🤓 How to manage up your 1:1 with your boss?

Thoughts by Ronen Shetelboim, #4・ Mar 15, 2022

I normally post only once every 2 weeks.

But!..

Last week I wrote about how managing up and sideways can make you a better leader.

And..

I got some great questions about how people can better manage up their boss.. specifically, 1:1 meetings with their boss.

So..

I decided to write a short bonus post this week.

I am super passionate about this topic.. mostly because I think it’s important for personal growth, development and career advancement of managers and leaders.

But, also because.. well.. I made some mistakes in the past 😅 , so I hope you can use my 2 cents here and avoid those mistakes. 😉

So.. without further ado, let’s get into it.👇

11 things you can do right now to better manage up your 1:1 with your boss

1. Shift your mindset. You should think about your 1:1 meetings with your boss as the most important meeting of the week! If you don’t know what to talk about, the meeting ends early or you are not taking plenty of notes.. something is wrong.

2. Come prepared. Prepare for your 1:1 meetings with your boss in advance, at least the night before. You should come to every meeting with at least 1-3 topics to discuss. When building the agenda for your meeting with your boss, consider these ideas:

   • Is there anything specific you need help with?

   • Is there anything you want them to know?

   • Can you anticipate what questions they might have for you? 💡 Pro tip! It’s always good to review numbers, data and projects statuses before your 1:1 with your boss and have your data accessible during the meeting. You never want to be surprised, you want to show that you are in control, in case they want an update on something specific.

   • Do you know what’s top of mind for them? If yes, great! Make sure you touch on relevant items. If not, ask, so you know for the future. 

   • Is there anything you can do right now to make them look good in front of their boss?

   • Is there anything they asked you to check, read or follow up on? If so, make sure you follow up and close the loop. Yes.. even if they didn’t ask you about it. Be proactive!

   • Send a meeting agenda in advance, at least the night before. It can be short and sweet, just highlight the topics you want to cover. 💡 Pro tip! Keep the agenda focused on maximum 3-5 items. It’s better to cover less topics and go deep on each topic, rather than to try to cover too much at once.

3. Own the meeting & manage time wisely. People often think that their boss is the owner of the 1:1 meetings, so the boss should lead it. But that’s not true. This is valuable time that your boss dedicates to you. The time is for you. Use it wisely. Make sure you are in control of the time, the agenda and you drive the discussion. Consider the following agenda for 30 minutes 1:1 meeting:

   • 5 minutes chit chat

   • 10 minutes to go over 1-3 key items on your list

   • 10 minutes to go over 1-3 key items on your boss’s list

   • 5 min keep it open in case you want to expand on any topic

4. Don’t be late! In fact.. Get there 5 minutes early, so you can start right on time. Yes.. even if your boss is late. Getting there early shows that you are in control, that you respect your boss’s time, it will also give you a few more minutes to organize your thoughts and make sure you have everything you need with you (for example: your laptop is working, you have wifi, slides are working, reports are ready to share, pen and paper, glass of water.. you get the idea). 💡 Pro tip! If you change your mindset and think about this meeting as the most important meeting of the week, you won’t be late, you’ll be ready and right on time. 😉

5. Over communication is key! It’s always good to over-communicate. Over communication before and after your 1:1 meeting with your boss will ensure a successful 1:1 meeting. It’s especially important if you just started a new job, if you are trying to build relationship with your boss, or if you have a new boss. Think about it for a second, no one ever complained that they knew too much about what’s going on in the company. The more insights you have, the better you are setting your boss up for success, the better you are setting your company for success and yourself. You can also use over-communication to showcase what you've been working on, in case they are not aware.  Rule of thumb is to over-communicate unless you are told that you don’t need to anymore. Here are 2 ways you can over-communicate effectively:

   • Monthly or bi-weekly written status updates. Send those to your boss and your team. Written updates will help you think through your world in detail, writing provides clarity, clarity shows that you are in control. These updates can include the following topics: progress vs. targets, what’s working / not working, any other insights or observations. 

   • The FYI.. for your visibility email. There might be scenarios where you don’t really need your boss’s input. But, you want them to be aware of something, ensure they are in the loop, or to show them you are simply making progress on something they care about. So.. you can always forward them the latest communication on a topic and just say “FYI.. for your visibility’’.

6. I don’t know, but I’ll get back to you. What if your boss asked you a question that you don’t know the answer to?  Say you don’t know, and follow up after you get the answer. Don’t guess, don’t make up an answer, and don’t forget to follow up. 😉

7. Make requests, not complaints. Show that you are solution oriented and be clear on what you need. For example, you can say: 

   • This is a problem I am seeing.. (describe the problem)

   • It’s a problem because.. (explain why it’s a problem and why it’s important)

   • Here is a solution I propose.. (describe your solution)

   • Here is what I need from you (be clear on action you are asking from your manager)

8. The pre-read written 1-pager memo (the Amazon way). If you are working on a big or complex project, you should create a 1 pager written memo and share it with your boss in advance to get their feedback. If your boss doesn’t have time to pre-read, you should use your 1:1 meeting to go over the memo. You can let your boss know that you want to dedicate 10 minutes at the beginning of your meeting for them to read the memo and comment in the doc. You can discuss their comments in the same meeting (1:1) or schedule a follow up. This is pretty much how they run meetings at Amazon. (you can read about it here).

9. Ask for feedback, don’t wait to get feedback. Assume your boss has millions of projects on their plate and perhaps they are trying to manage up their own boss. So.. if you want feedback on something ask for it. Don’t wait for it. 

10. Your own career growth. Explain where you want to go and see if your boss can guide you on how to get there. You know yourself best, don’t wait for your boss to tell you where they want you to go, be proactive. If you don’t have time to discuss this topic in your 1:1, consider having a monthly / quarterly cadence where you discuss your growth and career path.

11. Building a strong personal relationship with your boss is important. You can read more about why building relationships is important and how to do it, in one of my previous posts - “Most Underrated Secret of Success”.

That’s it! Enjoy the process, let me know if you have any questions.

P.s. if you like my newsletter and find it helpful, it will mean the world to me if you can share it 🙌, so it can help other managers and leaders 💛 . I tried to make it super easy for you to share.. below you have 2 options for sharing: 

• Option 1: copy the text below and paste into a text message, Linkedin post, twitter, email or any of your favorite networks:  “I really enjoy reading the newsletter Thoughts by Ronen Shetelboim, you should subscribe, I think you’ll enjoy it as well”. 

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