Re-learning how to ask for help

Why did we decide to focus this newsletter particularly on Founding Ops?

Partly because it’s what we know. Both Jonni and I are the first and only operators at our companies and we only want to share perspectives based on our experiences.

But more fundamentally, being the founding operator is different than being part of an established ops team and we believe that this differentiator is worth exploring.

One of the key differences for me in founding ops was re-learning how to ask for help. In previous roles, if I didn’t know how to do something, I would ask someone else on my team for help. The same is true now - I just need to change my understanding of who was on my 'team.'

Of course, your first resource should always be within your own company. Some of the best advice that I’ve received on pricing strategy at Plain has come from our engineers (a vent about pricing will definitely be a future post from me). Your colleagues provide a fresh and invaluable perspective, even if it feels unrelated to the work that they are focused on.

The next step is learning how (and where) to seek help outside the company, which is much more ambiguous.

Here are a few resources that have become really useful to me:

• ChatGPT - I was admittedly late to the game here because I was too stubborn to admit needing an LLM’s help. I’ve very quickly gotten over this and use ChatGPT on a daily basis to speed up my work. I’ve found ChatGPT especially helpful for frameworks when I’m starting with a blank page - How should an invoice be structured? What documents are required for GDPR compliance? etc.

• Community resources (like this one!) - There are a ton of community resources about being in operations in a start-up. Hopefully this one is somewhat helpful so far 😉. Other communities that I really like are - Operations Nation, Operators Guild, and OG Next.

• Mentor/mentee relationships - Leaning on mentors gives you a fresh perspective and advice from someone who has already conquered similar challenges. Ask around your network for introductions to people who might be a good fit and when you find someone that you have a good rapport with, invest in the relationship. Do prep work before calls, use your mentor’s time sparingly, and show gratitude for the time they’re investing.

Disclaimer: Being great in a founding operator role requires an enormous amount of trust from your founders and your team. There are many things that should not be shared outside the company so be mindful 😇.

As founding operators, we’re often stubborn enough to think we can handle every task by ourselves. This isn’t scalable, neither for your own career or for your company’s growth. Luckily, all of us are in the same position and as eager to help as we are to receive help. As soon as you start looking around, the flood gates will open.