Change your swim lane: how I made the leap from big tech to startups then VC

- July 25, 2023 8 MIN READ
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Transitioning from a tech giant like Microsoft to an early-stage startup can be a daunting but exciting experience.

Before joining Tidal, I made this leap to become the fourth employee and founding marketer at hyper-growth startup Dovetail.

In this article, I’ll share the valuable insights I learnt along the way, I’ll share my critical realisations during this transition, and offer advice for thriving in a startup environment.

Swim lanes

When I was thinking through the process of moving from big to small, I chatted with a load of different people about it.

One conversation in particular stuck out—it was with venture capitalist, self-professed dumbest guy at the table and founder of Australia’s first unicorn David Shein.

He asked me why I wanted to join a pre-seed startup, and my response was that I was sick of swimming in my own swim lane.

At Microsoft, job descriptions often define our roles and responsibilities pretty concretely. But I found at startups that these descriptions are more like starting points based on the team’s assumptions and best guesses.

I realised that swimming in my own swim lane, confined by a job description, was nowhere near as fulfilling as the prospect of joining a pre-seed startup and, in turn, embracing ambiguity and being open to taking on tasks outside of the traditional boundaries of a role.

It required me to shift my mindset to view job descriptions as evolving representations rather than fixed roles.

Clarity is king

We often walk around our workplaces making assumptions and filling in knowledge gaps all day.

That’s kind of how our brains work—we save energy by forming patterns. At startups, you don’t have time for your brain to make an assumption and send you down some random path for you to finally come up for air on the entirely wrong track.

It’s in your best interest to ask all the questions that make the implicit explicit—which requires a rather painful brain retraining. We’re used to expressing our efficiency and intellect as how quickly we can grok a concept and run with it, but that won’t do you any good at startup; you don’t have time to play Russian roulette with your strategy hoping your assumptions are valid.

So be willing to sound like an idiot with all your clarifying questions; your successful future self will thank you.

Socialise your ideas

From my experience, larger organisations are fans of the big reveal. I found the opposite true at a startup—even before you’ve done anything, begin to seed your strategies to your colleagues to get their feedback and source indicators.

Suppose you throw something out there and get crickets from someone who needs to be bought down the track.

In that case, you might have a problem with your idea or the way you’re selling it—either way, you know a hell of a lot more than when you were walking around with that idea bouncing around your own echo chamber of a brain. This is a finger-in-the-air estimate, but by the time you’re set to formally ‘announce’ something, 75% of people in that session should already be somewhat familiar with what you’re suggesting.

Buy-in is not guaranteed when there’s a big reveal, but if you’ve made a bunch of micro course corrections based on the indicators you’ve received, it should set you on the right track.

Communicate openly

When I say open communication, I don’t mean open your heart and communicate freely; I mean post shit in a public Slack channel so people can see it.

People are often okay with sharing things in specific meetings or with certain people, but 86% of people blame lack of collaboration or ineffective communication for workplace failures.

So if someone else could benefit from the background you’re providing, if it would help align something strategically, or if that information could assist someone in doing their job (rather than hinder their direction)—then what’s the harm in opting for a public Slack channel. It saves time on reposting, provides context, and allows others to play along at home and amass information about what you’re doing and how that may affect their role.

There’s a certain point where this breaks, and the noise would be too much, but that’s much further down the track than one might think. Weigh up the benefit of sharing context with entire teams and empowering people to take control of their Slack/Notion alerts versus the cost to the business of each and every 10-minute context-sharing rabbit hole you have to go down because you kept everything closed until that point.

Share early, share often, and cop the feedback—you’ll be less wedded to the project if you share it before you’ve added your blood, sweat, and tears.

Context switch

Context-switching refers to stopping work on one project and resuming after performing a different task on another.

Context-switching is shown to negatively impact productivity and cause mental fatigue. On average, it takes about nine and a half minutes to regain a productive workflow after switching between digital apps.

Google context switching, and you’ll find many articles explaining how it kills your productivity, saps your energy and increases cortisol levels.

That may very well be true, but what you’re going to need to do at a startup is get really good at it so that it doesn’t have those same detrimental impacts.

Maybe what I’m talking about isn’t so much task-switching but fundamental mindset alterations you’ll need to make continuously throughout your day. It is no way easy; it takes immense amounts of practice and is really tiring when you first start but challenge yourself—how quickly can you be deep in a task, then switch to being 100% present when someone asks you a question, to then going back deeply into that task.

It also turns you into a live executor who starts to execute a task while you’re discussing it, knowing you’re 100% present at that moment for the time it requires. I’m not saying it’s sustainable, but building this capability allows you to oscillate between different states of concentration—it gives you an engagement superpower, a solid commodity in startups.

Fire yourself

Fire yourself in your current role and rehire yourself in a completely new capacity every 90 days.

First, change is constant, and the phases of a scaling business are relentless, so your job is to self-regulate. There are loads of growing pains in startups, and you often won’t find formal performance reviews taking place. You’re constantly doing a job that you’ve never done before, so critical analysis of how you’re going and what you need to do to grow into the new iteration of your role in three months is imperative.

You might need to take the step to imagine that you’re your own boss and critically evaluate your own work.

Imagine you were considering firing yourself and hiring someone else; what skills would they have? Do you have those skills? What’s the delta?

And when someone new joins the team, consider what responsibilities you want to give away to enable you to focus on new things.

View feedback as data

Feedback’s a gift, right? WRONG!

Feedback is a data point. Actively challenge the notion that feedback is always a gift.

Feedback is subjective and influenced by the giver’s perspective. Consider the intent and expertise of the person delivering feedback to determine its value and relevance.

There can still be value in the data if you acknowledge its potential distortion and understand that it requires a cost-benefit analysis.

That way, you can be more intentional about responding to feedback.

Customers are your greatest allies

Deep empathy and understanding of the customer are crucial for every startup team member.

Tidal VC Liz Ross

Tidal VC’s Liz Ross

To achieve this, it is essential that each team member actively engages with the customer. This involvement can take various forms, such as joining customer calls, shadowing support team members, and participating in customer interviews.

After all, the customer is the very reason that you’re building the product. Being closer to the customer makes you more motivated, especially when you witness your impact on their lives.

Customer satisfaction and appreciation make startup life’s challenges and fluctuations worthwhile. They serve as your greatest weapon in discussions about the focus of your strategy. In fact, customer feedback often outweighs internal discussions.

By leveraging the insights you receive from customers, you can shape your strategy more effectively and cater to their needs and desires.

Be all in

An imagined future payday is not enough to sustain you day in and day out. Gnarly problems will inevitably arise, and if your motivation is solely driven by equity, they will quickly leave you feeling defeated.

It’s essential to recognise that this journey is an emotionally challenging rollercoaster ride with its fair share of highs and lows. To navigate it successfully, caring deeply is critical. If you find yourself losing that sense of caring, it’s a clear sign that it’s time to move on.

Company values hold a lot of importance in startups, and your personal values should be mapped to the company’s if you want things to work. By nurturing this harmony between your individual and the organisational values, you pave the way for a more fulfilling and prosperous journey.

Create your own boundaries

Creating boundaries is never more important than at a startup; the lifeless legal entity that is a startup will take every one of your waking moments to fuel its own growth if you let it.

An inanimate legal entity can’t identify when you’re at capacity or close to burnout, so establishing and maintaining boundaries is crucial for productivity and velocity. Understanding the concept of diminishing returns is essential, realising that excessive work hours hinder productivity and create a pile-up of tasks in your personal life.

Applying yourself to the most critical jobs early in the morning and leaving work despite any urgent issues is crucial. Setting and encouraging boundaries establishes some clear guardrails for everyone you work with—clearly communicate your availability and stick to it; humans love nothing more than clarity and clear expectations.

Learning to respectfully say “no” and trusting your intuition before committing to additional tasks or responsibilities.

Setting boundaries from the beginning is more straightforward than establishing them later on, as it is challenging to regain respect once you’ve shown a lack of boundaries.

Let it fester

Most of the time, when you see a problem in a startup, you consider the steps you can take to solve it, and if needed, you might bring others in—there are just so many little holes you’re trying to fill. It’s often the case that you’ll try to address a problem head-on to prevent it from getting worse. There are a few important exceptions to that rule.

Nick Crocker from Blackbird once shared some insightful advice with me; he said that 9 times out of 10, you rally around a problem, but there are some systemic problems you might want to let fester if you want them to get fixed.

You have to make sure that everyone has experienced them, so the onus is on the collective to make a change–after all, how can people change what they fundamentally don’t know about.

I liken it to the act of “paper-mâché’ing over cracks” in concrete; it’s a temporary solution that hides the issue rather than bringing it to light for everyone so you can collectively create a genuine and lasting fix.

You’ve got to discern whether a problem falls under your personal responsibility or whether solving it correctly requires exposure to others. It’s crucial to assess whether the issue lies outside the boundaries of your circle of influence, as focusing on a temporary solution might divert your attention from your actual responsibilities.

Concealing the problem with a quick fix can also hinder Founders from acknowledging its existence, potentially leading to further complications for all parties involved and frustration that they weren’t aware of the problem in the first place.

When the problem goes beyond our personal purview, it may be more prudent to allow it to persist so that it can be comprehensively addressed.

Create MVPs for everything

To address current challenges and prioritise rapid growth, it is crucial to minimise time spent on hypothetical future problems and avoid excessive investment in far-fetched scenarios. Put your head down and focus on executing well, learning from past experiences, and embracing speed in decision-making and execution.

You can sustainably fuel your growth by dedicating 80% of your focus to immediate growth projects and reserving 20% for future initiatives. Simplicity, adaptability, and a willingness to embrace challenges are essential in this fast-paced environment, where learning occurs at an accelerated pace.

Think of a version 1 for everything you do and iterate on what you’ve ‘productised’ if need be, just like your product team does with the product you’re selling.

Transitioning environments requires a significant shift in mindset and approach—you want to embrace uncertainty, open communication, continuous learning, and nurture a deep understanding of the customer. Job descriptions become fluid, and one must seek clarity and challenge assumptions.

Sharing ideas early and frequently, seeking feedback as valuable data, and actively engaging with customers become fundamental practices.

Your ability to context switch efficiently and create personal boundaries is crucial for maintaining productivity and avoiding burnout.

Recognising the need for self-evaluation, adapting to evolving roles, and aligning personal values with the company’s mission is vital for success. It’s a long journey but well worth it.

  • Liz Ross is marketing lead at Tidal Ventures, Australia’s leading seed-stage venture capital firm.