FounderFuel: 7 questions to ask yourself as a founder

As founders we so often spend our lives charging from one thing to the next – driven by that invisible internal force to make progress – that moments of reflection can be even more valuable when we do them. At certain times of year (the New Year, the summer slow-down) there’s a natural cadence shift that encourages this kind of check-in, and given the fast-pace we usually operate at, it’s worth taking a moment to focus on what will serve you for the months ahead.

Inspired by many of the coaching conversations we have with you all, here are 7 questions to ask yourself as a founder. Think of it like giving yourself a virtual founder-offsite. Make it an annual endeavour, or revisit and reset every three or six months.

Looking back

What have been my biggest wins?

This will come as no surprise to many of our founders since Wins is one of the daily resilience-building habits we advocate, and it’s a natural starting point for your reflections. Being achievement-focused types as founders, we tend to just move to the next task on the list (and then the next and the next) at a relentless pace. In short – we’re not great at celebrating the milestones! And let’s face it, in the role of founder there’s very rarely anyone there to say “hey, good job!” either, like there is in conventional jobs – so take a moment to just reflect on this question and actually feel a sense of achievement for what’s been achieved.

What have been my biggest challenges and how did I overcome them?

Strength and resilience do not just appear, they are borne out of encountering challenges and overcoming them. Consider the way in which the body gains muscle through strength training: you make tiny tears in the muscles from lifting weights, in order for the growth-hormone to rebuild those muscles stronger. Resilience is the same. We need to encounter challenges to stretch our mettle to build our resilience. So as a founder, consider the challenges you overcame and take comfort in the fact that these challenges are making you more resilient too. In addition, look for the lessons: Identify how you overcame the challenges and ask yourself what can you learn from this. 

What got in my way that was in my control?

We all know that we can get in our own way sometimes, so this question is a way of taking an honest look at this and seeing where we might be holding ourselves back. Reflect on what might have stopped you (or slowed you down) from making progress on your top priorities. It can sometimes help to consider times you might drift to something comfortable, rather than doing the ‘main thing’. In addition, dive into what habits are serving you well and then consider the counter question – what habits are not serving me at all?

Taking stock

What and who gives me the most energy?

This is such an under-utilised question and yet it uncovers a great deal, especially for founders where we inevitably end up wearing so many hats (and are often slow to shed them even as the team scales). It really helps to go granular with this one – consider moments in time where you’ve felt in the flow or where you‘ve been thriving. What was it about those situations that gave you energy? What were you doing? Who were you with? What were the things that really fuelled you?

What and who steals my energy?

On the flip-side, pull up the moments and situations that sapped your energy. Go into the detail again – look for tasks, environments, people and activities that kill your energy. Tell-tail signs are the things you procrastinate from doing, or the things that you dread dealing with. It’s easy to forget those monotonous activities, and when we do you just play the same story year after year.

With both of these questions, it worth reviewing your findings and seeing if there are any patterns that emerge.

Looking forward

What will I be most proud of achieving 3/6/12 months from today?

It’s likely that you’ll do plenty of strategizing and objective setting for the business, so hone in here on you and your role. The most sustainable founders might consider their role as founder and start-up leader (i.e. things you want to achieve professionally) but also what they want to achieve personally – whether it’s to run a marathon, or dedicate specific time to loved ones. You can start with a long list (personally I like to get everything out my head first, so I feel that I can consider everything) and then start to prioritise. Really consider that word ‘proud’ – it’s a strong acid test for what should make your top three or five focus areas.

So what?

What do I need to do to make it happen?

All this reflection is fruitless unless we ask So What? at the end of your virtual founder-offsite. For every answer and entry to your previous six questions, run through the list and ask ‘So what?’. What are you going to do differently? What are the steps to actually make something happen? And one of my absolute favourites… what are you going to NOT do – which can cover those habits and energy sappers, but also projects and responsibilities that are not aligned with your main priorities. At the end of the day, time is a finite resource, so you need to decide what you won’t do in order to have the space to achieve what you do.

FounderCircle members can access the worksheet for this framework here.