What I learned about email newsletters: some advice for writers

Why write a newsletter?

Newsletters are the big things at the moment. Blog readership is down. So the logic of email newsletters is that people are more likely to read your content if you a) get them to subscribe to your newsletter because they are already making an investment, and b) send your content to them rather than expecting them to come to your blog.

The business owner/marketer idea behind newsletters is building an audience and collecting email addresses. It’s an owned audience, different from an audience built on a social media site. If you choose to move to a different email newsletter platform you can take your audience with you. If you choose to move to a different social media platform you have to start with no audience.

Does that strategy actually play out over time? We won’t know until the popularity of newsletters declines and we all move on to something else. The same idea used to be thought of for blogs and RSS feeds. If you really want to build an audience (because you have something to sell them) then do it through multiple channels.

I started subscribing to newsletters because I wasn’t getting enough good stuff to read just by scrolling through Twitter. So if you’re writing a newsletter that should tell you two things about me as an audience; a) I want to read good content, and b) I’m to lazy to go looking for it myself.

What should you write about?

Fixed or flexible subject? Should you write about only one subject (or one subject per newsletter and have multiple newsletters) or should you write about a few different things. As a reader, it depends on why I’ve subscribed. Did I subscribe to you because I think you’re an interesting person and I want to hear what you have to say, or did I subscribe to the subject because that’s what I’m interested in. Personally, I’d rather subscribe to someone who is interesting even if they sometimes write about something I’m not interested in. And typically, writing is interesting when its about the intersection of two things that don’t normally go together.

How often should you send?

Fixed or flexible schedule? Should you send your newsletter at same time every week or whenever you’ve got something to say? I’m sure most of the newsletters I get have a publishing schedule but I don’t pay enough attention to know. I’d rather get good newsletters than regular newsletters, but in most cases your audience won’t even notice (unless they are paying you) so don’t worry about it too much.

So writers have a choice: fixed schedule fixed subject, fixed schedule flexible subject, flexible schedule flexible subject, or flexible schedule fixed subject. How you choose depends on how much you have to write about and how much time you have to write it.

What makes newsletters unique?

Some newsletters aren’t really newsletters, they just an intro to a blog post and a link. These are missed opportunity. Only one of the newsletters I subscribe to does this and I hardly ever click the link. It’s ok to link to a blog post version of the newsletter (in fact I’d recommend it as it makes sharing or bookmarking easier) but the days of newsletters just being an acquisition channel have passed. Newsletters are a distribution channel.

Newsletters are less temporary than a tweet but less permanent than a blog post. Personally, I want content in newsletters that is of blog post quality, I don’t want to read stuff you’re testing out to figure out whether to write a blog post about it (and you probably aren’t going to learn anything useful if that’s your tactic because newsletters suffer from the information good value problem; I only know if it’s any good after I’ve read it, and so I’ve read it even if it was rubbish or the idea was nonsense).

Newsletters provide an immediate way to distribute medium to high quality content to an invested audience. Make the most of it.

What makes your newsletter unique?

It’s easier to stop going to a blog than it is to unsubscribe from a newsletter, but its still not that hard to unsubscribe from a newsletter. I guess there’s an argument for ensuring your writing stands out, whether through the subject matter, your take on the subject, your writing personality, or whatever it is that makes someone recognise your writing.

Adding to the point above about whether I’m subscribing to you (the person with interesting things to say) or the subject you are talking about, I guess it’s a bit of both, but it’s you that makes your newsletter memorable. Of all the newsletters I subscribe to there are only a few where the personality of the writer comes out in the writing, and these are the only newsletters where I can tell you the name of the person who sends them. That might be an interesting measure of success; does your audience like ‘you’ enough to look you up on twitter and follow you without you asking them to?

Weeknotes #199

This week I did some stuff…

Online mentoring

I’ve been working how we can use Microsoft Teams to facilitate online mentoring. Fundamentally, Teams is built as an enterprise collaboration platform with certain assumptions built-in, things such as everyone in the organisation knowing who each other is, which don’t always meet the needs of mentoring where safeguarding and privacy is really important. Our challenge is that Teams is the tool we have, and we won’t let not having the right tool stop us from enabling mentors to support young people, so we have to find ways to make it work. 

One of the things I like about my role is that I get to do a lot of zooming-in and zooming-out, so I move my thinking from almost philosophical ponderings about the value young people get from one-to-one mentoring to the technical details of how Teams handles permissions for certain types of users, and the organisational stance on safeguarding and the volunteers experience of using Teams in between. I think finding the best solution to a problem comes from being able to hold all those different and sometimes conflicting perspectives and figuring out which parts trade-off against which other parts. 

Teachers using Teams

Microsoft wants to get Teams into 27,000 schools across the UK. Lots of people don’t like MS Teams, and it certainly has its product peculiarities, especially if you are used to ‘one-product-one-function’ approach like using Slack for messaging, but Teams is a far more complex product, and I wonder if the hate comes from not taking the time to learn how it works and how to use it. I’m sure this is something all those teachers will go through as more schools introduce Teams.

If the schools had good IT people to teach the teachers, or if Microsoft provided really good onboarding, then Teams would make a huge impact on digitising schools, but I worry that it’ll come up against the same old problem of expecting the tech to solve/change everything and not do enough for the people using the tech. When Teams is used as part of an ecosystem with other MS products it could take a huge chunk of what schools do onto the internet. Teams and Sharepoint could be a far more effective intranet than lots of companies have. Timetables could be managed in Shifts. All school work could be done within documents in Teams, allowing teachers to provide fast feedback and students to iterate on their work. Lessons delivered via video could be recorded so that students can watch them again later if they missed anything or was absent. Chat between students and teachers would be secure and monitored for safeguarding issues. There are so many benefits schools could get from Teams and I can see a future of education where location is irrelevant and rather than attending a school because they live near it, students will attend ‘the school’ because it will be the one and only online education platform.

Anyway, back to real life. We’re using Sharepoint to build a content repository for teachers working with young people outside of mainstream education. Sharepoint can be used to produce some quite interesting public facing websites, but the question of whether Teams is the right frontend is an interesting one. On one hand, if teachers are using Teams in their school then they will be familiar with how it works and can switch accounts to access our content easily. One the other hand, it doesn’t look like a marketable product and something that will encourage adoption, especially if teachers have had a bad experience with their Teams. So, as with so many product decisions, deciding what to make trade-offs between is part of the challenge.


I’ve become a bit obsessed with cookies (the website tracking files, not the confectionery) and how websites handle them. GDPR and the ICO say users should be given the choice about whether to accept non-essential cookies (those used for analytics, advertising, etc.) but the vast majority of websites don’t do this. I think it’s an interesting moral choice; should you respect your visitors enough to not track them without their permission, or as you own the website should you be able to implement things that work for your business objectives? 

It makes me think back to my old ‘hierarchy of compliance’ that says comply with laws first, e.g. GDPR, then industry specific regulations e.g. PCI-DSS, then your organisation’s policies, e.g. security, then your organisation’s procedures and practices. Should morals be first and above laws, or does it belong alongside every layer?

Browsers don’t differentiate between essential and non-essential cookies. If you block them all, some stuff on the site won’t work, and then you have to allow all cookies again. Browser controls are too blunt a tool. When Chrome shows that cookies are blocked on a page it uses a red square with an X in it, the universal sign for something bad or wrong. Interesting, but not surprising that Chrome tries to signal to us that blocking cookies is bad given Google advertising business model. 

But the Cookiepocalypse is coming. Before too long cookies won’t be a means of tracking users on a website. Some browsers block third-party cookies by default already. And Google looks like it’ll follow suit in time, but probably not before they’ve introduced a means to track users without cookies and so lock-in websites to using Google Analytics.

There’s so much to those little cookies, if I get time I’d like to write up all the stuff I’ve learned.

User Guides

I wrote some more for my Whiteboard product user guide, and tested how formatting in Google Docs renders as an ePub file. I’m keen to make my little shop of user guides the next project I put my time into after I’ve finished this term for my masters.

I’ve also started thinking about how this might evolve into online courses for using products more effectively, and how a course could be delivered by email, perhaps with a button in the email that triggers the next part of the course so that learners can control their own pace.

And studied some stuff…

Reinforcing business design decisions

An effective business model is made up of “business design choices that reinforce one another” (Osterwalder, 2005). This week’s lecture was about business models. Something that lots of people talk about and very few can explain. I like Osterwalder’s definition. It helps us understand that a business model isn’t a finished, discrete thing that exists ‘over there’, but actually is made up of lots of choices that in order to be successful need to reinforce each other. Lots of organisations, that probably don’t do enough business model thinking, seem to make choices that have them competing internally or one department requiring a level of support from another department that they don’t have the skills or people to do. A business with a good business model makes choices that makes the parts work together.

There are no rational agents

I listened to the recording of last week’s lecture about the nature of digital goods. It was about the nature of different types of goods and how defining them along the lines of excludability and rivalrousness leads to four types of goods: Private, which are things that a person can own and so prevent another from using and can only be used by one person at a time, e.g. a car, Public, such as street lighting which anyone can use and using it doesn’t stop anyone else from using it, Common-pool resources, which anyone can use but if they are that prevents anyone else from using them, and Club goods, like television which requires particular access and you watching a show doesn’t prevent anyone else from also watching it. It’s a bit of a revelation to me to think about the model for providing a product or service being driven at the micro level from the nature of the goods themselves and not from the marco level of whether the government or the commercial sector should provide it. Internet access (see Cassie’s tweet below) is an interesting example of this. Currently my access to the internet is somewhere between a private good and a club good, because I can prevent anyone else from using it, and has some technical limitations on how many people can all use it at the same time. To shift internet access to being a public good would require tackling the technical limitations that then mean everyone could access the internet and no one accessing it prevents anyone else from accessing.

As lectures this term have been digital, starting as video meetings with the lecturer presenting the slides and moving to recorded lectures for pre-watching and then group exercises and discussions over video calls, it has made me consider the format of lectures as a means of providing information. I got a lot more out of listening to the recording of the lecture and listening live, perhaps because the lecturer was more focused. Lectures often seem to have tensions between providing information because it’s part of the curriculum, providing some context and real-life examples to aid with learning, but not biasing the content. I have to sometimes remind myself not to get lost in exploring ideas.

The economics says that Public Goods shouldn’t work because a rational agent should free ride as they get all the benefits without any of the costs, but people aren’t rational agents they are social creatures which is why we have Public Goods paid for indirectly through taxes.

Bigger and better

Worked on my analysis of Shopify’s business model, digital product offering and pricing strategy. Shopify announced its partnership with Facebook and their stock price jumped up. I saw a tweet that said investing in Shopify after their IPO would have given you better returns than investing when they were at Series A funding, which is usually not the way those things work, and perhaps shows . Anyway, it’s been interesting to work on something that feels so ‘now’ but still uses economic thinking from the seventies.

And thought about a few things…

The business of charity 

Over the years there have been a few occurrences of business people thinking they can apply business thinking and techniques to make charities work more efficiently. It never works because charities are obviously different to businesses in lots of ways. Having been thinking about the nature of economic goods I wondered whether part of the reason for this misunderstanding is that the nature of the services charities provide are excludable and rival, like many commercial services. Being excludable means the services provided by a charity aren’t available equally to everyone, and being rivalrous means that if the service is already being used by someone it can’t be used by anyone else.

In contrast, a service that is non-excludable and non-rivalrous (the classic examples are lighthouses and streetlights) can be used openly by anyone regardless of whether anyone else is also using it. So I started thinking about how charity services could be public goods. The closest example I could think of was Citizens Advice, whose services are available to anyone via their website. They came from, and still have a rivalrous & excludable aspect in the face-to-face advice sessions that they provide, and I’m not suggesting that any charity should get rid of the face-to-face work they do if its meeting a need, but most service delivery charities haven’t figured how to make the shift, and arguably because most charities tackle issues that affect a small segment of society, but it’s interesting to think about the thinking of how they would scale services as public goods if they need to.

New news

I’ve got into email newsletters lately. Email, and so email newsletters seem to be making a come back. The idea that web messaging was going to kill email didn’t happen, instead email evolved, and I think for the better. I’ve mentioned before the trend of emails becoming more like an editable document that passes between people, so that’s one trend of improvement. The other trend is in improving how people use email, something hey.com is working on solving. And then the third trend is in the quality of content that utilises email’s unique features. Emails aren’t limited in size like a tweet, and can either contain all the content for the reader or links to more content. They can be read at a time that suits you and are easier to find later if you want to go back to something interesting.

Email newsletters are also a great means of building an audience as even if you took a no-tracking approach you’d still know how many people are sign-up to receive your newsletter. If email could solve the problem of being able to select which content you want to read before you get it (usually informational products problem) then I would definitely rather have the ‘our content/thoughts/opinions sent to me’ approach rather than ‘we put our content on our website and expect you to find it if you search hard enough. Also, an idea for a product, imagine getting search results by email rather than websites. Describe in greater detail what you are actually looking for and get a high-quality curated list of links emailed to you for you to read at any time. That’s pretty much how I search for things, it’s just that I do the work of copy-and-pasting into my notes.

And some people tweeted…

Internet for everyone 

Cassie Robinson tweeted, “Digital infrastructure should be considered a vital 21st century public good “We need to build a digital landscape that provides world-class connection to all, is sustainable, privacy-enhancing, rights-preserving, innovative & democratic by design.” Having studied public, private & club goods, and common-pool resources, it makes sense to me that access to the internet should be a public good (in the economic sense) that is available to everyone. If Raymond Coase was right when he wrote The Lighthouse Economics then existing purely for the good of society is enough of a justification for making a good public, and it would be hard to argue that internet access isn’t good for everyone. 

Limiting meetings in progress 

Woody Zull tweeted “Heuristic: If you spend “too much time in meetings”, it is likely that you have too much work in process. Limit WIP for a week and see how it affects your meeting time. Adjust accordingly.” ~@duarte_vasco

One of the replies to the tweet was about how many problems vanish when work in progress is reduced. I think this is because it reduces complexity across the whole system of work rather than just allowing individuals to focus more.

Fluid office 

The Verge tweetedMicrosoft’s new Fluid Office document is Google Docs on steroids”. Microsoft is getting into blocks in a similar way to tools like Notion, where a document (if there will even be such a discrete object in the future of work tools) is made up of lots of blocks from different sources that pull content and functionality into the ‘document’ you are working on. 

I think it’s another step in the journey of information moving from being centralied to be decentralised and distributed in an internet-y way, and the next step will be in how content is made discoverable to pull into a document, so the author doesn’t have to write original content that becomes locked into the document if someone else has already written it or the data is already available. Rather than having to go and find last year’s sales data and create a chart to then create an image to be embedded in the document, you would import the live data into the document and the chart would be up-to-date in real time.

The To/CC rule for sending email

When sending an email:

‘To’ is for action

If you want someone to do something, then you send the email to them.

‘CC’ is for information

If there is something in the email you are sending that you think someone should know, but they don’t have to do anything with that information, CC them.

If the reply is likely to contain some information that you think someone should know, then CC them and hope the person replying clicks ‘Reply-all’.

The challenge of transactional emails: achieving context

I’ve been doing a piece of work to improve the transactional emails that we send to customers.

The challenge of transactional emails: achieving context

At first glance transactional emails seem simple. They are just about providing simple information to update a customer, right? Actually, the more you think about it the more complex it becomes. Does the email contain the right information? Is it presented in the right way? Does it clearly indicate if the customer needs to do something, and if so does it explain how to do and what will happen because of it? Is the email sent at the right time? Does the email contain too much information or not enough? Do customers want to receive an email as soon as an update on the status of their order is available or would they prefer it at the most convenient time, especially if they need to do something? Should the email be trying to seamlessly fit into the customers life and just be there when they need it or should it be trying to interrupt them and get them to pay attention to the message in the email?

Trying to understand the context of transactional emails for all customers is really interesting and difficult. I don’t know if it’s something you could ever get right for everyone. That’s the challenge of context.

An awful email from my bank 

I received an email from my bank. It’s the same email I get every month. That’s the only reason I know it isn’t spam, because looking at it, it sure looks a lot like spam.

“Dear Customer”! What do you mean,” Dear Customer”? Don’t you even know my name? When it comes to email personalisation, that’s day one stuff. You have so much data about me that could be used to personalise the emails I receive and yet you’re not even capable of putting my name in an email.

“Your latest statement is ready for you online now” – But if I want to see it I’m going to have to open a browser, search for your website, click on the result to load your website, navigate to login page, then find this month’s statement, when all you had to do to make it easier for me was to include a link. It’s almost like you don’t want me to look at my statement.

“It will be ready to download as a pdf two days after the statement date” – Does it really take two days to generate a pdf? And what makes you think I even want a pdf, you haven’t asked me? What if I want a .csv? What if I want to connect my account with Google Drive or an Expenses Tracking system and have my statement exported to either of them? It’s the twenty first century. This is not complicated stuff.

“Log in to Online Banking to see more information on your account.” – I could probably do that a little bit more easily if you bothered to include a link to the login page on your website. If you are trying to encourage your customers to use Online Banking rather than high street branches, why make it difficult for them?

“Remember,within Online Banking” – When I went to school commas had spaces after them. A major high street bank sending emails to hundreds of thousands of customers with grammatical errors like this doesn’t exactly inspire confidence that they’ll be correct and accurate with my money.

Was this email really worth sending?