The top 5 operational mistakes founders make - with Kirstin Hunter

Kirstin Hunter, Managing Director of Techstars Tech Central Sydney, shares the top mistakes she’s seen in her time as a founder and senior startup executive – and how to avoid them
May 10, 2023
Katarina Throssell

Kirstin Hunter knows how it feels to navigate the chaos and ambiguity of running a startup. As co-founder and former CEO of Future Super, former Chief People, Risk and Legal Officer at Brighte, and former Chief of Staff at Human, she has lived it from the inside, several times over. 

Hannah Mourney and I recently asked Kirstin for her advice on what early-stage founders should focus on to set themselves up for long term success. Her deep experience in the ecosystem has taught her that getting the unsexy, operational elements of your business right is the real, and often overlooked, secret. 

Here are Kirstin’s top operational mistakes that she sees founders make, and her advice on how to avoid them. 

Mistake 1: Assuming the company vision and purpose are self-evident 

We all know that having a strong purpose, mission and vision are prerequisites to startup success. The purpose is your ‘why’, the mission is the ‘how’, and the vision is what the world will look like once you’ve succeeded. 

Founders are rarely short on vision. Where they can trip up is by failing to clearly and succinctly define the ‘what’ and the ‘why’, right from the start. It can be easy to assume that the purpose and mission are so obvious to others that you forget to articulate them out loud.

Clearly defining the purpose and mission is essential to ensuring that a rapidly growing team is working from the same starting point. Your definition will help empower each member of your team to make decisions based on what will deliver the greatest impact against your purpose. A divergence of even one degree can push you in different strategic directions and, by the end of a thousand mile journey, will see you end up in a completely different place. 

How to avoid it? 

Define the purpose and mission in writing so that each co-founder and new hire is 100% clear on what you are all working towards. This is best summed up in a few sentences, or, at most, in a crisp 30-second sell. 

Do this as early as possible, ideally at the company’s inception. You’ll know its time to reset if you see divergence within the team, when the team grows significantly, or when the mission needs to evolve to better reflect the business as it actually operates after a pivot or two. 

Mistake 2: Leaving the company culture to chance 

Kirstin has seen many founders fall into the trap of thinking that investing in culture is something that only big companies need to do. While this is often a fair reaction to the inauthentic attempts at “culture-building” that many of us have witnessed in past corporate lives, a startup also experiences cultural shifts as it scales from 5 employees, to 10, to 50, to 150, and beyond. 

Founders should be thinking about defining values and setting the ideal culture from day one. This means outlining both how the team encourages and rewards behaviour that aligns with the cultural vision, and how it corrects behaviour that does not. 

How to avoid it? 

Doing this well means making the hard calls. When you’re in a small team and have an archetypal ‘brilliant asshole’ employee who delivers outstanding work but is terrible to work with, founders need to do the hard thing and correct their behaviour or move them on. Their negative impact on culture will likely cause more damage in the long term than the benefit gained from their technically strong skills, and how you handle the situation as a leader will always speak louder than words

Kirstin also recommends thinking not just about what your values look like when they're just right, but also what they look like when they’re absent or present in excess. For example, if one of your values is to “get shit done”, the goldilocks state will be everyone working productivity towards your core goals. In absence, this looks like stasis, and in excess, it’s just furious busy work (aka getting shit done).

Mistake 3: Hiring when you should really be prioritising 

Kirstin has often seen founders make this mistake in the ‘growth at all costs’ stage of a startup’s journey, when it’s easy to think that the solution to any problem is just hiring someone new to come in and solve it. This often doesn’t work. Founders can scramble to hire a specialist in the problem area that may not actually have the generalist skills or scrappy attitude needed to be a successful early-stage startup operator. 

Her advice for not being able to do as much as you want to do, as fast as you want to do it? Don’t hire - prioritise instead. You can’t win by trying to do everything, and the best companies are highly focused on what they do and don’t do. 

How to avoid it? 

Start with the team and capability you already have, and figure out what the top priorities in the business are within these constraints. Work on developing your generalist staff to help them tackle the problems you’re facing, rather than searching for the illusive ‘unicorn’ employee with deep specialisation. Chances are, a unicorn won’t be able to leverage their skills in the way they want to in a messy, ambiguous startup environment. Your job as a manager and leader is to shape your existing people into what you’re looking for and help them unlock their full potential. 

Only once you’ve doubled down on your existing priorities and helped support your team, should you mindfully expand capacity to new priorities and roles. 

Mistake 4: Not focusing on the unsexy stuff 

When a founder or CEO forgets that it’s their job to think about the un-sexy stuff, everyone suffers. Kirstin has often seen founders forget about HR, finance and legals (including ESOP), particularly in the early days. The longer you leave it to get these operational elements fully set up, the harder it will be to fix them down the line (not to mention the compliance risk!). 

Kirstin’s advice is to bring on someone who can take the icky stuff off your plate as early as possible, such as an internally-focused COO, and empower them to do an amazing job. They can make sure your business runs as a well-oiled machine, freeing up time for the founder to focus on product, investors, marketing, and everything else.

How to avoid it? 

Kirstin’s top tip: bring on a COO earlier than you think you need one. Find someone who finds the un-sexy stuff sexy and relinquish control to them. Doing this early will help knowledge transfer and ease the stress of letting go that all founders face as a company scales. 

Mistake 5: Focusing too much on being a founder, and not on being a leader 

Not every day-one founder can be the leader of a $40 billion business. Success for a founder and CEO looks very different at the stage of 1 employee, to 5 employees, to 50, and to 100. 

As a founder who is also the CEO, you need to make sure that your leadership skills evolve at least as fast as your business is growing, and ideally a few steps faster. 

Some founders just can’t make this transition - and that’s completely fine! Some of the best founders have gone on to take functional leadership roles (e.g. CTO, Product) rather than trying to fill the CEO shoes. The most important thing to helping your company succeed in the long term is being honest with yourself and your team about your skills and capabilities, and about what stage of the startup process you are most suited to. 

Core to this is seeing yourself as a leader, rather than just a founder. This is a mindset shift that every founder has to face as their company grows, and for some founders, it may eventually be better to step aside and get in a new CEO instead. 

How to avoid it? 

Start by accepting that this is a challenge all founders face. Take yourself on the journey by actively seeking out the support that you as an individual human need to grow. Kirstin swears by executive coaching and finding a peer mentor, especially with someone who has experienced operating in a fast-paced startup environment. 

Kirstin Hunter is currently the Managing Director of Techstars Tech Central Sydney. She is an experienced start-up and high-growth business executive with a particular focus on fintech businesses at the intersection of activism and capitalism: co-founder and former CEO at Future Super, former executive at Brighte, former Chief of Staff at Human, and long-time mentor with Blackbird’s Giant program and Startmate fellowships. Kirstin is passionate about purpose-driven startups and helping founders build businesses that make the world better. 

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