Communicating Work Expectations to Avoid Misunderstandings

When onboarding a new team member, a recent experience with asynchronous collaboration brought a humbling revelation. As I was onboarding her to our tech stack, I uncovered a blind spot in communications within our project management software, Asana. 📝 In the meticulous notes I left for myself a while ago in one of the Asana projects, I had cut and pasted some language from an email to a client that included the word "YOU". 🤔 I failed to consider the potential confusion for my new team member. It hadn't occurred to me that she would interpret that "YOU" to be referencing her. ⚠️ What I had put in Asana as notes became unintended directives for the new Virtual Work Insider team member! The result? 📉 A cascade of actions on her end, each based on a misinterpretation of my notes. ⏳ This was an inefficient use of her time and effort that were invested in tasks that weren't needed or intended. The fix? 🔄 Once I realized what had happened we had a great discussion about how I would change my note-taking behavior in shared Asana projects to make the async communication clearer and we refined on our norms for how new requests would come through to her. My aha moment made we want to share some actionable insights for seamless onboarding in asynchronous settings. ✅ Precision in Messaging: Avoid vague language and ensure that your notes are explicitly for personal use and directives to others are clearly marked as tasks. ✅ Establish Communication Norms: Kickstart the collaboration by setting expectations on how tools like Asana are used. Establish a shared understanding of communication conventions to avoid misinterpretations. ✅ Feedback Loop: Create an open channel for feedback. Encourage your team to seek clarification if something seems ambiguous. This proactive approach can avoid potential misunderstandings. What would you add to this list? 👇 #virtualleadership #hybridleadership #hybridwork #async

If you think overcommunication is annoying, wait until you have to redo your work because of a simple misunderstanding. Guess which one is worse. As an entry-level engineer, you might feel that overcommunication is unnecessary. You might think, "This could be straightforward, why bother bringing it up?" But here’s the truth: overcommunication can save you time and effort. I learned this the hard way. 💬 I was working on a ticket and followed its description to the letter. I shared my approach during the team standup, got inputs, and started implementing. Everything seemed fine. But as I was close to completing it, I realized the planned outcome wasn’t possible. When I raised this, my manager stepped in and explained that we needed a completely different approach. It turned out she wasn't in the standup where I shared my plan. I assumed approval from the team was enough, but in hindsight, a quick confirmation from my manager could have saved me a lot of rework. This wasn’t a high-priority task, so there was no major impact. But it taught me that overcommunicating isn’t a burden, it’s a safety net. ✅ Takeaway: How to avoid this situation in the future 💡 Use Team Channels. If you’ve shared your approach verbally, follow up in the team’s messaging channel. Write something like: “Here’s how I’m planning to approach Ticket #123. Please let me know if there’s anything I should reconsider or if this doesn’t align with expectations.” 💡 Document Assumptions. When you’re not 100% sure about something, spell it out. This invites corrections early. 💡 Confirm with Stakeholders. If someone wasn’t part of the discussion, proactively loop them in with a summary. 💡 Don’t Be Shy. Remember, you’re not being annoying, you’re ensuring success for the entire team.

William Shakespeare said that expectation is the root of all heartache for communications professionals. Wait, he didn’t have those last three words? Well, what I’ve seen over and over is that expectations indeed create misery for those in communications. This realization re-smacked me over the head in a communications workshop I was facilitating. The comms team was struggling. Was it writing? Planning? TIme? Need for training? Those were all the assumptions we had going in. Turns out, it was expectations that created heartache. The CEO had different expectations for what the communications efforts would look like, the tone/voice and the outcomes --  and the team didn’t know those expectations. Naturally, when those expectations aren’t met, there is tension. Following that workshop, the topic of expectations became a first step in every workshop, communications assessment, CEO coaching/messaging, or fractional/gap-filler guy work. One of the most important jobs for any communications professional is to get in the heads of leadership teams and align on expectations. A few ways to do so include: - Series of questions for leaders on what trying to accomplish, the desired outcome, and what want to see in writing. When is deadline? Try to understand their expected end result. - Also try to understand the strategy and why important: what is the “wow,” how fit with organizational plan, what does it mean for organization? - Try to head misalignment off at the pass. What are the CEO must haves/what is not optional or can’t be changed? Likewise, same questions for legal, marketing, etc. Sometimes a CEO wants something and legal/other disagrees, and you're in the middle. - If time allows, prior to writing, share an expectation overview. Here’s what I heard you want, here’s what we must include, here are legal parameters, here’s the SME that will review the technical details, etc. If time doesn’t allow, drop that in front of the document they will review. If we can align expectations and reality, we won’t have as many heartaches. Curious if others have ways to align on expectations when it comes to driving communications for a leader and/or organization?

Have you ever found yourself giving the same feedback over and over again—whether it's about a presentation, a newsletter, or a meeting? It can feel frustrating. You might think, Why don’t they know by now? Maybe they should. But they don’t. Here’s how to think about it. Clarity upfront saves time later: Instead of making corrections after the fact, take time to explain your expectations in advance. Whether it’s the layout of a newsletter or a framework for strategy, be clear on what you want from the beginning. Start with dialogue:  Have a conversation about the process. Don’t assume your team knows exactly how you want things done. Ask them what they know and what they think. Provide specifics about what you expect and why, allowing room for a back-and-forth discussion. Prevent, don’t react:  Setting clear guidelines early means you won't find yourself in a cycle of constant corrections. That’s valuable time saved for everyone. I’ve felt the frustration of repetitive feedback loops, and I’ve seen how powerful it can be when leaders shift from reactive to proactive communication. It transforms team dynamics, builds trust, and empowers everyone to perform at their best. What’s your approach to ensuring your team understands your expectations upfront? #leadership  #startups  #business  #strategy