Career conversations with your boss

I get it. It can be tough to have the courage to talk to your boss about what you need when it comes to career growth. But whether you seek money, higher status, increased visibility, additional resources or more time off, you likely won’t get it if you don’t specifically ask your boss for it. Here’s the good news: if done right, it shows both self confidence and respect for your boss by acknowledging that you are requesting, not just expecting, help.

We talk a lot about how to have meaningful career conversations in our Dare to be Deliberate workshops. It’s a skill that will propel you throughout your career by ensuring that you are clear about where you want to go, and you know how to enlist others to help you get there.

Five Steps to Career Conversations

1.      What outcome are you trying to achieve? Be clear about what outcome you are seeking. Example: salary, title, scope of responsibility, stretch assignments, oversees opportunities, flex time, etc.

2.      What do you do to prepare? Rarely will it work to just walk in to your manager’s office and ask for a raise. This is a process. Know your value in the marketplace by speaking with mentors, recruiters in your specialty area and others with knowledge of your industry/region/function.  

Gather feedback from stakeholders with whom you work closely or prepare them that you would like to give your manager their names to provide input during performance review time. If this is not a process already in place in your company, ensure you ask permission of stakeholder to share their names and willingness to share their experience working with you.

Be mindful of your company’s compensation cycles (i.e., have a salary conversation 6-8 weeks before salary review process starts instead of a week before those decisions are communicated…it is typically too late to influence the outcome then). Also think about how your company views titles. Some organizations are very flat, so there may be a wide salary band for a given title. Others may require a title bump to get the pay bump you are seeking. Identify standard practices in preparation for the conversation.

3.      How do you initiate the conversation? Request a meeting with your manager and indicate you would like to have a career conversation. (Even if your company does not have a formal program to have quarterly career conversations, I recommend asking to create a routine for a focused career discussion. Most leaders will welcome the initiative if you come prepared. Help them help you!) Your manager will likely ask if you want to talk about something specific (especially if it’s not a routine conversation). Provide context so they can also prepare for the conversation.

4.      What are your key messages? Questions? Proof points? Just like when preparing for an interview, know what questions to ask and have your key messages and proof points ready.

5.      How do you follow up after a career conversation with your boss? Write up a summary of your conversation with an action plan that the two of you can agree upon. The action plan should cover those things discussed that will help you achieve your career goals. There will be mostly items that you will be committing to, but also include those things your boss agreed to do for you.

Create a cadence of quarterly career conversations. These conversations should be a way to share your career vision and enlist their help to get you there. Review progress on your action plan and gain commitment on timelines for the requested raise or promotion.