Conversations at Obvious – Part 2 : One-on-One Conversations

9 minute read
Conversations 2 3 column

Dedicated time with your manager, focused on what’s important to you.

One-on-one meetings are an opportunity for individuals to meet with their manager and discuss anything they want, in private. If you're one such individual, then this is your time! You set the agenda, format, and location. During this time, you can give feedback, build and enhance trust with your manager, discuss new ideas and problems, and brainstorm on ways to advance your career.

The Why

At Obvious, our goal is to create an environment where everyone feels empowered, supported, and heard. To accomplish this objective, we must create a safe setting for you to discuss your ambitions, concerns, and suggestions.


The direct report decides the agenda of the one-to-one with their manager. If you're a direct report, we recommend creating a format that works best for you, and it may change each time, depending on your priorities. We also recommend focusing on topics that pertain only to you. In other words, things you are not ready to discuss in front of the entire team might be a good fit for discussion here.

We suggest covering: positive work events, negative work events, manager feedback and outside life. Each one-on-one, though, does not need to cover all four areas. These proposed topics provide general guidance, but the direct report has ultimate control.

Outside Life

We try not to pry into the personal lives of direct reports but, sometimes, it is beneficial to share what goes on in life outside of work. As an organisation, we may realise that a direct report is going through something personally that causes distractions, or is dealing with a health issue that sometimes requires time away from work during normal business hours. We'd encourage all direct reports to speak as freeely as possible and know that information shared will always be confidential.

In addition, it is helpful for managers to know what motivates direct reports. If an individual's life’s goal is to open a design school, we could talk about the skills necessary for that to become a reality and how we can develop those during the time spent at Obvious. We understand that people’s aspirations change. One may not want to be in a current job forever. If an individual wants to do something else in life, we'd like to support that and help them see success in that goal.

One-on-ones are the time for direct reports to speak about whatever they want. Each meeting may focus on a different topic or could be a continuation of a previous conversation. If you're a direct report, you call the shots!

Positive Work Events

Discussing what drives individuals shows managers what each person enjoys and wants to do. By conveying this information, it makes it easier for managers to provide more of those opportunities. Here are some factors that direct reports can consider sharing during this one-one-one:


We always encourage answering the following question during our one-on-ones: What motivates you to come to work? When we're excited to come into the office, then we're likely to be more productive, and that energy is contagious! At Obvious, we want to do what we can to keep everyone motivated, and we'd say this comes of learning about each individual's motivation.

New Ideas

New ideas are like infants: innocent and fragile. They need care and nurturing before they stand on their own. This one-on-one time is great to understand any new ideas that an employee may have, then brainstorm and ask for constructive guidance before rolling it out on a larger scale. These ideas could be small items — like a new type of coffee — or larger suggestions, such as a new way to work with a client. At Obvious, creativity is crucial, so we always recommend using this time to strengthen ideas at their inception.


We encourage direct reports to share their aspirations and areas that they're trying to improve. We then offer guidance, if they want it, on what they can do to move in that direction. This discussion will not replace the bi-yearly Career Conversations or day-to-day feedback, but rather, it may serve as a midpoint check-in to ensure progress regarding each individual's path.

Negative Work Events

We spend a lot of time at work, so we try to make the experience a pleasant one. To do that, managers also needs to know what is not working for their direct reports. While we don't want these meetings to turn into gripe sessions, we'd still recommend voicing frustrations so that the manager and direct report can find a solution together.


Here's another question that we think needs to be asked at these one-on-ones: What do you dread about coming into work? If you're the direct report, let your manager know what that is. Odds are you and your manager together can resolve the issue. It's handy to come in with possible solutions, but if there isn't any in mind, that's fine too because you can then brainstorm together.


If, as a direct report, you experience roadblocks that impede doing your job or make you feel unproductive, we'd recommend letting your manager know. This way, you can look for answers or workarounds together. It may take a few attempts, but it works as long as you continue to address the problem.


Bring up things that are in the back of your mind. Sometimes it could be something you can't quite put your finger on, but understand that something isn’t quite right or could be improved. Or maybe the problem is clear but there's a need for external support and advice. In either case, it's best to be as honest as you can!


Feedback for the Manager

It's good practice for individuals to provide their managers with immediate, personal one-on-one feedback regularly, whether after a meeting, privately, or through written communication. However, sometimes you might need more time. We'd recommend that every individual use these meetings to give advice on how the manager can better their impact. We also suggest using this time to follow up on previous advice given, in the interest of continued growth for everyone. We recommend using the Situation → Behaviour → Impact (SBI) model. It can be highly rewarding to tell managers what impact, both positive and negative, their behaviour had on you, as a direct report, in the context of a particular situation.

What can the manager do more of?

Ask yourself the question: what can your manager do to make you more productive and happy? When possible, use the SBI model and be as specific as you can.

What can the manager do less of?

Tell the manager what they could stop doing to make your job easier. Remember to use the SBI model and avoid talking about the personality of the manager.


Use the following tips to make the most of your one-on-ones:


Use one-on-ones as a time to release the pressure you might be under. For instance, at Obvious, we like these meetings to be collaborative and relaxed, not something dreaded. Look at it as a time to reset yourself. So, we'd recommend choosing a format that puts you at ease, such as having coffee or tea, taking a walk or going to lunch.


These meetings occur once a month for 60 minutes and are scheduled at roughly the same time. The one-on-ones can be rescheduled when necessary but not cancelled.

Resist Work Critique

We encourage specific feedback using the SBI model to occur in three to five-minute conversations right after the situation instead of in the one-on-ones. Instead of saving up that feedback, deliver it when it has the most impact.

Keep a List

Instead of preparing a list of things to talk about at the last minute, keep an on-going list. This could be a separate list from the one you share with your manager or not. When a thought pops into your head during the week, add it immediately instead of trying to remember it.

Shared Feedback Document

Keep a written account of your meetings so that you can look back and see progress. Share the document with your manager where they can make comments and track your growth. Either take notes during your one-on-one or add notes after the meeting. In addition, add notes throughout the week. This master list of your yearly progress will be helpful when the Career Conversation comes around!

OBV0414 Edit

Bullsh*t Meter

As in everything we do, it is important to measure how well the one-on-ones are working. The following are indications that the process is not going smoothly.

Only Good News

If you, as a direct report, only talk about how positive everything is and how well you are doing, you limit the feedback your manager can provide. Bring issues up as soon as possible so that the two of you can plan a course of action.

Lack of Criticism for the Manager

Praise is great but constructive criticism and suggestions are crucial as well. It is how we grow as individuals and as a team. Managers make mistakes and want to know when it happens. In fact, we encourage it. If you feel uncomfortable critiquing, then talk it through at these one-on-ones.

No Agenda

While we encourage free-flowing meetings, the direct report, who sets the agenda, needs to have a general idea of what to talk about. We recommend specifically carving out time for these meetings because we feel strongly that they will increase the effectiveness of everyone involved, on a personal and professional level.


If you have the same conversation with your manager month after month with no progress, then something is wrong. Use the guidance in this document and to mix it up a little bit.

One-on-ones provide direct reports a genuine opportunity to feel included, supported and understood. It also is the best way to give managers direct feedback about how they're doing and what could be improved. As an organisation, we can testify to the positive impact of these career conversations, and we'd love to see the approach catching on in similar organisations!

Notes and Definitions

Situation → Behaviour → Impact Model

The best way to provide constructive feedback, both positive and negative, is by putting your comments in context instead of being vague. For maximum effect, state the situation, the behaviour you liked or disliked, and how it impacted you. We call this the SBI model. Use it to offer sincere praise, or seek clarification before delivering critical feedback.

Let’s look at two examples:

Positive Feedback

Vague: You did an excellent job with that client this morning!

SBI: During the meeting this morning when the client suggested changing the home-screen (situation), the approach you took to walk him through how the modifications would negatively affect users (behaviour) saved us from creating a poor user experience and also helped him understand how important it is to keep users in mind at all times (impact). Thanks for taking the time to walk him through it.

Negative Feedback

Vague: That client will never hire us thanks to you!

SBI: When we met with the client this morning and she asked how our team would decide how we find candidates for the user studies (situation), you told her that we will not discuss that today and that it was not relevant to the conversation (behaviour). She stopped participating and cut short our proposal meeting (impact). She wanted a better understanding of our process, and she felt that her questions were not considered important. I would love to hear your take on the situation.

In both these conversations, the SBI approach provides the one receiving the feedback with concrete information that allows them to either change their behaviour in the future or receive the compliment knowing that it is sincere.