4 things I’ve learnt from working in a startup as I prepare to run my own

PSA: At the end of September, after almost 18 months as sole legal counsel, I’ll be leaving Wefarm for pastures new (or, in fact, pastures old). I’m going full-time as CEO of CareerEar!

I’m very excited about being in this position and very much recognising the privilege that I have to build my startup and have a major impact on the world. As I am preparing? to finally have one key focus (kinda), I took some time to reflect on how my experience working within a startup has prepared me to be better at running my own. I'm sharing my key lessons here in case they’re of use to anyone out there who is also thinking about becoming a full-time founder.

My role as a leader

I’ve learnt that the role of in-house counsel and CEO share a key similarity: like the leader of a company, I was required to be an enabler. My role wasn’t to build products, acquire users or perform QA tests, it was to enable the teams doing all of these things to operate without putting the business at risk. This meant that I was always at risk of becoming a “blocker” and holding colleagues back from executing. What I noticed was that it’s all too easy to get really deep in a particular topic instead of tactfully balancing the demands of multiple teams (which can sometimes conflict!) and making sure everyone is unblocked to do their best work. I had to learn how to not be the bottleneck. I will be looking at my role as CEO through this lens: how can I best empower my team to execute to their fullest potential?

Building company culture from the ground up

Despite attending numerous workshops on how to build your startup’s culture, engaging in discussions about culture and so on, if I’m honest, I didn’t ever think that culture could possibly be a priority for an early stage startup - there’s already enough to do and there aren’t enough people to need to start thinking about culture. Wrong!

I’m now a firm believer of building your company culture from your very first team member joining your team i.e. you.

Your “company of one” should have a culture.

If you are not clear on the culture that you want to build and the values that frame it, it will be near impossible for you to find the right people as you grow. We have our core values at CareerEar and we’ve been doing some work with the team to revisit these and ensure that we’re all aligned and are the right people to take CareerEar forward. For more on this, I’d strongly encourage you to read “Traction” by Gino Wickman, kindly recommended to me by one of my incredible mentors, Dan Kirby (thanks, Dan!).

Wefarm has really worked hard on revisiting, reframing and rebuilding its culture and I totally get why. I feel inspired by Wefarm’s efforts on this and will certainly be taking away some of the day to day tools such as the public praise channel on Slack, the shoutouts to colleagues during All Hands and the iterative approach of learning from processes adopted and working collaboratively to improve these going forward.

OKRs are only as valuable as the buy-in they receive?

A lot has been written about the value of OKRs, but much less has been written about how to make OKRs valuable. My experience working within a startup environment has been invaluable in developing this knowledge about the work required to truly embed OKRs into the fabric of an organisation and get sufficient buy-in so as to have each individual team member genuinely taking ownership of their OKR and driving forward each quarter. I’ve witnessed an iterative approach taken to learning about ways to better improve the implementation of the OKR framework with:

• company wide sessions;
• different ways of structuring setting OKRs in a remote working environment;
• 1:1s with leaders;
• facilitating and empowering cross-collaboration across teams; and?
• using technology to enable transparency and tracking.?

These efforts take time and multiple cycles but result in a greater shared understanding of what OKRs are and how they are valuable. When every individual understands how valuable they can be and feels accountable to their OKR, that’s when the magic happens.

Building a team

Building a high quality, diverse team is HARD. To be fair, I already knew this, but it’s difficult to truly contemplate the real impact of this without being on the inside and seeing it play out for yourself. Talent is truly everywhere but so are other employers! The current job market is such that every single employer has to have solid employer branding (check out Wiser for help on this), competitive salaries and be attractive to potential candidates over and above other employers. In addition, employers have to work on casting their net further and wider than they are used to in order to attract a diverse pool of candidates. I’ve seen the impact that unfilled vacancies can have, I’ve seen candidates slip away at the final hurdle due to other offers and I’ve seen the impact that staff leaving a business can have.

In a way, it’s strangely comforting to know that this is just how it goes. Transitioning into my full-time role at CareerEar, I can be mentally prepared for it all because I’ve seen it and I know it happens across all startups. On the positive side, in my current role, I’ve been able to observe some of the solutions in action - the transition to being remote first; opening up opportunities to hire from anywhere in the world, from Kenya to Spain; and taking steps to understand, from the data, how diversity within the business can be improved.

What I’ll be doing at CareerEar is focusing on creating a positive workplace environment (which includes operating a 4 day week (more on that soon)) and doing our part to support other employers to hire fantastic talent from underserved communities (cheeky plug to promote CareerEar's job ad service - check it out here).

I’d love to hear from other founders who spent time working within a startup first. How did it prepare you for the realities of full-time founder life? What did you take away from your experience?