Fruitful 1:1s with your manager

In the past year, I’ve spent a lot of time with my manager in weekly and monthly 1:1s. There was a short period of time when I consecutively cancelled my time with him for various reasons viz. no agenda, unavailability, or just sheer guilt to face my unproductive week or a month. However, I soon realised, skipping this time with them is one of the worst negatively-compounding decision you can make for your career. Since then, I ensured that each 1:1 has a great agenda to talk about.

Below, I’ll dive into my ways of driving 1:1s. I hope you learn a thing or two, and make yours more fruitful.

What’s a prerequisite for having a fruitful 1:1 with your manager?

Each point below acts as a prerequisite for the following one.

  1. Self-reflect: As Socrates said, “To know thyself is the beginning of wisdom.” The more you understand where you struggled or excelled, your strengths and weaknesses, the better you can help your manager to help you. You need to know where you need the most help; you need to know what you did really well. Give your manager an opportunity to learn from your failures and successes.
  2. Trust manager and process: To begin with, you need to put a complete faith in your manager to give you continuous and helpful feedback. Manager is equally responsible for earning your trust. You may find yourself reporting to someone newly hired or promoted manager. In that case, you both need to start with complete trust in each other to be a great manager, and a great report. Additionally, you need to trust that 1:1s are a great way to help you grow.
  3. Ask for help: It’s easy to fall into the trap of I should know it all. It’s important know that you’re hired to find out the answers; not to have all of them. The sooner you learn to ask for help on the right thing at the right time, the more successful you will be. Your manager is best suited to help you find the answer. Again, they may or may not have all the answers. But they too are hired for finding all the answers and not having them.
  4. Prioritise: You may have a single problem at hand or many. You need to learn to prioritise the most important one for the day, week, or a month. If you talk about all problems at once, you will end up having high-level conversations – which may lead to generic conversation and advice. If you prioritise well, you can go deeper and leave the conversations with effective and actionable plan.
  5. Document: This needs no explanation. Write down what you want to talk about, the advice you received, action items, open questions, and everything.
  6. Show ROI: Your manager has an overflowing plate of work. They have (and should have) a vested interest in helping you level-up. Because that’s how they can delegate more things to you, make an away for you to grow and move onto different challenges. However, it’s critical that you show progress when they give you an advice and plan of action. The higher the returns you show, the more they would want to invest their time in you.

What’s the secret ingredient for great 1:1s?

Answer: Great questions!

The key to wisdom is knowing all the right questions. John A. Simone, Sr.

I have relied quite a bit on the interviews of great people. They are invited on many podcasts and shows but only some of them truly stand out. Over the time, I realised, it’s not the speaker but the host… It’s not just the host but their great questions! They ask great questions and let the wisdom from the great unfold for the next hour or two. That’s why Lenny’s Podcast, Tim Ferris, The Knowledge Project and alike are so densely packed with timeless material.

What are some of the questions I ask during my 1:1s?

  1. What is your definition of X?
    X = Being strategic, Strong Craft Person, Being a great manager etc.
  2. We discussed 2 goals in our last meeting. Here’s the update so far. How do you think I’ve been doing? What can I do better? What do I need to change?
  3. I see myself being X / doing Y in next 2 years. What do you think about it? Do you think I’ve what it takes to be there?
    X = Sr. Designer, Design Manager, Visual Designers etc.
    Y = 1:1 mentorship, leading a vertical, establishing a research practices etc.
  4. What are the key milestones you want me to achieve in next X time that gives you confidence of me being on-track?
    X time = 15 days, 2 months, 1 year etc.
  5. Here is my plan of action to achieve X. Do you think this will work?
    X = Completing this project, improve my strategic muscle, better visual design, clear writing etc.
  6. What are the most common pitfalls you and others have fallen into when you were on the same track as I am?
  7. Who should I look up to in Postman for being the best at X person?
    X = Product thinker, Craft person, Manager, Coach etc.
  8. What changes do you want to notice in my team in the next X time to give you a confidence that this is a winning team?
    X time = 15 days, 2 months, 1 year etc.
  9. What’s on your plate that you need help with? Can you delegate that to me? To flip this, you may also observe what is on their plate and say, “Can I pick up this task from your plate?”
  10. How can I help you become a better leader for all of us?

This is not an exhaustive list. I don’t repeat these questions in every 1:1. Consider these as guiding questions and think what you need from your manager; rather, think what you need from anyone and your manager can help you with the answer or the right people or resources. Depending on your rapport with your manager, consider asking them questions that helps you see the person behind the title, and beyond the company.

To conclude, 1:1s should be considered as a sacred time between a manager and report. They are never cancelled and only rescheduled if needed. It’s the only way to ensure alignment, motivation, coaching, two-way feedback, and becoming a better professional than you were yesterday.

Thank you for reading till here. Here’s one more tip for you…

Your manager is not perfect; never will be. There are a few things they may not be able to help you with and you would know when that’s the case. It doesn’t mean they are bad managers; it means they are human. Understand that you need help to unblock yourself or to grow. Identify who else in the company is better suited to help you. It’s probably your manager’s manager, one of your peers, head of some vertical, or someone outside the company. Learn to ask for help for your growth depends on it.