The Engineering Manager

If you’ve had periods in your leadership journey where you feel like you’re generating more to-do items than you can handle, then you’re not alone.

Every day, you might add five or ten items to your list, each representing an entire project that could take weeks or even months to complete.

For example, after a busy Monday your list might have the following items added to it:

• Review increasing infrastructure costs and propose optimizations.
• Plan team offsite for next quarter including budget and agenda.
• Look into security audit findings and create action plan.
• Prepare for upcoming performance reviews and set criteria.

Sigh.

And that’s on top of the existing huge items that you already have on your list from last week which you haven’t had the time to deal with yet.

This can lead to a feeling of being overwhelmed, like you’re carrying around a heavy mental load. Each item on your list feels like a weight, and the more you add, the heavier it gets.

Although the pragmatist may say that the solution is simply to put time aside to properly triage, prioritize, and delegate or action these items, this is easier said than done. At the end of a busy day I’m usually pretty tired, and the creative juice that I need to properly think through these items is often in short supply.

My own mental resistance to dealing with these items is often the biggest barrier to getting them done, rather than the actual complexity of the items themselves. Long days with lots of context switching can seriously deplete my mental capacity. I wrote about managing this capacity in a previous article, noting how it can expand and contract based on the demands of the day.

In order to better manage my capacity and energy, and also leaning on creative ways to use LLMs, like in my mind meld technique from the last article I’ve been trying a new approach to deal with this problem, which I call “the bag of worries”.

Separating to-dos from worries

The first problem I have is that the big, gnarly, and unprioritized items on my to-do list are not really to-dos, but larger, unsorted worries, like in the example list at the beginning of the article: a discussion in a meeting making me worried about projected infrastructure costs, or some known bottlenecks in the system that require deeper investigation.

These tasks are not five minute jobs.

Compared to the other things on my to-do list which are often small, actionable items that I can rattle through sequentially, these larger items are more like worries that I carry around with me. They require a fair bit of unpacking and thought before I can even start to think about how to tackle them.

As a result, I’ve separated out my to-do list into two parts: a “to-do” list for actionable items, and a “worries” list for these larger, more complex items that need more thought and planning. Because the to-do list is typically sorted by priority, and the worries list is not, I call my worries list “the bag of worries”, as they’re all jumbled together in a single place.

I wrote previously about my second-brain system of gather, decide, execute, in which I use Logseq to continually make notes and gather information, and then decide what to do with it. The bag of worries is a natural extension of this system (it’s just a page in Logseq), and it allows me to keep track of these larger items without them cluttering up my to-do list.

As I go through my day and see things that worry me, or that need looking into further, I just throw them into the bag of worries. I don’t worry (no pun intended) about whether they’re important or not, or whether I should be doing them now or later. I just add them to the bag.

I’m feeling lucky

But hang on, isn’t that just procrastination? Well, kind of. Based on self-observation, if I have these kinds of big worrisome items staring me in the face alongside my to-do list, I tend to begin to feel a little overwhelmed, and I find it hard to focus on the essential tasks that I need to get done. So tucking them away in the bag of worries is a way to declutter my mind and focus on the immediate tasks at hand.

However, the bag of worries is not just a dumping ground, and I’ve been experimenting with picking one big thing from it each day to break down and then make a plan from.

Since these items in the bag of worries often are large and require a lot of unpacking, I’ve been enlisting the help of LLMs to kickstart my thinking and planning process.

In the last article I wrote about how to use the Prompt Engineering whitepaper as an input to your own GPT or Gemini Gem (or other equivalent), enabling you to generate significantly better prompts than you might write unassisted.

To save clicking away from this article, I’ll reproduce the Gem/GPT here, of which you attach the PDF to as additional context:

You are a tool to generate excellent prompts that will greatly improve output compared to what is given as input. You will use the attached book on Prompt Engineering to formulate these prompts and you will return the improved prompt along with your reasoning for why it is better.

You are always helping a CTO do their job, so frame the prompts as such.

I then use this to generate a prompt for the bag of worries: it helps me select one at random, unpack it, and then generate a plan of action.

As a CTO, I'm managing a 'bag of worries' – a list of pressing technical and strategic issues that require my attention. You are my expert executive assistant. I need your assistance to systematically tackle these.

My current bag of worries is:

[insert list of worries here, e.g. "increasing infrastructure costs", "team offsite planning", "security audit findings", "performance reviews preparation"]

Your task is to: 

* **Randomly Select One Worry**: From the provided list, please choose a single worry at random. Clearly state the selected worry. 
* **Generate a Comprehensive Action Plan**: For the selected worry, develop a detailed and actionable plan to help me, as the CTO, take positive and effective action. 

This plan should be structured and include the following elements:

* **Objective**: A clear, concise statement of what successful resolution of this worry looks like. 
* **Key Actionable Steps**: A sequence of 3-5 primary steps to address the worry. For each step, provide a brief description of the action. 
* **Stakeholder Identification**: List key individuals or teams (e.g., Head of Engineering, Security Lead, Product Management, specific engineering squads) that need to be involved, and their general role in the action plan. 
* **Potential Challenges & Mitigation Strategies**: Identify 1-2 potential roadblocks or challenges that might arise and suggest a proactive mitigation strategy for each. 
* **Resource Considerations**: Briefly mention any critical resources (e.g., budget allocation, specialized tools, external consultants, dedicated time from specific teams) that might be necessary. 
* **Success Metrics**: Define 1-2 measurable indicators that would signify progress or successful resolution of the worry. 
* **Suggested Initial Timeline/Focus for the Next 2 Weeks**: Outline what realistically can be initiated or achieved in the immediate short term (e.g., initial meetings, data gathering, preliminary assessments). 

Output Format: Please present the selected worry first, followed by the detailed action plan with clear headings for each of the elements listed above. 

Tone and Style: Strategic, decisive, and action-oriented, suitable for a CTO's executive advisor.

This works surprisingly well for plucking something out of the bag of worries and removing the initial mental effort to turn it into a real action plan.

The generated action plans are fairly long, so I didn’t want to copy and paste it verbatim into this article. However, I do recommend trying this out for yourself, as I have found that it’s been the best way of taking a big scary worry and having me able to actually do something about it in a fast and structured way.

Or, you could prioritize

Another way to tackle the bag of worries is following the classic Eisenhower Matrix prioritization exercise, except you let the LLM do it for you. Here’s a prompt for that:

Assume the role of an expert executive assistant, highly skilled in productivity and prioritization frameworks. I am your CTO, and I'm providing you with my current 'bag of worries' – an unsorted list of tasks, concerns, and observations that require my attention.

Your task is to:
1.  **Analyze each item** from my provided list of worries.
2.  **Categorize each item** according to the Eisenhower Matrix. For clarity, these categories are:
    * **Urgent and Important (Do First):** Tasks that demand immediate attention and are critical for achieving significant goals.
    * **Important but Not Urgent (Schedule):** Tasks that are vital for long-term success and strategic objectives but do not require immediate action; these should be planned and scheduled.
    * **Urgent but Not Important (Delegate):** Tasks that require prompt handling but do not necessitate my direct involvement and can be effectively assigned to someone else.
    * **Neither Urgent nor Important (Eliminate/Delay):** Tasks that contribute minimally to our objectives and can likely be removed from the list or significantly deferred.
3.  **Present the categorized list clearly.** Please use distinct headings for each of the four Eisenhower Matrix quadrants.
4.  **Provide a brief rationale (1-2 sentences) for each item's categorization.** Explain the thinking behind placing it in that specific quadrant, especially if urgency or importance might be ambiguous. (Adopt a 'think step-by-step' approach for your reasoning).
5.  After categorizing all items, **identify and recommend the single most critical item** from the 'Urgent and Important' quadrant that I should address first.
6.  **Explain your reasoning** for selecting this top-priority item over any others in the 'Urgent and Important' quadrant.

My 'bag of worries' is as follows:
[Insert your comma-separated or bulleted list of worries here.]

Please process this list and provide your categorized output and recommendation.

Try it out yourself

Before going back to whatever else you were doing with the rest of your day, try this out for yourself:

1. Take a moment to write down the top three or four big worries that you have at work right now. Perhaps these are upcoming performance reviews, a design document that needs writing, or perhaps you need to come up with a plan for analyzing the current budget and finding 5% savings.
2. Open up your favorite LLM, such as ChatGPT or Gemini, and paste in the bag of worries prompt above (you can choose between the random selection or prioritization version).
3. Copy your worries into the prompt at the place with the square brackets in either.
4. Hit send and see what comes back.
5. Look at the action plan, and see if you then have a clearer idea of what to do next.
6. If you do, then congratulations! You’ve just taken a step towards tackling one of your big worries. That was easy, wasn’t it?
7. If you don’t, then try tweaking the prompt a little bit to better suit your needs. You could do this by using the reusable prompt engineering gem above, or by just changing the wording.

Congratulations on having a new executive assistant.

You might find that it helps to have a version of this for your home life too, as it’s rare that you only carry around a bag of worries for work. There’s DIY to do, insurance to renew, and family events to plan.

Every day I find more neat tricks that LLMs can do in order to help me be more productive at work. I find you get out what you put in.

How are you managing your own ‘bag of worries’? Have you found other creative, non-obvious applications for LLMs in your managerial work? Let me know if you have.