5 Questions to Assess Leadership Readiness for Growth

A company can have a strong strategy, talented people, and real opportunities for growth and still struggle to execute. Usually, the challenge is whether the leadership team is prepared for what’s next. 

According to DDI’s 2025 Global Leadership Forecast, only 20% of CHROs report having leaders ready to step into critical roles. 

Five questions can help identify leadership risk before it impacts performance. 

Does the team match where the organization is headed?

The leaders who built the company aren’t automatically right for its next chapter. A team built for $20M in revenue isn’t necessarily right for $100M. This doesn’t always mean replacing leaders, it means adding capability alongside them.

Are key responsibilities put on one person?

When too much knowledge or authority sits with one executive, the whole organization is exposed if that person leaves. Ask: which roles affect performance the most, and who could step in if that person were gone tomorrow?

Is there a real succession plan for critical roles?

Succession planning must start before someone announces they’re leaving. Naming a possible successor isn’t enough. That person usually needs development and real experience first, so the transition happens on the organization’s timeline, not one forced by circumstance.

Can this team actually lead people through change?

Growth brings change, new systems, structures, and markets. Leading through it takes more than technical skill. In a McKinsey survey of 750+ executives, only 56% said their transformation met most of its goals initially, and just 12% said the gains lasted more than three years. Starting a change can be easy, but sustaining it is difficult.

Is the leadership team built for what’s next, or what came before?

A leader can be highly capable and still be the wrong fit. The skills that drove success in the past, like efficiency, stability, and deep functional expertise, aren’t the skills that drive transformation now. Transformation calls for comfort with ambiguity, cross-functional influence, and the ability to bring people along through disruption. The question is whether the team is equipped for the next stage 

Start Before It’s Urgent 

Leadership planning works best before a critical role becomes vacant. Regular assessments help catch risk early and keep the leadership team aligned with where the business is going. 

The problem is that most leaders skip the assessment step entirely, relying on gut feel instead of data. 

“Over the course of my career, I’ve watched many leaders rely on subjective progress updates rather than examining the underlying realities,” says Tino Mantella, President & Managing Partner of Retained. “The principle ‘what gets measured gets done’ is not a cliché; it’s a discipline. Leaders who consistently benchmark performance gain the insight needed to make precise, in-flight adjustments that keep initiatives on track. Nearly every leader claims to do this, yet many are still caught off guard when targets are missed.” 

Retained helps organizations identify and secure senior leaders who support growth, transformation, and long-term success. If you’re evaluating your leadership needs, contact Retained to start the conversation.