An one on one guide when talking to leadership

How to make the most of your time when talking to leadership.


  1. Introduction
  2. How to make the most when 1:1s to leadership
    1. It’s not about updates
    2. It’s the best time to be listened
    3. It’s all about you!
    4. Career, long-term and guidance are all connected
    5. Half of the mood is up to you!
    6. It’s a time for new ideas, bring them all!
    7. Challenge and be challenged
  3. Technical mentorship
    1. Kick-off
    2. Catch ups
  4. A lot of words, how to objectively do it?


The 1:1s put together two things Data Science people usually fear: meetings and personal interactions. But just as strongly as we fear investing our time in useless meetings, we all also wish to be productive and deliver great work. The price is fixed since you can’t have 1:1s without meeting a person. However, the benefit is unlimited, and that’s what we want to maximize here.

Will we get rid of the uncomfortable silences?

Though some might have managers focused on their career and tech leads on their technical development, notice it’s hard to provide career guidance without technical talk. Just like it’s hard to do technical mentoring without talking about your career, so you can use the tips here when talking to both.

This guide is composed of content from Radical Candor book, my experience in Nubank, and Pragmatic Engineer blog. Special thanks to Caique Lima and Paulo Rossi - both Nubankers - for reviewing and suggesting changes.

How to make the most when 1:1s to leadership

One of the roles of the people you’re reporting to is to make your life better at work. It means helping you be productive, make the most of your time, and deliver the best outcome possible. It also means contributing to your development and integrating you into a collaborative environment.

It’s not about updates

It’s common to update your manager, tech lead, or squad lead about the progress of things you’ve been working on. Though that’s useful, it’s not what 1:1s are meant to be about.

Update progress in stand-ups, pack meetings and… update meetings.

For your 1:1s, bring the obstacles, bureaucracy, crisis, doubts, anxieties, and political issues.


How updating instead of addressing problems looks like.

It’s the best time to be listened

Your manager will be there to listen to you, primarily. You’re the one with the best perspective to describe your day-to-day work and talk about what is working and what is not.

What are your expectations? What has been blocking you?

But if I only bring problems to my manager, it’s going to look like I’m not a problem solver, just a complainer!

Not at all! Your manager knows what has been accomplished - either they are already part of your squad, or they communicate with people who are. Not bringing anything going bad is way more suspicious since we all struggle during self-development. It’s natural to have a couple of issues to talk about.

It’s all about you!

The 1:1s are the most personal it can get. In the end, it’s all about you. Don’t be afraid to bring everything in your mind, don’t worry if you think it’s not “work stuff” - if it’s in your head while at work, it’s certainly something you can bring to the other person during the 1:1.

Think about it as a conversation during a coffee and not a work meeting. Your manager is willing to know you better, so there’s no reason to block whatever you consider not appropriate.

You should leave a 1:1 more calm, with issues clarified and relieved.

Career, long-term, and guidance are all connected

You probably have a couple of career goals. And you also have some objectives and dreams to achieve in the long term. How do they connect?

Remember, work is a day-to-day activity and a large part of your life. To achieve more significant objectives, you need to move constantly in that direction.

It’s your manager’s goal to provide guidance, but to make it match your expectations and objectives, they need to be clear. So talk about it. For those whose goals are unknown, any guidance seems to fit.

If you don't know where you are going, any road will get you there.

Half of the mood is up to you!

It’s a conversation between two people. Both moods can completely change the outcome. So make sure you bring your best self to it. If it’s not scheduled in the best time for you, talk to your manager to find out when it’s better for both, but try your best to be present, energized, and open to talk.

This shouldn't be the reaction when a calendar notification with "1:1" appears.

It’s a time for new ideas. Bring them all!

It’s hard to make new ideas stick in a work environment. Everybody is busy doing something the team agrees is important, and new ideas are as fragile as a newborn.

An unpolished new idea on senior hands.

Take the 1:1 as an opportunity to discuss and prepare new ideas to be delivered to a broader audience.

Challenge and be challenged

During the 1:1, it’s a perfect time to challenge the other person directly. It doesn’t mean it’s supposed to be a fight, discussion, or anything aggressive. Instead, it’s time to be open and shift towards a better direction and a closer relationship.

Notice this should happen in both directions! So it’s expected to say something like “Hey, I lack some updates from upper management. I don’t know what is happening, and when something changes, it seems it comes from nowhere, like when ‘A’ was announced. Can we make the information flow better?”.

You can expect to hear from the other person something like “When that bug happened, I think you’ve lacked ownership during its investigation. Getting more involved is expected.”.

However, it’s not a unique moment to get and provide feedback and challenge. Feedback should be present seamlessly in your day-to-day.

Technical mentorship

Mentorship happens in the day-to-day work, but formalizing it can help you grow faster and focus on specific areas you care about the most. However, it requires more effort from you and the mentor.

Be clear in a 1:1 that you want to be technically mentored and bring in the areas you want to develop.

If the person considers they can’t help you on that, they can point someone else who could. It’s part of the tech lead role to mentor, but if you need to look to another person for some specific knowledge, please mind they may not be readily available to mentor you.

Focus can make evolution faster

To establish the formal relationship, use the 1:1s to structure the mentorship. It can be used to kick off and then on for the catch-ups.


  1. Share your background on the topics that need to be covered.
  2. Share where you want to get and where the other person can get from what you can offer. Think of it as an exchange.
  3. Share the challenges you’re facing. Clarify what makes you insecure. Is this the first time as a mentee? What are essential projects on your plate?
  4. Discuss roles. Discuss what you expect from the mentor and what is expected from you, like PR reviews, work evaluation, content suggestion, etc.
  5. Cover all topics and the areas you want to push.
  6. Agree on cadence. How often will you meet for the tech mentorship?
  7. Discuss communication between catch-ups: Can you ping on slack anytime? Should you come to talk in person? Is it possible to schedule an extra time when needed?
  8. Establish short-term wins. What is the first thing to get better at, and what are milestones to identify success?
  9. Agree on progress evaluation. What are the criteria to assess if the mentorship is working?

Catch ups

In the 1:1s, bring the challenges, wins, subjects you want to have their opinion, etc. Use your agenda to take note of the top things you want to go through and ask for inputs. Again, the agenda is a doc you can drop subjects between the 1:1s, so you remember everything valuable to discuss. By preparing beforehand, you show you value the other person’s time. If you don’t think it’s necessary to prepare, the chances are you do not appreciate it as much as it is needed to make it effective.

A good way to think about what to bring to it is:

  1. Key things that happened since the last 1:1, as short updates to relevant items to the areas being developed.
  2. Reflect on action items, guidances, and discussions from the last 1:1: share results on things you have acted, like trying an approach, reading a book, and so on. This is interesting since it can also teach something to the mentor.
  3. Challenges you’re facing: expose and discuss how to approach it.
  4. Recent successes: describe a situation you have handled and ask how the mentor would approach it. It’s good to get feedback and other points of view.

Many words, how to objectively do it?

You need to bring things to this conversation. It’s yours. Create a file you can share with your manager/tech lead to work as an agenda. It can be on Drive (or whatever tool you like) and put items on the next 1:1 as the week/month passes by. This way to control it is a recommendation but talk to the leadership to find out what best suits you.

It’s hard to remember everything on top of your head, so prepare for it.

I can’t think about anything! My 1:1 starts in 10 minutes, and my list is empty. Please help me!

Don’t worry. Try to ask yourself these questions, and soon you’ll have something:

All those questions could bring some discomfort, doubts, and anxiety. Take them to the 1:1, talk about the questions, talk about how you feel about them.

It takes some time until things run smooth and natural, but embrace the awkwardness at the beginning and focus on the benefits!