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Is Your Team Getting What They Want on Trello? 7 Tips For Virtual Collaboration & Negotiation

Where do you get work done with your remote colleagues? For many of us, work now happens within project management boards, tagging comments, pushing projects to new phases, uploading deliverables for approval, etc. And a lot of this work is negotiation: how do we communally agree on the allocation of resources to achieve business goals, while also hitting our personal goals? Which means you have to consider how your negotiation techniques change when it’s all happening on Jira/Trello/Monday.com.



The idea of project management software as a communal space is probably only to become more prevalent as work evolves. Being able to communicate about projects in an asynchronous, medium-rich, communal way will be even more integral going forward.



The value of documentation and knowledge retention in a virtual workplace is clear. Tools like Jira or Trello are where we go to push projects forward, complete our tasks and let others know the status. This means that either overtly or passively, these communications are full of negotiation.


Assigning a task to someone. Approving a deliverable. Agreeing to next quarter’s priorities. All of these usually require some level of negotiation, in that there are multiple parties with different viewpoints, but there has to be one, agreed-upon result.


In general, written communication is complicated. It’s more transactional. It seems more official, after all, contracts are written documents. There are far fewer non-verbal cues to add a layer of nuance to our words. And some people are more comfortable with the written word than others.


So what are the pros and cons of written negotiation, and what can we do to make this better for all of us?



Here are some pros of written negotiations, specifically on communal project platforms:

  • Well prioritized: Written comms allow you to make priorities more clear. There’s a record, and it’s black and white.

  • Hides your emotions: You don’t risk looking overly happy. One study showed when people expressed happiness after negotiation, the other party believed that the deal was not in their favor, and this led to less-generous subsequent actions.* This is far less of an issue over text-based comms.

  • Timing control: Research suggests that if you’re in a disadvantaged situation, having more control over timing, as you do with asynchronous communications, helps you make better choices and achieve better outcomes.**

Here are some cons of written negotiations:

  • Multiple streams: If your team isn’t disciplined, there can be verbal, email, and Trello negotiations going on at the same. Messages can get lost, people can feel out of the loop, and it’s not scalable to communicate this way.

  • Lies: Contrary to actual face-to-face, people are more likely to exaggerate or alter facts over email.*** Project management software is likely prone to the same issues.

  • Overly contractual: Given it’s alphanumerical nature, text-based exchanges can be seen much like a contract. Seeing the entire exchange “permanently” and communally recorded in black and white makes negotiators less flexible, less willing to get involved in the kind of give and take that’s normal in more personal communications.

  • One shot: Readers can gloss or skim over text-based communication, missing key details or making assumptions, even if the post is perfectly written. There’s less chance to repeat back what the other is saying and clarify points. This is doubly true if the medium is two-pronged, like you get an email from your project management software, but it doesn't show you the entirety of the text. If you don’t click through, you could miss critical points.


What can we do to make these negotiations more effective and more pleasant for all involved.


First, we can practice Digital Empathy. What do the people looking at this board or ticket see when their eyes first land on it, and what do they think? You need to provide the information they need to know in the simplest way. That might mean clear labeling, (overly) comprehensive back stories or explanations, or quick syncs to make sure that short hands are well understood by all involved. If your boss’s boss can't quickly see the project’s progress, your efforts probably aren’t digitally empathetic enough.

  • What aspects of a brief or update are always necessary? The more specific everyone can be, the easier it is to stay on the same page.

  • Who needs to know what? Make it clear from the outset of every project, using a RACI chart (Responsible, Accountable, Consulted, Informed) or other, to make sure you know who needs to be told what when

  • What does tagging without commenting mean? Little actions that might be obvious to one person, e.g., “ Hey, I want you to see this, “ might come off as passive aggressive to another.

  • What’s your joke and sarcasm lexicon? Many have argued, “we need a sarcasm font.” Or we could agree that’s what the eye roll emoji is for?

  • Agreed upon notifications. Does everyone get updates emailed to them immediately? Weekly? When do colleagues see comments they are tagged in? You can’t move forward if you don’t understand how synchronous or asynchronous your communications are.

  • Highlight great examples. Some people, myself included, need to see a good example to be able to make one themselves. When you have a comprehensive project plan that has worked really well, document it, annotate it, and share it.

  • Be generous. Another tool of digital empathy is to assume your colleagues are always out to give you their best in the most altruistic and loving way. I get it; this may not always be true! But if you think it’s true, it’s more likely to be true and will make getting through your workdays more pleasant in the meantime.



As we continue to evolve remote work, creating explicit behavior frameworks will help us communicate more effectively, richly, and kindly with our colleagues. Ultimately, we’ll get more done and be happier for it with better communication.


*Thompson, Leigh, Kathleen L. Valley, and Roderick M. Kramer. “The Bittersweet Feeling of Success: An Examination of Social Perception in Negotiation.” Journal of Experimental Social Psychology 31, no. 6 (1995): 467–92. https://doi.org/10.1006/jesp.1995.1021.

**Loewenstein, Jeffrey, Michael W. Morris, Agnish Chakravarti, Leigh Thompson, and Shirli Kopelman. “At a Loss for Words: Dominating the Conversation and the Outcome in Negotiation as a Function of Intricate Arguments and Communication Media.” Organizational Behavior and Human Decision Processes 98, no. 1 (2005): 28–38. https://doi.org/10.1016/j.obhdp.2005.03.007.

*** ZIMBLER, MATTITIYAHU, and ROBERT S. FELDMAN. “Liar, Liar, Hard Drive on Fire: How Media Context Affects Lying Behavior.” Journal of Applied Social Psychology 41, no. 10 (2011): 2492–2507. https://doi.org/10.1111/j.1559-1816.2011.00827.x.



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