Cube vs. Corner: Employer and Employee views on Career Planning

Cube vs Corner


When I was new in the workforce there was a big emphasis on “Career Planning”. You would have a big meeting with your boss to discuss your “career goals”. You were supposed to already have some idea of where you wanted to end up in 5-10 years, then work backwards from there and decide what developmental assignments or skills you needed to learn in order to get there.

Looking back on it now, it feels a little out of place — like something they do in communist countries. You want to be an engineer? Okay, we’ll get you on that path and that is what you will BE, for the rest of your life. I’m guessing the jobs that will be in the market 5 years from now don’t even exist today!

career planning with the boss

That said, thinking ahead about what my long term career goals were, and what skills I needed to develop or learn in order to reach those goals, wasn’t such a bad thing. It meant that I felt really in control of my career — I knew what I had to do now in order to end up where I wanted to go (or where I thought I wanted to go). Information in this case is some kind of power.

Is having a career planning conversation with your boss taboo? How are younger people in today’s workforce approaching career planning? How do you know what skills or experiences you want to pursue? How do you even set career goals in a marketplace that’s changing so rapidly?



My initial reaction was, “Why would I talk to my boss about that?” If you were looking to leave a company or move into a different field, it’s not something you’d want to tell your employer. Otherwise you’d be afraid of getting fired. If I’m on the fence about my career or job, it makes more sense to go to peers or a mentor to help figure it out. Telling the boss seems like a big no-no, communicating a lot of stuff to my boss that would make it look like I’m not committed to my role or the company.

I think I could speak on behalf of a lot of my peers that I think most of us would like to be able to have career planning conversations with our bosses. But I really think that’s in the boss’s court to build trust and transparency in the relationship to make it possible to have an honest and comfortable conversation about it.

As for how do we go about career planning? I don’t think a lot of us really have any specific way we figure it out. We’ll read articles and talk to friends and mentors to get advice, but don’t have any main source of direction. I think that might attribute some to Gen Ys feeling “lost” a lot of the time with their careers or what they want to do.



So it looks like Forbes columnist Paul Brown agrees with you. But it makes me a little sad. Other than you, who has the most to gain from an open an honest career conversation? I think your boss does! If he/she can understand where you think you want to go, then she can help you to get the assignments and training you need to get there. If there is outside the company they can also plan for that (at the appropriate time). I don’t know about you, but a plan that includes leaving the company, but spans across 6-months to a couple of years is better than two week’s notice any day of the week. I wonder, too, if you are right about the perception of disloyalty — you might be. But I’m always telling business owners that it’s OK for people to move on — you can’t keep everyone. If someone’s interests aren’t aligned with what you need for your business, better to find that out sooner rather than later. Maybe another senior person in the company, who’s not your boss, might work…

Because this discussion does require trust and if you have a “crappy boss” then it’s not going to work. Still, I have to wonder, why stay with a crappy boss? The #1 reason people change jobs is because they don’t feel supported by their bosses. Come to think of it — that’s a pretty good reason for bosses to have more of these career planning discussions. If you can actually have this conversation without getting resentful, or taking it personally that people might think of working somewhere else, you might win some trust from your team and actually make it LESS likely that they will leave.

Which leaves me right where I started, is it worth the risk to try?




Yes and no. I think you can take a different spin on it to help you get some information though.

I tell friends that they need to take control of their career (because no one else will do it for you). So when looking for jobs, and in your current one, find out what opportunities exist in the company that you can strive to move up to. And maybe, to feel out how your boss would respond to a “career conversation”, ask him/her what the next position opportunity might be and find out what you can do to become a good candidate for that position. Maybe you’ll be surprised to find how easy it is to expand the conversation from there!

But even then, I think it is hard to get around that fear that you might accidentally offend or freak out your current boss.

How would you talk to employers that are like the ones I described? What reasons would you give them for why they should meet with their employees on Career Planning?


  1. Every situation is different. It depends on the leader of the organization.

    If they’re authentic, really care about the future of their constituents, they’ll welcome career discussions with the team.

    On the other hand, if the leader is not transparent, or inauthentic, Gen Y won’t want to broach the subject.

    One company that gets an A+ in this area is Zappos.

    After an introduction period, say four weeks or so, they offer the new hire money to leave. That’s right. Here’s a check for $400 or $1K, depending on the position, to leave the company. Zappos does this to make sure they have someone on the team that really wants to be there.

    They also have an internal trained ICF coach ( like me ) who meets regularly with staff to learn what they want to accomplish both personally and professionally.

    In fact, if someone wants to start their own business, Zappos management will try to help the employee find a way to make this happen sooner vs. later.

    Cool huh?

    • Steve;

      That is cool!

      Your comment is telling because the company is working to build that trust with employees from the very FIRST DAY of work.

      I think where people get in trouble is when they wake up one day and say, “Hey, let’s talk about your career!”

      I still wonder about the uncertainty though. Do you feel like your career is likely to follow a “straight line” or is it possible that your next job hasn’t even been invented yet.

      • Most are ambivalent about their future.

        Management should encourage upward mobility in the organization.

        The people that are intentional about where they want to be are the future leaders within the company.

        I was surprised to hear GE does a very good job of grooming future leaders very early in their careers.

        Management constantly scans those with leadership potential. Then, they feed the individual with what they need to be great.

  2. Hi Brad,
    Thanks for the great conversation in this blog post. I’d say that, even if your employees move on, it’s not a bad idea to have career discussions with them. My experience has been that there are some employers (and entrepreneurs) who have learned the benefits of gaining a reputation for fostering talent. It can make it easier to recruit, especially if you can’t compete on salary or other compensation. Thanks for sharing with the BizSugar community.

    • Heather;

      Some small business owners are very good a growing talent — and these types of conversations are terrific for those. I agree that even if some team members leave (Weren’t they going to anyway?) when the other team members see that you are serious about investing in their growth they will frequently respond with greater engagement.

      Thanks for commenting, Heather!

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