Q.“I was recently assigned to co-lead a major project with a colleague who has a completely different work style from mine. I’m a planner (I like to map things out, set clear milestones, and work toward deadlines). She’s NOT a planner and constantly pushes things off until we’re under pressure, then goes into overdrive and expects me to drop everything to keep up with her pace. It’s starting to create tension. I feel anxious when things aren’t organized, and sometimes I feel like I’m micromanaging her even though we’re peers. The frustrating part is that she does good work in the end, but it feels like she needs the stress to execute, when I’m the opposite.
How do I work effectively with someone whose style is so different from mine without compromising the project or constantly feeling stressed? And how do I even have that conversation without sounding like I’m better than she is or criticizing how she works? – Kaitlyn, 29
A. You’re a planner. She’s not.
You map things out. She waits until the pressure cooker hits max heat, then expects you to drop everything and keep up.
I get it.
This is one of the most common (and most frustrating!) dynamics at work. And it gets even trickier when you’re co-leading. No hierarchy to hide behind. Just two different people who need to get stuff done together.
She’s not doing it wrong. Neither are you.
Some people do their best work with a plan and a runway (that’s me most of the time). Others need the adrenaline of a deadline to fire on all cylinders. Both styles exist. (And a mix of styles exists.) Each style can produce great work. The issue is when they collide.
So how do you fix it?
- Stop waiting for her to change. Design around the difference by setting your own internal deadlines before the real ones. That way, when she kicks into overdrive at the last minute, you don’t have to scramble because you’re already mostly finished. You protect your process. She gets her pressure. Problem (somewhat) solved.
- Have the conversation, but do it skillfully. This is where most people get it wrong. They either avoid it entirely (and quietly seethe) or they go in guns blazing and unintentionally make their colleague feel judged or less than.
The key? Make it about you, not her.
Instead of: “You always wait until the last minute, and it stresses me out.”
You could try: “Hey, I want to flag something before it becomes a real issue between us. I get anxious when things feel up in the air. It’s just how I’m wired. I do my best work when there’s a clear plan in place with concrete deadlines. I’m sure you have your own rhythm too. Can we figure out a working agreement that lets us both do our best work and meet the deadlines without unnecessary stress?”
See the difference? You’re not criticizing her. You’re inviting a conversation. That’s much harder to get defensive about. - Negotiate the non-negotiables. Once you’re in that conversation, agree on a few shared checkpoints. That way, you’re never blindsided. Think: a quick weekly check-in, a shared doc where you both track progress, a mutual agreement on key deadlines, and what “crunch time” requires from each of you. For example, you may have other obligations after 6:00 pm, so let that be known upfront.
Send a simple email summary after the conversation. - Give yourself some grace. You’re doing your job. The anxiety you feel when things are unorganized is real, and it’s telling you something. Honor it. Build the structure you need, even if she doesn’t.
You can’t control her wiring, but you can control how much her chaos actually impacts you. The goal is to build a system that lets you both show up at your best.
That’s good for you. That’s good for her. That’s good for the project. (I love a win/win/win.)
You’re equipt to navigate different work styles.
