Writing Concise Notes for Weekly Check-Ins

One of the most valuable habits I picked up in my career didn’t come from a book or a course. It came from Anthony Kennada when I worked with him at AudiencePlus. He taught me a simple but powerful practice: send a weekly roundup. Wins. What moved forward. What’s blocked. At AudiencePlus, I called it “Sunday Thoughts.” Every Sunday evening, I’d write Anthony a quick email while organizing my week. It wasn’t long or exhaustive. Just enough to show progress, highlight priorities, and flag obstacles. That habit stuck. At Circle, it’s evolved into my “Friday Roundup.” It only takes 20 minutes, and I’ve tailored it over time to cover exactly what my founders care most about. The feedback has been clear. They find it valuable to have a quick pulse on where key initiatives stand. Over the years, it’s also surfaced misalignment early, which let us course-correct before things got off track. And this isn’t just for leaders. If you’re an IC, try it with your manager. A short weekly update makes their job easier, shows initiative, and gives you more visibility than you might think. I’ve found this to be especially important in a remote environment. Without hallway chats or quick drop-ins, communication has to be intentional. Otherwise, silos can form fast. This isn’t just a status update. It’s a way to keep the right people aligned week after week. Shoutout to Anthony for inspiring a practice I still use today. Alright, time to go write this week’s roundup.

One of the biggest struggles for new sales managers is figuring out how much to coach and how often to check in. You do not want to micromanage.  You also do not want to be caught off guard when deals fall through or reps miss quota. Here is a simple habit I recommend to every field sales leader I coach.  Ask for a weekly report. Just a short summary from each rep:  What they accomplished.  What they are focused on for next week.  Where they are stuck. It takes five minutes to write.  And it completely changes the quality of your one-on-ones. Here is the quick template I share with my clients: Wins: Closed renewal with XYZ account. Had a great first meeting with a new lead from last week’s conference.  Focus for next week: Follow-up on demo feedback from ABC Corp and set up Q4 planning call with two top accounts.  Stuck on: Unsure who the decision-maker is at DEF Inc. Need help navigating their org chart. Three bullet points. Simple.  But it gives their manager everything they need to lead well. Consistency builds visibility.  And visibility builds trust. 

Weekly reports? BOOORING! Just kidding.  In fact, they are a misunderstood high-powered secret super tool. Leaders in any organization are like nodes in an information network. If the nodes are clogged, information isn't distributed well. This leads to stress, chaos, and failure in the system. If you write a weekly report every week that is public towards your leadership and your team, you turn from a clogged up node into an information super highway.  The reports shows achievements, how well we are performing towards a goal, and how unexpected events are handled immediately.  The team loves it because they see how you tell the team’s story. Leadership likes it because they have absolute peace of mind around what your team is doing and they can chime in if they can contribute a useful piece of information (enabling information flow again here).  Here is a template you can use: -- # 1 Big Thing: <title_of_big_thing> There is mostly one big topic that was most important that week. That big topic gets prime real estate in your report. Describe what happened in a short, clear paragraph here. ## <smaller_topic> Underneath the the 1 Big Thing, put other topics that were important this week and write short, succinct paragraphs about them. ## <another_topic> Topics could be: - Challenges and how the team addressed them (super important) - Describing decisions and their reasoning - Celebrating achievements - Progress updates towards a goal ## <third_topic> 3 to 5 topics is a good amount. Make sure you list only the most important stuff. Mind your audience. Regularly check-in with your audience to see if this report is useful for them.  ## <misc_topics> You can add a short list of miscellaneous topics at the end.  ## <fun_links_section> I like to close the report with a few links that were useful this week. It could be internal documentation or an interesting article on the web, etc.  -- Try it. You won’t regret it. P.S. As always: consistency is 🔑

One habit that changed the way I worked (and even got me 2x promotions in 3 years): designing a great check-in document. Most of the time, we walk into 1:1s and updates with a jumble of things in our head. The conversation ends up being tactical, rushed, or missing the bigger picture. Here’s the structure I use, and it worked like magic for me: 1️⃣ How am I feeling this week What gave me energy? What was worrying me (work + personal)? Starting with this makes the check-in human, not just a task list. 2️⃣ Highlights + concerns This sets the tone for the discussion. What I am proud of, and what needs attention. It also subtly shows progress. 3️⃣ Projects Updates on all and questions on those that need discussion. This kept meetings focused on decisions, not updates. 4️⃣ Time spent It gives visibility and builds alignment, avoiding the “why did you spend so much time here?” conversations at appraisal time. 5️⃣ Gratitude Calling out people who helped me every week. It shows I am a team player and spotlights my tribe in the org. It takes a good 1-2 hours to fill in. But the results are too good to not do it. Manager shows up prepared. You reflect on weekly progress. Your projects are organized. And nothing slips through the cracks. PS: Would you add anything to this list? #Leadership #Productivity #Habits #ChiefOfStaff #Growth

As the week winds down, I’ve learned that keeping weekly updates steady and straightforward makes project work easier for everyone. You don’t need long reports or fancy slides. What people really need is clear, short information about where things stand and what’s coming next. A useful weekly update starts with a short reflection on what was completed. This isn’t a place for every task, just the meaningful steps that moved the work forward. Naming these wins helps teams see progress, especially in weeks that felt chaotic. Next comes a clear look at what’s being worked on in the coming days. This helps the team and stakeholders understand the immediate focus and the reasoning behind it. When people know what’s ahead, they make better decisions and avoid unnecessary back and forth. Every project will have its slow points, so the update should also include anything blocked or at risk. Keeping this section honest prevents small delays from turning into bigger issues. It’s a gentle way of saying, “Here’s where we need to pay attention.” From there, it helps to state any asks directly, approvals, information, alignment, or decisions waiting on someone’s desk. When people know exactly what’s expected from them, the work moves faster and with less friction. And finally, a short reminder of key dates, deadlines, or upcoming moments that the team should keep in view. It’s a small detail that creates a lot of calm, especially when schedules start to fill up. This simple structure, what we completed, what’s next, what’s blocked, what we need, and what to remember, keeps weekly updates clear and predictable. It’s a steady way to end the week: one page, a few lines, and enough clarity to walk into Monday with a level head. Have an amazing weekend 🌸