Vanessa O'Mahony
6 min readMay 11, 2021


Ramblings of a Slacker — one year on. 🚀

In preparation for this note, I asked myself “had I known then what I know now, what would I have done differently?”, and the answer is, in fact, very little.

What a year! I wonder how many times we have uttered these words as we reflect on the unexpected turn of events that this global pandemic has thrown upon us. Thankfully, the tone of the statement feels less scary now as we look ahead to continued success with the vaccine rollout, the re-opening of economies and society, and the ability for us to connect physically with our nearest and dearest.

Today, I also say the words “what a year” in a different but connected context — it’s my 1 Year Slackiversary — and what a year that has been! It’s hard to believe that, one year “in the door”, with the benefit of one lunch date with my management team and two walking 1–1’s, that I could feel in any way immersed in the business. And yet that is exactly what I feel. When I penned this note three weeks into my Slack journey last May, it’s probably best I didn’t envisage my spare room was to be my digital HQ for quite so long. ;-) The path was meandering for sure, I had to lean on people differently than if we had been in the physical office, and I had to trust both myself and those around me to get me to where I needed to be. I’ve jotted down some thoughts and experiences from along the way, which may be useful to those behind me on this remote journey, and to those perhaps considering the uncertainty that moving companies in a remote environment presents.

In no particular order:

  1. Remote On-boarding is a potential breeding ground for Imposter Syndrome — spot it, challenge it, and talk about it. With nobody alongside you to endorse you in the day to day, I certainly observed self doubt creep up regularly and unexpectedly in the early months. This is natural when you’re learning and finding your feet in a new business, and is often what drives us to achieve goals in a new environment. When there is extra chaos however, it’s more important to be crisp with your expectations, and structured in how you are measuring and recognising success to yourself. I found documenting my priorities and discussing these with my teams and peers useful in filling the gap of being physically “in” the business, which in turn lessened the creep of self doubt. Talking about Imposter Syndrome and other forms of self doubt is important not just in managing your own process, but it also serves as a support community for the many people around you who can relate to these new obstacles

2. Feedback — Seek it!

Connected to the above, self validation skills are fragile in the absence of an organic feedback environment where you pick up on cues from your peers, your team, your boss about the course you’re taking and the progress you’re making. In order to compensate for this gap, I recommend you are deliberate around seeking this feedback. I’m generally fairly self-sufficient and can assess how I’m doing but certainly felt the uncertainty of a physical feedback surrounding in those early months. Letting people know about this gap and inviting feedback is a great way to get closer to your business while also validating your work, or indeed course correcting if necessary

3. Prioritisation — Be hyper-focused and super-disciplined

There is so much meaningful work to get stuck into at Slack that you could be really busy doing great stuff, but still not be invested in the most meaningful work. This is the beauty and the challenge of being at a company in scale up mode, where the market opportunity is great, the people are smart, and the innovations for progress are all around you. Pick your priorities wisely, define the path towards them and the metrics for success, and then structure your bandwidth with these to the fore. I have a broad role at Slack so initially had to “go wide” into the organisation as part of my immersion in the business. This took me to some fascinating corners of the business and has given me great insight into the wider org, but at some point it was crucial to my personal remit that I define where I invest my energy, and commit to these most impactful to my commitments.

4. Silver Linings:

Find them, embrace them, celebrate them! Being authentic and bringing the whole self to work are no longer hypothetical goals for the corporate world — it’s a must to create an environment that works for your people, and creating your own ideal environment is leading by example. I’ve joked many times this year that I don’t have time to be anything other than my whole self — warts and all — and that manifests itself in me being open about both the challenges the pandemic has sent, as well as the really great nuggets we now have. My husband, Rónán and I get to drop and collect our girls to/from school this year, and catch moments of connection and live insights into their day we previously didn’t have. Dinner is a priority time where we value togetherness and not just the eating, and while homeschooling is something I have no desire to repeat, it was an opportunity to be close as a family in a new way too. Also, we got a puppy! The kids put in a couple of hard years begging for a little puppy — being at home means we could seriously consider this and Púca has honestly taken all our hearts in the last few months

Púca 💙

5. Empathy — lead with it, connect with it, treat yourself with it. Always.

The culture at Slack is special. There is a warmth and sense of genuine goodness about how people go about their best work that is remarkable. Not only does this make it a wonderful place to work (even from afar), it makes business sense cultivating an environment where people are motivated to find creative ways for continuous improvement and ambitious goal setting

6. Recruiting at Slack is an art — one which seeks to not only commit to finding the exact right people for the job at hand, but one which commits to sourcing and hiring with a visible diversity agenda to the fore. The last year has insisted that now is the time for people to step up and make a difference in the world, for society in general to do better, and I am proud to be in a place where advocating for diversity is not only welcomed but insisted upon.

7. Done is better than perfect — when there’s so much to do, we need to trust our gut to run, and be ok with failing — otherwise the opportunity is gone and you’re deliberating about the right way forward. Don’t be afraid to go forward, and therefore risk staying put. Also, leaders should be committed to creating that culture where innovation is cherished and “failure” is part of the journey.

8. Asynchronous and digital-first work is the future — technology is innovating to facilitate this, and remote work is here to stay in some shape or form. Play a role in what that new world looks like — speak up and insist on your point of view being part of this evolving conversation. For me, Slack is where my work happens; where I engage, collaborate, challenge, celebrate and muse. I do long for a time where there is face to face opportunity, however this year has demonstrated organically that the pivot to a digital-first world is here to stay and I’m excited about how empowering this is to both our working and personal environments.

9. And finally — Laugh! And play! And stay curious — who knows what’s around that next corner?

Oh, and Schitt’s creek — just ‘cos!

Also — we are hiring lots! And have nailed the remote on-boarding.

Check out our career page to see more.