Startups and change go hand in hand. The people who build them have to be able to grow quickly for the startup to reach its potential, and founders are pushed to change during their time building a company no matter what their personal story might be.
Yet there’s one part of change we rarely talk about: grief, without which you can never change. Any founder building a company needs to get comfortable with loss and leaving things behind.
A growing startup demands that the founder goes from doing everything to letting go and leaning into management and leadership. It demands that whole functions are created from scratch where nothing existed before. It demands that features are iterated, scrapped or built again. For a company to move forward employees need to leave, get promoted, experience a new boss. The list goes on.
It’s easy enough to deal with grief when a feature or a strategy dies. It’s harder when you have to let go of an early team member. It’s even harder when it’s a part of your identity, or the DNA of the company itself.
Every few years you need to smash up your business and start again
A mentor of mine, Simon Rogerson, founder of Octopus Group once said to me: “every few years you need to smash up your business and start again”. I was horrified; he was right.
I struggled with this when building Sanctus, the workplace coaching company I started in 2016. We took shape as a services-led offering and quickly reached £1m ARR+ — our coaches were also placed in the offices of our partner businesses. Over time I knew we needed to be a tech-enabled marketplace to reach new heights. Yet for the first phase of our build, our team, product and business reflected a bootstrapped agency.
But over time the market moved on. Our customers were about to get more educated and, to grow further, we needed to adapt. We needed to start again.
I struggled to let go of the early version of the business. It meant saying goodbye to employees who wouldn’t be the right fit for our next chapter; changing relationships with our early customers who valued us as a hands on wellbeing partner; and adapting the ethos of our company from a bootstrapped coaching practice to a marketplace that could 10x the impact we were having.
I needed to grieve the founder who’d got this thing off the ground and step into a new set of clothes. The founder who was going to take Sanctus from £1m-10m, was a new James.
When you’re scaling you have to change the belief system you started with.
There were a new set of rules and conditions compared to when I started the company. My old world view needed to be left behind so that I could welcome in a new one. Practically, this can often look like conversations with employees where you call out that the company is changing, roles are changing and what the future looks like. You constantly have to recontract with employees. Celebrating milestones is important too, when you hit a revenue or funding milestone — celebrate it, this naturally marks the end of one chapter. Strategy days, all hands and offsites are important too — not just to talk about what you’re going to do, but what you’re not going to do anymore.
When you’re scaling you have to change the belief system you started with. You have to let that die. For example “I need to do everything myself” is a belief that might serve you and the company in the embryonic stages. That won’t scale and, at some point, needs to die. You have to grieve for it. Grieve that you knew every customer by their name. Grieve that you and the early team all felt like mates. Grieve what your company is now, because if you want it to evolve — it needs to look very different.
Founders have to get really good at letting things go. This can include:
- Getting really good at having ending conversations. Learn to embrace the discomfort of letting someone go or changing their role in the company (hiring above them).
- Being better at communicating what you’re not going to be doing anymore. This is just as important as saying what you are going to be doing and clearly marks a change from the old to the new.
- Being better at celebrating what you’ve achieved so far. Celebration helps people feel proud of what they’ve contributed and can help people move on long term.
- Taking holidays at key jump off points to ritualise the transition from one chapter to the next. Taking a holiday after a fundraise is never a great look, but holidays at key points allow you to come back refreshed ready for a new chapter.
- Celebrating and saying goodbye to team members who played key roles in your journey. Making sure key team members get credit, recognition and reward is key, so people feel good and more open to conversations about change.
- Killing features, departments, ways of working. It’s not easy killing a feature product or strategy you loved, but you need to learn to celebrate the end of things as much as you celebrate the new stuff.
When you get better at letting stuff go, you create more space for the new. You free up more energy to go into a new chapter feeling resourced and excited. You make it clear to the people around you who you are becoming and what the priorities are.
Lean into the sadness. Lean into the growing pains and don’t underestimate the emotion that change can cause within you and your team. Create rituals, celebrate, reflect and end well — I promise you. You won’t regret it.
