As co-founder and former CEO of Future Super, former Chief People, Risk and Legal Officer at Brighte, and former chief of staff of Human, she’s seen it from the inside out several times.
Hannah Morney and I recently asked Kirstin for her advice on what budding founders should focus on to achieve long-term success. Her deep experience in the ecosystem has taught her that the real, and often overlooked, secret is getting the non-sexy, operational elements of your business right.
Here are Hunter’s top operational mistakes she sees founders make, and her advice for avoiding them.
Mistake 1: Assuming the company’s vision and purpose are self-evident
We all know that having a strong purpose, mission and vision are prerequisites for the success of a startup. The goal is your ‘why’, the mission is the ‘how’ and the vision is what the world will look like once you succeed.
Founders rarely lack vision. Where they can stumble is past not clearly and concisely defining the ‘what’ and the ‘why’, right of the get started. It can be easy to assume that the purpose and mission are so obvious to others that you forget to state them out loud.
Clearly defining the purpose and mission is essential to ensure that a fast-growing team works from the same starting point. Your definition helps each member of your team make decisions based on what will have the greatest impact on your goal. A deviation of even one degree can push you in different strategic directions and, at the end of a thousand mile journey, you will end up in a completely different place.
How to avoid it?
Define the goal and mission written so every 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 sharp 30-second sale.
Do this as early as possible, ideally when the company is founded. You know it’s time to reset when you see divergence within the team, when the team is growing significantly, or when the mission needs to evolve to better reflect the company as it actually operates after a few pivotal years.
Mistake 2: Leaving company culture to chance
Kirstin has seen many founders fall into the trap of thinking that investing in culture is something only big companies should do. While this is often a valid response to the inauthentic “culture building” attempts many of us have witnessed in corporate history, a startup also experiences cultural shifts as it scales from 5 employees to 10, to 50, to 150, and beyond.
Founders need to think defining values and determining the ideal culture from day one. This means setting out how the team encourages and rewards behavior that aligns with the cultural vision, and how it corrects behavior that doesn’t.
How to avoid it?
Doing this well means make the tough calls. When you’re on a small team and have an archetypal “brilliant asshole” employee who does a great job but is horrible to work with, founders need to do the hard thing and either correct their behavior or help them move on. Their negative impact on culture is likely to do more damage in the long run than the benefit they derive from their technically strong skills, and Hhow you handle the situation, because a leader will always say more than words.
Kirstin also recommends thinking about not only what your values look like when they’re just right, but also what they look like when they’re absent or overly present. For example, if one of your values is to “get shit done,” the state of goldilocks will be everyone working productively toward your core goals. In its absence, this looks like stasis, and in excess, it’s just furiously busy work (aka getting shit finished).
Mistake 3: Assume when you really should be prioritizing
Kirstin has seen founders make this mistake many times in the “grow at all costs” stage of a startup’s journey, when it’s easy to think that the solution to any problem is to just hire someone new to take it on. to solve. This often does not work. Founders may rush to hire a specialist in the problem area who may not have the generalist skills or sloppy attitude necessary to be a successful novice startup operator.
Her advice for not being able to do as much as you want, as fast as you want? Don’t hire people, but set priorities. You can’t win by trying everything, and the best companies are very focused on what they do and don’t do.
How to avoid it?
Start with the team and the capabilities you already have, and find out what the company’s top priorities are within these constraints. Work on developing your generalist employees to help them address the issues you face, rather than looking for the elusive “unicorn” employee with deep specialization. Chances are a unicorn won’t be able to utilize its skills the way it wants in a cluttered, ambiguous start-up environment. It is your job as a manager and leader to mold your existing people to what you are looking for and help them unlock their full potential.
Only when you’ve doubled down on your existing priorities and helped your team should you consciously expand capacity into new priorities and roles.
Mistake 4: Not focusing on the unsexy stuff
When a founder or CEO forgets it’s their job to think about non-sexy things, everyone suffers. Kirstin has often seen founders forget HR, finance, and legal (including ESOP), especially in the early days. The longer you wait to fully set up these operational elements, the harder it will be to fix them later (not to mention the compliance risk!).
Kirstin’s advice is to hire someone who can take the nasty stuff off your plate ASAP, like an internally-facing COO, and empower them to do a great job. They can keep your business running like a well-oiled machine, freeing up the founder’s time to focus on the product, investors, marketing, and everything else.
How to avoid it?
Kirstin’s best tip: hire a COO sooner than you think you need one. Find someone who finds the non-sexy things sexy and hand over control to them. Doing this early will help foster 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, not being a leader
Not every day-one founder can be the leader of a $40 billion company. Success for a founder and CEO looks very different at the 1 employee, to 5 employees, to 50 and to 100 stage.
As a founder who is also the CEO, you must make sure your leadership skills evolve at least as fast as your business growsand ideally a few steps faster.
Some founders just can’t make this transition – and that’s totally fine! Some of the best founders have moved on to functional leadership roles (e.g. CTO, Product) rather than trying to fill the CEO’s shoes. The most important thing to help your business succeed in the long run is being honest with yourself and your team about your skills and abilities, and the stage of the start-up process for which you are best suited.
The core of this is seeing yourself as one leader, rather than just a founder. This is a mindset shift that every founder faces as their business grows, and for some founders it may ultimately be better to step aside and hire a new CEO instead.
How to avoid it?
Start on accept that this is a challenge that all founders face. Join us on this journey by actively looking for the support you need as an individual to grow. Kirstin swears by executive coaching and finding a peer mentor, especially one who has experience working in a fast-paced startup environment.