Work Diaries: A Daily Reflective Practice That Helps Your Team Scale Without Burning Out

There’s a lot asked of our creative teams. 

As much as we strive for our teams to be strategic, proactive partners for the brands and companies we support, the reality is we also field a lot of requests. A 👏 lot 👏. Moving from project to project, meeting to meeting, and from one “quick question” on Slack to the next, work can start to feel like one big blur.

Balancing proactive, strategic planning with reacting to the day-to-day needs of the brands we support is part of the job. Without the right guardrails, it can also lead to burnout and frustration for both you and your team. 

When work is overly hyper-reactive, there isn’t space for our teams to reflect on how they are feeling about the work they are doing. Not about the result of the project, but instead how they felt during the process. That distinction matters. If we don’t understand the moments that energize us versus the ones that drain us, we can’t grow. We can’t improve our team processes, set better boundaries, and we, as Creative Leaders, definitely can’t coach others through their own development.

This is why I developed Work Diaries. 

A Work Diary is a simple, yet powerful tool. This isn’t about tracking productivity. It’s about uncovering patterns.

It’s a space for self-reflection to help improve insight into how we work and how that work affects us. Over time, these diary entries form a larger picture that helps individual team members and their managers to better understand what lights them up as well as what drains them at work. 

From these insights, you and your team can start to co-create a healthier, more intentional way of working. One that not only supports creative output but also helps each person develop the self-awareness to lead themselves. Whether that means setting new boundaries, refining how they approach their work, or naming what they need to thrive, this process puts reflection into action.

Important Note: This post will focus more on you as the creative leader guiding your team through this process. That’s not to say that you can’t do this yourself, but the real power behind this tool lies in the guided facilitation. You can certainly do this process on your own (or maybe even using AI or a trusted colleague to support uncovering your own themes), but for the purposes of this post, we will focus on the tool, the process, and how to guide your team through it. 

“You and your team can start to co-create a healthier, more intentional way of working. One that not only supports creative output but also helps each person develop the self-awareness to lead themselves.”

This process is all about your mindset, so proceed with caution.

Before we start, there are four critical mindsets for you to bring to this exercise if it is going to work:

1. This is NOT a work tracking tool: If your team thinks your intentions are anything other than supporting their development, they will feel misled and you will lose their trust. Make sure to address this directly with your team at the onset of your work together. Reinforce the purpose of this, and hold yourself accountable to it. While this process helps you guide your individual team members to build more awareness around how they work, it’s also an opportunity to build trust. 
2. We listen, and we DON’T judge: The magic of this process is the candid and vulnerable conversations that arise during this process, which is only possible if your team members feel psychologically safe. That starts with how you show up in this process. If you immediately jump into problem-solving mode or get frustrated, the space to explore potential themes and build a meaningful, trusting relationship is gone. Check in with yourself before you get started. Can you create a safe space for exploration where you ask the necessary questions to help draw out the larger themes for each of your team members? Are you able to listen and stay curious? 
3. This is NOT a requirement: This is a journey of exploration that requires a great deal of trust and vulnerability for it to be successful. Meaning, it has to be a journey THEY choose to join you on. You can’t force them to do this. Don’t be surprised to find team members who sign up, but then fall behind or completely off on keeping up with their diary. You can’t force them to do this. Instead, you can be there to encourage them and remind them that you are here to pick this up with them when they are ready. It’s okay to table this discussion for a month or so and then revisit it with them. Some just need a bit more time to warm up to the process. 
4. Respect their privacy: I include this last bullet as more of a best practice suggestion to remind your team members that whatever is shared during this process can be as private as they feel comfortable with (I take the same approach with 1:1s as well). 

The Anatomy of a Work Diary

Every work diary has three important parts for your team members to focus on. Most parts are flexible while others are not, so it’s crucial that you and your team members understand these sections correctly before you get started. 

Part 1: Data Collection

For this to work, we need data, and in this instance, our data will be diary entries (or events, as I like to refer to them).

An event can be anything work-related that your team member wants to add to their diary, comment on, and score (I’ll explain the scoring system more a bit later). When it comes to your team members’ entries, I find it’s best to leave this part of the process open to whatever they choose to include. What’s most important is that they are using it as much as possible. I don’t like limiting them to WHAT they add, as what they choose to include can be just as enlightening as the actual work. This is also why I like to refer to them as events, as it doesn’t have to be just a project; it could be a team member interaction, a specific project management issue, or something that popped up unexpectedly. 

For example, I had one team member who had multiple events that were scored very low. On closer examination, many of the low-scored events were due to her being interrupted by tech difficulties. Now, that is a very obvious thing to be annoyed by and this may not be important at first glance, but after deeper reflection together (and also when held up against her other entries) we were able to uncover that she placed a high value on being able to achieve flow state with work, and these tech hiccups were keeping her from being able to do that. On face value, a fairly trivial and common issue, when pooled with her other entries, it helped to illuminate a larger, more important picture about how she prefers to work—in an uninterrupted state of flow. 

How much data is too much data? 

Good question. It really depends on the person. The team member I referenced above loved adding to their work diary, and we ended up having way more data than was needed, causing our theme exploration process to take a bit longer than planned. A rule of thumb I follow is to give my team members around 4 weeks to fill in their Work Diary, and then use our weekly 1:1 meetings to check in on progress and answer any questions. This way, you can gauge their progress and decide if more time is needed. 

I wish I could give you a firm number here, but it really depends on the person, and how they interact with the diary. That is why the weekly check-ins are so crucial. This is where you can get a sense of how things are going and reinforce that this process is not only important for them, it’s important to you as well. 

“It’s only when we truly understand what conditions will maximize our team members’ productivity…that we can provide the necessary support as leaders to create the environment for these conditions to flourish.”

Part 2: Scoring & Sentiment

For each diary entry, we want our team members to associate a score with that event. While we have been flexible around what defines an event, our scoring structure is the only part of this process that is rigid and uniform across all Work Diaries you do with your team. 

The scoring will range from 1 (the lowest) to 10 (the highest). Much like any survey you may have done, 5 is your neutral score. This means the experience was neither good nor bad, while anything above a 5 is progressively better and vice versa. 

While facilitating this process, keep in mind that scoring will serve two purposes in this process. 

1. Individual Project Experience: Scoring each diary entry provides a quick snapshot of how they felt during the event. A score on its own is not enough, which is why, along with the score, we want them to give an explanation of this score (more on that next). 
   
2. Overall Team Member Sentiment: As you will see in the Work Diary example included with this post, there is a space at the bottom that automatically provides the overall score average. After a full month of filling out their diary, this score will reflect your team members’ overall work satisfaction score for the last month. As I am sure you would expect, there’s a big if to follow that statement. If your team member is engaged in the process and does their best to add to it daily, then this is (in my humble opinion) the best, objective view into how satisfied your team member is at work.

When thinking about scoring, I aim to keep my team in the average range of 6-8. Why not 9-10, Chris? Well, easy. It’s not the reality of our work. Creative work is demanding and emotionally challenging. Priorities can change rapidly. Stakeholders can be difficult and confusing. If they’re regularly in this range, that tells me they are, more often than not, satisfied. Satisfaction in their work means they retain engagement and have the energy needed to continue making refinements in how they work. Would I prefer them to be in the 9-10 range, absolutely, but as a leader, you know that making false promises and under-delivering is a sure-fire way to lose their trust in you. Let’s shoot for the stars and land on the moon.

That said, if you choose to rate reading this post as a 10 in your diary…now, that wouldn’t bother me one bit 😉

Part 3: Explanations & Context

This is pretty straightforward, but as I mentioned above, it’s crucial for each entry to have a short explanation of why they scored it this way. 

Much like the other parts of this process, don’t put too many rules on what this entails. This is about them doing a quick brain dump around what influenced this score while everything is still fresh in their minds. Some people jot down short notes, and others can write small novellas. The important thing here is for them to add context around the score to help facilitate the theme exploration process. 

Remember, aside from the score, let your team members make this their own. The freedom to explore their own thoughts and feelings is where the magic happens.

“Let your team members make this their own. The freedom to explore their own thoughts and feelings is where the magic happens.”

Guided Work Diary Theme Exploration

At this point, you have been having regular check-ins to see how your team members are progressing with their work diary, and feel confident that you have enough data to move to the final stage of this process. Now it’s time to set up a special 1-hour meeting (or Zoom call, for my remote homies) to dig into what they have been putting into their diary. 

This is the part that truly sets this process apart from others, but is also the hardest to teach. The important thing to remember is that this isn’t about problem-solving or finding quick fixes. It’s about holding space, being curious, and exploring insights together. 

Here’s my approach to this stage of the process;

• Set the stage: To kick things off, I like to reiterate that the goal of this process is for us to gain improved awareness around how they work. This is not a performance review or to track their work, and my responsibility is to help facilitate the process and that they should expect me to challenge them to dig a little deeper. I also let them know that I will be taking notes in their work diary to help track patterns and that anything they share during this process is private.  
• Individual event review: Next, we go line by line through all of their entries. This is where they get a chance to share their experience and why that event received that specific score. 
• Be an active listener: You can’t be passive here. This part of the process requires full presence. You’re listening for more than just words. You’re noticing tone, pauses, or when someone’s brushing past something that might matter. Stay present.
• On-going note taking: As they talk, take notes and jot down key words or phrases that stand out. These are your clues to deeper patterns. Trust your instincts. Sometimes a word or phrase will stand out to you, but you won’t know quite why. Much like an incomplete puzzle, the picture becomes clearer as more pieces fall into place. 
• Ask questions and don’t be afraid to push: If an answer feels vague, or if a score doesn’t quite add up, this is your cue to gently challenge them to go deeper. Remember, your role here is to help uncover parts of themselves that they weren’t initially aware of. 
• Zoom in or move on:  Not every event is going to be useful or illuminating. Some may need to be probed further, while others are simple and don’t have much to reveal. That’s normal, so don’t be afraid to keep things moving. The more you practice this, the better you’ll get at sensing which is which.
• Spot and name patterns: As you move through the diary, what keeps showing up? What stands out in the highs or lows? You don’t need to wait till the end to start identifying patterns, but also don’t force it too soon. The goal is to keep your aperture open wide enough to identify themes as they arise. 
• Action Plan & Next Steps: Work together to name a few insights or themes that feel true. Do this together by asking them often if these insights resonate with them. End by deciding together what small experiments or shifts they want to try. This isn’t about adding more work, it’s about testing what you’ve already uncovered. As always, agree to revisit and refine during future 1:1s.

The Wrap Up

So far, we have discussed how Work Diaries are an invaluable reflection tool for creative leaders. They not only help you understand what keeps them engaged and inspired at work, but it also helps to continue to solidify trust and emotional safety within your team.

There is one last important aspect of this tool that I want to leave you with. 

It helps grow future leaders. 

Through this process, your team members are able to unlock an awareness within themselves that they didn’t have before. This, paired with your modeling around communicating for their own needs and healthy boundary setting, gives them the ability to self-lead instead of coming to you first. That kind of self-leadership is what allows you to sustainably scale your team’s output without burning them (or yourself) out. They can spot misalignment, name what’s not working, and have the tools to make changes on their own. 

Especially now, with shrinking budgets and headcounts, leaders can’t afford to be the only source of clarity and direction. The ability to meaningfully scale how our team operates doesn’t happen by accident. It takes reflection, trust, and clarity. We need to equip our teams to have the tools to self-lead and that only happens when leaders create space for them to reflect and grow. 

One diary entry at a time.