10 Tips for Having 1 on 1 Meetings with Your Boss

I recently asked readers to submit their burning leadership development questions. Those that get picked for a post will receive a free copy of my eBook.

This question from Jennifer:

“Can you give us some tips and tricks for 1X1 meetings with your boss, including how to prepare for the meeting and ways to discuss your career and goals?”

Sure can!

I’ve written a post on the same topic for managers: How to Have an Effective 1 on 1. So, I’d suggest starting with reading that in order to get an understanding of what your boss is looking for.

However, let’s assume most bosses haven’t read that post. After you anonymously leave it on their desk, here are some “tips and tricks” written from the employee’s perspective, on how to have an effective one on one meeting with your boss:

1. Request regular one-on-ones with your boss. I’ve only had one boss where I had a hard time nailing him down for regular meetings, but most have readily agreed. You don’t have to sit back and wait. Everyone, at any level, from entry-level to executive, should be having regularly scheduled meetings with their bosses. The frequency, duration, agenda, and style may vary, but it’s a must!

2. Prepare an agenda. Many bosses don’t – they expect you to. They see it as your meeting. And if they are the type of boss that sees it their meeting, with their own agendas, then request to add your agenda items to theirs.
I like to send my boss a copy ahead of time so they have a little time to prepare, even if it’s the same day. But if not, at least bring two copies to the meeting with you. It helps put you in the driver’s seat, and from a practical standpoint, gives your boss something to take notes on, put in your file, and refer to for your next meeting.

3. Keep your boss appropriately informed. By “appropriately”, I mean a very succinct, high level summary of all of the key things you have been working on. This is your boss’s chance to ask questions, coach, and reinforce. This is also a chance to highlight your accomplishments. Hey, if you don’t, no one else will! You can, and should “toot your own horn” in a very humble, matter-of-fact way.

4. Cliché alert…… if you bring a problem, always bring your recommended solution. If you need a decision made, always bring your recommended decision. Yes, it’s getting to be a horrible cliché used by the Pointy Haired Boss in Dilbert, but alas, it’s true. Yes, there may be problems in which you really have no clue where to begin (maybe you’re new in the job), but they really should be the exception.

5. Own up to your mistakes. Read How to be Accountable and Hold Others Accountable. If you screwed up, make sure your boss hears about it first from you. No surprises, no finger pointing, and no excuses!

6. Don’t ask your boss to prioritize your work. If you’re swamped and feeling overwhelmed, it’s OK to let your boss know that (again, but not on a regular basis). However, unless you want to be micromanaged or seen as incapable of managing your own time and priorities, don’t show up with a list of projects and ask your boss to rank them.  Better to rank them yourself, and ask your boss to verify (“I just want to make sure we’re on the same page here as far as my priorities”).

7. Always come and leave with a positive attitude. Yes, some will say it’s your boss’s job to pump you up and keep you motivated – and if you read the post I wrote for bosses, I said it is too. But that doesn’t let you off the hook – bosses – and coworkers – would much rather work with competent and positive people. No one likes a Debbie Downer. As a manager, I’ve had employees that I’ve looked forward to meeting with and those that made me want to hide under my desk.

8. Make sure you include development (including career development) as a regular agenda item. Whether your company or boss requires one or not, ask your boss to help you create an individual development plan (IDP). It’s a chance to ask for feedback (before it’s too late), enlist his/her support in your development, and demonstrate that you are ambitious, self-aware, and have a desire to improve. You create the first draft, and then get your bosses input. Bring it with you to your meetings 3-4 times per year to show progress and keep it updated.

9. Occasionally ask for feedback (read18 Tips for Receiving Feedback first). Sure, again, that should be your boss’s job to give you feedback, but most don’t, and if they do, they find it terribly uncomfortable. However, if you ask them for it, you are opening the door and making it much easier for them. Hey, they may even turn around and ask you for feedback in return! When that starts to happen on a regular basis, you’ve got a really good trusting and supportive relationship.

10. Let your boss know what you need from them in order to be successful. Don’t assume they know. Not all managers are intuitive, sensitive, or can read your mind. And some experts suggest that women don’t ask as often as they should. If you let them know in a constructive way, most will do what they can to support you. After all, your success is their success, and then they get to go home feeling like they did their job as a manager.

If you do 1-7, then you are more likely to establish a foundation to discuss 8-10 and get your own needs met.

Follow all 10 tips and you might even help turn your average boss into a great one!