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How to Have A Career Conversation With Your Boss

julieaverillshore

Updated: Aug 1, 2024

What do careers and grass have in common?


You have to water them - for them to grow.


Last week I read this quote which has really stuck with me (something to the effect of):

The grass is greener where you water it.

 


Many times my career clients wonder if there is a better boss, job or organization OUT THERE... SOMEWHERE for them.


Maybe. Maybe not.


Often times, that is part of my work as a career coach- should my client stay or should they go?


The short answer: it depends.


Are you empowered to have a

'career conversation' and do you want to?

Are you brave enough?


Performance reviews are becoming obsolete.


  • Raise your hand if you love to give and/or receive a performance review?


  • Raise your hand if you love completing a self evaluation?


According to a recent Gallup survey, only 1 in 5 employees feel that their current performance review system at their organization is inspirational, fair or transparent.


Enter- career conversations.


There doesn't have to be a set time or rigid system. Now, granted, not all leaders/managers do this naturally. So, perhaps some guidance, coaching or guard rails on this would be helpful.


And the data continues to be abysmal... as we know that approximately 85% of employees are NOT engaged at work.


What does it mean for an employee to be engaged?


Well, typically an engaged employee will:

  • Take initiative

  • Care about their work

  • Ask thoughtful questions

  • Be proactive and is often an open communicator

  • Analyze a situation or data and provide recommendations

  • Has a positive, optimistic attitude

  • Keeps the big picture in mind while focusing on the day to day


So, quite the opposite you will find in a dis-engaged employee:

  • Makes excuses / plays the victim

  • Doesn't openly share information with peers, colleagues or bosses

  • May not put in full effort; may do the minimum to get by

  • Isn't responsive or communicative

  • Could be late or have attendance issues

  • Tends to drop problems at your door


With one out of three people being unmotivated and dissatisfied in their work (and this has been for quite some time) doesn’t it behoove us to be proactive and have a career conversation at work? No matter if you ARE THE BOSS reading this, or you are trying to summon some courage to have a conversation with your boss...


Ask yourself:

  1. Can I afford to NOT have a career conversation at work with my boss or employees?

  2. What is the consequence of looking the other way?

 

Too often for the people I coach I hear of a story of them being paid what they feel they deserve when they finally raise their hand and say they’re going to leave. And then, they second guess themselves, their values and their decisions.


While changing jobs may be what you need most right now or a healthy option to help you grow further in your career, don't make a move pre-maturely because you are too afraid or don’t know how to have a career conversation.


Here are five tips for being proactive and managing your career to have a career conversation.

 

  1. What's your why? This is often the root of much job dis-satisfaction. Your 'why' or key motivators have shifted since you first took your job.

    1. What do you value?

    2. How do you define meaningful work?

  2. Are your goals within reach that you are striving for? Daily tasks or issues will always arise, but what are you truly pushing for? In other words, why does your job exist?

 

Outside of the performance review, you should be checking in at least quarterly to see if you’re on track or off track with key goals or initiatives.


A goal only in your mind is hazy at best.

 

3. Ask to get involved.


If you see a new initiative or perhaps you even sense some bad news coming down the line, ask how you can help or add value. Proactivity is always better than reactivity.

  • Can you lead a committee?

  • Can you do jump start some research?

4. Don’t be afraid to discuss things you’re excited about as well as disappointments.

 

Too many times I've seen employees and managers/leaders alike (both in my corporate HR role as well as in my current role as a career coach) wait until that dreaded annual performance review where it is too late to course correct how an employee has been spending their time, or change a process or shift focus on something that better aligns with expectations. And often times these hard conversations are dreaded by everyone; personality conflicts arise; and good employees may even quit.


5. Bring data. Know your accomplishments. Be able to quantify how you’ve been spending your time and what you have accomplished, or the value you’ve added. Then, you will be in a much better spot to proactively ask for what you need at work whether it’s compensation, another team member, more physical, monetary or human resources, etc.

 

6. Map out the plan. Based upon what you know the organization's priorities are, be proactive and map out your key initiatives that you propose over the next 6 weeks, 90 days, 3 months and 6 months and beyond.

 

TIP: And whether you realize it or not- a natural byproduct of being proactive and having a brave career conversation is, you are essentially updating your résumé at the same time!


If you don’t ask, the answer is always no.


Who will YOU schedule a career conversation with in the month of August?



 
 
 

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