“Founders can be blinded by ambition” shared a CMO from a Series C start-up, “so occasionally you need to ground them with a ‘meanwhile on Reality Ranch’ response.” Marveling at this CMO’s chutzpah, my mind exploded with questions.

Reality Ranch: Grounding Ambitious Founders

The first question is, “Do ambitious founders need to visit Reality Ranch, and if so under what circumstances? Steve Jobs famously used a “reality distortion field” to bend the company, shareholders, and Apple products to his vision. That worked out well for shareholders though it didn’t make Jobs a model boss.

Legendary founder Ted Turner (CNN, Cartoon Network, TBS, TNT, etc.) knew he was on the right track the more “experts” told him he was delusional and a victim of “magical thinking.”

Successful founders are visionary. They have to be. Unfortunately, they are also rare.

The Ambition-Vision Confusion

Your more typical founder easily confuses ambition with vision. They also confuse ambition with leadership. Such was the case for our Reality Ranch-resident CMO. Their CEO had led the company to $50 million in ARR by personally driving product development and being the lead salesperson. They identified a niche, filled an unmet need, raised tons of VC funding, and then hit a wall. No amount of wishful thinking could help them cross the proverbial chasm.

This founder hadn’t built an enduring company. They launched a product.

The Challenge of Unrealistic Requests

Now back to our daring CMO. Was trying to ground this ambitious CEO in reality an effective play? It depends. In this case, it felt right because the CEO had just requested that the CMO increase the inbound pipeline by 30% while cutting the budget by an equal percentage. As I covered in an earlier post, CMOs are not miracle workers. No amount of distorted reality could fill the delta between the upward goal and the downward budget.

I asked former FBI hostage negotiator and bestselling author Chris Voss (Never Split the Difference), how he would respond to such a request from a CEO. His first suggestion was to say, “Do you want me to fail?” This reframes the CEO’s request as a fruitless exercise and connects the CEO with the undesired outcome. Visionary or not, most CEOs do not want their employees to fail.

Reframing for Success

Reframing challenging requests is a skill, that all leaders, especially CMOs need to hone. Voss talks about this at length in his book. He successfully stalled various kidnapper demands for large sums of money in 24 hours by asking, “How am I supposed to do that?” While the CMOs listening to Voss and my conversation admired this response, they didn’t think it would be effective with their CEO.

They imagined that conversation going down like this:

CMO responds to a crazy request from the CEO, with, “How am I supposed to do that?”

The CEO says, “That’s your problem, figure it out, or I’ll find someone who can.”

When times are tough, it can get ugly. Fast.

Finding the right words to move your CEO from an untenable position, isn’t easy. What words have you used to bring a boss back from the brink?

Written by Drew Neisser