How to start One-on-Ones with your Boss

Tip: Get a best practice email invite for a one on one meetings with your boss here.

If you’ve had a boss who did regular, high quality One on One meetings with employees (like this process here) then you know how important these meetings are. Because they keep things moving forward, they keep priorities aligned and they keep relationships running sweet. Good bosses invest time in 1 on 1 meetings because they know how to use them to get a lot more back than the time they invest. But it’s not just about the bosses because One 2 One meetings are essential for employees too because this is how you:

  • Let your boss know what you’ve achieved,
  • Problem solve with your boss,
  • Make sure you’re working on the right things in the right way and,
  • Work on your future.

If you’re not sure how, I show you in this free short course on 121s for employees (which include agendas and templates). The course also gives you the best tips on how to manage up.

But the question is what do you do when your boss doesn’t have one on one meetings with you? Well like all things in life, you can passively wait for it to happen or you can take control of your destiny and ask. Here are some tips to avoid getting a no answer. Including an email request for a One on One meeting with your boss for you to download. Don’t miss the super user tip at the end.

Before emailing is your boss a texter or a talker?

But before you send an email, does your boss prefer spoken communication? That’s because a one way email is not really communication. You will have better results when you speak to people face to face. If you do choose to speak instead of email you can still use the email template as a guide to what you should cover in the conversation. But if you do prefer to speak first then follow up with the email as a reminder and reference.

P.S. this article has guidance for how you can go about starting one on one meetings with your boss. To get the email template for a one on one meeting with your boss, download it here

Firstly It’s Your Boss so You Can’t Tell Them What to do

The first thing is a little bad news and that is you can’t tell your boss how you would like them to manage you. Your boss is in charge and that means they make the final decisions. And my experience is that bosses are sensitive to criticism about how they manage people. And the messed up thing is that the less they know about being a boss the more likely they are to get defensive.

If you have a boss who isn’t doing One on One meetings with you this is a sign that your boss hasn’t had any manager training. I know because I never used to do proper One on One meetings with my staff until someone showed me how. But even if you have a boss who has no idea about what they are meant to be doing, you can take personal responsibility to improve things because there are still things that are in your power to control.

Trust in the process and engage your boss in the vision

Firstly accept that you will not achieve perfection straight away. And maybe you never will achieve perfection. There’s a lot going on in a one on one meeting and I’ve been doing One on Ones for years and I don’t claim to be perfect at them. But you can still get most of the benefits by starting off small and building. Instead of telling your boss what to do, engage your boss by telling them what you’re trying to achieve and asking for their input on the process.

You could call it a status update meeting but..

Now some people recommend that you shouldn’t ask for a one on one meeting with your boss. They say you should instead ask for time to give “Status Updates”. Now I don’t like this because I think it’s condescending to your boss. And you run the risk of being bundled into a team status update meeting or getting told to “just email it” instead. It’s not a one on one meeting if it’s with the team or if it’s not even a meeting! But if you have to call it a status meeting to start off with then do what you need to do.

You don’t have to ask for a yes - you only need to ask them to try it

Now you may be sold in your head and ready to book the next years worth of meetings. But your boss isn’t in the same place as you and wants to avoid adding tons of meetings to their calendar. Instead of trying to do the hard sell to get your boss to commit a year's worth of meetings, it’s so much easier to ask your boss to try the process.

Don’t ask for a recurring meeting straight away

So before your boss sees the tangible benefits of meeting with you they are unlikely to want to commit to recurring meetings. So what you can do is book the first meetings on an ad-hoc basis. And in each meeting finish up by asking your boss if they found the meeting helpful and what they’d like to change for the next meeting.

Show your boss what’s in it for them, keep the meetings valuable and soon your boss will be asking you

Like any sales job, it’s going to be easier if you show your boss what is in it for them. And then it’s up to you to keep the meetings valuable by being focused and fast. When you demonstrate the value of one on ones to your boss then instead of you asking your boss, your boss will be the one that wants to have one on one meetings with you.

You don’t have to do everything at once either. Start small and build up

Now you’re probably keen to talk to your boss about your growth and next promotion. But if that’s the first thing that you ask your boss then they’re going to feel like the one on one meeting is entirely about you. Start off small, make sure your boss get’s the value. Later on you can progress to more complicated topics such as training and career development. And this makes it simpler for you too - because change is always easier when you can break it up into more manageable chunks.

Super User Tip: Take it over from your boss

Bosses like employees who take initiative to make things happen. Most bosses have a lot of demands on them to do all sorts of things that sound like a good idea but they simply don’t have enough time to do everything. If you want something the best way is often to take over the administration that’s required to make it happen. For your boss all the administration around running a One on One meeting process such as finding time slots, setting agendas, recording follow up etc. is a small bit of stiction that stops the process from starting and gaining momentum. So offer to take ownership for this and you will gain greater power over your destiny.

Next Steps:

So your next steps are to download the email invite for a one on one meeting with your boss. Make sure that you have signed up to the short course (121s with your Boss) to:

  • Find out how you can have great 121 meetings with your boss,
  • Improve your growth,
  • Get better bonuses, promotions and increases,
  • What mistakes to avoid.

Remember when asking your boss for a One on One meeting, don’t come across as critical or condescending, show your boss how they benefit. Be concise with a clear explanation of exactly what it is you want your boss to do.


Comments:

Do you have any questions, comments or tips about starting One on One Meetings With Your Boss? Do you have any good tips on how to manage up? Please share in the comments below.


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