Allison Cheston, Career Connector


Career Connector Blog

Get the Feedback You Need to Get Better at Your Job


I have a 23-year old client who is doing a one year, post-graduate fellowship. During our call this morning he told me that while he enjoys his work it can be slow and that his bosses don’t give him as much work as he’d like. In fact, they expect him to take initiative and suggest work he thinks needs to be done. While he has some ideas for new projects he struggles with how to initiate conversations with his boss who seems so busy with more important work.

Millennials have been criticized for being the product of helicopter parents who have scheduled their every waking hour throughout their young lives. Once they are old enough to have an internship or a job, they can be uncomfortable taking initiative and may be anxious about making mistakes and therefore avoid taking risks. Employers, on the other hand, are looking for those who move confidently ahead and can get a lot done. Ideally they are also creative risk-takers – those who are willing to fail in the name of a great idea.

So what should recent grads keep in mind when navigating new jobs where roles and responsibilities are not always completely clear and expectations can make them uncomfortable?

Schedule the feedback you need.
I hear this all the time from millennial clients. Unsure of whether they are on the right track at work they are afraid to annoy their boss with requests for hand-holding or feedback. But without that feedback their insecurity paralyzes them and they end up doing a less than stellar job.

Mitigate against feeling anxious by making periodic appointments with your boss to check in and get feedback. Do not wait for or expect your boss to make appointments with you; most bosses are too busy with their own work and managing their own bosses to worry about giving you feedback or knowing when you’re struggling. I know this can be disappointing to high-achieving Millennials accustomed to regular and well-intentioned feedback but this is not the norm at work. I heard someone say once that in moving from college to the working world you go from being asked what others can do for you to being asked what you can do for others. Your job is to make your boss look good and alleviate her stress, so start thinking about how you can be of service, not the other way around.

Don’t be afraid to ask questions.
But make sure you’ve done thorough research – gone as far as you can –  before you do. The last thing you want to do is add work for your boss by interrupting her with questions you should be able to figure out on your own. There’s a difference between interrupting and clarifying; more clarity leads to better learning and better work. And next time you won’t need as much help.

Don’t take initiative just for the sake of it.
Yes, you should focus on developing new ideas and working on bringing them to fruition. But taking initiative isn’t always a good idea – there should be a good reason behind it. Before you bring your great new plan to your boss, make sure you’ve done the research and talked with as many helpful contacts as possible to determine whether it’s an idea worth executing on.

The more thoughtful and well-documented your proposal, the better chance you’ll have of being able to act on it – and maybe really move the needle on your career. Craft a one-pager with the business case for your idea, ideally with a rough forecast of how it will save or make the organization money, to enhance your chances of success.

Participate in Millennial networking events to gain insights.
The more you talk with others your age and at your experience level, the more confident you’ll become at managing your career. Take advantage of the substantial programming targeted at young professionals, both virtual and even better, in-person. Attend talks about managing your career and make contacts. Read blogs like The Daily Muse and check out organizations like FindSpark for advice, jobs and events. Contact the career office from your college or grad school and attend alumni events in your city. The more you hear and share with others your age, the better you’ll become at maneuvering around common pitfalls. Most importantly, you’ll enjoy work more as you become more successful.

Send me your questions and stories about managing your career and I’ll respond in this blog, at