Ben Stewart

Opinions, definitely not facts

Managing - Up, Up, Down, Down, Left, Right

Posted at — Aug 3, 2020

*Left, Right, B, A, Start! Sorry, couldn’t not finish that

Delivering communications to anyone in your organisation should have come with some serious thought and experience behind it. While there are most definitely diminishing returns on going over your email to CEO thirty-five times, it definitely helps to know and think about a few things before you send something out from your brain into the world.

How do you want to say?
When do you want to say it?
Who do you say it to?

I often ask myself these three questions whenever I am thinking of delivering a message of any kind. It’s also important to say that the answer to those questions will drastically change the content, style and the execution of how I end up delivering that communication.

How do you want to say?

The actual delivery mechanism of your message likely depends on your previous experience with these things and also whether you have been burnt in the past with saying or receiving communications.

If you need to tell your team you’ve booked the second week in September for a vacation; it’s hopefully quite evident that you shouldn’t book a company all-hands for it. You would use Slack/Teams, email or even just a OoO message for folks so that they know.

On the other hand, if you need to announce a company wide re-org… it’s probably best you don’t do that in a Slack thread finished with a 👍. For one of those you want to plan out exactly how, when and where folks are going to hear the news.

Understanding the weight and potential reaction of what you want to say should allow you to exercise empathy for those receiving the message. Once you do that, you can then plan on what method of delivery your message should take.

Side note; with everyone WFH at the moment you may think Slack is a good idea for most things. However you should have a serious think about if that really helps convey the seriousness of your message. I’ve also had experience were messages on Slack/Teams/Email don’t truly land on the nose of what you want to achieve, which leads to panic.

Similarly, booking a meeting next week may be over the top for what you want to communicate. It really is a fine balance that you should spend some time thinking about in your org.

When do you want to say it?

So we know you have something to say but the timing of it can be crucial.

As an IC, you would fully expect your boss to give you information as soon as they have it. We should be transparent, open and honest with everyone right? Obviously the answer to that question is yes but I would be lying if I didn’t suggest that this is a grey area.

While it’s perfectly valid to say that your team should be given information as soon as you get it but sometimes that isn’t always the best approach. I’ll admit that this is something I still struggle with to this day, but it’s a part of leadership that sometimes needs to happen. Delaying the delivery of information shouldn’t be based on any malice or bad intent; instead it should be based on empathy and an understanding of how teams perform.

When I have something to tell my teams, I usually go through the following questions in my head;

Do I have enough information yet to give my team the full story?
When will I have enough information?
Will this disrupt the organisation and if so, when is it safer to deliver this message?
Do my team need to know this right now?
Who needs to know first to help deliver the message?

I’ve experienced very few circumstances, luckily, were I need to send a message out at 4.30pm on a Friday.

Who are you saying it to?

Whether you are talking to your team, your leadership peers or your grand-boss will shape the narrative of the message you are trying to send. It takes a lot of practise and experience to be able to deliver communications ‘down’ to teams and ‘up’ to the company board. It’s shouldn’t come as a shock that delivering communications to a mid-level engineer in Squad X is very different from delivering a 15 minute presentation to an executive board.

Let’s take the example of introducing continuous integration to your teams;

Zoom Hair

Giving a presentation to senior leadership is something that only gets better with practise. From personal experience, it also helps to practise a few times to get comfortable with the flow and overall delivery but not too much. I’ve sat the night before practising a presentation only to be interrupted in the first five minutes which then put be completely off. Prepare your narrative and your ask for senior leadership, not the run order of your slides. You will be interrupted and questioned… probably more than once.

Sending a message to any colleague in your organisation should come with some thought. It’s the job of a leader to make sure that everyone understands what you are saying and why you are saying it. So the next time you have something to say think about the three questions to understand how best to deliver what you want to say; how, when and who?

With that understanding you’ll be more likely to improve a key part of being a leader in any organisation.