New advice for aspiring managers

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Q&A

I had a conversation with a colleague the other week who is interested in moving into management. It was during this conversation that I realized just how different my advice is now compared to even a few years ago, so I thought it would be worth writing down and sharing more broadly.

What hasn’t changed

Before getting into everything that has changed, I wanted to point out something that is still important and true: the world needs more great leaders.

It is something that I believed when I thought I’d give the job a shot myself many years ago, and it is the reason that my books and this newsletter exist (especially when I write it right up to the deadline…)

Managing teams is hard but can be incredibly rewarding. It gives you the opportunity to help people grow, succeed, and be happy. It lets you build great products that you couldn’t build alone. And, over time, as you look back at all of the people that you mentored and see how they’ve all gone on to do great things, it can be one of the most fulfilling things you can do in your career.

So, there is a place for you in management if all of that sounds appealing to you. But the manner in which you will do it, and the environment that you will be doing it in, is very different.

Companies reflect the world around them

Managers exist within a new world. A lot has changed. We’ve been though a pandemic, a recession, and for the first time in a long time, interest rates are high and there is far less cheap capital for companies to use in the form of investment or credit.

For anyone that got into management in the last 15 years, fiscally, it couldn’t be more distinct. Over the ZIRP period, cheap capital meant plenty of investment into technology companies, and that meant a lot budget and a lot of hiring.

Lots of hiring needs lots of managers, and that meant that there were plenty of opportunities for people to make the switch, and it was a safe environment to do so: all these new people needed to report to someone, after all.

Fast forward to today, after years of post-pandemic layoffs, you can see a number of key differences:

  • Managers have been specifically targeted in reporting on major tech layoffs. The term “flattening” has entered the vernacular, meaning that companies are looking to reduce the number of managers and layers in the organization.
  • Related to the above, there is a lot more scrutiny on the value that managers provide. Despite hiring flurries creating management roles in the first place, managers are now being asked to justify their existence.
  • And, following that, the wave of new AI tooling that can make engineers more productive is making companies optimize for either having fewer people do more work, or for more individual contributors than managers to increase raw output.

Now, back to the premise of this article: yes, it is still possible to get into management. But the environment is more challenging and you really need to be invested in it to succeed.

Growth is expanding impact, not headcount

Whereas the previous focus of managers was to rapidly hire and scale their teams, today’s focus is on expanding impact. This is because in today’s macroeconomic environment, output is key.

In the eyes of a 2025 company, the more that you can do with fewer people, the better. There are very few additional people to go around, so the focus is on how you can help your team do more with less.

This may have some consequences for the new manager:

  • They may not be able to hire as many people as they would like, or at all. This means that they will need to focus on how to get the most out of their existing team.
  • They will likely need to remain more hands-on with their smaller team, rather than fully delegating work to others. I wrote about this before in an article titled Being In The Details. You don’t become a manager to become hands-off in 2025: that’s a surefire way to be seen as underperforming.
  • As a result of the above, the pure (fully delegated) manager may not even be a thing any more in front-line teams. Thus, managers are often more of a hybrid role, where they are still doing some of the work themselves, while also managing others.
  • If new managers are expecting to grow to a Director or VP role, they may need to adjust their expectations. The path to those roles is still there, but it is going to be a lot harder and take longer than it did in the past. In the same way that there are only 20 Premier League managers, there are only so many senior roles to go around, and they are being created far less frequently than they were before.

So, to the new manager: do it if you are happy to be hands-on and focused on running one team for some time. If you are going to be disappointed that you can’t make VP in two years, then maybe now isn’t the right time for you to make the switch.

Efficiency is the new growth

In a capital-constrained environment, the focus is on efficiency. Whereas a growth-mode manager may have had a primary focus on hiring and coaching, now engineering managers are expected to be all-in on efficiency.

This means optimizing processes, eliminating bottlenecks, shipping quickly, and maximizing the productivity of their developers.

Efficiency is proven though measurement, so new managers should expect that they will need to be able to measure the output of their team in ways that they may not have had to before.

This can span operational measurements such as DORA metrics through to strategic measurements via OKRs or KPIs.

The more that you can measure, the more that you can optimize, and the more that a manager be sure that they are providing value to the company. This is a good thing to be able to do.

Quantitative measurements are essential: new managers should have the conversation straight away about how they will be measured, and therefore what the expectations are for them and their team.

Headcount is a liability until proven otherwise

Whereas new hires flowed liberally in the past, meaning that future roadmaps were built on the assumption that more people would be available to do the work, today, headcount is heavily scrutinized.

This means that every single new hire needs to be justified, and the manager needs to be able to show that they can get the most out of their existing team before they can even think about hiring more people. Some companies have even stated that managers will have to justify that AI can’t do the work before they can hire a new person.

Headcount scrutiny equally affects existing team members. Given the financial constraints, managers are expected to be proactively raising the bar on their team, and that those that are not performing at the expected level will need to be let go to make room for new hires. I wrote about this in a previous article: Performance Management: The Rising Tide.

The skeptical reader may be thinking “surely this is no different than before?”, but the reality is that it is: performance management expectations now are far higher than they have been in the past. During ZIRP, the member of staff who’s performance was on the fence of acceptable was often tolerated, and now they certainly are not.

If you are aiming to be a new manager, realize that the unsexy part of the job isn’t something you need to deal with once a year: it’s something that you will feel the pressure to do all of the time, else you’ll be the underperformer.

Scrappy is back in fashion

Being entrepreneurial and scrappy is now essential. It goes hand in hand with the efficiency focus, but it is also a mindset that is increasingly expected of those leading teams.

Your company will want you and your team to be able to show progress and value as quickly as possible, likely every single week.

This means:

  • Building prototypes and MVPs to show value quickly, rather than waiting for a fully polished product. The urge for executives to see something as proof of progress has never been higher, especially when you can vibe code a prototype in a few hours.
  • Cutting scope aggressively to ship as soon as possible. We’re back in a zero-waste environment, so continually ask yourself “what is the minimum that I can ship to deliver value?” and then do that.
  • Debates about the “right” way to do things hold little value: instead, show progress. Show a prototype, some code, or a demo. Create rather than debate.
  • Acting as an operator, not just a manager. Think of your team has a small business unit, and you are the CEO. You need to be able to make decisions quickly, pivot when necessary, and show results. Pointing at others in the company as a reason why you can’t do something doesn’t cut it: do it yourself, or find a way to get it done.

This can be either good or bad for a new manager: I know many people who love operating in this manner, and they’d certainly enjoy getting into management now. However, I equally know many people who have a different style, and they may find today’s environment a lot more challenging.

AI is now table stakes

The final key piece of advice that I would give to new managers is that use of AI is now required.

Of course, this isn’t particularly surprising given where we are in 2025, but importantly, as a manager you will be expected to increase and optimize the use of AI in your team.

What this means is that you will need to:

  • Ensure that all of your engineers are using AI in their workflows, both from use of prompting to improve research, thinking and decision making, to using AI to accelerate the production and testing of code.
  • Be able to measure the impact of AI on your team’s productivity, and be able to show how it is improving output. This may mean that you need to track metrics such as time saved, code quality improvements, or reduced cycle times; this was covered in the efficiency section above.
  • Be able to coach your team on how to use AI effectively, which means that you need to be able to use it effectively yourself.
  • Be creative in how you use AI in your own work. I wrote a few previous articles on this, such as LLMs: An Operator’s ViewA weekly mind meld, and A bag of worries: tackling overwhelm with LLMs. Get creative and inspire your team.
  • Likely treat AI skeptics as underperformers. Although it makes me feel somewhat uncomfortable writing this, there really is no place for people who refuse to use AI in today’s software engineering roles: it is evident that productivity is significantly higher when it is used, and so it is a key part of your job to ensure that your team is using it effectively.

So, do you still want to be a manager?

Remember, and I said it at the start: the world needs more great leaders, and if you want to do it, I’m sure that you can. The issue is that the world has changed outside of our control, so we have to adapt and operate differently.

If you’re excited by the prospect of being scrappy, hard on performance, resourceful and able to do more with less, and want to help teams level up in their use of AI, then maybe now is a good time for you to make the switch. After all, if an opportunity presents itself, remember that these opportunities are far rarer than before.

Best of luck.

A bag of worries: tackling overwhelm with LLMs

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Growth

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.