Get good at reading the room
Know how to get your boss’s attention
Turn that attention into buy-in (i.e. more YESes)
"Convince Your Boss is a gem! I had avoided workshops for many years, but I feel fortunate I took a chance with this one. It was full of aha moments. I can't recommend it enough!"
– Thuan Nguyen, Sr. Product Designer, Equip
Convincing your boss is f*cking hard
You’ve likely spent hours painstakingly tweaking, adjusting, and refining your argument, hoping next time it works…
But instead, you leave meetings feeling frustrated, wondering why your ideas aren't being considered.
And we bet you’ve tried the advice of the gurus, using “proven techniques”, short cuts, and hot vibes. And yet…
Your ideas got shut down. Again.
Getting shut down is soul crushing!
It’s not your fault though. The truth is you’ve been lied to by the experts.
What worked for them won’t work for you.
Chances are their challenges were totally different than yours, right?
There is a better way…
Do you want to have influence?
You must become CONVINCING
It’s simple. But not easy…
You don’t need more beginner advice.
You've wasted a lot of time looking for the perfect answer. You bought the frameworks and read all the LinkedIn posts. That didn’t help.
You don't need more people telling you to "put yourself out there more" or "learn how to network better." You already know that stuff.
Let's get real. Your current approach isn’t working.
The problem isn’t your ideas. It's that humans are designed to resist change.
If you want to grow your influence, be listened to, or drive strategic decisions… something has to change.
That ‘something’ is YOU.
"Convince Your Boss is a treasure trove of tools, frameworks, and hands-on practice! This helped me cut through with clarity and purpose. I can't recommend it enough."
Thuan Nguyen
Sr. Product Designer
"I wish I could carry Tim and Ryan around in my pocket. This was very thoughtfully planned and we left with templates we could use out of the box. Invaluable!"
Allison Lei
Sr. Product Designer
"This broke patterns of my own thinking, and showed me how to reframe my ideas so they are heard. The interplay between Timothy and Ryan's different styles showed how this can be done."
Timothy McKenna
Director of Product Design
What you'll learn
Convince Your Boss isn’t another online course that you’ll buy and forget about. It's a 21-day group challenge for experts who want to grow influence.
We’ll show you what works today and teach you WHY it works based on timeless psychology principles.
Rather than ask or guess what your boss wants, we'll help you:
- Observe what they do
- Learn their "love language"
- Frame new options
- Sell your idea
The best part? You won’t have to do it alone.
You’ll apply everything you learn with support from us and other experienced experts.
Foundations of Buy-In
- Sources of Tension
- Choice alternatives
- Negotiation Canvas
- Influence is Political
Verbal Communication Fundamentals
- Coaching
- Imago Dialogue
- Active Listening
Written Communication Fundamentals
- SCR
- Email vs. Presentation
- SWOT
Managing Up
- Finding a coalition
- Learning the “love language” they receive
- Rational vs. Relational
- Champion or Challenger
Ready to learn unignorable skills?
Ready to learn unignorable skills?
The kind of content that builds your confidence and trust in you?
How it works
Bite-sized lessons and exercises
You’re busy. We get that. Most courses take pride in selling you “80 hours of video content” or multi-week, full-day sessions that you have to attend.
Honestly, that’s insane. Who has the time (or energy) for that? The answer: no one.
We’re flipping career growth on its head. Each day, you’ll watch a short video lesson–usually less than 10 minutes–and complete an exercise to act on what you learned.
Here’s a small taste of what we’ll cover:
- Get good at reading the room
- Discover your boss’s “love language”
- Learn how to gauge your (and your boss’s) emotional energy before you try to change their mind
- Know which communication formats to focus on… and which ones to ignore
- Position yourself as the person others want to hear from
- Learn the science of influence and timeless communication techniques
- Learn “the rules” of presenting… so you know when to break them
- Develop a system for easily and repeatedly making new arguments
- Feel confident selling your ideas your boss (or anyone else for that matter) and look like a genius doing it
Learn the WHY behind the HOW
There are countless influence courses out there. Most are taught by creators who built a large following and show you HOW they did it.
But here’s the issue: they all focus on how to do exactly what they did. Their templates, their formulas, etc.
Which leads to issue #2: you don’t understand WHY those tactics worked to begin with.
Convince Your Boss focuses on the WHY behind the HOW. We’ll explain the art and science behind influence based on timeless psychological principles.
The result? Consistent, repeatable results for where you are now and where you'll go in the future.
Hands-on learning to tackle a real-world situation you’re facing
During the challenge you will:
- Pick one idea you want to get buy-in for
- Diagnose the source of tension between you and your boss
- Identify your boss's "love language" so you can match their leadership style
- Shape your argument in 4 different formats: email, presentation deck, verbal, and coaching
- Check-in on your emotional capacity
- Make a plan to sell your ideas
Time-tested frameworks and templates
Wait—didn't we just criticize templates? In a way, yes. While frameworks and templates serve an important purpose—providing a solid starting point to develop from—we steer clear of flashy, short-lived gimmicks because they suck. Instead, we’ll share proven, time-tested tactics based on our own personal experiences and a thorough understanding of human nature. Doesn’t that sound better? Yes, and that's exactly what we’ll give you.
You'll walk away with:
- Ready-to-use email templates for presenting your ideas to resistant stakeholders
- Storytelling frameworks that connect your idea to outcomes executives care about
- Reusable Figma boards to practice and prepare your arguments
- Insights and guidance from a close cohort of peers
Finally, practical tricks that help you read the room
Let's be real - the best arguments don't come from fancy structures or processes. They happen when you crack the toughest workplace puzzle... people.
We'll hook you up with practical psychology hacks to figure out which boss to prioritize, what actually makes them tick, and the perfect moment to pitch your brilliant idea.
Say goodbye to the guessing game. Say hello to actual results.
Live sessions with Tim and Ryan
Sure, you can learn a ton on your own. But nothing beats working directly with people who have made things happen, getting real feedback, and peeking inside their thought process. Every week, you'll get to do exactly that.
Peers that have your back
You'll be part of a tight-knit cohort of peers. Learn from each other. Share feedback. Boost each other's progress ← psst: this is secretly more practice for your skills!
Let's face it - going alone makes it way too easy to quit. But with the support of your peers who keep you accountable, you'll actually follow through.
Your Hosts
Your Hosts
Hi, I'm Tim Yeo
Before Convince Your Boss, I have been a designer, leader and chief introvert at The Quiet Achiever (TQA). Best known for saying complex things simply, Tim has been 18 years a designer and leader, and 40 years an introvert.
Design Director of IBM Consulting, Founder of the Quiet Achiever and proud introvert, Tim Yeo, shares his personal journey of being an introverted designer and design leader and how he’s now helping other introverts have better impact and influence without pretending to be extroverts.
An introvert with over four decades of experience he was previously a Design Director at IBM Consulting, Head of Design @finder, and Head of Design at fintech startups @OFX, @Prospa.
Hi, I'm Ryan Rumsey
I made my way up from Designer to Executive. I worked in Design Led- companies. I transformed Design Immature orgs. Now, I'm an Entrepreneur, Author, and Founder.
Over the last 25 years, I designed software at Apple. I built and led in-house teams at EA, Nestlé and USAA. I’ve presented and led workshops around the world. I've delivered in-house training to small teams, and for huge multinational companies. My book Business Thinking for Designers has been read by 60K people. I coach some of the best design leaders in the business. And, I teach everything I know to help you position design to win.
Is Convince Your Boss right for you?
Is Convince Your Boss right for you?
- Are you very experienced, yet struggle to be taken seriously?
- Have your best ideas died because you couldn't get buy-in?
- Have you tried pitching ideas on your own without getting much traction?
- Has imposter syndrome or self-doubt kept you from speaking up?
- Have you had moments of success… only to see the results vanish into thin air?
- Do you want to build influence the smart way—without becoming someone you're not or playing political games you hate?
- Want techniques that work with YOUR natural communication style?
- Ready to take the plunge but don't want to do it alone?
If you can relate to any of these, Convince Your Boss is for you.
Pricing
Pricing
4 weeks · Bite-sized Daily Exercises · Weekly Office Hours
Next cohort starts in August 2025
$599
Included:
- Step-by-step exercises to build your personal brand strategy
- 20 bite-sized video/text lessons: Learn how to create Convinceable arguments (~10 mins each).
- Co-writing sessions: Stay accountable by hopping on co-working sessions with your peers.
- Fast feedback sessions: Join live breakout sessions with your peers to talk through challenges and critique each other's work.
- Multi-time-zone office hours: Join us live for 60-minute Q&A sessions to get answers to your burning questions.
- Engagement squad: You'll join a small, ambitious group of smart peers to exchange feedback and support each other’s audience growth efforts.
- Accountability to help you stay on track with projects.
- Access to a community forum to get feedback on your work and collaborate on projects.
- Channel cheatsheets: Learn what's working today on each social media channel.
- A reusable content planning system to ensure you never run out of ideas.
FAQs
FAQs
When does it start?
The first cohort will kick off on May 19, 2025 🙌
What’s the schedule and time commitment?
Convince Your Boss is a 21-day challenge. Starting May 19 and ending June 16, 2025.
It includes short lessons spread over 21 days (M-F only). Each video lesson is ~10 mins and you’ll complete exercises and mini challenges to put what you learned into practice. All in, expect to invest up to 1 hour per day Monday to Friday.
You’ll also have the option to join weekly live sessions, with time-zone friendly options. These live sessions happen every Thursday at 2p ET (10a PT) and Thursday at 2pm AEST.
And if you can’t make it to the live sessions, don’t sweat! You’ll get recordings of each one so you don’t miss a thing.
Am I a fit for Convince Your Boss?
Convince Your Boss is best suited for:
- Senior Experts whose ideas get overlooked despite their technical merit or domain expertise.
- Managers who need stakeholder buy-in to move projects forward.
- Anyone tired of seeing less qualified ideas win simply because they were presented "better"
To get the most out of the program, you should have basic familiarity and experience with presenting your work. If you have zero experience presenting your work, this program isn’t right for you yet. Come back when you’ve got a little experience presenting under your belt.
Worried because you can't think of a specific argument yet?
We’ve all been there. That "blank slate" feeling. How do you get good at selling your ideas when you're starting from zero?
It can feel like climbing a mountain without gear. And honestly, it stops many beginners in their tracks.
But that's exactly what makes Convince Your Boss different. You're not just learning to frame one argument. You'll learn how to do this again, and again. You'll have people to engage with and amplify each other's work. Think of it as having your own personal cheer squad from day one.
I am a boss–what about me?
First off, congratulations! Now, to answer your question: yes. Are you happy with your rate of growth? Do you feel confident that you’ll know how to pivot if a big algorithm change comes, or the current tactics you’re using no longer work?
If you’ve answered yes to both of these questions, then you may be too experienced for Convince Your Boss. Otherwise, we think you’ll get a ton of value from the program.
And if you’re on the fence, we’d encourage you to jump in and give it a shot. Worst case, you realize it’s not a fit and we’ll give you a full refund (within 5 days after we start).
Is this just another online course? I’ve seen a ton of those lately.
So have we. And that’s a big reason we felt compelled to create Convince Your Boss.
There are countless communication and storytelling courses out there. Most of them are looooonnggg or require A LOT of your time and energy, with little progress made.
A lot of them are taught by professional creators who have built a large following, but haven’t had YOUR JOB. They show you HOW they did it, and tell you to use the exact tactics they use without teaching you WHY their methods work.
Without a deep understanding of the WHY, you’re completely trapped and totally dependent on single techniques to get any results.
Convince Your Boss focuses on the WHY behind the HOW. We’ll explain the art and science behind earning trust based on timeless psychological principles and street smarts. We’ll show you how to adapt your approach based on different scenarios.
The result? Consistent, repeatable results. You’ll be able to adapt while growing undeniable arguments, and the trust that comes along with them.
No, really… how is Convince Your Boss different?
For six years, we have studied why talented people struggle to gain influence despite their expertise and know-how. Separately, we've taught and coached 3000+ experienced tech professionals actionable ways to get buy-in.
Together, we’ve combined our knowledge and developed new, proven-techniques you won't find anywhere else.
You'll focus on what's missing from other courses out there – understanding political capital, timing for emotional capacity, framing arguments in multiple ways, and the written/verbal communication skills that no one teaches you.
Rather than ask or guess what your boss wants, we'll help you:
- Observe what they do
- Learn their "love language"
- Gauge your emotional capacity
- Frame new options
- Sell your idea
- Test your results
The best part? It’s very practical and doable. While other people just talk about the ‘messy middle’, we’ll help you decode how to push through it.
When you get this right, magical things happen. 🪄🎩🐇
Is there a refund policy?
You bet! If, after the 5 days, you realize Convince Your Boss isn’t right for you, we’ll give you a full refund – no questions asked.