TBM 252: How to Troubleshoot Status Updates and Syncs

I've often wondered why some companies can develop strong habits around introspection, weekly goals, weekly reviews, progress logs, and regular updates. Meanwhile, other companies never stick to those habits or do some sort of performative version of the habits without any real value.

It is not for lack of trying! I've personally been on many teams over the years that have committed to one cadence or another, done the work for a while, and have let it slip.

At the day job, I’m also in the business of helping healthy habits form and troubleshoot when they don’t. It’s incredible how hard it can be to make some things stick, even when teams have the best intentions.

Here are some roadblocks to look out for.

"Feels like déjà vu. We're discussing the same issues every week."

If nothing changes week after week, then you'll end up talking about the same things over and over again. For these rituals to be valuable, something has to change. There has to be something to talk about.

Try This: If, for some reason, it's difficult to make meaningful progress in a week or two in your environment, that's a bigger problem than status updates. Discuss what got in your way and what needs to happen to make progress.

"We're busy, but it feels like we're running in circles without getting anywhere."

On the flip side, if you have a situation where there's lots of news but nothing is news—none of the updates are material or convey any progress—teams will have a lot to report, but Nothing is happening.

Try This: Be more selective about your goals. What signifies a stepping stone or point of progress?

"I'm not sure why we are doing any of this. We ship stuff. And yes, [some metric] goes up. But is any of it related?"

Related to either too little or too much information, lots of teams (and companies) have trouble aligning teams against actionable levers or inputs. Therefore, when they give updates, it is way too delivery-focused ("this long project is on track"), or it is impossibly laggy ("the goals that we don't control or impact seem to be going ok.") Nothing the team discusses feels relevant.

Try This: Consider more actionable input metrics to help guide your team. Yes, delivery matters. And yes, those laggy metrics probably matter. But you need to find the sweet spot.

"Every week, it's a new direction. It's hard to feel like there's progress when the goalpost keeps moving."

When a team's focus is constantly being challenged or changed, it becomes very discouraging to start over by giving updates on new things. It's depressing, especially since when you start something new, it might be difficult to make regular progress, and you have to try to get your momentum going all over again.

Try This: Agree on a timebox for the current area of focus. Figure out why priorities keep changing, and start removing those blockers.

"I spend 10% of my time on this, yet it feels like it's the only thing we ever discuss."

Sometimes, the work people provide status updates on is just a small percentage of their workload. They have a ton of other stuff to worry about. If what you're providing an update about is only a small part of your job, then you aren't getting the opportunity to convey the breadth and depth of what you're doing and get feedback on it.

Try This: Run an experiment where you provide an update on everything. Ask yourself (and others) to give a real overview. When faced with that reality, people often take action to reduce WIP.

"I'm not sure why we must be here for this. I can't relate to half of the updates."

When you have a bunch of individuals giving individual status updates for personal projects that are of no real interest to the other people in the meeting, the whole activity takes on a more formal and less useful format. Except for maybe the manager who's hearing everyone's updates, the fact that everyone needs to do it together seems a bit redundant. People don't need to collaborate on everything closely, but ideally, the information is useful to everyone.

Try This: Don't waste people's time. Give 1:1 updates. And maybe ask yourself if running a workgroup is your goal or whether you want to have a team. Workgroups don’t need performative team-like activities.

"It's clear they're not invested in our updates. Maybe there's a better platform or method for this."

For the update audience, if understanding progress isn't their job and they've got a lot of other stuff on their mind or plate, the update isn't providing them with any material value. It's only a small part of their week. A leader/manager in this situation will appear aloof; they may acknowledge the update, but their mind is elsewhere, and it shows.

Try This: Be honest with yourself about whether you will take action on what you're hearing in the meeting. If your mind is elsewhere, call the kettle black and cancel the meeting. Participate! What are YOUR updates?

"It's like we're writing our story but constantly erasing the previous chapter. How can we learn from our past if we don't keep a record?"

It's incredible how many teams essentially overwrite their updates and don't keep a record of past updates. There's a practice in bullet journaling that revolves around rewriting your action items repeatedly, and this works for a reason. That repetition forces reflection. You have to put something back on your list actively, and that forces you to ask the right questions.

Try This: Start rewriting your goals, milestones, etc., with each update/review. Don't copy and paste. Keep a record. I met a team recently with an incredible 200 page “log” recently, and there was so much love and obvious value baked into the work and communication.

"Everyone seems swamped, so our updates feel more like venting sessions than strategic check-ins."

When people are busy and overwhelmed, they don't have time to prepare for these updates, and it can seem like they're sort of phoning it in at the last minute. This situation is difficult because these types of updates aren't useful. People are typically sympathetic to the idea that everyone is overwhelmed. So, when you have a situation where everyone is overwhelmed, and the updates aren't actionable or useful, no one is in a position to call it out.

Try This: Spend the first 10 minutes of the meeting writing your updates. Call out that people are too busy to make their updates useful.

"The updates are all over the place. We need a clearer thread to tie them together."

"Why are we still using this format? It doesn't reflect our current goals or challenges."

It's helpful to return to similar themes, goals, metrics, or anything that adds a consistent thread to these updates. If you're giving updates at a very tactical level but not linking them to the overarching goals, it can be not very helpful for people, and they lose interest. Similarly, if you dogmatically return to the same format repeatedly, and that format doesn't fit the current shape of work or mission, it can turn people off.

Try This:

1. Experiment with a new format each quarter. Rotate the meeting design owner.

2. Keep what works.

3. Always try to revisit certain goals and "pillars."

"It's just a list of what we did, not a reflection on where we're heading or how we're feeling."

Part of the value of these check-ins is that they trigger reflection and self-assessment for the team. And action. If none of that is happening, and people are only communicating things that are already known or knowable, then there are no surprises. It's the deltas, the things that aren't going right, or the things that are going right, where there's a lot of value for people.

Try This: Ask each person in the meeting to bring one puzzle they are trying to unravel. Timebox some feedback. Invite feedback from other members.

"Why even bother mentioning it? Nothing ever changes."

When a team keeps asking for help and doesn't get any, there's not much motivation left to keep bringing up the same issue. So, updates start getting sugar-coated, and everyone knows there's this big elephant in the room. Miss a few meetings, and soon, people aren't even showing up. When everyone keeps getting blocked, and there's Nothing you can do about it, who wants to keep talking about being blocked all the time?

Try This: At the start of the next meeting, ask everyone to share one ignored issue openly. Make a plan to tackle it together.

It is all about value and meeting people's needs. Value can take lots of forms. Value can be incisive feedback. Value can involve support and congratulations. Value can focus on unblocking something or making someone's life easier. Value can be a trigger for a new collaboration. Value can sound like a leader explaining that the context has changed. Value can also be internal introspection and maybe surfacing new insights about what you're doing.

There's also an important community component. In companies that get a lot of value from regular syncs, regular goal setting (e.g., weekly goals), etc., I tend to hear feedback like:

These things motivate us!

It is incredible to see how much we can all collectively achieve together!

I get inspired by seeing other teams cranking.

It feels like we keep our promises to each other.

It is the habit of reflection that truly counts.

These quotes speak to the idea that people are willing to put in the time not only when they see individual value, or maybe value to their immediate team members, but also when they see it connected to the success of their company. 

In these companies, it's not about the framework or process in isolation; it's about the value and impact it brings to individuals, teams, and the organization.

It's the difference between tasks/processes and rituals.