I am about six years into a career that puts the “individual” in individual contributor (nonprofit fundraising, in case it matters). I have good relations with my colleagues and we work collaboratively when possible, but our projects are completely solo. I have always known that I want to spend my career in a role that involves organizational leadership and people management. I’m good at the work I do now, but I feel so much more fulfilled when I have the opportunity to coach and support others, and my deepest goal is to be part of the team that sets the strategic direction of an organization.
The problem is there’s no way for me to build management experience in my current role. The organizational structure is rigid and there is not likely to be a director-level position opening for many, many years. Even when something does open up, I might not qualify because, you guessed it, I don’t have management experience. The scope of my role is intentionally kept very narrow, and while I’m fully independent in my work, the management here likes to keep us at arm’s length from any real conversations about the organization’s strategic direction.
I keep an eye on postings outside my organization, but the positions are either what I already have (individual contributions only) or require a decade of strategic oversight and people management to even be considered. If I wanted to take an intermediary step by finding a lateral move that incorporates the work I do now and also organizational and people management, it would invariably involve moving to a smaller, less prestigious organization and taking a serious pay cut, which I really can’t afford.
I’m looking for a volunteer position that would include people management (such as a nonprofit board), but these are hard to come by. I also don’t have hours every week or deep pockets to contribute to an organization the way board members are often expected to. I do respect and trust my boss and have considered discussing it with her, but I’m afraid the answer will be there’s no way for me to get the experience I want in this role, or that it would damage my reputation here to indicate I might not be in it for the long haul.
So what gives? In some ways, this feels like a repeat of the difficulties of finding a first job when all entry-level positions require five years of experience. How can I land a job managing people when I don’t have any experience managing people?
Yeah, this is tricky!
It’s understandable — very understandable — that employers want to hire managers who already have experience managing because bad managers can have a huge impact, from an unhappy staff to lower work quality to legal headaches. And managing is hard and takes a long time to learn to do well. It’s a role that you really have to learn on the job, and so it’s easier to bring in someone who won’t be starting from scratch. Plus, the stakes are high enough when you’re hiring someone to lead a team that you want to be able to look at a candidate’s track record and see what kind of manager they really are, not just what kind of manager they hope to be.
Which, of course, raises the question you’re bumping into: How, then, are you supposed to get management experience in the first place?
Often people do it by starting in smaller ways: They lead a project, or manage an intern, or fill in for their own manager when she’s on leave, or work as a team lead. They build their skills through those sorts of responsibilities and get some initial experience with the range of challenges that come up in managing (like having tough conversations, giving feedback, setting clear expectations, correcting mistakes, and getting comfortable exercising authority without being a wimp or a tyrant). Once you’ve demonstrated your skills in those situations, it’s often easier to convince someone to hire you for a more formal management role. You’ll have specific examples you can point to showing how you’ve operated in a management context, and when interviewers want to talk about the mechanics of the job, you’ll be able to ground your answers in those experiences.
It can also be easier to get moved into a management role at a company you’re already at, because decision-makers have seen you in action and have an idea of whether you have the raw material that’s useful in a manager (like a willingness to confront problems and have hard conversations, an orientation toward making things happen and getting results, good instincts for dealing with people, and a high bar for performance). When people know you from working together, it can be easier to get them to take a chance on you. (Although the flip side of that is true too! In some cases, you might know from working with someone that you don’t want to put them in a management role.)
It’s also true that not every employer is as particular about requiring past management experience. In some cases, if you’re good at X, an employer will give you a shot at managing the people who do X. I’d argue that can be a sign that they devalue how hard managing well is and that it won’t necessarily be an ideal place to learn and get support as a new manager, but that’s not always the case and it’s definitely an option that’s out there.
So, where does that leave you? As a first step, talk to your manager! Tell her you’re interested in getting leadership experience and ask if she’d be open to things like you leading a project or managing an intern. It’s possible she’ll say that there’s just no opportunity for those things in your current role, but even if that’s the case, it’s unlikely to damage the relationship or your reputation. Obviously don’t frame it as “I need this experience or I’m leaving”; just say it’s increasingly an area of interest to you and you’re hoping there could be ways to incorporate it into your work. If your boss is a decent manager herself, she knows that people have ambitions beyond their current roles and that part of retaining good people is giving them opportunities to develop their skills. It won’t be shocking to hear that you’re thinking about this.
You might be surprised by what that produces! If she values you and thinks you have potential to do the work well, it’s not often that there would truly be no opportunities to give you more leadership experience, even if it’s just helping to coordinate a big project or being the point of contact for the rest of your team when your manager is out. And if she seems stumped, be prepared to make specific suggestions like that.
But if that’s a no-go, then your idea of volunteering is a good one too. I’d look less at board membership (which is often highly competitive and time-consuming and comes with fundraising obligations) and more at plain old volunteering, probably at a small organization that doesn’t have a management structure of full-timers.
The other option, of course, is to move to a job that has more room for advancement. I know you’re concerned that a lateral move to a role doing what you do now plus people management would only be available at less prestigious employers and for less money, but you might be able to move to a job that doesn’t include the people management yet but doesn’t have the same obstacles to advancement that your current job has.
So there are a bunch of options to consider! But start with your manager, since that could end up being the easiest and fastest way to move in the direction you want.
Order Alison Green’s book Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work here. Got a question for her? Email firstname.lastname@example.org. Her advice column appears here every Tuesday.