Steering clear of all-too-common career pitfalls

Conventional wisdom doesn’t always apply to you and your career moves

(This article accompanies Episode 2 of the Skip podcast. Listen to it here for additional depth.)

Higher compensation, phases of a company, skills growth, work-life balance. You’ve done a lot of self-reflection and analysis of these themes in an effort to to shape your career framework, and yet new doubts seem to arise. Just as you make one decision, you face another. Rest assured, you are not alone in this discovery – I have been approached with certain questions time and again throughout my decade of coaching and managing dozens of tech executives. I’d like to highlight some of these questions in this article, along with my responses, which aren’t so much answers as approaches to maximizing growth. Think of these “career growth hacks” as a baseline for some of our future conversations. 

Prioritize speed to success over the size of your next role

First, let’s consider the idea of starting fast and collecting some quick wins. I’ll meet with someone, and they’ll explain that they’re looking at taking a certain role, but they’re wondering if it’s the right choice. I’ve long recommended that people consider all of the positions they might hold at a company, not just the initial one, when evaluating a new job offer. People rarely consider these subsequent roles. But a great company that’s worth considering is often growing, and new roles will emerge, and many of those opportunities will go to internal candidates. On the flip side, companies aren’t static – and if you do encounter one that is, that’s probably not the best company to join. You need to think about that second job. So I’ll always ask – where can this go?

This advice goes counter to conventional wisdom. Often, people come to me and say, hey, I want to make sure I start in the biggest role possible.  They don’t consider that large companies are unusually complex, and especially for leadership roles, it will take substantial time to get to flow and nail some initial wins. But these monster roles are alluring, and people end up favoring them over “smaller roles,” which they feel are lateral moves and make them feel like cogs in the wheel. What I’d tell that person is – maybe that smaller role is the right way to go. You’ll get seen, and perhaps it will mean a quicker path to leadership. In a couple of years, a new job might emerge and be available only to those who are more tenured because the best roles in a larger company go to trusted employees – meaning the company isn’t interested in brand-new people, who won’t be able to hit the ground running. Since it takes a while to get context and an organization’s language, and to understand the culture itself, why not learn these first and then expand your responsibility?

You can have a much stronger story this way, right? If you are considering a larger, complex company, I prefer the idea of taking a smaller position in which you can easily exceed expectations. And if you can really crush it, that sets you up for success and the next opportunity. Oftentimes, if you look at it from a promotion point of view, fast promotions are noticed and result in an opportunity to take on larger roles more central to a company’s top priorities.

When the going gets tough, the tough don’t always get going

This leads me to one of the most common dilemmas: Should I stay, or should I go? Well, I would lean toward sticking it out and staying, particularly if you’re in your first year or two. Otherwise, you end up with a short tenure (potentially over and over again) and less opportunity to make a durable impact. Plus, each time you move to a new company you waste a lot of time – almost like a 12-month penalty box – to absorb the culture, build context, et cetera. And this is before you can have any substantive impact. So before you let dissatisfaction or the pull of the “Great Resignation” sway you, think of the longer term picture, particularly if your end goal is to be in leadership. 

If your eye is on leadership, you need to consider how jumping around prevents you from learning how to drive meaningful impact. How might a company look at your story when you’re mid-career or late career? Durability tends to come from having some patience and “gritting it out” past the exciting initial launch phase. There comes a bit of a slog when you’re dealing with growth constraints and users who have issues. But, frankly, that’s where a real amount of leadership skills are developed. And companies know that. Through each of these phases you glean new insight, and you gain a new playbook. By going this route, when you say you’ve built something, you haven’t just launched it – you really have built it. So jumping around is undesirable, though perhaps not for the reasons that people initially think. It’s for the learning, and showing grit and durability, all of which will help you in that leadership career. 

Great products or missions won’t always translate into great companies or enjoyable work

I think this third FAQ is one of the more interesting: Boring is not a bug. It might be a feature. Boring products and companies can be highly career additive. Okay, let me back up a bit. There was a time back in the ’90s – when I was starting out – when most of the tech opportunities could actually be classified as reasonably boring. The internet was being built, but there were few apps and no mobile phones and very few end-user experiences. My early jobs were a lot like plumbing jobs: infrastructure for what was coming. You see that in AI today, and crypto. These new platforms are starting to come to bear right now. “Boring” roles may involve working with customers that are businesses or maybe even businesses of businesses. Perhaps you can’t easily explain the products to your friends or use the products yourself, but they’re really healthy, successful businesses.

I think people can get too focused on only being at a company that has a product that they can personally use and be proud of. This notion comes up in a lot of career frameworks. It’s not a bad thing, but I think it’s heavily overweighted. When I worked at Credit Karma, the power of the mission of helping people who were struggling with money was a big, exciting piece of the role. But in reality, 99 percent of the day job has very little to do with that part. No – you’re managing people, working through constraints, trying to scale and monetize the company. And just because a company is mission-based doesn’t mean it’s incredibly well-run and the values extend all the way to how they treat their employees. At the same time, a company that isn’t mission-driven may treat its employees really well. The correlation doesn’t necessarily exist. The best career frameworks, in my opinion, weight the product area low on the wish list. It’s better to be more agnostic about the type of company you work for in terms of product, and to factor in other elements that might drive your career over the long haul – like the culture, the people, the values, the learning, and the speed at which you might grow.

It may be hard to square devoting a huge chunk of your life – to advance your career – to developing a product or scaling a company that doesn’t represent you. Some people might say this is selfish. But it isn’t black and white. And I respond to this (fair) criticism by highlighting that your professional life should be more than your day job. One of the best parts about being in technology is that you’re not stuck doing one, all-in job. You have the opportunity to cultivate interests and pursue projects or experiences that are adjacent to your day job and scratch that itch to make the world a better place. You may even encounter fewer constraints following these other paths. And you may even be able to diversify your compensation by taking on an advisory role or a side opportunity that grants equity. The options are many: Scratch that itch to help others by becoming a mentor, or connect with an organization that needs your skill set. And rather than attending a slew of conferences, which I think can be somewhat generic, make meaningful connections by finding a mentor yourself or carve out two to three hours a month (at least) to sit down one-on-one with founders or colleagues. All of this can lift you up and pull you forward.

Who you know might be as important as what you know

Of course, being in roles that naturally connect you to people will “generate luck” and help your career over the long term. But some roles and some workplaces are simply isolated – not to mention the pandemic and increase in remote work. In short, how to connect on a more human level has become a common question. No matter the situation, making one-on-one connections can counterbalance isolation and be career additive. It’s worth putting in the effort to make that call. I find that people who tend to have “fortune” in their careers tend to know a lot of individuals. You hear stories of, I just happened to know that person, and they were doing something amazing. They could have called anyone, but I was a known entity. The reverse can happen as well, and you are able to reach out to a peer who is a “known entity” to quickly fill out a team you’re building. You also learn from listening to other people’s stories. So connecting isn’t necessarily about networking. It’s about engaging and growing professionally. 

Surround yourself with talent that will pull you forward

The last hack I want to touch on in this article has to do with a misconception about companies and talent – that the most successful companies always have the highest, most successful band of talent, and that the weakest companies have the weakest band of talent. The coupling is much looser than this, and a lot has to do with luck and determining what success looks like. I think there are companies that may have average talent, but they have done exceptionally well because they managed to find the right “recipe.” One thing leads to another, and they shift their talent. As they become more successful, they attract higher-quality employees. But as they scale, they lose some of their best people. So there’s a talent band that exists in every company and it shifts as the company grows so you have to continue to recalibrate.  I think you want to have a bit of a nose for the current talent level. And ask yourself: Realistically, where do I fit in? Which band of talent do I want to be in: below, middle, or above?

I can speak from experience about starting from below. It’s not easy, but it can really pull you forward. Right out of college I went to a startup. I had no work experience, and yet I was working alongside these people who were almost legendary in status. The bar was high, and I just kept telling myself, ya gotta keep up. I had to make the decision to take on that challenge, to find my niche there. If I’d chosen something where I was in the middle of the pack, I might have found flow more easily. At the time, however, I chose to bet on myself, hoping I’ll have some quick wins within weeks of being hired. And in my case, it worked and I moved into leadership years earlier than my peers at other companies. 

Alternatively, being more talented than your peers can be career additive, despite conventional wisdom. You’re quickly seen, you’re trusted to make decisions and have outsized responsibility. You definitely won’t feel like a cog in a wheel. Why do these opportunities emerge? As an example of different talent bands, consider a startup that is trying to navigate product market fit.  During these early stages, it might have to hire anyone who is willing to help. But then let’s assume this company finally hits some success. It has a real business, needs to scale, and starts interviewing experienced professionals. But instead of interviewing there and getting turned off by the weaker talent, you should get excited about the opportunity to uplevel the team and shape the future. You have more to lose in being rigid about “your brand” than you have in missing an opportunity to leapfrog your peers. Consider what’s right for you at this stage of your career because ultimately it’s a matter of being seen, getting to flow, and getting to growth. 

Ensure you build a custom plan for yourself and take advantage of these growth hacks. Here is a quick recap: 

• Consider the double-jump, because the best roles aren’t often available to outsiders.

• Long tenures at your current company can be good to ensure that you are showing grit and learning.

• Boring is not a bug, it might be the most career additive.

• Your professional life should be more than your day job (lower pace might be smart).

• Meet the people you work with and stay in touch with them.

• Consider the talent band and ensure you are intentional about where you fit.