Founder Check-ins: Honest conversations for stronger foundations

When you start a company with friends or close contacts, it adds an extra layer of complexity – a layer built on shared history, mutual trust, and (hopefully!) a healthy dose of camaraderie.

I’m an advocate of regular founder check-ins in any start-up or scale-up. But when discussing the future, it's important to think about both the company, and your individual motivations. Remember, you all likely embarked on this journey for different reasons.

The key question: Are you all still on the same page?

Here's the thing: as your company evolves, so do you and your friends-turned-cofounders. It's natural for priorities to shift, aspirations to change, life to take people in different directions. That's why open and honest conversations are vital to avoid resentment, burnout, and potentially, the breakdown of your partnership.  This is your time to focus on the core group, the engine that keeps the business running and do some maintenance.

Here are some questions to consider during your check-in:

• Are you happy? Is the business giving you life satisfaction, happiness and contentment you crave?

• Do you see yourself at this company in the long term? Be honest about your career goals and how this company fits into them. Just because you started it, doesn’t mean you have to stick around

• Are you itching for a new experience? Perhaps a larger company with training opportunities would be a better fit right now

• Do you long for a change of scenery? Relocation might be something you’re looking for, but how does that fit in with the company goals?

• Is the entrepreneurial fire still burning? Did you enjoy the buzz of the start up life and want to start something new?

• Is it turning into ‘work’? For some, starting a company is a way to escape the feeling of ‘work’, the corporate life, the day-to-day drudgery. As a start up starts to scale, it is necessary to have documentation, processes, strategies and plans. For some, this building up stage is exciting but for others it is what they wanted to escape.

• Have your priorities changed? If you fell into entrepreneurship due to circumstances or being in a particular stage of life. If those circumstances or life stages change, it can mean you start to view your journey differently. 

Creating a safe space for open dialogue

Have open conversations, all cards on the table and approach them with empathy and understanding:

• Take the opportunity to get together away from the office, find somewhere with a relaxed atmosphere - and no laptops! Talk to each other as individuals rather than your job titles or functions

• Establish a safe space where everyone can speak honestly about where they are at in their life, how they are feeling about the business at that moment in time. Regular check-ins mean it should be easier to raise things as they arise without dropping anything unexpected into the group

• Focus on solutions that address peoples’ needs, where possible. Perhaps a sabbatical, reduced hours, more challenges, or a temporary relocation are options to keep everyone on board

By having these crucial conversations, you can navigate the inevitable changes in your personal and professional goals. An open dialogue will strengthen your friendship, ensure everyone feels valued, and ultimately, set your company on a path to sustainable success.