How, when and why to have performance and career discussions with your boss

Are you comfortable having a discussion with your boss about your performance and career goals? If not, it does not necessarily mean you have a poor relationship with your boss, it could also be that you are shy or awkward talking about yourself.

With a little bit of preparation, you will feel more confident having a discussion with your boss or manager.

What are the top five things a person should do to prepare for a discussion with their boss?

  1. List the areas you want to discuss.
  2. Rank their importance. If you run out of time, you want to cover what is important before you leave the meeting.
  3. Conduct a pro/con analysis about the subject. Think through the options.
  4. Know what action(s) or outcome(s) you want out of the discussion. Are you looking for feedback, support, background information or direction?
  5. Make a concrete plan and gain their commitment.

Who should initiate a discussion? There is nothing wrong with you asking to meet with your boss to discuss your performance or career goals, even if it is not during the company’s standard review time.

You may catch them off guard if it is something that other employees do not approach them with during the year. It is always a good idea to give them a “heads up” about the discussion ahead of time so that they are prepared to give you the coaching or feedback you need to be successful.

How often should I discuss my performance with my boss? If you believe your performance is off track, schedule a meeting now even though it may be difficult. It will be much easier to gain their insight and support to get yourself back on course.

A good manager will help with removing roadblocks that prevent someone from being successful.

Removing roadblocks is not doing your work; it is running interference in organizations that may inadvertently make getting things done more difficult and create more work.

If there is no urgency for manager intervention, keep your boss informed of your progress at periodic times – it might be weekly, monthly or quarterly.

The timing will depend on your experience and how often your boss likes to be updated. When in doubt, ask him or her how often they prefer to meet or communicate with you.

Sometimes bosses become unavailable, it is up to you to make it happen.

How often should an employee discuss their career or development objectives with their boss? If you are talking to your boss about your career on a daily basis, I can guarantee it is too much. The message you are sending is that it is all about YOU and not about what you can do.

The company wants to know you are able to perform in your job and take on increasing levels of responsibilities before they contemplate promoting or moving you into a new position.

A good rule of thumb is to initiate a career discussion about every six months to discuss your progress – not to ask for a promotion.

Consider calling it an “update meeting” to discuss the skills you have learned and how you have applied those to specific projects, tasks or initiatives.

Companies are not interested in knowing that you checked the box to learn a skill. What you learn can become dormant if it is not used.

However, applying your skills to a new and unique situation shows that you have the capacity to work in more complex situations. Those kinds of discussions will make an impact and will keep you top of mind when the next promotion or big project comes around.

About Lynn Dessert (415 Posts)

Lynn Dessert is an ICF trained certified NLP Coach specializing in Executive, Career and Life coaching based in Rochester, N.Y. She works with individuals and organizations to maximize personal effectiveness skills—a cornerstone to career advancement. Lynn is the author of What To Do After Being Fired and The Secerts to Successful Job On-Boarding. Start your discovery process by contacting her at 585.249.5149 today.


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