One on One

Many folks I know lament doing 1 on 1s at work, and the trepidation is often on both sides of the conversation.

Is my boss/coworker/direct report supposed to be my friend? Do we only talk about work? How much of my life do they really need to know? How much of their life do I need to know? Does any of it matter?

Personally I have been on both ends of the spectrum. As an engineer I usually want nothing more than uninterrupted time to do my work, and recurring meetings break into that. Throw in a 1 on 1 where the agenda might be nebulous and the meeting performative then the whole thing seems like a waste of time. As a manager, the number of 1 on 1s can be overwhelming if you are doing direct reports, skip levels, lateral peers, your boss and dotted lines. Also, the higher up you get the more relationships you have to manage, and the success of your organization becomes increasingly predicated on these relationships.

That said, at a fundamental level, businesses are about people. It is about your customer and their problems that you solve. It is about your team that solves those problems. It is about the vendors your business relies on to operate. It is about the communities in which you operate. It is about you, your life, and the value you provide to the business and the value the business provides to you.

I would suggest everyone take this to heart, and doubly so for managers. The goal in all situations is to meet people where they are, understand their wants and needs, and figure out how that fits into the context in which you both operate. One on ones are a very good tool for this. Yes, talk about work and business in your one on one, but also talk about whats going on in your life and the world, the challenges you face, the things you are excited about, and what opportunities you can craft together to maximize value across the board.

As a leader you occasionally need to have hard conversations, and you don’t want these conversations to be your only interaction with people. If people are terrified anywhere you show up then you have a problem. One on ones are good way to address the sense of unease many folks have by creating repeated positive, genuine, and low-stakes interactions with people. This helps both parties have a more open and honest dialogue when shit gets real.

I continue to be amazed at the value that comes from these conversations. Through these conversations we have helped people take life changing sabbaticals, make proper space for people to deal with grief and loss, support team members immigrating between countries, save people at risk of churning from the company, support people starting families and make sure we don’t annoy them while they are out, fix communication problems between teams and individuals, totally reform technologies/architectures/processes, create plans for people to be promoted, identify opportunities and connections for people, and generally build a much stronger team that likes working together and supports each other.

Achieving productive one on ones are an essential piece of building a culture and environment where people can do their best work, and that is where the magic happens.