Using Career Aspiration Conversations to Increase Employee Engagement and Retention

We live in a day and age where job-hopping is not only a trend, it’s the norm.

So how are managers supposed to retain talent and keep their employees engaged at work?

While reading The Alliance by Reid Hoffman (founder of LinkedIn), a specific story stood out to me —

Reid convinced an early candidate who wanted to get a job in venture capital, but lacked startup experience, to come work for him at LinkedIn for a few years. In exchange, Reid offered him the experience he needed and a personal letter of recommendation to get into a top-tier VC firm in the future.

Reid Hoffman knew up front that this employee was going to leave (and he did, for Facebook and eventually a top-tier VC firm) and that this was only going to be a “tour of duty,” but in return, Reid received an “engaged employee who’s striving to produce tangible achievements for the firm.”

No one goes to work for one company for life anymore, so why should we pretend that they do? Why are we afraid to to talk to our employees about what they want next in their career?

We’re probably afraid they’re going to leave, but what I’ve personally found is that focusing on what is next on an employee’s career horizon might actually keep that employee more engaged and more likely to stay.

Now, this career-aspiration conversation is one of the first ones I have with new employees and direct reports, for a few reasons:

First, recognizing and admitting that an employee is going to leave one day for bigger and better things not only shows that you are invested in your report’s career, but it immediately builds trust between you and your report — because if you can talk about quitting your current job with your boss, what can’t you talk about?

Second, by offering up what your own next career step might be as a manager and engaging in this “what do you want to be when you grow up?” conversation, you build rapport with your employee and get to know them on a personal level AKA their hopes and dreams.

Third — and most importantly — once you understand their career aspirations, you can use that knowledge to identify business problems/opportunities that line up with their larger career goals, which will ultimately keep them more engaged and excited about their current job.

I manage teams of over 50 employees at Uber that talk to new drivers. To date we have interacted with hundreds of thousands of drivers across the U.S. and Canada. This team is one of the most diverse teams at Uber, with people from all different backgrounds and professional experiences.

One of my reports (let’s call her Sarah) wants to become an HR Business Partner (HRBP) at a large company one day — that’s her “North star” career goal.

Knowing this, I’ve been able to identify business needs on my team — interviewing and training — that align with her own personal and professional goals. Sarah now leads on-boarding for all new hires on our team.

I’ve also connected her to our company’s HRBP and she has been completing small projects with her on the side, and is actually traveling to another office next week to help present the work and research she’s conducted for that HR team.

Sarah is a top-performer on the team, which (as I like to say) “affords her the opportunity” to work on these side projects. These projects help our team and also serve as growth opportunities to enhance her career. It’s a very clear win-win.

Another one of my reports (let’s call him James) is very interested in Product Management and wants to explore that as a potential career path.

As it turns out, a large portion of my job includes interacting and collaborating with Product Managers and Engineers across multiple product teams at Uber based in San Francisco, Seattle and New York City.

Since I know that James is interested in becoming a PM one day from our career-aspiration conversation, I’ve been able to get him involved in those interactions, and now he is responsible for gathering user feedback from our drivers and creating valuable feedback loops with those teams.

We’ve also talked about making his schedule more flexible at work so he can attend UX/UI courses after work to continue his exploration into the world of product design and development.

By doing this simple act (being flexible and allowing him to leave 30 minutes early 1–2 days a week), I’m showing James that I care and that I’m willing to invest in his career.

As a result, I’ve provided myself more bandwidth by getting James involved in these areas, and more importantly, provided a valuable growth opportunity for James that keeps him more engaged because he’s working on projects that he finds to be personally valuable.


I know that one day Sarah and James are going to go off and do bigger and better things in their careers (and if they don’t, then I’m honestly not doing my job).

But since I genuinely care about them and show interest in their career aspirations, they are more engaged, and in turn, are much more likely to continue working on my team because I’m creating valuable experiences for them.

Do you know what the next career step is for each of your employees?

When was the last time you had conversations with your reports about their career aspirations?

Do you agree with this, or do you take a different approach?

I’d love to hear about it!