Leadership pitfalls

Can Your Executives Grow with Your Company?

Editor’s Note: This article was first published on Inc. here.

As you build your startup, one of the most difficult choices you have to make is about your existing executives. Can they scale with the company or is it the right time to bring in people with more experience to lead?

The problem is that many people who join startups in the early stage like the dynamics of that stage. They like getting involved in everything and they like problems that they can solve. Themselves. Right away. Those are wonderful qualities for executives early on. Over time they turn out to be bugs, not features.

Here are five questions to ask yourself to identify if an executive is oriented towards scale.

1. Does She Tend to Fix Things “Right Here and Now” or Does She Step Back to Look at the System?

A bias for action is a good trait, especially in a startup. In the early days when an executive is managing three or five people, she often can and should take care of things herself. The problem is that when she needs to manage a team of, say, 30, doing things herself is simply not sustainable. Even more importantly, if she is doing things herself or asking her team to do immediate one-off fixes, you can safely assume that she is not thinking enough about process or efficiency.

2. Has He Demonstrated an Ability to Handle and Simplify Complexity?

Alongside scale comes new products, new customers and competing priorities. Having more people means more communication to make sure everyone is on the same page. All of this adds more complexity. Leaders who can simplify tend to be the ones who know how to pause. They are leaders who ask, “What is the one thing we can implement that will solve 10 things at once?” They also know that over-communication is the only way to get their message out to their team so they stay aligned.

3. Does She Create and Maintain an Excellent External Network?

An executive’s lifeblood is his network. Having a strong network of contacts inside and outside of his domain area helps him get answers quickly, think through best practices and hire great people. If your leader has a great network and added to it over the years, that’s a strong marker that he is also growing and learning.

4. How Is He as a Boss?

An executive who can scale must be someone who can manage other managers. This requires many micro skills. Can he identify and then hire good managers who can lead processes and people? Does he then delegate, empower and hold them accountable? Is his leadership style more asking questions rather than telling people what to do? Can he communicate a consistent, clear, big picture message? If he has demonstrated these skills or looks like he can, he likely has the capacity to scale.

5. Is She a Great Role Model?

As your company gets bigger and you elevate your executives, they get more and more attention. They are on display. What do your employees see when they watch this leader? If they see a strong cultural steward, a competent and mature professional, someone approachable, someone who owns her mistakes, then you have an executive who seems ready to scale.

Executive Coach

Alisa Cohn is an Executive Coach who works with startup executives to help them develop the leadership skills they need to scale their companies successfully. She has worked with companies from very early stage to Fortune 50. Her clients include Venmo, Foursquare, Facebook, Google, Cisco and Dell. She is based in New York City.
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