectives and metrics connect and influence business outcomes and you’re able to communicate that to colleagues clearly and concisely.

Who is this best suited for?

• Managers, Directors, Operators, and Executives

When will we meet?

• Tuesdays, 3:30-4:30p ET, September 19 - October 17

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Cohort 3: Define What Good Design Is; Baseline Quality with Scorecards and ROI Math

In this cohort, you’ll baseline what good design is with rubrics, ratings, and scorecards. You’ll establish a scorecard to monitor and track the health of your product, service, or portfolio. Our goal is that you clearly understand the ROI math behind your initiatives and convert your insights into measurable numbers.

Who is this best suited for?

• Managers, Directors, Operators, and Executives

When will we meet?

• Wednesdays, 1-2p ET, September 20 - October 18

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Cohort 4: Get Good at Managing Up, Down, and Out; Find Your Sidekicks and Champions and Learn their Love Languages

In this cohort, you’ll be able to speak the love languages of your colleagues and coach them to understand you better. You’ll understand how your partners perceive your work and how to support or change that perception. Our goal is that you can assess when you need to change your argument vs. when you need to make something easier to understand and to communicate in the languages to make either a reality.

Who is this best suited for?

• Managers, Directors, Operators, and Executives

When will we meet?

• Wednesdays, 3:30-4:30p ET, September 20 - October 18

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Cohort 5: Stand out in the Job Market; Position Yourself as a Differentiator

In this cohort, you will develop a strongly held position on "what is unique about you" within resumes, portfolios, and interview conversations. You’ll craft new stories about your experience and how you are uniquely positioned compared to others in the job market. Our goal is that you clearly understand how you create and deliver value to a company, and a structured story to communicate that value to hiring managers and teams.

Who is this best suited for?

• All levels

When will we meet?

• Thursdays, 11a-12p ET, September 20 - October 19

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Cohort 6: Raise the Performance Bar! Develop Your People More Effectively

In this cohort, you will extend your knowledge of job skills frameworks and focus on specific approaches to develop your team. You’ll practice delivering difficult news in meaningful and productive ways. Our goal is that you clearly understand how you can better develop and mature the humans on your team to meet your and their expectations better.

Who is this best suited for?

• Managers, Directors, Operators, and Executives

When will we meet?

• Thursdays, 3:30-4:30p ET, September 20 - October 19

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Apply to join a September cohort

Joining CDO School is the only way to attend a cohort. It's not the cheapest program out there (it's $2000 USD), but it's also not the most expensive. And you get a lot of bang for your buck. When you join, you also get:

✔︎ 11 on-demand courses

✔︎ A pass to attend a different cohort in April 2024

✔︎ 40+ downloadable templates

✔︎ 45+ video replays from prior community events

✔︎ 100s of resources

✔︎ 400+ active community members

✔︎ Weekly community events and syncs

Apply to attend

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If you've gotten this far, I appreciate you reading. I want you to know you're doing a good job. A lot is going on, and you're doing your best. That's good enough. If you've read this far, I'd love to hear your biggest challenge right now. Hit reply and let me know what one thing you'd like to be doing better at work tomorrow.

Cheers,
Ryan

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