Lead with Confidence!

I am researching like a madman how to turn people into confident engineering leaders! I finally feel confident that I can make this happen for others!

My goal is to help new and aspiring engineering leaders transform from uncertain, overwhelmed, and stressed into confident leaders so that they can successfully guide their teams and drive results.

To make this happen my first step is building a course for these new or aspiring leaders. Anyone considering the leap into becoming a tech lead or manager, or who stepped into that role in the last 1-2~ years. If you are interested or know someone who is, sign up for Lead Kindly to receive all the updates and free guidance along that path while I put the course together!

You can also follow my shorter form exploits on LinkedIn.

Why a Course?

My favorite way to help people is one-on-one. I love meeting with people, getting to know them, and seeing how I can share my knowledge and skills for them to solve problems. I frequently mentor managers and engineers in my job, and it’s definitely my favorite thing to do at work.

However, this has a scale problem. I have 5 kids, a full time job, and a ton of interests that I want to explore. I want to go to the gym, and read books, build apps, do woodworking, fix my 3D printer, dance in the rain, etc. If I were to trade my non-work time I’d need to charge at least $500/hour to make it worth it to me. While I do think I could find some folks who would pay that much for 1:1 work, if we could find mutually free schedules to meet, I think it would take 10-20 hours to achieve the transformation we’re looking for, and I would only be able to work with 1 or 2 people at a time T_T.

There’s nothing wrong with that approach, but I think I can scale to help many more people by directing my effort into a course, at a fraction of the price.

Why THIS course?

When I read Andy Grove’s book High Output Management, it completely changed my career trajectory. I was a software engineer just kind of getting by, learning, trying to make an impact, watching some videos on tech things, learning about writing, etc.

One thing that really ruined my week was my 1:1 with my manager. It wasn’t bad, it just interrupted my day, and I got nothing out of it. I felt anxious going into it, convinced I would say the wrong thing and get fired. As if my manager would realize that I was a phony and cut the fat.

Reading HOM made me realize that the manager 1:1 was FOR ME. My manager wanted to help me be productive and happy. An unhappy engineer is not going to do good work. My manager also had exposure to many parts of the business I didn’t, and I could learn from that.

WHY HAD NOBODY EXPLAINED THIS TO ME!?

That question burned into my brain. Once I realized that meeting was for me, anxiety gone. I looked forward to it every week, I sometimes asked for more time, or to meet a second time later int he week.

I created a Google Doc for me and my manager. Each week I would create a heading with the date of our next 1:1. Throughout the week I would put my thoughts down. Everything I learned, all the questions I had, and things I wanted to know. Some of these didn’t end up being relevant and were an FYI for my manager, but others led to amazing conversations.

I started adding things I wanted to my doc, and when opportunities came up, my manager already knew I was interested and I was the first one they thought about. When our project lead left the team, my manager already knew I wanted to lead more so he asked me to do it.

It’s simple and probably not earth shattering to most people, but it changed my career.

From that point I wanted to be a manager, and help other engineers recognize why they have 1:1s. How they can leverage their manager to be happier and more productive. How they can make a bigger impact.

As an engineer I gave talks on how to have better 1:1s with your manager, and I gave similar talks to EMs begging them to explain 1:1s to their direct reports.

Now that I’ve spent years being a manager I can help new managers thrive in their “scary” new role and start helping engineers just like old-me be happier and become wiser!

Why a Confidence Focus?

I was very very nervous to become an Engineering Manager.

As an engineer, when I let my manager know I wanted to become an EM, I had a plan to study for 1-2 years before I took on the role. I had this detailed doc on all the EMs at Yelp I would interview, I had a long list of books to read, and a ton of newsletters and blog posts and podcasts to listen to. I wanted to hit the ground running when I became an EM. I wanted to CRUSH IT!

A few months after letting my EM know my intentions, an EM on the Design Systems team left the company, and there was a void. This was a big team (10 engineers) and they needed someone yesterday. Did I want the job?

Panic.

Panic panic panic.

The team was incredibly strong, was in the Engineering Effectiveness org which I loved, and was responsible for so many great pieces of tech in the company.

It was kind of a dream team for me.

It was a really hard decision, and I won’t bore you with the process, but I eventually decided this: I can spend 6-24 more months learning about eng leadership before I start, which would help me be a better EM when I started, or I could take the role now and start learning by doing the actual job.

The rubric I used to score the decision was, in 3-5 years which path makes me the more confident and strong manager?

After I framed it this way, the decision was easy. I said yes and never looked back. No regrets.

But you know what would have been nice? Some training! Even a 4-8 week course to learn the basics. Even if it was alongside my journey as an EM.

I am a strong self-learner. I used videos and blogs to learn enough construction to build a really amazing Duck house. It was a bit over-engineered, but that thing was a beast.

There are some things as an EM or tech lead you will really only learn by doing the job, and I think this fact prevents people from making truly useful resources because nothing you make will “cover everything”.

However, as a prolific self-learner who overcame his introversion and anxiety to become an EM, I think there is a good compromise. I am a confident leader. I can step into any engineering team and help lead the way. This is not because I know everything, far from it, but I no longer believe I need to know everything to be effective. It’s not my job to have all the answers, but I know I can work with my team to figure it out. I know I can help coach people to improve. I know how to communicate with stakeholders and get results.

I may not be able to make a course that tells you how to handle every single thing that will come up — that’s impossible — but what I can do is give you the necessary skills to be able to figure it out.

I’ve searched for years and have not found anything that does what I am setting out to accomplish, so I am going to make it myself, because I know there are managers out there who would really love a course that teaches them all the fundamentals, and helps them go from “Sorry, I don’t know what I’m doing yet” to “I don’t know the exact answer, but I know how to figure it out”.

If this sounds like something you’re interested in, or know someone who might be:

If you made it this far, what are things that helped you become a confident leader? And if you don’t identify as a confident leader, why not? What’s holding you back? What do you think you need?