I make a new Spotify playlist at the beginning of every year, and I keep adding songs I enjoy throughout the year.

Now that it’s September the 2023 edition is nice and ripe.

You can also listen to the 2022, 2021, and 2020 editions.

The Trusted Advisor is a book focused on trust and relationships in professional services but feels applicable to any work partnership.

I’ve collected a few choice quotes below.

Show, don’t tell

To make anyone believe something about you, you must demonstrate, not assert. What you claim about yourself, your colleagues, or your firm will always be received skeptically, if it is listened to at all. In Emerson’s words, “Your actions speak so loudly, I cannot hear what you are saying,”

Listen first

We must listen effectively, and be perceived to be listening effectively, before we can proceed with any advisory process. Cutting to the chase without having earned the right to do so will usually be interpreted as arrogance.

Interruptions and reordering

…if the listener breaks up our sense of story (insists on interrupting, or rearranging, or imposing his or her own sense of story line), the meaning we intend is disrupted. It feels inappropriate when someone jumps to a conclusion, or misses a connection, or gets things out of sequence. All these are forms of not “getting it.” Good listening respects the speaker by respecting the sequence of the story he or she chooses to tell us.

Listen for what’s different

At the core of earning someone’s trust is convincing them that you are dealing with them as a human being, and not as a member of a group or class or subset. Accordingly, as you listen to a client talk, the question on your mind should be, “What makes this person different from any other client I’ve served? What does that mean for what I should say and how I should behave?”

Unfortunately, this is hard work. The natural tendency for most of us is to do the exact opposite: We listen for the situations we recognize, so that we can draw upon past experience to use the words, approaches, and tools that we already know well. It’s the way most of us work, but it doesn’t always serve us well.

Sincere interest in others

So much of our time is spent focusing on ourselves, and so much of other people’s time is spent focusing on themselves, that it is a rare and surprising event whenever someone breaks the veil. Sincere interest in another person comes across strikingly simply because it is unusual.

Be sure advice is being sought

One of the biggest mistakes that advisors make is to think that their client always wants their advice. This is dangerously wrong.

…

What the advice receiver wanted was a combination of a sympathetic ear, emotional support, an understanding of the difficulties faced, and the opportunity to collect his or her own thoughts by talking them through in a non-threatening environment.

Long-term vs short-term

It’s near impossible for any professional to hide his or her true motives, whatever they may be. And if those motives are rooted in naked self-interest, they will be duly noted and reciprocated. We are not loyal to self interested people we don’t trust them. Which means we are always likely to leave them for a better price-or for someone we actually trust.

Which in turn means longterm success is compromised by such behaviour. And since the long term is nothing but a series of short terms, short-term results themselves are being harmed, not improved, by slavish adherence to short-term goals.

The truth is, both long-term and short-term results are maximised by long-term behaviour on our part. The old Goldman Sachs mantra expressed this well: “We are longterm selfish.” It is in the long-term that our goals and our clients’ goals merge and that merging reveals itself over a series of short terms.

Steps to develop trust

We suggest that there are five distinct steps in the development of a trusted relationship. In this chapter we will define each of these In the succeeding chapters, we will explore each stage in detail.

Expressed in their simplest form, the five stages are:

• Engage. “Let’s talk about…”
• Listen. “Tell me more…”
• Frame. “So the issue is…”
• Envision. “Let’s imagine…”
• Commit. “I suggest we…”

How to Decide digs into the characteristics of decision making and provides tools for making better decisions.

I took away loads of things to try and recommend the book.

Below are some of the salient points that stood out to me.

Traits of good decision making

Two things determine how your life turns out: luck and the quality of your decisions. You can only control the second.

Any decision is essentially a prediction about the future.

When making a decision your objective is to choose the option that gains you the most ground in achieving your goals, taking into account how much you’re willing to risk.

You need to develop a decision process that improves your decision quality and helps you sort your decisions to identify which are larger and which are smaller.

A good decision tool seeks to reduce the impact of cognitive biases.

Determining whether a decision is good or bad means examining the quality of the beliefs informing the decision, the available options, and how the future might turn out given any choice you make.

Using the quality of the outcome to judge the quality of the decision causes you to learn the wrong lessons and is called resulting.

Uncertainty and decision making

Imperfect information is a kind of uncertainty that interferes before a decision.

Luck is a kind of uncertainty that can interfere after the decision is made but before the outcome.

Chasing certainty causes analysis paralysis.

Biases

Hindsight bias is the tendency to believe an event, after it occurs, was predictable or inevitable.

Memory creep is when what you know after the fact creeps into your memory of what you knew before the fact.

Tilt is when a bad outcome causes you to be in an emotionally hot state that compromises the quality of your decision making.

Quitting

Quitting is a powerful tool for defraying opportunity cost and gathering intel, intel that will allow you to make higher-quality decisions about the things you decide to stick to.

Tools and Techniques

There are quite a few in the book. Here are some that resonated with me.

Use a Knowledge tracker to avoid hindsight bias.

Use Decision trees for evaluating past decisions and improving the quality of new ones.

Repeating options are when the same type of decision comes up over and over again you get repeated chances to choose options, including options you may have rejected in the past.

When a decision is hard, that means it’s easy. When you’re weighing two options that are close it can feel like the decision is difficult. The decision is actually easy, because whichever one you choose you can’t be that wrong since the difference between the two is so small.

The lower the cost to quit, the faster you can go, because it’s easier to unwind the decision and choose a different option, including options you may have rejected in the past.

I’m a sicko for trawling the internet and loading up Instapaper with things to read later.

Which means, you’ll be shocked to hear, my reading queue can get large and unmanageble.

Longer articles tend to stay in the queue unread for quite a while.

Often, as with my productivity system, I’ll declare read later bankruptcy, archive a bunch of the stale articles, and walk away a little disappointed in myself.

Kagi’s Universal Summariser to the rescue!

Now, when I scroll through my queue and see those intransient “40 minutes to read” articles, I put their URL into the Kagi summariser.

If the concise summary it provides piques my interest I’ll ask for the key moments summary.

Then…I’ll usually still archive it. But! I feel a little better about life. 😎

I like the sound of these “now” pages so I added one here.

I was having an after-work chat with Simon a while ago. We were discussing how we can cultivate a more resilient culture at work, specifically enhancing the capacity of individuals to constructively handle feedback.

He mentioned that he’d been reading Thanks for the Feedback which emphasises that, contrary to popular advice, it’s better to focus on helping people get better at receiving feedback rather than giving it.

This reminded me of a design principle in software engineering called the “Robustness principle” or “Postel’s law”. This principle guides how software systems should be designed to communicate with each other.

It’s often summarised as: “Be conservative in what you send, be liberal in what you accept”.

It felt like when it came to feedback and people working better together we were talking about the same thing, i.e. Postel’s law for people.

This makes me wonder what other software design principles might be useful when applied to people.

One of my favourite features of Artifact is the ability to use machine learning to replace clickbait titles.

It’s good that you can trigger it from the listing page so that you can choose whether it’s worth reading an article or not.

It’s great that if enough people report the same article, a human reviewer may decide to make it the default title for all Artifact users.

It’s a very helpful feature for internet trawlers such as myself.

I just binged season two of The Bear.

Intense and roaring. Loads of heart. Loved it.

Definitely recommended.

Update: This Spotify playlist for season two is great listening for children of the 90s.

I wrestled Hugo to the mat¹ and set up separate RSS and JSON feeds for my Posts and Links.

I also got feeds set up for individual tags.

The combined feed is still available as the simplest subscription option.

You can find all the details in feeds.

Viva la RSS.

I spend too much time reading online.

I tend to trawl content from a variety of sources, save the shiny ones in Instapaper, and read them later.

The majority of the articles I read are sourced from RSS feeds in Feedbin. I’ve organized these feeds into three categories: ‘full read’, ‘skimmable’, and ‘skippable’. This system means that if I ever feel overwhelmed by the volume of content, I can quickly mark a large number of articles as read and move on with life.

I like to complement these feeds with articles from elsewhere. I used to route specific Twitter accounts into Feedbin for this but that option is gone since the Twitter API ‘asplosion¹.

Around the same time as that feature disappeared I started using Artifact. It’s from the founders of Instagram and the early development cycle has been impressive. At its core is a machine curated personalised news feed². The recommendation engine feels like it still has room for improvement, I’d love to be presented with more “surprising” articles, but it still manages to throw the odd interesting articles into the mix. Using it feels like panning for gold.

The latest version of Photoshop Beta now includes a feature called generative fill.

I can imagine it’s easy to compromise the authenticity in your photography if you overuse these kinds of tools. With that said, and I know it’s potentially a slippery slide, there are situations where they can be incredibly useful.

For instance, I sometimes want to adjust a crop and need to fill in some areas to maintain the balance of the composition, and my Photoshop pixel-surfing chops aren’t up to the task.

I had a crack at using generative fill on a photo I recently took that I wished had more foreground.

The results look usable.

I also tried a prompt that removed the shadow on the left but the results of that were less natural.

Experimenting with various prompts and browsing their outcomes is far more enjoyable than swearing at the healing and clone brush tools 😂.

Keep a journal for work, champions.

It’s pretty easy to get started—just create a text file.

Throw in a new heading each day and write down whatever you did—a single line for each task is usually enough. I put the newer dates at the top so it’s less scrolling to get to the most recent content. Over time you end up with your own little private reverse-chronological blog-in-a-file.

Each day, dump in commands you’ve run; links to documents you’ve created, reviewed, or read; tasks you want to get done; or goals you want to achieve.

You’re building a little outboard brain where your work history is just a short grep away.

When that Friday afternoon ennui kicks in, and I’m trying to work out what I’ve contributed, I go back over my work journal for the week.

I’m the rigorous¹ type, so each Friday, I summarise my achievements and impediments of the week in a separate note.

When it’s performance review time, I run over these weekly notes and pull together the story for the year.

My journal used to be a bunch of text files saved to a folder in Dropbox. That’s honestly all you need. Use Markdown or Org mode or whatever, and opening a window into what you’ve done is a ⌘f keystroke away.

NotePlan as a work journal

I used text files for years, and then, about a year ago, I switched to NotePlan.

I switched to it mainly because it has built-in daily and weekly notes², search, sync, an iOS app, and stores everything in plain Markdown files.

It integrates with your calendar (not that I use that feature much) and includes tasks and tagging in the style of Bullet Journaling.

I’m more accustomed to the GTD productivity approach but have found having tasks alongside my journal to be worth tolerating some of the rougher edges on the task management side³.

Eyes on the prize

Knowing that I have a home for all the minutiae of work leaves me more space to dedicate my brain to what’s actually important. 🫡

It’s often necessary to roll out organisational changes in a business, e.g. new reporting structures, goal setting frameworks, or planning processes. Each change introduced requires time for people to adapt and normalise.

When businesses introduce a series of changes in quick succession, people deal with them like a swimmer facing a tight set of waves. As they adjust to the wake of one change, they are immediately destabilised by the onset of another.

This situation can make it difficult for people to build their capability and improve performance. Leaders spend most of their coaching effort on dealing with the impact of the changes rather than improving an individual’s performance.

If you find managers in your team are spending the majority of their time coaching people through change it’s likely a sign that you are trading off rolling out change over coaching performance.

I’ve journaled in various forms over the years ¹.

About ten years ago, I migrated my journaling to the Day One app.

I love how Day One is available on my Mac and my iPhone. I post text, photos, audio, links, or quotes as they pop into my head. I tag posts and even store posts into separately themed journals.

In the last six months, I’ve added reviewing my journal to my morning ritual.

Each morning, before I knock out the day’s Wordle, I review the posts “on this day” in Day One.

It’s been a delight.

On some days, I have posts dating back ten years. It’s like jumping into a time machine to a previous life. Reading back over challenges at work, holidays we’ve taken, or photos of my family always brings a smile to my dial.

Once a month, I choose a random tag and review the journal posts under that. It’s illuminating to see the evolution of my mood or feelings on a particular topic over time.

Regularly reviewing my posts has made writing posts feel more valuable too.

So yeah, journaling is like a tricked-out DeLorean.

Product development is a team sport mostly carried out through meetings and conversations.

Two practical things you can try to help create clarity and reduce chaos in particularly complex conversations:

1. Consolidate progress with a series of summaries.
2. Crystallise outcomes in writing.

These might seem obvious, but they don’t happen as often as I’d hoped.

Consolidate progress with a series of summaries

Do you find yourself in meetings with multiple people discussing complex topics?

Does a series of tangents and related issues emerge as the conversation progresses?

In the end, are you unsure of where things are at?

Are you confident that you understand the situation but are uncertain if it’s the same for others?

Taking complex, meandering conversations and providing clear, structured summaries throughout is incredibly valuable ¹.

I think of each summary as incrementally locking in consensus or taking a collective step up the ladder of inference, as described in Crucial Conversations.

Sometimes the state of play seems obvious, and therefore it feels unnecessary to summarise. I suggest pushing through this feeling and doing it anyway to ensure alignment and avoid pluralistic ignorance.

Crystallise outcomes in writing

As soon as you leave the conversation, you are immediately misaligned again ².

You can reduce this misalignment by sharing a written conversation summary including decisions and actions.

Given the volume of conversations leaders tend to be in, capturing the outcomes becomes essential for rebooting context later or remembering which decisions were made and why.