Crafting a successful career framework

Five questions that you should consider before any transition

(This article accompanies Episode 1 of the Skip Podcast. Listen to it here for additional depth.)

I’m not sure my current thing is working, but is making a move right now worth it? This is one of the most common concerns I encounter as a career adviser, and one of the biggest decisions you’ll make in your work life.

But the spreadsheet you’ve created – a wish list of sorts – to organize what you think you want in your next role isn’t going to help you make (or not make) any leap, particularly over the long haul. I suspect your list – to have an amazing manager, high compensation, a strong brand, a worthy product, and wide job scope – is pretty generic.

You’re planning for a whole career, not just the next job, so you need something personal to you. Dig deep to ask yourself what is at the heart of your drive to make this change. After reading this article, you may realize that the right jobs for you don’t even include some of the five items on your spreadsheet-slash-wish list. Figuring this out begins by building what I call a career framework. 

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I have three ground rules, or key principles, that I see as the backbone of this discussion about framing a career. For starters, the name “The Skip” wasn’t chosen arbitrarily. To me, “skip” refers to the job after the next one. Working backwards can actually be the most effective way to plot out a career. You may be considering transitioning from job 1 to job 2, so you need to be thinking about what job 3 might look like and what skills it will require. You skip ahead to then reverse engineer your plan, so to speak.

Second, do you realize that you could have 20 – yes, 20 – jobs over a 50-year span in the always-changing, always-moving tech world? I suggest thinking about each job as a chapter of a whole book. As a chapter ends, it should set up for the next one. And the chapters toward the end of most books are typically much more substantive and critical than those near the beginning. 

And the last ground rule is more multifaceted and applies specifically to careers in leadership. Decisions about movement or changes become far more complicated because leaders are managed differently. Compensation, for example, is dramatically higher. And tenures are likely shorter because roles toward the top of the pyramid depend less on competence and more on mutual fit based on chemistry and soft skills and the current needs of an organization. So to have an elite career, optimize for becoming a leader sooner rather than later. This might mean focusing less on core skills and more on how to go about increasing your scope, managing a team, and being seen as a leader. At the same time, the higher you climb, the less “management” you might receive. Those in the top echelon aren’t necessarily there based on excellence in management skills, with an acumen for teaching or explaining things. They might be senior in the company because they made successful bets or have a hyper-skill, like driving growth. These types of positions may equal shorter tenures, but they can be big accelerants due to their high impact –  which “skips” you ahead.  

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Okay, the ground rules are set. Time to set aside your spreadsheet (the one that looks like so many other folks’ spreadsheets). Maybe brand isn’t quite as important? Perhaps having an amazing manager isn’t as critical as you thought?

Instead, I’m offering up five questions, or jumping-off points, that can help you be more intentional about any transition you are considering. The answers to these questions can help distill down what is driving you and be the framework you need. All the while, it’s important to keep the book-chapter analogy in mind: Each job, like a chapter, should have a purpose and motivate the reader (you) to turn the page.

Of course, a book is nothing without a story – and that’s where I like to start. I ask people, what is your story about what you have built? What did you learn? What challenges did you navigate? What ambiguities did you overcome? This isn’t about what promotions you earned or the glamor of the product. It’s about what you learned and the experience you gained. If all you can talk about in your next interview is what you launched or another brief experience without seeing it become a success – well, that’s not a great story. But sharing your experiences encompassed in a successful story can help ensure your next role is career additive. Some may say what I’m asking for is a pretty tall order, especially if a person is just getting their start. I get that. Choosing to work at a startup might generate a lot of good stories if the company succeeds – or none at all if the company’s struggles limit your ability to make headway. But maybe you choose to work at a big company, with a prominent brand. Perhaps you are considering a role at a big company – think about the stories you can tell with regards to scaling success, best practices, the struggles to bring something new to light.  

The second question I pose is, how fast do you think you will find “flow” in your next role? Say you have two job opportunities, and one is centered around a relatively complex role. Expectations are high. The project is on fire. You’ll need to quickly hire a team and set a direction or shape a culture. And, by the way, you don’t really know anything about this stuff. Not to mention the product is new. But it’s a huge opportunity! Both the brand and the sheer scope scream “career additive!” Then there is the “other” job, which is at a new company and seems familiar and consists of performing skills you’ve demonstrated in the past. Some people might see it as a very lateral move. Now stop and imagine yourself six months out. In the first case, you might feel very much like you’re not in flow. You’re struggling to find your sea legs, and the context is missing. Even after a year you might feel like you’ve not found your rhythm and that you’re not your true self. So given the urgency of showing success, it’s unlikely you’ll be trusted to take on other, bigger roles.

Sometimes it’s better to find a little smaller role in which you can crush it. You feel like yourself. In six months you are seen. People love the work you’re doing, and then you get thrust into the next new opportunity. That “skip” opportunity might be much more challenging, offer much more scope. You come into that next role with confidence and with support, and in that second job is where you really do your damage. Remember, you will likely take multiple roles at your next company. So it’s better to consider all of the opportunities at the company, and then at what the entry role looks like. Make a match according to what you can reasonably achieve. Put all the risk on your ability to optimize your speed to flow. 

Just as speed to flow can have an impact on your career trajectory, the speed at which your company (or the one you’re interested in) is growing can have an effect. There are times when jumping into a fast-moving company is right, but don’t assume this. Perhaps that environment isn’t right for learning the skills you need to master at that moment. If a company is growing more slowly than you are, that might actually give you a reason to leave. The same can be said if the projects themselves aren’t growing. The sweet spot seems to be if you are slightly behind your company in terms of growth and can be pulled forward.

Another spin on growth is to ensure that you experience different phases of growth, from projects that are just starting out to those that are starting to scale, and eventually to market leaders. Each additional new experience makes for terrific learning opportunities. Personally, some of the best, most effective learning during my career has come when moving between companies that are at different stages of growth themselves. Those experiences bring opportunities to build playbooks.

This is where the fourth element of your career framework comes in: diversity of roles. With each different role you take – whether it’s in a different market or type of business, or in an entirely new location – you’ll gain a unique playbook. And as you build this library of playbooks, you’ll become a more attractive candidate, and leader. When you come to the table as a leader, you can say, oh, I understand the problem you’re facing – it’s a little different from perhaps others we’ve seen, but it’s similar to what I’ve encountered. And, you add, that maybe someone from your network can provide some assistance.

The last – and an often overlooked – factor that’s very worth considering as you’re building a career framework is pace of work. People almost put blinders on and say, well, I want the biggest job at the best company with the highest compensation. I will do what it takes. And perhaps that’s actually correct. Perhaps that is actually your best next job. But before you think through a job decision, determine what the right pace of work is for you given your lifestyle. And that answer might change depending on who you are and where you are in life.

If you start asking questions around pace, people get a little bit skittish. They’re like, well, what is this guy or gal asking? Maybe they’re afraid to work hard? So you do have to be careful. It isn’t out of line to ask in an interview, however, the hours your peers (and your managers) tend to work, perhaps after you receive the offer and they are selling you. And then there is no shame in admitting to yourself, hey, that pace is too much for me right now in my life. Otherwise, this might lead to such churn or high anxiety that you actually pull back in your career. Burning out in this next job isn’t going to be good for your future.

In short, revise your career framework to make one that’s personal to you. This means going beyond the basics everyone uses. Great compensation is, well, great – but leaders make more, so accelerate your path to leadership, which will have you making more money in fewer years. Meanwhile, don’t hold out for a great manager, which may not come along. Growth, in fact, might teach you more. And big, hot companies sound exciting, but if that environment doesn’t match where you are at the moment, you’ll have poor flow. 

Instead, focus on how the next job sets up the next one – and ensure it’s on a path to a leadership role – and consider:

1. The story of what your role will enable

2. How fast you’ll hit your stride and get noticed

3. Growth rate and ensuring you are getting pulled forward

4. Adding new corporate experiences since each one is highly career additive

5. Ensuring work pace fits intentionally into your life