A deep dive into my business journal prompts and how they help me make better decisions everyday

My business journal has become the single biggest needle-mover when it comes to generating  ideas, keeping goals on track, and reflecting on the them.

In my previous post, I've laid out how the business journal works. This is a follow-up post to dive into all the prompts I’ve included in my business journal template.

Let’s get started.

Prompt intervals and types

The journaling prompts are split into three main intervals:

1. Daily prompts: These are daily questions I’m asking myself to keep me on track with my goals and values on a day-to-day basis.
2. Quarterly prompts: These prompts can be done on either a monthly or quarterly basis.
3. Annual prompts: These are questions I ask myself at least once every year. They’re deeper questions that take longer to think, but are also reveal more about what I want to get out of my business in the upcoming 12 months.

I’ve also separated my business journal prompts into three main types:

1. Reflection prompts
2. Mission and value prompts
3. Idea generation prompts

More on these below.

1. Reflection prompts

Reflection prompts are aimed at helping me learn more about myself, the actions I’ve taken, and appreciate those around me. Most importantly, they help keep me on track on my long-term goals.

All of these questions are answered in relation to where I am towards my goal.

Below is my full set of reflection prompts for the daily, quarterly and annual journal.

Daily reflection prompts

1. What was something that went well today?

2. What’s one challenge I’ve faced today?

3. Name one decision I’ve made today, what was your decision-making process and what factors were considered?

• Thanks to this prompt, I become more aware of the ‘micro-decisions’ I make that affect the business everyday. Contemplating on many of these decisions allows me to question whether I’m delegating enough and what intentions or emotions were underlying my decision-making process.

4. Name at least one thing I was grateful for today

• Intentionally practicing gratitude in the workplace, not only at home

Quarterly reflection prompts

1. What was a seemingly inconsequential decision that made a big impact on the business?

2. What were some good investments that I’ve made along the way?

3. What can I learn from investments that weren’t so great?

Annual reflection prompts

1. Write down 10 things that are true about your business today. Don’t think too much, just jot down whatever comes to mind.

• A great prompt to reflect on where things are. It made me realize and acknowledge achievements that I may have looked over in the past 12 months otherwise.

2. Write down 10 things you want to be true about your business in the next 12 months. Write it down in present tense as if you’ve already achieved it.

• Following the last prompt, this one helps me figure out where I want to take the business in the next 12 months. It forces me to visualize where things will be, making me become aware of what I want to get out of work in the next year.

3. Write down 1-3 things that bought you a sense of fulfillment. It has to meet these three criteria: It’s an action you took, you believe you did it well, it brought you a sense of fulfillment.

• Fulfillment stories have become a great tool to remind me why I come to work everyday. It works particularly well on days where friction is high and motivation is low. I credit it as one of the single most impactful prompts I've ever come across.

2. Mission & value prompts

Mission and value prompts add an element of accountability in keeping my in line with our core values. For instance, they question whether my actions are team-centric or whether I’m making an effort to form new connections with others.

These prompts are also reminders that goals change and values evolve.

In the past, I’ve realized our goals have shifted gradually overtime without us being aware of it, leading to wrong decisions being made, even when they felt right.

Being more cognizant of changes in objectives and values means are can make the right adjustments to our business early on to stay on track.

Daily mission & value prompts

1. Name at least one thing I did that was aligned with the company’s core values

2. What’s one thing I did to better serve my team?

• This prompt helps me do two things. First, it allows me to better empathize with the team, identifying friction points they’re facing and how they can grow from their experiences. Secondly, it keeps me accountable as a leader, making sure that I’m investing my time and effort for the betterment of the team.

3. What’s something new I’ve learnt or a major realization I’ve had today?

Quarterly mission & value prompts

1. Name at least 3 people I want to connect or reconnect with, name at least one old and one new connection.

2. Write a thank you note to someone. Sending it is optional.

• I sometimes prefer vocalizing these notes during 1:1s.

Annual mission & value prompts

1. Have my objectives changed from when I first started? What are those?

2. Describe what an ideal day at work looks like. Has that changed?

These two prompts help me track and identify gradual shifts in goals and objectives, preventing them from going unnoticed. The second prompt, in particular, forces me to visualize what an ideal day looks like. Over the past two years, I’ve been surprised by how my answer to this question has signed ever so slightly each time.

3. Idea generation prompts

The final set of journal prompts are designed to generate new ideas for the business.

One mistake I’ve made in the past was working too much in the business, and not enough on the business.

These prompts allow me to be more intentional on working to improve how we run things at Criclabs, focusing on pain points, areas of opportunities and open-ended questions.

Daily idea generation prompts

1. Name a task that I’ve been dreading. How can I break it up into the smallest possible steps?

• To identify micro-stressors I face on a daily basis and come up with better ways of attacking them.

2. What’s a piece of feedback I’d like to give to a team member based on today’s work?

• These are stored as key takeaways in future performance reviews with each team member, allowing me to offer detailed examples for each piece of feedback I give.

3. How did the team collaborate today? Were there any conflicts or areas for improvement in communication or teamwork?

4. Name one thing that happened with a client today, how did it go and what did you learn from it?

• Treating every client interaction as an opportunity to learn.

Quarterly idea generation prompts

1. What's the biggest bottleneck to achieving my next goal?

• A problem-solution orientated prompt to identify a hidden or overlooked bottleneck at work.

2. What is something FUN that I want to do with the business in the next three months?

• A personal one here. Prioritizing ‘fun’ at work has been central to how we run our business at Cric, even if it comes at the cost of efficiency and margins at times. It’s what keeps us going, it’s what allows us to enjoy the journey.

Annual idea generation prompts

1. Think about a “what if?” or worst-case scenario and work your way through the problem, identifying your options to get through it if it were to happen.

2. Name one thing I wish I could do more quickly

3. Name one aspect of our service that we need to improve the most.

• These are annual review prompts which are incorporated into our annual management retreat. More on that in an upcoming post.