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How to have one on one meetings with your manager

One-on-one meetings are one of the most overlooked pieces of real estate when it comes to growing your career and growing your business. The one-on-one is incredibly valuable time that is often misused for the wrong topics and both parties lose in that equation. The employee loses because they're not getting enough advice and support to grow their career. And the company loses because the team member is not performing up to their full potential to help the business go forward.

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One of the best pieces of advice that I've ever heard on this topic came from Harley Finkelstein, who is the COO of Shopify, on Cameron Harold's COO Alliance Podcast, where Harley shared my one-on-one with Toby is my opportunity to get what I need for Toby to have a bigger impact and do my job better.

Let's look at what Harley says once again. He talks about the one on one as his opportunity to get what he needs to help Toby do his job better and for himself to have a bigger impact. The goal of your one-on-one is to figure out how you can do your job better and help your manager with his/her objectives. You need to be thinking about this every time you enter into that room to have a meeting with your manager.

In order to be able to do that, you need to make sure that you come prepared. You need to:

  • Bring an agenda of topics to discuss
  • Share updates on key items from your previous meeting
  • Progress on strategic initiatives
  • Business lessons learned
  • Failures and course corrections
  • People related topics
  • Resource related topics.

Notice the underlying theme of these topics. These are all directly connected to what is a priority for the entire business, and therefore, it's also what your manager would be accountable for and should impact what your priorities are on a day to day basis.

By coming into this meeting prepared with all of these topics you are communicating up. When communication is talked about, people often talk about communicating down to team members in terms of what they need. But one of the most important elements of being a leader or emerging as one is communicating upwards so that the people who are in more senior positions as you know what you're up to and know the impact that it's having on the business so they can figure out how to allocate resources and make more strategic decisions.

By constantly communicating up, you're keeping your key stakeholders in the loop and you're building trust. You're able to extract knowledge, insight and feedback from your manager. You're reducing micromanagement because as you communicate and build trust, people feel less of a need to come and get involved in the day to day. And you'll increase the amount of capital and freedom you have because people will realize whenever something important that requires their involvement comes up, you will be sure to loop them in.

And this is great, right? We all want more freedom. We want more autonomy to grow our careers. We want to be able to express ourselves creatively and be able to make decisions. So by communicating up, you're setting up that framework of trust so that you can go about doing your job even better.

Now, regardless of how often you're scheduled one-on-ones are, whether it's weekly, biweekly, monthly, you have to make sure you check in as often as possible in between. During your one-on-one, you're going to give all these updates and then there's radio silence until your next one-on-one. And that's the worst, right? 

So whenever important items come up, such as major milestones, critical changes to projects or iterations, you have to give transparency to the people that you're working with by regularly checking in. And that checking can be just five minutes, right? So either going in or finding five minutes on the calendar where you can just give the person a quick update, it can go a long way to help you build more trust and gain more autonomy to work on the items that you're working on.

A key thing to realize is that communication is one of your key job responsibilities, regardless of where you are in the organization. As you communicate and deliver more results, you will inevitably get more trust inside the organization. The conversations that you get to be a part of will become more strategic. You'll gain more freedom in your domain. You'll get more resources for your initiatives. You might get bigger teams to manage, and your responsibility will widen.

Over time, if you keep doing this over and over again, you'll slowly see yourself move from manager to director to VP, and eventually to a C level executive. All it comes down to is making sure that you're communicating well and delivering on the items that you're promising to the people that you're constantly working with. Every manager's dream is to have team members who over-communicate so that they themselves don't have to go chasing after team members. If you're that proactive team member and you're constantly bringing the right information at the right time to the table without getting caught up in the micro or the minutia of tasks, you will have incredible value to whichever organization that you work in.

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