A couple of months ago, my co-founder came to NYC for our board meeting.

During that week, we took a day to sync up with everyone on the team—literally. We had 14 conversations, each lasting up to 30 minutes. Apart from lunch, we did all these back-to-back.

The goal of this exercise was 2-fold:

1. Check up on the team. Basically, a more in-depth version of:
   https://openbb.co/company/open/team

2. Have the team share anything they want with leadership or ask any questions openly.

Structure

Part 1 - 20 minutes

For the first 20 minutes, we asked the following questions to each team member:

1. How do you feel working for OpenBB today?

2. What do you enjoy the most about working at this company?

3. Who do you get along the best? and why?

4. Who do you feel like you have a not-so-close relationship with? and why?

5. What does your day-to-day look like?

6. How would you describe the relationship with your manager/team lead?

7. It’s 2028 and OpenBB didn’t make it. What are potential reasons that you would bet on that lead to this?

8. If you had to tell us what your biggest achievement is since being in the company, which one would you pick?

9. What was your lowest moment during company time - and why? What could we have done better?

10. (for managers/team leads) How do you feel about the team you have today?

Part 2 - 10 minutes

During the last 10 minutes, the team could ask us about anything.

Funnily enough, we learned just as much (if not more) from the questions the team asked than the ones from Part 1.

Results

Lack of focus is the biggest risk/challenge that we face as a company.

Culture

• Handbook is important (folks didn’t know about personal development budget, PIP, etc…)

• The team’s main reasons for being happy at OpenBB are autonomy, ownership, smart team, transparency and freedom - very aligned with our values.

• Remote work is a benefit that more people should take advantage of. Celebrate it even more.

• It’s vital to set boundaries when overworking and know when to decompress to avoid burnout

Management

• It’s key to consider that each person has different preferences in terms of management style - execution vs contributing to discussion.

• 1:1s are essential and everyone should have them set.

• 1:1s should be focused on the direct report and not necessarily on tasks at hand. Several people highlighted that they felt that their manager cared about them based on conversations about their personal life and personal development.

• Feedback should go both ways, the manager/leader appreciates when feedback is provided.

• Setting up expectations clearly for each individual is critical. People appreciate when they know exactly what is expected of them, so they understand how their value is perceived from the company's perspective.

Rituals

• Monthly update emails are very good. Sometimes even more details would be better.

• Some people are so focused on execution that they try to protect their time at all costs. It’s important to respect this decision and default to async text-based conversations instead of setting up a meeting

• Dogfood the product from people from different backgrounds is important as it gives different points of view that we can leverage to make our product better

Communications

• Be aware of different comms styles throughout org. In general, people have shared that they appreciate when others send them a DM with feedback based on a conversation in a public channel.

• Sometimes team members need to put themselves in the shoes of other people first instead of defaulting to defence.

• We shouldn't compromise on quality. We should aim to agree first on the best solution and then adapt if there’s a lack of resources, but knowing what the best solution is and what is the trade-off that is being made

• When a conversation is taking a few messages back and forth, sometimes a quick huddle should be done

• Making sure that all stakeholders are involved regarding features or changes in the product before any green light is given to execute. It happened that a green light was given, mockups were created based on that context and the engineering team added the feature. Only for that to get pushed back because a stakeholder that wasn’t involved in the discussion saw the final result on Slack chat.

Transparency

• More transparency when deals are closed - e.g. what are they interested in, how many seats, what do they do on a day-to-day basis

• When mentioning increased transparency, the vast majority of people think that our level of transparency is very high.

• A common answer: “If I have any questions I know can just DM you and you will answer”

• Add a Q&A at the end of the status update where everyone can put questions to be answered

• A common answer: “I don’t like when someone leaves out of a sudden”. Unfortunately, we can’t do anything here. We’ve also asked for feedback on what we could do better, but people understood that there’s not much we can do. This is a conversation between the person and the manager and it’s unfair for the person being let go if we share their personal information. There’s a PIP and that means that before everyone leaves the company they are in 3-4 weeks PIP, where expectations are set clearly and their continuity depends on their output.

• People appreciate feedback a lot, regardless of if it’s positive or not. It’s the best way for them to improve.

Thoughts

I think, at an early stage, everyone should do this. And maybe even at a later stage but in each subset of the org.

One of the reasons I think this worked so well is that for the first 20 minutes, you are asking the exact same questions to everyone and so that allows you to get answers that you can compare across the board.

Then, once those 20 minutes are over, the team member feels that they have already been so transparent that they openly ask questions that they are curious about.

The final result was a presentation with all the combined learnings and actionable.

What do you think?