How to Enjoy Working with People

Jenn Dodd
Jenn Dodd
May 23 · 5 min read
Photo by Brooke Cagle on Unsplash

I love working with people. It’s the most fulfilling, draining, inspiring, challenging, awesome, and dreadful thing.

Over my decade of working (already?!), I have been a student, a contributor, a designer, a teammate, a freelancer, a consultant, a coach, a mentor, a mentee, a report, a facilitator, and a manager both onsite and remote. That’s a lot of roles, that’s a lot of people to work with, that’s a lot of lessons learned.

Over the past few months, I’ve been reflecting on what it is that makes working with people so great, and through that, how can I more consistently remember that it’s great on those days where it feels terrible.

What I realized was:

What I thought about myself and the people I worked with, determined how successful and satisfying the experience was.

Boom! Now, if you’re like me and lean ‘half empty,’ that gives you a whole new reason to feel guilty. But if you try to see it a bit more ‘half full,’ it can be incredibly empowering.

Applying that can feel less tangible when you’re in the moment, so I keep this list of 4 notes-to-self to help me put on a new mindset when I’m struggling to enjoy the people stuff (and it’s all people stuff.)

Show up. (And do what you say you will.)

This one is my favorite. It can be an imperative when starting something or changing course (“Show up.” or “How do I want to show up?”), or it can be a diagnostic tool when you want to understand why something feels good or bad (“How have I been showing up?” or “Am I following through?”).

The two parts of this go hand in hand. By doing what you say you will do, it will confirm how you are showing up.

For example, one time as a freelancer I was struggling. I took the project on because I thought I should (should + anything = red flag.) I showed up grudgingly in this case, which lead to me putting off the work. A milestone loomed and I rushed through the work due, not doing my best. I showed up as someone who didn’t try, and I barely finished the work for the first milestone. I wound up quitting and not finishing the project, so in the end I didn’t do what I said I would do. I never really showed up. I didn’t like the work, I didn’t like the people, but really… I didn’t like myself.

You choose how you show up (consciously or unconsciously) always. It gets really fun when you realize you get to pick.

Assume the best. (Always.)

I once had a coworker who I thought didn’t like me (impossible, I know!) I would read into everything they did as a slight against me. At best, they were selfish and thoughtless, at worst they were actively trying to undermine and destroy me. That looks incredibly dramatic as I write it down, but it’s really how I felt. The result was that I avoided them, was passive aggressive towards them, I sulked, I dreaded any interaction with them, I complained and vented to friends (see “Show Up.”) I suffered.

Know who didn’t suffer? Them. Turns out they weren’t thinking about me at all (which, again, impossible.)

It was all unnecessary. Once I decided to start assuming the best, all the drama I built up in my head went away. I showed up how I wanted to be, and assumed they were showing up doing their best, which meant I treated them differently. Even if they did want to destroy me (they didn’t), at least I didn’t spend all that extra time spiraling and feeling anxious.

So just do it. Assume the best. Not because it’s “nice” or what “good people” do, do it because it’s way easier. You will suffer so much less and have way more fun if you just decide to assume the best of everyone and everything.

Listen. (And actually hear.)

I’m a really good listener. I’m told that all the time. I’m so good, actually, that sometimes I’ll think about what’s for dinner, that meeting I just left, and also what I’m going to say when you’re done talking all at the same time. Kidding! Mostly.

Listening without hearing is just temporarily being quiet.

Back in my consulting days, I learned the difference between listening and hearing. As a consultant on a mission to help transform the way the world builds software, I would come to projects with a potentially very different mindset and expectations than what the client had. Sometimes it was exciting and easy to collaborate. Other times it was extremely frustrating and difficult to align.

We had a lot of rituals that encouraged sharing and communicating, but sometimes the resistance would persist after retro, through the weekend, and show up again on Monday. I eventually realized that working together was so much easier if we truly gave space for hearing not just listening. Whether or not we talked about it in a retro didn’t matter if the client (or anyone on the team) didn’t trust their thoughts would be seriously considered and understood. If clients didn’t feel like they had the space or the attention to have their concerns and ideas truly heard, they would have a harder time collaborating. And rightly so.

Feeling heard builds trust and connection, which can lead to much more satisfying and successful interactions with people. Without the trust and connection, working together can feel really painful.

When in doubt, ask.

I’m not sure why I feel like I need to know all the things all the time. Or why I prefer to sit and replay interactions over and over guessing at what the other person meant or thought. Or why I forget that people generally want and like to help. Or why I wait for people to notice what I want.

There’s another option. I could ask.

A while ago I was struggling at work (Me? Struggle? No!) balancing two sets of responsibilities. I felt like I wasn’t showing up how I wanted, that I was letting people (ahem, myself included) down, and it was starting to make me feel both ragey and sad. After being frustrated for what felt like forever I finally let my manager know what was going on, so sure that they would agree I was failing.

Instead they asked why I was doing both and if I wanted to stop doing one of them. Over all those weeks it never occurred to me that I could ask for what I wanted. Of course they could have said no, but then I would have had a good reason to be frustrated. Instead, I was frustrated for no reason.

I now view asking as a shortcut. Probably the most obvious lifehack. It can be uncomfortable, and potentially a bit of a risk, but it seems better to know for sure, to be clear, and to skip all the useless effort, frustration, and pain and just ask.

I really hope these notes-to-self all glaringly and painfully obvious. Hopefully these things come to you naturally and easily.

But in case they don’t (they obviously didn’t for me), in case you feel frustration, or anger, or dread bubble up from time to time when you’re working with people, I hope they help.

Note to self: Don’t forget, people really are the best. ❤

Jenn Dodd

Written by

Jenn Dodd

Product designer. Manager. Coach. Maker. Seltzer Enthusiast.