The Job Experience Paradox
What do you do when you “need experience to get experience”?
A Puzzle to Solve…
A few weeks ago, I was chatting with a friend who is looking to make a jump in his career. He asked a question that everyone confronts at some point (especially after they’ve spent several years developing a unique expertise or skill set).
“How does anyone get a position managing people when they’ve never done it before, and the management job you want requires you to already have significant time in a prior management position?”
This is what I call the “Job Experience Paradox”. Aka you “need experience to get experience.”
It looks a little something like this…
Anyone trying to break through to the next level, whether that is working in a new function, a new industry, or in my friend’s case trying to manage people for the first time, runs into some variant of the Experience Paradox. It can be deeply frustrating. You feel as though you’re caught in an infinite loop.
Solving the Experience Paradox
So how do you break through the Paradox? At its core, the short answer is that you have to convince someone to take a bet on you.
When someone in leadership gives you a new role, they are in many ways staking their reputation on you. They are being judged (by their bosses) on the output of their team, and they have to “place their chips” on your ability to deliver. For many leaders that is a risky proposition when the outcome is uncertain. Oftentimes a boss’s reluctance to give you a new opportunity is primarily about their fear of a failed result (which would reflect poorly on them). You’ve never done this exact work before (e.g., managing a team, working in a new function) and so you can’t simply point to your resume as evidence that you are a “low risk bet”.
The tricky part is convincing a leader at your company to take that risk, especially since you’re an unproven commodity. I’ve seen a few paths for doing this successfully:
(Let’s use the example of trying to get a first-time people manager role for illustration)
Path #1 (probably the easiest) = Use the “Snowball Method”
You need to help the company (or your boss) be willing to “place their chips” on your ability to lead a team (likely a small one at first). If you can prove competence in your first small “pilot test”, you’ll be entrusted with a larger opportunity. Prove it there again, and you’ll be trusted with an even larger scope to manage (e.g the snowball principle)
Raise your hand for opportunities to manage others internally in your department / existing team and then up-level. What you’re looking for is a “Pilot Experience” (even if it’s just for cross-functional projects and not an official role change). Every department and company has a large number of projects that simply need someone willing to herd the cats and get the work done. Some examples include:
Leading a small internal team doing competitive intelligence research
Organizing a small company event
Being the one in charge of pulling together the PowerPoint slides for an important presentation (aka “the deckmaster”)
Planning a team retreat
Taking charge of gathering updates from all your team members and consolidating into a executive weekly update for your department leader
Etc…
These projects can be unglamorous, but that is why they’re excellent candidates for your purposes. You just need an opportunity (that no one else really wants) to demonstrate to your boss that you know how to get others organized to accomplish a task. You want to get the snowball rolling.
The basic principle = start small → get results → ask for a slightly bigger opportunity next time.
Remember your goal is to reduce the risk in your boss’s mind that you won’t succeed. A series of small, but growing wins, is an excellent way to do just that.
Make it clear to your boss that you want the opportunity to manage people in your career as part of your growth plan and want to start having experiences managing others right now (even if only on internal projects). Do an excellent job in those small/internal roles and then keep asking for more. Hand raisers get noticed.
Once you have a few of these under your belt, you will either (A) get promoted to a position officially leading a team at your current company, or (B) can leverage that experience on your resume when applying for a position elsewhere (as you can now point to these small “mini projects” as evidence that you’re capable of doing management to some degree).
If your current company isn’t willing to give you these pilot experiences (even at the project level) that is a giant red flag that they are not invested in your growth. You probably need to find a boss/company who will ASAP
If you do need to switch companies, here are some quick tips…
Find a role similar to yours where your subject matter expertise is strongest (ex: if you’re a digital marketer, look for roles leading a small digital marketing team).
Tailor your resume to highlight (A) the depth of your subject matter expertise, and (B) anyway to highlight how you led cross-functionally on projects (similar to path 1). This often works if you’re coming from a larger company to a smaller one (but this rule isn’t exclusive).
Leverage personal connections if at all possible (people who can speak to your leadership in other areas like sports, extracurriculars, community work, etc.) For example, I have a friend who was captain on her university’s soccer team and used that leadership experience as evidence she’d be a great people manager despite only being an individual contributor (IC) beforehand. You likely have similar experiences you can leverage.
Path #2 (harder) = Lateral into Management Role in a Different Department
This one frankly isn’t as common, but I’ve seen it happen. If you feel there isn’t a management track in your current department, see if there is an internal opening somewhere else in your company.
Oftentimes if you are known as an excellent individual contributor with a solid reputation in the organization, other company leaders will be eager to “poach” you for their own department (as they would prefer to trust a known commodity who already “knows the ropes” instead of bringing in a relative unknown to lead one of their teams from outside). Use the fact that you know how the company works to your advantage here.
Note: There are a couple of risks with this strategy that you need to mitigate…
Make sure you don’t burn any bridges with the department/team you’re leaving. It can be a bit awkward when you leave one team for another (even if it’s the right move for your career).
Remember that while you may know the company well, you’re likely stepping into a new function (ex: switching from marketing to product management) and there is going to be a learning curve. You’ll need to do some off-hours homework to get up to speed quickly, especially if you’re to gain the trust of the new team members you’re now managing.
Conclusion
The most important thing to remember when trying to solve the “Experience Paradox” is to avoid discouragement.
On a cross-country trip a few years ago I was talking with my Dad (easily the wisest man I know) about my own fears of not being able to level up in my current role. I was worried that I lacked the experience and talent to become a leader at a company. He listened patiently and then simply said:
“Son, in all of my years of working as a professional I’ve learned one lesson over and over again: the cream always rises to the top; These things have a way of working out for those who are giving it their best and are patient”
That’s advice that’s carried me through the years. And as I've grown older I’ve come to realize how very right he was.