When your startup needs to scale – the execs

It’s been over a decade since I joined my first startup. During that decade I’ve certainly learnt a lot, and one of the biggest takeaways is that at different stages of startup life you need to bring different people on board.

In my experience the biggest blocker for startup’s growth is a stagnant mindset of its founders, who resist making changes in their leadership team. Often, it’s exactly an ability to make tough calls of this nature that differentiates startups who thrive and the struggling ones.

It is super tough to part ways with the people who helped you get to the place you’re at now. Even working with them on transition to different roles and responsibilities is tough. After many wins and losses, after years of grind people get accustomed to their position and you get accustomed to working arm in arm with them.

Yet as a startup founder, an executive or a board member, you need to do the necessary and make peace with the truth being that what brought you here won’t take you to the next level. And it’s always about the right people in the right roles.

I myself stay away from early stage startups for exactly this reason. I’ve realized that having had spent most of my career working on startups who have already found their market fit and needed people to coordinate startup’s accelerated growth, I should stick to my guns and work with startups which are already there.

It’s easy to fall for an idea that if you grew organizations to hundreds of employees, then managing the early-stage startup from the ground up is going to be nothing but a peanut. I’ve met many wildly successful executives who made this exact mistake. They overestimated their ability to adapt and underestimated the nature of challenges bothering early-stage startups.
You could say that if I’ve seen other people fail I’d grow wiser, right? Yet there you go, I’ve made this very mistake myself.

See, it’s hard to operate on a very tight budget, even more so if you’re used to being more relaxed with money. Just because you grew one organization from 14 to 70+ employees, another from 80 to 120+ employees doesn’t mean you’ll be as capable when you join a startup having 6 employees and able to hire maybe one or two employees per quarter.

While the middle-management can adjust quite easily, the people in senior leadership positions often have built a certain mindset and skillset which allows them to repetitively achieve success while joining organizations of the same level; at the same time being the reason for their crash and burn situation at startups on a different level of maturity.

Your first software architect could’ve been the greatest technology leader even when you were starting out, but it doesn’t mean she/he will be able to manage the technology organization which grows fivefold – which is when you need to bring in a seasoned CTO.
Your CMO who helped you find your market fit, may not be a leader you need if your ambition is to expand globally and build a product for tens of thousands of users vs current hundreds.

Next time you find your organization stuck with seemingly no ways to grow, look at your leadership team, including yourself. It’s easy to miss the right moment in which you should re-evaluate your team, because you may trick yourself into thinking that any growth is good and even tho slow, you’re moving forward so you’ll somehow make it all work out in the end. You may or may not and hope has never been a good strategy.

That’s why I recommend startup operators to evaluate the leadership team on at least quarterly basis. It’s unusual that your needs in terms of staff would change drastically over 3 months, and that’s why it’s valuable to have this process in place because it allows you to take action and react to a situation which could become a problem few more quarters down the road. When you know that your startup will be in need of leaders capable of exploiting new market opportunities, you can start coaching them or have them work with someone who’s been there and learn how to prepare for what’s coming. Being prepared has never been a bad strategy.

Still, it’s easier said than done. It’s hard to change people’s habits. It’s even harder to change people’s mindset. And nine out of ten times it’s completely unnecessary, because people who’ll be struggling in a forced transition could be working on a success of a different early-stage startup. Letting people go sometimes is just the only right thing to do, for the benefit of all of you.

So, bring in the experts. Bring in the seasoned professionals who’ve been there and done that.
It’s never too early to start thinking about challenges of this nature, because changes in top leadership team will affect the culture, stability of your company and overall atmosphere.
You need or will need to make the necessary changes, so don’t leave it to a chance. Embrace the startup nature and know the necessary.

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