Jason and Eiso share the frameworks that have helped them navigate big and small decisions through the years and look back at how key decision-making moments shaped how they operate as leaders today.

Making good decisions is one of the pillars of exceptional leadership and a practice that can make or break an organization at any stage. Through company politics, difficult conversations, promoting employees, and raising equity, there are several approaches to staying grounded and keeping your team in sync as you navigate the turbulent tides of organizational change.


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If I'm giving any advice to engineering leaders, there's a two-fold thing, which is: you've got to think of yourself as your department and your department's efficiencies. But if I were to flip it around I'd say: think of yourself as a functional leader second, and an executive first.

If you're thinking about yourself as an executive first, you're thinking about a business, you're thinking about the new CAC multiples, you're thinking about sales efficiencies, you're thinking about all the stuff that's going on in finance. Not that you have to actually know those things, but you're interested when the CFO is talking at the LT staff meeting or the exec staff meeting about what's happening in procurement. You're still interested. You don't tune out and just think about "we need to start talking about database tuning". Think about those things second. And the reason why is because then you'll actually pick up on a bunch of these things and care about the entirety of the business.

The first time someone gets promoted or a raise or more equity or they’re "teacher's pet", you're starting to enter political land. So you've gotta be a lot more explicit about communication to root out politics. And sometimes you have to be a real hardass. Like you have to say, "sorry, you actually are probably one of the most capable engineers we have, but we're not going to make you staff because you've got five different things over here or two different things that we can't tacitly endorse of your behavior. If we do that, that becomes the norm. That becomes the standard by which everyone else will act. And we can't have that."

I speak to hundreds of engineering leaders and I come away from it that many people, humans in general, but I'm very much exposed to those that work in software engineering, are great kindhearted people who are passionate about technology. That's why they got into the field. They found themselves in management because there was some aptitude towards it or they got the opportunity to do so. And when asked, they want to do the right thing.

But all of a sudden, they find themselves in situations where the money all of a sudden becomes a topic. And early on in any of our careers in engineering, money is not a topic. It's not something are really thinking about when it's very early on, at least maybe 10, 15 years ago. So, what do you do? What do you do when you have the right things in mind? What do you advise to someone who right now is at a company that just, you know, got their first billion-dollar valuation, the environment is changing and you're an engineering leader and you're trying to do right by you by your organization? (hear Jason's advice on minute 23:21)

Don't assume that anyone is going to be looking out for you. Don't assume that anyone's going to look out for your employees. Don't assume anyone's going to be actively seeking to give away more of the company to those people. You have to be that champion for your people and you. You have a boss who is not going to give you more equity. I can almost guarantee it, unless people listening to this become that person in their organization and actively start to do that, just don't assume it. So, have a conversation with them. Be that person for your employees though. The only way that this changes generally, as an industry, is that a hundred people see the example from one person and ten of those people go on to lead more organizations who inspire more people to be that way. And it may not be there ever for you in your career, but that doesn't mean you shouldn't do it anyway.

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