Working with others
Work through a problem side by side
A simple exercise to get unstuck together when messages keep going back and forth
When a problem keeps bouncing between you in messages, book thirty minutes with the other person and solve it together, looking at the same thing.
- 30 minutes
- You and one person
- When a thread stalls
- Conversation
Why this can work
Some problems are hard to solve in writing, because each reply answers the last message rather than the actual question. Sitting down together lets you both see the same thing at the same time, catch a misunderstanding in seconds, and try ideas out loud. Thirty minutes can end what days of messages couldn't.
Read moreHow to work through a problem with a coworker
You’ll come away with a problem settled, and a short note of who does what next.
- Notice when the thread has stopped working.
Three or four rounds without progress, the same question asked twice, or a reply that answers a question nobody asked. Any of those is the signal.
- Ask for thirty minutes, and say what you'll solve.
Name the problem in the invite, so the other person knows it's a working session and not a sign something's wrong.
To: the person you've been going back and forth withThis one's been going back and forth for a while, and I think we'd get further together than in messages.
Could we grab thirty minutes when and work through the problem side by side? I'll bring what I have so far.
Swap the highlighted parts for your thing. Works on Slack, in email, or said out loud. - Start by writing the problem down together.
One or two sentences at the top of a shared doc or whiteboard: what you're trying to decide or fix, and what done looks like. If you can't agree on those sentences, you've just found the real issue.
Tip: Five minutes spent here tends to save the other twenty-five.
- Work on one screen, and think out loud.
One person drives, the other talks. Try things, say what you're assuming, and ask why when something surprises you. Swap halfway if it helps.
- End with what's decided and who does what.
Write it at the bottom of the same doc and send it to anyone else who was in the thread, so the conversation doesn't restart without you.
Good times to repeat it: when a thread goes three rounds without progressat the start of a tricky piece of shared workwhen a problem needs both of your halves to solve
Making it work for you
Every workplace is different. Here’s what to think about before you start, and what might get in the way.
Things to think about
A thread with your manager that keeps circling is often really about unclear priorities. Half an hour side by side tends to surface that faster than another message.
What might make this harder
Offer two short slots across the next two days, or take fifteen minutes right now. A shorter session soon beats a perfect one next week.
Questions people ask
How do I know when a problem is too tangled for messages?
When a thread has gone a few rounds without progress, when the same question keeps coming back, or when you're explaining something that would be quicker to show. Half an hour working on it together usually settles it.
What is pairing at work?
Two people working on the same task at the same time, often on one screen. It's common in software development, and the same idea works for any problem that's hard to untangle alone or in messages.
How do I ask a coworker to work on something together?
Say what you'd like to solve and suggest a short, specific slot. Framing it as faster than messaging keeps it from sounding like a problem is coming.
Isn't this just another meeting?
Not if it's two people, one problem and a clear end. A working session produces a decision or a fix, not a status update.
Why this works, and where it comes from
Writing is a fine tool for some problems and a poor one for others. The poor fits tend to share a shape: a few moving parts, some ambiguity, and two people who each understand half of it. In writing, every small misunderstanding costs a full round trip, and tangled problems are mostly made of small misunderstandings. By the fourth reply, each person is answering what they think the other meant.
The other person is probably as frustrated as you are, and may be wondering whether you're being difficult. Working side by side changes that quickly. You see how they reason, where they hesitate, what they know that you don't. A lot of what looked like stubbornness in the thread turns out to be a missing piece of context that takes ten seconds to share out loud.
This is a cousin of pairing, which software teams have used for a long time: two people, one problem, one screen. The version here is short and works for any shared problem. It adds two bookends that tend to get skipped, writing the problem down before you start and writing the outcome down before you leave.
Not every thread needs rescuing. When the question has one right answer that one person already knows, a single clear message beats a meeting. Tension between you is a different matter, and it deserves a conversation of its own before you try to solve anything together.
Other simple things to consider
What to do next
More in Working with others
A few minutes that compound
Do it with Truest and it goes on your permanent record, in a Career Vault your employer doesn’t own.
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- It comes back if it slipsA missed one comes back around instead of disappearing.
- On your recordWhen it's done, it goes on your record with your priorities and progress.
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An exercise written by Truest, based on our experience. Last updated September 25, 2026. We sell a career membership; where that’s relevant above, we say so.