The Question I Regret Not Asking Every CSM Candidate

I’m a big fan of Ben Horowitz’s no bullshit, “call it as it is” attitude and mentality of building, scaling, and investing in software companies.

In particular, there’s a section of Ben Horowitz’s book, The Hard Thing About Hard Things (and corresponding blog post, and youtube video) that talks about peacetime and wartime in startups. In particular, peacetime and wartime CEOs, and how leadership styles must adapt to each condition when the market demands. Ben gives a great definition of the two:

Peacetime in business means those times when a company has a large advantage vs. the competition in its core market, and its market is growing. In times of peace, the company can focus on expanding the market and reinforcing the company’s strengths.

In wartime, a company is fending off an imminent existential threat. Such a threat can come from a wide range of sources including competition, dramatic macro economic change, market change, supply chain change, and so forth. The great wartime CEO Andy Grove marvelously describes the forces that can take a company from peacetime to wartime in his book Only The Paranoid Survive.

I often reference customer success managers as being CEOs of their own business. Businesses being… their set of customers for which they’re responsible. And, being a CEO means you must flip on peacetime and wartime CEO.

Wartime when there’s an active Risk Mitigation play in the works. When the champion leaves, when the project stalls, when the adoption is low. Most CSMs are able to turn on Wartime with ease. They jump into escalation calls, assume authority, and ensure we’re making progress against defined deliverables. This makes sense. It’s where CS was born, out of a reactionary muscle of responding back to customer needs, requests, issues.

But only the best CSMs can flip into Peacetime when the escalation is resolved. Instead of naturally gravitating to the next fire (the next war with the next highest value customer), the best CSMs are the ones that lean into success. They’re able to strategically plan for the future. They’re whitespace mapping the next use-case, doing a deep dive on the latest feature, and continuously ensuring we have not one, not two, but double digit key champions within an account for relationship redundancy.

The ability for a CSM to flip from wartime to peacetime is a true test of a proactive CSM. It’s an area I hadn’t tested, despite 5+ years of looking for excellent Customer Succes talent. It’s one I missed.

And a question, if I were starting from scratch, that I’d be asking 100% of my CSM potentials.

“Suppose you have a customer at a 65 health score. They have active usage. They’re engaged with support (3 tickets per week). They just renewed last week. Tell me your plan for how you’d collaborate with this customer”

This aides in my understanding of this CSM’s ability to put on their Peacetime CEO hat and focus on building additional relationships, discovering additional valuable use-cases, and increasing the current maturity of use.

Because at the end of the day, it’s the CSM that can engage customers proactively as a Peacetime CEO who will wage less wars.