Ryan Walker 🚀


Sharing everything I learn

Reflections from the Online World

2021 is one of the years I've felt most connected to friends whilst spending more time online than ever before.

December 13, 20217 min read

A long-standing opinion I've had is that to make great connections with colleagues friends, the kind that I would classify as an "old friend" is based on:

✅ - The number of meaningful interactions, ideally in different circumstances.

❌ - Not the time that has passed since first meaningful interaction with an individual

My definition of "Meaningful interaction":

  • Collaboration on a project
  • Collaborating on a problem...and hopefully solving it together
  • Sharing personal lives
  • Buying in and supporting each others growth

2021 is one of the years I've felt most connected to friends, in the most part due to the number of meaningful interactions I've had with them. I've also spent more time online than ever before, with some of my favourite moments being:

  • Demo Day W21, followed closed by Demo Day S21
  • SFF1 Founder’s Fellowship Showcases
  • Blackbird & Startmate Q3 Offsites

All of the examples above were times where I was online collaborating with friends, sharing experiences, and delivering on great work. Ultimately in reflection, what I believe made them great (vs merely good) was the power of effective online communication.

Online Communication

As mentioned before this has been the year of only online internal communication and a small amount of external in-person communication. With the unfortunate reality that I've been unable to meet the rest of the Startmate team IRL since starting 290 days ago (23rd Feb - 10th Dec) and that since moving to Auckland we've been in lockdown a total of 136 days this year, online was really the only choice.

External Communication

I want to create a seperate blog post about this but for the most part, I can group my external communication by the groups below:

  • Founder Scouting Meeting founders virtually (in most cases for the first time) to learn more about their startup and evangelise the Startmate Accelerator.
  • Founder's Fellowship Facilitating an online program for a cohort of fellows taking the leap into being founders.

For some reason, perhaps because of Covid induced social isolation, I've found that by in large we've almost forgotten how to interact when meeting new people online, as though the computer screen wants us to skip the beauties of getting to know someone in favour of efficiency. Well, I say let's swing the pendulum back to its equilibrium...

It's just like a first date, those first impressions are the most nerve-racking and you're trying to build your credibility and connection as fast as possible.

When meeting people for the first time, especially online when the social dynamic may be unequal from the outset, creating psychological safety and equality is paramount. For example when Founder Scouting often founders start off nervous, and rightfully so... putting myself in their shoes - "I'm pitching my company, something that I've spent countless hours, money and sleep crafting, at this point it's almost entirely entwined with my personal and professional identity and all I want is for you to understand my perspective of how important it is".

Creating psychological safety therefore takes time but setting a good precedent is a great way to put us on the right track. Every call starts with this question, "How are you doing?". My gut reaction is that the only reply to that question can be "Good, how about yourself?" But in reality, this is the perfect opportunity to set a good precedent by replying instead with:

"I’m actually surprisingly hungry. I've had far more walking meetings than my body is used to today, so I may need to grab a snack later but I have been really looking forward to this chat, so how are you doing?"

What I'm trying to do here is set the tone that it’s alright to overshare and be vulnerable. They don't need to be perfect or read off a script, we are all human after all...

A final great piece of advice I heard earlier this year at Festival of the Future, is that inevitably when I reciprocate by asking "how they're doing?" and IF they reply with only "good" they're indicating they're still not comfortable and I should dig in to get them to open up “Oh yeah, what have you had on this week so far?” The goal is to not continue on in the conversation till I've given them a fair chance to be comfortable and perhaps vulnerable.

Internal Communication

Getting used to an always-online office was quite the communication challenge - unlike most workplaces, I can't see and hear my colleagues on a day-to-day basis, so I miss out on being able to see what someone is working on or how they're feeling. Therefore reading between the digital lines becomes a required skillset, and something I definitely took for granted.

"If a tree falls in the forest, does it make a sound?" It's easy to say, do good work and the rewards will follow, but in the online world, if you're unable to communicate it, does the digital falling tree ping a Slack notification?

Coming to the realisation that having a skillset in online communication is not only important for my wellbeing but also for my career, it makes me ponder what “leveling up” also means at a career and individual level, something that’s more tangible than a high-level growth framework... something I can really sink my teeth into.

There’s no checklist to being GREAT, I can't just run a program 10 times or put in 1000 hours into coding and then I'll be great...or will I? In the time it takes at Startmate to run 10 iterations of the same program, 5 years would have passed (assuming they've been run twice per year). By then I probably would know a thing or two...

So then it comes down to the question,

How do I believe I can become GREAT at my job?

To evangelise change and get maximum buy in, you need to communicate consistently with leaders and stakeholders to ensure everyone stays excited about the product" - Marty Cagan, Inspired

I’ve come to my 2021 conclusion that to be GOOD at my job I need to have the basics, an above-average skillset in a defined job description, the know-how to use it, and a decent level of emotional intelligence (soft skills).

Therefore to be GREAT, I need to pair that with a maturity of strategic experience that comes from synthesising primary and secondary information, articulating insight-driven opinions whether that's in the form of a blog, or interpersonally. And above all else consistently communicating to all involved leaders & stakeholders.

Let me break that down:

Experimentation, involvement, and experience

The following steps don't work unless I have:

  • Informed the strategy for the experiment's success criteria and goals prior to the build
  • Built the experiment
  • Watched the experiment unfold first-hand

Being involved in one of the above is better than none, but having a stake in each is the only way I can set myself up for success. On a few occasions this year, I found myself joining projects late and missing steps that have in hindsight reduced my own buy-in and understanding of the project's purpose.

Synthesising primary and secondary information

Collecting and reading feedback/information is one thing but asking the right questions, whether those are success criteria, business objectives, or hunches, inform the grouping and segment the data to see what stories it tells.

Articulating insight-driven opinions

My main area of development this year has been to build confidence by forming strong opinions informed by the data, held loosely, and having feedback requested upon.

Above all else, consistently communicating to all involved leaders & stakeholders.

So many things happen at Startmate, and in the virtual environment, it becomes hard to keep track of where things are at. Communicating first and foremost with those who are involved is vital, as is keeping leaders excited so they can be brought along for the ride too.

This year has gone by quicker than I would have ever expected, it feels like just yesterday Auckland went into lockdown, and the day before that Lauren was ringing me to say I got the job.

It's easier to say time moves differently here at Startmate, some often refer to it as living in the exponential curve (myself included). But in reality, in reflecting back on the work that I've been involved with over the last year it's been a staircase of tightly laid-out steps, no step much bigger than the last.

It's only when I look back do I appreciate how much we've achieved as a team.


What it felt like vs Reality

Has it been a straightforward year? Not necessarily, we did the things we set out to achieve but getting there was perhaps a different story.

In the day-to-day I found myself commonly in a reactive state of mind, coming into projects after planning and strategy were mostly complete or handing off projects before they had finished.

🚀 When this works well, we are a cross-disciplinary, high executing machine.

🚧 Where it doesn't, is when I'm coming in to drive projects after they're started to try to meet success criteria that I had no involvement or buy-in and at the end having a 3rd party report on my behalf.

Just like Startmate, I'm on the same journey of continuous improvement, this year has brought along so many new growth opportunities and friends, that I'm grateful for. As long as we keep iterating and improving our ways of working, there isn't much we can't achieve. Looking forward to tackling 2022.


P.S. I've never written a blog before, and I'm not much of a writer but you need to start from somewhere right?

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