Mistakes to Avoid When Hiring a Seasoned Executive at Your ScaleUp

How do you limit the risks in this and hire the best person to help you scale?

learn more about Jena Booher, Ph.D.

By Jena Booher, Ph.D.

Opinions expressed by Entrepreneur contributors are their own.

You're a first-time founder and you've never run a company before. You've already raised significant capital, and it's becoming clear to your board that your current leadership — who gave their blood, sweat, and tears to get you to this point — aren't the same people who will take your company to scale. You need to find a few executives who have done this before. Extensive experience is table stakes, but how will you know someone is right for your company outside of their track record?

Of course, there are considerable risks. Choosing the wrong executive will be a waste of time, money and opportunity cost if they're unable to move the business forward in a meaningful way. Plus, you'll let down your most loyal employees who are already disappointed that you're putting someone above them. To complicate matters further, time is working against you. You're in the ScaleUp phase, which requires a new level of speed and precision. How do you limit the risk in this decision and hire the best person to help you scale?

As a business psychologist and advisor to many high-growth companies, I've seen CEOs make great hires — and costly mistakes. These are my recommendations for what to look for during the interview process:

1. Look for adaptability and willingness to think outside of their playbook

A seasoned executive should never rest on their laurels. Sure, they should be able to identify the ways they drove success in previous roles. For example, a Chief Revenue Officer should explain a specific methodology that enabled their sales team to surpass revenue targets. A Chief Product Officer should detail the philosophy that helped them move from delivering one product to multi-products. But this is just the tip of the iceberg.

Beware of candidates who say their playbook is "bulletproof" or "can be deployed at any organization." Instead, look for answers like, "While this process or framework was successful in the past, it might not be the best approach at your company. I need to understand the ins and outs of your business before I start making wide-scale changes."

I once worked with two CROs at different SaaS companies. One came in brimming with confidence, telling the CEO and his new executive peers that his sales methodology is tried-and-true and can be adopted by any B2B vertical SaaS organization. This CRO failed to identify the pitfalls of adapting his playbook at the new company and was terminated within one year.

The other CRO had over 25 years of experience and a sales process he believed in. He tried to implement the framework in the first three months, but realized it wasn't working. He spent the next six months learning the business and what differentiated it from any other company. This allowed him to create a new, distinct process that was right for the organization. Ultimately, his approach helped them reach scale.

Related: Hiring A CEO? Use These 5 Methods to Find A Leader You Can Trust

2. Look for vision and energy in addition to experience

Moving from a startup to ScaleUp is one of the hardest transitions high-growth companies have to make. It's imperative that new executives have the energy it takes to face the challenges coming their way.

But it's not just about stamina. They also need vision. The most successful executives aren't just functional leaders — they're business leaders. Experience and process are minimum requirements for ScaleUp executives. If the candidate has been through the scaling stage before, that's a good start. I've seen CEOs hire executives that spent 15-20 years at 50,000-person organizations, only to regret it. Sometimes these leaders work out, but many times, they don't. Companies like Oracle or Salesforce are considered stabilized businesses that moved through the ScaleUp phase a long time ago. Don't let recognizability be a red herring.

Related: The 4 Biggest Mistakes New Executives Make

3. Identify where their playbook is at odds with your culture

Sometimes an executive's method contrasts with your company's current climate, but that doesn't mean it's wrong for you. It just means you need to be smart about the implementation.

For example, I worked with a Chief Product Officer who subscribed to agile product management and building empowered product teams. He assured everyone that his philosophy was going to take the company to the next level. The founders agreed, but didn't factor in the ways that this methodology was radically different from their existing process. If they had recognized the fundamental differences sooner, they could have sped up the implementation of the new executive's better process. This cost them time and money.

It's easy to put off executive hiring decisions and promote from within. But you know by now that taking the easy road doesn't always drive success. Yes, you're new at this. However, that can be a strength in its own right. Take these strategies into the executive hiring process, and you'll be one step closer to finding the leader you need to scale your business.

Related: 9 Mistakes to Avoid When Hiring a Developer for a Product Team

Jena Booher, Ph.D.

Entrepreneur Leadership Network Contributor

Startup Advisor

Dr. Booher is a startup to ScaleUp expert, business psychologist, social scientist, and trusted advisor to startups across the country. Her mission is to help high-growth businesses transform their culture, build engaged teams, and chart the path for sustained success.

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