The Art of Scaling Yourself: Fuel Your FY2024 Leadership Career Strategy
“What Got You Here Won't Get You There”
This is a popular book title, but it's tricky to find out how to be successful in your career beyond the success you got so far.
That’s why on June 15, 2023 — I teamed up with Mounica Veggalam, AJ Stark, and Jen Iverson Kinkade (moderator) and hosted an in-person networking event to help people find answers to tough career questions.
We received positive feedback, so I want to share the information with you.
Below is the video recording.
The format includes 15min presentations from each of us followed by a Q&A.
For readers who prefer text, below are my answers from the Q&A in written form.
Note: I recommend watching the full recording to hear everyone’s different perspectives and career advice.
Q1: What part of scaling yourself is a science and what part do you consider art?
Ethan: Art vs Science. I’ve never thought of that before but I think it’s mostly science. The art part is incorporating it into your own personality, but there are a set of techniques (referenced in the presentations). Following those techniques will largely let you scale, the art part is how you make those your own so that you are comfortable with them.
Start with “There are things I can learn before I decide I have to make up my own solution.”
Q2: What’s a good resource or how do we continue to develop our questioning skills?
Ethan: The book Humble Inquiry by Edgar H. Schein.
The key to asking questions well is to not ask loaded questions.
When you’re asking a question that really is a statement cloaked with a question mark at the end, you’re not asking an honest question.
In the last single year, getting better at asking questions has been my biggest challenge and growth area. I wish I had gotten better at smart questions early.
Jeff Bezos at Amazon used to ask 3 questions (which he obviously honed) of any opportunity:
Is it real? Is the opportunity we are looking at real or is it a time machine or something in perpetual motion?
Is it worth it? Is it something that has money behind it?
Can we win? Is Amazon positioned (skills and talent) for that idea?
The idea is there are insightful questions for any problem.
Learn to find them (and that book will help).
Q3: What is one piece of wisdom you now know you wish you knew 10 years ago?
Ethan: That my career would have worked out without me stressing about it nearly as much as I did. The thing I want to encourage everyone is if you keep working hard, learning new skills, and learning like you are right now, the world generally delivers.
Have the belief that you will get there.
I read a book called Die with Zero by Bill Perkin about a guy who made a fortune and his goal now is how does he spend it all before he croaks because too many people don’t do that, they save and save and drive and drive.
Q4: What does great look like when you are scaling well?
Ethan: The first word that came to mind is it’s fun.
The second word is together.
When things are scaling well you do not feel alone. You have your whole team with you, they are hitting on all cylinders, your team members are growing with you, and everyone has heard of this so-called “Gel Team” — the team that does not necessarily have a bunch of superstars but because they all reinforce and back each other up they can do anything.
My greatest accomplishments came because a team pulled together and made it happen. It wasn’t anyone individual. Scaling requires bringing your team with you.
Scaling is not an alone game. Scaling is a team sport.
Q5: What happens when you are scaling but you are up against another important stakeholder, peer, or leader who does NOT know how to scale or is actively trying to get you not to scale because they want you to stay in your lane?
Ethan: Bad scaling looks like people regressing to their Individual Contributor (IC) skills, people being frantic, overwhelmed, distraught, dropping things, and looks like people trying to do it all alone.
Try to help them see.
Hold up a gentle mirror that says “Can I help you with this, have you thought about that.” Guide them to see there’s another way and offer help.
People like this need a lifeline.
Yes, you are suffering because they are not scaling. But the way out is not to criticize, it is to help and earn trust. Most likely they do not want to be in that painful situation, they just don’t know what to do.
So help them out.
Q6: How do you scale yourself as an Individual Contributor (IC)?
Ethan: Prioritization. You only control yourself and your own time.
There will always be more than you can do. You have to pick and choose.
It’s Thursday, can you quickly itemize what you accomplished Monday morning (right now, tip of your tongue)? Second question, just three days later, did that really matter? If you cannot remember what it was, it probably did not matter much.
So much of what we do ends up being wasted. Some of that is overhead, and some is corporate structure. If you work alone (e.g. Small Business Owner), try to have a set of systems to work on what really matters.
The world is full of distractions. Cut it off.
For example, if my content does not deliver enough value to you, fire me from your reading list, because I will step up and earn it.
You have to be ruthless.
Q7: How did you tame the beast of wanting to please others?
Ethan: I care. I don’t enjoy negative feedback. I don’t enjoy critics and attacks. So it still impacts me.
Honestly, it was being quick to jump in.
Some of my biggest career achievements were when I spoke up before I took time to consider what I was about to say. I opened my mouth and committed or suggested an idea before I considered the social implications.
Sometimes that burned me.
But the result is, I didn’t censor myself.
I try never to traffic in the world of fair or unfair because I do not cover that, just is and not is. What is true (backed by science), is the first person to speak is often considered by the audience to be smarter than the person who has the best answer.
Fact is, jumping in and being heard counts for a lot.
Q8: What is an “aha moment” you witnessed with a senior leader breaking through their scaling opportunity?
Ethan: I had a client whose struggle was getting angry and frustrated with colleagues who were not living up to his standard, getting in conflict with them, then alienating them, and then having the blowback such as performance feedback of “you are difficult to work with.”
Helping him see his self-sabotaging behavior and how that was driven by issues of performance very early in childhood (big influence).
My client broke through and at least now has awareness.
Awareness is only the first step.
Learning to lead differently is the next.
Note. To help you chart the course for successful leadership, I co-wrote 10 hard truths about tech leadership with a former Twitch colleague.
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