Somewhere in the beginning of 2020, amidst the whole Covid 19 pandemic chaos, everyone in my company was forced to move to a “remote-first” scenario. What once started as a fearful period of what a pandemic scenario might mean for us as a company — how it would affect sales, team cohesion, deliverables, recruitment — eventually turned into the most unexpected personally calm period of the last 10 years, by far.
Everyone was forced to step it up a notch and become more independent, clearer in communication, better at planning, at laying out expectations and flagging issues. We did a banger job at achieving this and it would ultimately pave our way to becoming a global team. Next to this, sales didn’t really get affected in any negative way for a decent period. Nothing was moving super fast but at the same time everything was just stable enough.
My role in the company besides bearing the “Founder” tag had always been a mixed bag of “anything but sales and finance,” which in practice meant that I was responsible for the Technical, Operations, Administration, Recruitment, HR and Culture flags, amongst everything else in between. On a company that used as flagships our amazing culture, above-standards technical quality, packed with soon-to-be rockstar people but with a combined near-to-zero experience on all fronts other than technical, this was a lot to learn and carry.
Suddenly, by having matured our way of working, by not being around 20 people in an office constantly battling for my attention, and due to an acceptable slower period in sales, I soon had very few fires to put out. I then realised that after spending 10 years having very clear goals and problems to solve, I simply had no MO for what Ben Horowitz calls “peace time.” This rapidly became the least productive period of my adult life.
The checklist
Because I’m naturally engaged with chaos and at solving it, I had to create and keep updating a checklist to drive my focus back to where it should go when there’s no obvious fire demanding attention. It’s focused on being critical about anything structural and creating longer-term investment plans that address any weaknesses or opportunities. I’ve maintained and updated it ever since, and it’s become one of the most useful tools I have.
I divide it into the following categories.
Technical
- Quality: From code quality to what and how we deliver it. Is it over or under-engineered? How are our clients perceiving this? Do we need to revisit our standards or are they not clear enough? Are we using the right tools in the right way? Are we missing out on any tools, processes or trends that could boost our deliverables?
- Efficiency: Challenge every single process, every intervenient, every duration, and see where we can optimise. Are there any bottlenecks or unnecessary steps?
- Scalability: If we needed to double capacity, would we need a structural change or simply time and resources?
- Productivity: Could we deliver something faster? Could we do a part of any process faster without affecting the perceived quality of the outcome?
- Opportunity: Is there a time and/or resource investment opportunity we can consider to benefit from in the future? Is there a market or strategy gap we can take advantage of?
People
- Communication: How are we relating and communicating? Are there any artificial or real boundaries? What is the tone and vibe of these exchanges? Do we have the right communication culture?
- Retention: Are we consciously taking care of our teams? Are we tracking and acting on their feedback? Do we have any blind spots? What is the pulse of the organisation? Where are we versus where our teams need and expect us to be, and is it a reasonable expectation? Are we attracting and retaining the right talent?
- Culture: Which behaviours are a natural consequence of the values we instil and the environment we created? Is it absolutely obvious what our expectations are? Do people follow our values or simply know them? Are we bettering people through our culture or stifling them? Are there imbalances in teams or departments?
Sales
- Strategy: Are we targeting the right markets or are there any shifts? Are we pitching the right angles or is there a different, differentiating one we can explore? Are we approaching the right people and businesses in the right way? Is our sales process conveying what we need to convey? Does it represent us?
- Marketing: Does it need to focus on or push a specific vertical? Is the communication style what we need? Is engagement growing or slowing? Which types of content have more traction? Are there any trends we can explore? Does it share what we need to share?
- Product or market ideas: Are there any problems that we are (or aren’t) solving that could be turned into a product? Are there any market or technology changes that could disrupt a specific space?
Documentation
This is a relatively recent obsession, but an obsession nonetheless. I check on a regular basis how thorough our documentation is, how complete it is, but also how concise. Documentation should be up to date, readable, easily understandable, easy to go back and double-check. Ultimately it should paint an exact picture of all the information you need your teams to fundamentally grasp. Too much and nobody reads it. Too little and it doesn’t serve its purpose.
Processes
For all of the above topics, there are processes associated with them. These should be fresh, organic, well documented, down to the point, efficient, and more importantly, relevant. Maintaining a process because it has existed for years is not a valid reason to keep it.
The thought exercise
One of the more interesting things I regularly do is try to bring other egos into the conversation, albeit only in my imagination. I’ll pick someone whose mindset I respect and ask myself how they would look at the current state of things.
A good combo I’ve used is to bring in Elon Musk’s surge mindset first — where I’ll come up with all sorts of borderline destructive changes and improvements to be done internally. Then I’ll bring in a Gary Vee to tone it down to a more human-focused approach at getting things communicated and executed. The point isn’t to roleplay as these people. It’s to break out of my own perspective and see the same problems through a radically different lens.
Push it down
Finally, an organisation needs a set of evangelists that share the enthusiasm around these priorities. These colleagues are my eyes and ears for all of the above and will, hopefully, keep things in check even when I’m not looking. I try to empower people to be as autonomous as possible in implementing, changing or completely removing any part of any process, as long as it moves us forward.
Autonomy, sense of ownership, and having these expectations clearly documented makes it surprisingly easy to keep the machine running in peace time. The irony is that the checklist was born from having nothing to do, and now it makes sure there’s always something to do. I haven’t had an unproductive peace-time period since.