When One of Your Key Leaders is Struggling to Keep Up

What do you do when one of the key leaders in your growing software business is struggling?

Struggling to build productive teams, hit reasonable goals, and keep up as your business organization evolves through its growth phases.

This topic comes up frequently in my Practical Founders Peer Group meetings with founders of SaaS businesses with an ARR between $2M and $12M who are scaling up.

There are enough senior leaders in these businesses that almost every month, someone has an “I don’t think one of my leaders is working out” conversation.

This conversation doesn’t happen very much in my other groups with founders of businesses striving for $1M ARR. They are still scrappy and figuring out their product-market fit, filling out their products, and tuning their business models.

Your business can only grow as far and fast as your leaders, including you. The bigger your company, the more it’s “all about your leaders. ”

All smart, capable people can figure out new things and grow.

Not all smart, capable leaders have the SELF-AWARENESS to hear they have a problem they need to address and the DESIRE to change and succeed in the new internal sport of your bigger company.

The first thing is to be clear about where your company is now, what’s working and what’s not, where the company is going next, and what new things will be required of all leaders, including the CEO.

Many first-time CEOs admit they aren’t as clear about all of those things with their teams as they should be. This clarity needs to be fixed first and fast.

Next, have continual conversations with your leaders about what needs to evolve and advance in their leadership and their teams.

Many first-time CEOs struggle with this regular and clear conversation with each of their leaders. Especially leaders or cofounders who are friends, relatives, or who made big contributions in the last crisis.

CEOs first need to be self-aware that the first responsibility for the success of their leaders is their own clarity and communication.

But when you have a clear vision, agreed approaches for the changing business, and frank communication, leadership conversations shouldn’t be a surprise to a struggling leader.

Many leaders, including the CEO, are self-aware enough to hear there is a problem and have the desire to change and fix it.

Other leaders can’t hear there is an issue. They are in their own heads or they want to keep running things like they used to last year.

You keep talking about it with them, repeating yourself, and nothing changes.

This happens. Most leaders don’t scale infinitely, from startup scrappers to corporate executives.

Getting through this is a big challenge for all CEOs, but new CEOs tend to be less clear about their communications and take more time to decide and pull the trigger.

It’s better to be decisive about firing senior leaders who are obviously slowing down the company and will not change than to wait another six months.

You’re late already.

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