Sitemate Blog Post – On How Sitemate Communicates
By 
Preface
Depending on what kind of environment you’ve operated in prior to joining the Sitemate team - I’ve been finding that most new starters are typically having one of two types of initial experiences.
First - for some, joining Sitemate can feel like you’ve been walking along the side of a motorway, with cars driving past you at one hundred miles an hour, until suddenly you are yanked inside one of them, leaving you with whiplash once you’re sitting inside.
And for others - you may feel as though the work environment is fast, but also less ‘noisy' in the day to day, particularly on Slack.
Even if the speed and frequency of communication isn’t new to you, nuances around norms, expectations and habits can lead to a similar feeling of whiplash.
As the current team is now acclimatised to the pace and these nuances, most of the time they don’t even realise the unique aspects, and it can be jarring for them to need to temporarily adjust their communication patterns as new starters phase into our team.
In-line with the above, this blog post is designed to help provide context for, and the history of, Sitemate’s communication system, hence lowering the likelihood of new starters experiencing whiplash.
As you will read below, there’s a lot more to creating and maintaining effective, modern and global communication infrastructure, systems and habits, than just “oh yeah we use Slack.”
Email, and Front
About six month’s after Greg our GM started in the London office, he messaged me out of blue;
“Just caught up with some friends for a barbecue, a couple of them work in tech.
The thing that surprised them most as I was talking about my experience at Sitemate so far, was when I told them I hadn’t received or sent a single email internally.
They just couldn’t comprehend it.”
So let’s start off with a bang - email is banned internally. Zero. Nada.
Except for calendar usage, email is exclusively used for external communication.
However, that’s not to say email is not important - for our Operations and GTM teams, our inboxes are supercharged with Front.
You can think of Front of like having Slack overlain on top of your inbox, it allows you to have internal conversations, about external conversations - discussing challenges, sharing information, reviewing drafts for critical communications and coaching on best practices during new starter onboarding.
We’ve been using Front for a long time - back in 2019, we were sitting in one of the very early Sydney offices one day, there was only 5 of us; Khanh, Sam, Lance, Terry and myself.
These were the days when Sam was acting as our Customer Success Manager, and over the course of about an hour, he asked Khanh to forward him multiple emails with questions from customers about billing.
It seemed inefficient, but I didn’t really have any better ideas, until a few days later I saw an ad for Front online, and I started a trial right away.
Front were themselves relatively early on in their journey at that time, I think they were around 50 employees, and now at the time of writing this blog, I believe around 500.
A week or so later, I called Sam, Lance and Khanh into a room, and was super excited to pitch them on Front - their response was simply… blank faces, skepticism and even some confusion.
Luckily, as CEO, I didn’t have to ask for their permission to trial it, and the rest is history!
Front is probably the tool that surprises people the most after they join Sitemate, with many wondering how they ever lived without it.
Asynchronous
Asynchronous, or ‘async’ communication and written communication go hand in hand, although it’s important to talk about the dynamics of async communication patterns specifically and why adjustment can be required.
In more traditional workplaces, communication often revolves around meetings, and email. Email is a form of asynchronous communication, but it’s fundamentally different to messaging based systems, as well as ‘on object’ communication systems within workflow and database systems.
Unless you’ve been living under a rock and have never used Messenger or Whatsapp, you will almost certainly have some level of experience with async comms.
The general theory is that you can send a message, or leave a note for someone, and they can reply back when it's convenient for them. This way, everyone can take their time to think about their answers and respond when they're ready, making it easier to manage conversations without disrupting what you're currently doing.
Leveraging async comms patterns allows you to progress projects, ideas, decisions and discussions across timezone boundaries, unlocking the potential of talented individuals across the world within globally distributed teams.
Async communication allows thoughts to simmer, evolve and mature, and you often end up with higher quality outcomes because of this.
However, there are a couple of triggers to look out for, which may indicate that you need to deviate away from async comms.
The first being when emotions like frustration and anger come into play, as writing under these conditions can be damaging and it’s best to write out your feelings on a personal note, and then discuss during a meeting.
The second being when there’s too much back and forth - usually indicating that the topic being discussed needs to instead be ported into a document summarising multiple options and perspectives.
Writing
About two weeks after Rob joined our Sydney office, he was starting to go live in his role as Sitemate’s first ever Enterprise AE, and like every other new starter - was through watching most of the ‘Sam from Sitemate’ product videos.
He was reporting to me at the time, things were looking good, we had heaps of larger leads coming through the inbound flow, but there was just one problem - he kept pinging me via Slack Direct Messages (DMs) asking for a call to talk about things.
This might seem like an obvious use of slack, but switching from primarily written communication, to primarily verbal communication, can quite disruptive - and when your manager is also the CEO, any disruptions don’t usually last long…
Speaking over the phone, video call, or of course face to face, requires real-time engagement from everyone involved, which means calendars need to be aligned and available.
In addition, unless well prepared for, typically internal phone calls, video calls and face to face meetings contain approximately 80% wastage for attendees, due to large amounts of ‘filler’ time.
The power of written communication is in the act of needing to write down your thoughts. When you are forced to write something out, it helps you construct a much clearer message, and sometimes, you can even answer your own question just through the process of trying to clarify what it is you are in fact looking to ask.
I have a strong personal belief that whatever someone writes, whether it be an internal message, or an external email, is a direct representation of what is happening inside of their mind at that point in time - meaning if it's messy and confusing, their thoughts are messy and confusing, and vice versa - if it’s clear and concise, their thoughts are clear and concise.
Writing helps you move from the former, to the latter, as most of the time you can look at what you’ve written, realise your thoughts are in fact a mess, and iterate on it yourself a couple of times to improve it.
Now to clarify - this is not to say that verbal communication is not important, it’s just as important as ever, particularly given how much written communication happens in modern workplaces, which are becoming increasingly digital.
There are certain scenarios where verbal communication should be the default - examples being; 1:1s covering personal updates/development discussions, feedback, as well as pulse check team meetings and rituals where it’s important for leaders to provide not just operational updates, but convey the general feeling, energy and mood at any given point in time - for example; weekly team meetings and the allhands.
In addition, and to contrast - there are also many scenarios where real-time collaboration is extremely valuable - primarily in creative contexts where the objective is not clear leading into the meeting or session. This could be exploratory research calls/meetings with customers and prospects, retrospectives, project objective and kick off meetings.
Needless to say, with the above being said - my response to Rob was a polite; “Can you write to me with what you want to ask?”
After another week or so of frustration due to me saying different versions of the above response, Rob finally reached the other side of the hill, where his written comms were flowing naturally and efficiently in written form.
The irony was that when our next new starter joined, Rob started getting frustrated because they were disrupting his daily workflow, doing the same thing that he did when he started, at which point he messaged me to say;
“Once you feel the efficiency of written comms, you can never go back.”
Put simply - in order to thrive at Sitemate, particularly as you start to move into leadership roles, your written communication skills will need to be very strong.
It’s ok if you’re not there right off the bat, there are plenty of examples day to day to learn from, as well as people on the team and resources (such as this blog post) that can help you start to build the muscles required.
Also, for the avoidance of doubt - if you ever have something personal or sensitive that you need to raise, please do not hesitate in using DMs to reach out to your manager, Annabel, Lisa or myself. The scenarios referred to above relate to project, task and account related communications only.
Messaging, and Slack
I remember the first time that I used Slack - it was during university, one of the classes that I was taking had a workspace setup to allow teachers and the cohort of students to communicate easily and openly.
I’ve been a part of a few Slack communities since then - Productboard power users, Startmate Accelerator, and some other miscellaneous workspaces. Some of them were very active, some of them had a few bright spots, and then fizzled out quickly.
The main learning for me has been that while the underlying system is important, ultimately it’s the people that make all of the difference.
As at the time of writing this blog, each week approximately 70% of messages read in slack are in public channels.
In-line with our value high vis, the guidance is that for anything project, task, account, case, opportunity related - never use DMs. But the question is why?
With our hybrid operating model, as detailed in our working arrangements, even for our office based team, who only see each other once per month, we are deprived of the value of spontaneous ‘water cooler’ conversations.
Conducting most communication in public internal areas such as channels, as well as onto the records of work, has many benefits. It builds visibility, trust, allows new members of the team to absorb what is happening, and increase the likelihood of spontaneous water cooler chats, albeit in a digital context.
However, this level of transparency can often be intimidating for new starters, due to concern of potentially saying something wrong, or asking a silly question.
I wanted to emphasise here - speed and visibility, is much more important than a perfect response.
Private strategy and tactics channels are used to allow senior members of the team to discuss raw ideas before they are ready for broader sharing, as in some cases, it can be confusing, distracting and broadly detrimental to share some things prematurely.
Direct Messages, or DMs, on Slack, should be used strictly for things such as personal/private discussions, general check in, banter with colleagues, etc. Meaning that DMs should never be used for discussion around tasks, projects, accounts, opportunities etc.
We originally started using country flags as our remote team started getting bigger and bigger, as a fun way of celebrating all of the different cultures that exist within Sitemate, and that is still the intention. Using your status in slack to indicate which office or country you’re based in, or where you’re traveling at the moment, or if you’re on leave - is an extremely efficient and effective way of communicating with people who may need to reach you.
It’s important that we continue to utilise this feature even more as our global team grows larger, particularly given how flexible our working arrangements are at Sitemate.
One final note for this section - please, please, pleeeeaaaase… “use threads”.
Daily Reports, or Standups
Unnecessary meetings are like rust that slows down the turning of gears inside of a company’s decision making engine.
I’ve heard horror stories of some companies running daily one hour zoom meetings to do a standup - every, single, morning, and it gives me shivers.
Broadly speaking, the guidance at Sitemate is to hold the absolute least number of meetings as possible - typically we aim for one single meeting per week per team, and managers should be aiming for 1:1s with their direct reports either weekly, fortnightly or monthly, depending on the stage of each person’s journey at Sitemate.
One of the tools that helps to minimise the need for meetings is our async daily reports, or daily standups - done by a tool such as geekbot or standuply, and posted in a #reports Slack channel.
We started doing daily reports each morning when we were less than 10 people, it was right around the time we started growing our remote team.
Coming from a construction and engineering background, where I was used to in-person briefings like pre-starts and toolbox talks, I not only had no idea what they were, but it felt a little odd writing down my daily update in private, and then pressing the send button into the abyss.
As it seemed to be a good practice for software and product teams, I thought I’d give it a go and that we should all be doing it, instead of just the software engineers on our team. I wanted it to be a tool for anyone in the company to feel like they have visibility into what is going on, instead of a tool for just software developers to report on their progress.
As we’ve grown, we’ve had to break up the various #reports Slack channels into smaller groups, to ensure that it’s relevant for each team.
When Khanh and I broke up the #reports channels the first time, at around 15 people, we saw that it was possible with the functionality available to send one person’s reports into multiple slack channels, and we decided to send my report into every channel.
Why did we do it? To be honest, we just looked at each other and said ‘Maybe one day Sitemate will be like 100 people, and wouldn’t it be cool if anyone could see what the CEO is working on every day?'
The expectations around the reports is pretty clear - of course every now and then there is a day where things get a little crazy, and you might forget, or miss it, and that’s fine. But, generally speaking - the goal is to do them daily.
Is anyone going to check on you day to day if you miss one? No - probably not, everyone else is too busy.
But, they are one of the key pillars that support the flexibility in our working arrangements, and as they’re one of our standard operating principles, it probably wouldn’t block progress on an individual contributor pathway, but it will likely block progress on a leadership path.
As a leader, either current or future - it’s a great way to easily and quickly keep your team up to date, as well as ‘manage up' if you’ve had any wins, good progress, or are experiencing any challenges.
‘On Object’
Probably the most difficult part of Sitemate’s communication system to grasp, and adjust to, and the part of which I believe Sitemate skews further towards uniqueness compared to most companies, is how communication happens 'on objects;.
But wait, what in the world is an object? And how do I communicate on it?!
In this context, the definition of an object is a record within a system - it could be a Jira Ticket, a Confluence Page, a Salesforce Account, or a Salesforce Opportunity.
These systems, and the records within them, are designed with embedded communication capabilities, however, even within technology companies, they are often not used to their full extent.
Our intention is to use the embedded communication capabilities as much as possible, for example - discussing Confluence pages on the page itself, discussing Jira tickets on the ticket itself, discussing Salesforce accounts on the account itself.
You communicate on them by using the native chatter, comments and @ mentioning capabilities.
Emoji Culture
Lance and I have discussed the theory of emojis being the modern day digital hieroglyphics a few times - hieroglyphics were used to communicate across different regions and cultures in the ancient world.
Emojis can now do the same - communicate deeper meaning, or a broader message, with just one symbol.
Let’s cover the base level of expected usage first - in order for our communication systems to function, there are a couple of base level requirements; acknowledging that you’ve seen things with a simple ‘:eyes:’ or ':thumbs-up:'.
On top of that, there are a couple of practical use cases, such as having emojis for each of Sitemate’s values, for example, :value-high-vis:, which allows us to indicate when someone is doing something in-line with one of the values.
Outside of those two things, pretty much everything else is just for fun - a bit of a laugh can really help take the edge off of what can be the grueling day to day of scaling up a company, with endless challenges and never ending to do lists.
Keep in mind though, Slack is intentionally designed to have some similar features to addictive social/consumer products, which is part of the reason why it’s such a powerful tool - but, it’s also important to set boundaries for yourself to ensure sustainability, and this will be covered below.
PS, a tip for anyone new to Slack, you can type a colon, or “:”, on your keyboard when inside of a text box, and it’s a shortcut to accessing any emoji by name.
Headshots
You might have noticed that Sitemate has a somewhat regular cadence for getting new photos and headshots for new starters on the team - for office based team members we’ve grown to start doing this once per quarter, and for remote team members we aim to do it at each annual offsite.
This section will answer two questions relating to this; (1) why do we do it? and (2) what does it have to do with communication?
On the why - this stems from a somewhat quirky theory that I have, which I’ve spoken to a couple of people about, but not many.
The theory is that people remember their careers in blocks of time, and their professional photo is like a shortcut to summarising each of the individual blocks of time.
Noting that a block of time doesn’t need to mean changing company, you can have multiple blocks of time within the same company, and in fact, this should arguably be a goal - it means you’re progressing.
If you are interested in testing the theory, pull up all of your previous professional head shots on a screen, and glance over them - you will likely have clusters of professional memories attached to each one as you do. Kind of like when you hear an old song that you used to love, and it takes you back to the major things that were happening in your life at the time when you first fell in love with it.
By getting a fresh new headshot, the goal is to start a new professional memory block - a clean start and signaling that you’re progressing, or have progressed, into a new stage.
If you hang around long enough, you might end up with multiple memory blocks from Sitemate alone - I know I’ve got four myself, and each time I see an old photo, I remember exactly what was happening at the company at that point in time.
So, how is this relevant to communication?
Due to the prevalence of digital systems, as well how significant your photo and image is, your headshot is your ‘digital hello’ or ‘digital handshake’, like a first impression, which as we know - always lasts.
It may seem like a small thing, and it’s a little hard to describe from my perspective, but for some reason - as our team has grown, and recruitment volume has picked up, it’s been surprisingly noticeable how important the way someone presents themself has been, both internally and externally.
The engineer in me doesn’t like that this is a thing, but optics are important - my recommendation would be two things; (1) always take a minute to present yourself in the best light (2) keep your presentation consistent across all digital platforms.
These are two very easy things to do - and it generally helps to make a good first impression, whether it be people internally, or external candidates.
It’s just like presenting yourself well in the real world and making a good first impression, and with so much now digital - why would you not do it there as well?
Expectations, Notifications and Sustainability
I’ve been asked probably a dozen times now by various people on the team, something along the lines of “How do you keep track of all the communications channels, across 5-6 product teams, 3-4 GTM teams, and everything else? How do you never miss anything, and respond so quickly?”.
Below is part of the answer.
Personally, I receive close to zero notifications on my phone and computer - no desktop notifications for slack or email, no push notifications on my phone, for both personal and work apps.
With Slack, I take it a step further, not only do I get zero notifications, but within the tool itself, I have 95%+ of my channels muted - public, private and DMs.
Literally the only way someone can reach/interrupt me is via a phone call or text message to my Australian mobile phone number, or through whatsapp.
If something is truly, truly urgent, which 99% of the time it is not - someone will call you.
I have also removed all duplicated notifications - many systems will send you an email when you get @ mentioned somewhere, e.g. “$Someone @ mentioned you on this Confluence page.” - these can usually be disabled with one click at the bottom of the email contents.
The above allows me to drive the systems, not to have them driving me - I work through each tool one at a time, and process the notifications from inside of that system, whilst I’m in that system.
I read in the news the other day that Australia passed a law giving people the right to disconnect from work communication systems, it made me laugh.
I will lean on a couple of analogies from operating like a pro sports team to help explain my thoughts on this topic.
Not having the right to disconnect, would be like expecting athletes to be playing on the field 24 hours a day, 7 days a week - insanity.
My perspective is probably still somewhat extreme, but on the other end of the spectrum - I would advise you, and I’ve done this multiple times to people on the Sitemate team, to uninstall Slack and Front/Email from your phone, or at a minimum - disable push notifications.
You do not need to be checking these systems 24/7, and it is typically easier to achieve this if you are processing them on your computer.
The ironic part here, is that people often keep notifications on because they’re worried about missing something, and I’ve found, now in dozens of cases, that it has the opposite effect.
The people who miss things, which causes friction, frustration and performance issues, are always the ones who get interrupted and distracted, and then forget to come back to things, instead of processing their notifications in a calm and systematic way.
As a general rule, it’s important to monitor critical comms channels at least every few hours, potentially more frequently depending on your role - Slack, Front, Jira, Confluence, Salesforce and Github.
There is only a very, very small number of scenarios where the expectations around monitoring communication channels change from the default described above, to a heightened level.
For product and engineering teams, this is when there are critical issues in your direct responsibility area - at which point, you are expected to be owning the work to drive this through to resolution, which could be either doing the work, or coordinating and project managing.
For GTM teams, this is when there are critical prospect/customer communications actively in progress - for example; closing a large and complex opportunity, or managing large customers in the case of any potential product outage.
However, even if the above occurs and you do need to go completely offline, for example, due to illness, or a special event such as birthday, wedding, travel, etc, the solution is simple - alert your team and/or line manager that there is something urgent that needs monitoring, and ask for their help to monitor during this period.
The only mistake you can make in these scenarios, is to not communicate.
Keen to learn more or join the Sitemate team?
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