Turning Product Designers into Outcome Designers
For B2B, B2E, & SaaS Product Designers
You don’t need a coach to grow your designers, but the right one can make it happen sooner. If your designers are capable but need to be more independent problem solvers, I might be that coach.
Let's see if we’re a fit.
Deeper Understanding
Outcome Designing
Increased Product Value
Do you feel like growing designers moves too slowly?
You have great product designers—they’re dedicated, willing, diligent, and working to make the features the best they can be for the product.
But somewhere along the way there is a disconnect between the designer's process and the value reaching the user’s hands.
You’ve tried giving them training through courses, books, and conferences. You've held internal lunch-and-learn sessions and workshops. The “product thinking” skill is slow going or not really sticking.
You’ve even carved out time to mentor designers one-on-one yourself, but there’s always that time constraint. They have great questions, but you can’t dedicate the time you’d like to really invest in them.
You look at the goals for the year and wonder:
“How can I get more consistency across our designs and features?”
“How can I get designers to ask better questions and dig deeper into requirements?”
“How can I get designers to take ownership of creativity and problem solving all the way to implemented feature?”
“How can I get designers to mature this year instead of over the next 5 years?”
The good news is you don’t have to figure this out alone.
“Darrell brought excellent mentorship skills to our team, always pushing to get to the ‘why’ and helping us unlock the right questions. He was a catalyst for great design conversations and jumped in to help us shape the best solution during feedback sessions. He brought valuable perspectives on research and helped us ask better questions to lead productive meetings with stakeholders.”
—Andreea, Product Designer
Let’s make Product Designers indispensable leaders
Many Design Managers are looking for better arguments, more statistics, or showing how they’re using cutting edge technology in order to have a seat at the leadership table.
Designers don’t need more justifications. They need to:
Offer deeper insights. So you can engage with stakeholders, engineers, and users and speak design in their language.
Visualize real possibilities. So you can demonstrate a broad array of solutions to show what works and what doesn’t before it gets expensive.
Deliver tangible value. So you can make the connection between design decisions and their effect on the business.
If a designer is dedicated, talented, and willing, you already have the core ingredients. You just need focus and a catalyst to become more effective.
What’s the catalyst? That’s where I come in.
Think of me as Lily Hevesh, except instead of setting up and knocking down dominoes, I’m coming in to establish patterns and habits that designers can keep coming back to perpetually.
This approach is how to enable designers to focus on what’s valuable in their daily work. It’s solving product problems visibly and often instead of having to justify their existence to the business with words.
63% of millennials say their leadership skills are not being fully developed.
—2016 Deloitte Millennial Survey
hello...
I’m Darrell Estabrook
I’ve been a UX Product Designer for 30 years. Yes, that’s before the web was young.
I designed (and coded) a regional coupon mailer web app using Photoshop 4 and Microsoft Active Server Pages in 1996. Stone knives and bear skins.
That’s right, it was the Wild West of the internet, but, it would have been awesome to have a mentor.
Instead, I pushed and pulled design through corporate intranets and websites. I integrated design practices into productivity web app product teams for insurance and financial startups and enterprises. I streamlined complex workflows and more complex business environments where design was scarce or was viewed as indifferent.
I hired, managed, and mentored a design team in our consulting firm and saw them grow into lead designers on client product teams, integrating Agile and design in harmony.
I took that to companies like IBM and Cigna and coached designers embedded on product teams where stakeholders relationships get complicated and design is foreign to engineering processes.
Now, I help other Product Designers and Team Managers address the same fundamental issues I faced. I bring this design approach to the next generation of Product Designers with realtime, interactive guidance.
Let’s see where you can grow. Start by applying for a complementary strategy session with me:
This is a no-pressure call, just people talking design
Here’s what designers say
See results in weeks not years
“What stood out most to me was his willingness to mentor and teach. He took the time to explain not just what the solution was, but why—from design system decisions to problem-solving approaches—helping me think more strategically and intentionally as a designer.”
Jill
Product Designer
“He pushed me to elevate how I frame problems, articulate trade-offs, and align design decisions with broader product and business goals. That shift changed how I lead stakeholder conversations and navigate ambiguity—moving from execution to influence!”
Grace
Product Designer
“In our 1:1s, Darrell wouldn't just give answers; he would demonstrate how to ask the right questions, to understand the complete picture, in order to produce the best result. His mentorship has been instrumental in my professional growth”
Joel
Product Designer
Who this is for
Previous Designers new to the product design role who are 1 to 2 years in the position
Product Designers from 2 to 15+ years experience looking to become invaluable to the team
Action-takers who are committed to making changes and trying new approaches
People who are detailed-oriented in their thinking and in producing their best designs for the product
Who this is not for
Non-designers with no previous design experience, including never using design tools, colors, typography, etc.
AI-only solution thinkers who prefer to generate solutions instead of digging in deep with stakeholders and users and getting into the heart of design
Anyone expecting an overnight transformation from a couple of meetings without stepping out and stepping up with action
You see the growth potential. Let’s make it real.
What you get
At the core, this is a focused 1–1 coaching relationship between me and a Product Designer. It’s my 30 years of product design experience customized to the designer's, team's, product's, and organization’s goals.
This isn’t a cookie-cutter program, but realtime, interactive, and product-specific guidance.
When a Product Designer has a Manager, I include a special kickoff meeting with only them to establish specific goals. Then I have regular touch point updates throughout the program. Of course, I’m always available for questions.
Here’s what you can expect if designers dedicate their time and effort to this:
A fundamental approach to product design beyond tools. There are many people and processes that affect design choices every day. You’ll be able to identify where you are and how to approach it with the tools of your choice.
A seriously professional, supportively fun design coach. Twelve (12) weekly sessions will keep you on task for what you’re learning, but also open design discussions and collaborations.
Slack-a-coach whenever you need me. You’ll have unlimited access to a private Designy Slack channel for asking questions, reviewing designs, or any quick chat between the weekly sessions. I typically reply within a business day.
The goal is to move the needle in your product design acumen. If you’re new to product design, let’s get you producing designs with value and talking to stakeholders. If you’re more seasoned, we’ll dive into the deeper issues of stakeholder feedback, UX design challenges on your plate, and larger, more complex ideas of scaling design thinking.
Designing is a blast, even while juggling the human interactions, conversations, and workflow challenges of a product team. I’ll take you as far as you’re willing to go, so let’s see if I’m a fit.
Investment
When it comes to traditional training options, my coaching will translate into a more effective approach.
Going to conferences, reading books, or taking online courses all have their place for specialty learning. However, I specialize in realtime, interactive, and product-specific coaching. This results in the designer applying theory in their actual daily work.
It’s a minimum of $3,800 per designer to work with me for three months when paid upfront.
Alternatively, you can pay $1,450 each month for 3 months.
Consider two-thirds of a 3-day conference investment is sunk into travel, lodging, and food. Once the conference is over, retention and application of the content is minimal.
However, my coaching is continuous, relevant, and will continually be used long after the coaching ends.
How it works
Many times my coaching spots are filled by returning designers.
Right now, I’m booking 2–4 weeks out. If we’re a fit, we can plan on the best start date that works with availability.
Step 1: Apply
Click the button and fill out the short application (takes under three minutes).
Step 2: Schedule
If you qualify, I’ll send you my calendar to book a call.
Step 3: Connect
We’ll meet for 45 minutes, talk about your goals, and see if we’re a fit.
This is not a commitment, just a conversation
“Darrell pushed me to elevate how I frame problems, articulate trade-offs, and align design decisions with broader product and business goals. That shift changed how I lead stakeholder conversations and navigate ambiguity—moving from execution to influence!”
—Grace, Product Designer
There’s no risk, except taking no action at all
Click the button below to apply.
It will take you less than three minutes to complete the application.
If you qualify, you'll be sent right to my calendar to book the complimentary strategy session.
There’s nothing hiding on the other side
Frequently asked questions
What’s the “unlimited Slack” feature
Between sessions, you’ll have direct access to me via a dedicated Designy Slack channel. You can reach out as often you need to for questions, updates, or feedback. I'll respond within one business day. This allows me to give you my full attention.
What if I miss a session, can I make it up?
The program is designed to meet over twelve weeks. We’ll plan for any upcoming vacation time and work around it. So, the overall program may total more than twelve calendar weeks.
If you have an illness, we’ll move the session to the following week. The goal is to use postponed sessions in the upcoming weeks alongside the planned weekly sessions whether as an additional whole hour, or divided into half hours.
However, postponed sessions can’t be carried beyond twelve weeks, and sessions not scheduled by the end of the twelve week window will expire and be reset if you extend to a new program.
What happens after the twelve-week program?
Many people find they want to continue the momentum they gain from the previous sessions. So, you can sign up for another three month program.
Do you offer a refund?
No, since this is a collaborative activity. It takes both of us to make this work. The investment you make up front is more than money, it’s time and commitment to apply and practice.
Before you commit to the program, set up a free call. We’ll talk about your current challenges and I’ll let you know if I can help you. Check out the details above on how to set that up.
Do you guarantee results?
Ooh, that would be great, but I can’t (and be wary of anyone who says they can). This is a dynamic program that relies on your performance to move the needle. I can guarantee I’ll be prepared, present, and giving you my best each and every time we meet. I’m cheering you all the way!
As a Design Team Manager, can I enroll more than one designer?
The short answer is—yes!
First, fill out the application and set up a strategy session. We can discuss your current needs and even a vision for where you’d like the team to move.
I’m a Design Team Manager, can I enroll myself?
I have also been a Design Team Manager and have been an advisor as well. Please fill out an application so I can schedule a strategy session. I can get more information on your goals and needs and if we’re a fit, we can go from there.
This is an awesome conversation about design, not a pressure pitch