The myth of the “playbook” in executive hiring, and how to work around it

I help mentor CEOs on executive hiring all the time. One common refrain I hear when we’re talking about requirements for the job is about something I like to call The Mythical Playbook. If I only had the exec with the right playbook, thinks the hiring CEO, all my problems in that executive’s area would be magically solved.

I once hired a senior executive with that same mentality. They had the pedigree. They had taken a similar SaaS company in an adjacent space from $50mm to $250mm in revenue in a sub-group within their functional area. They had killer references who said they were ready to graduate to the C-level job. They had The Playbook! 

Suffice to say, things did not go as planned. I ignored an early sign of trouble, at my own peril. The exec came to me with a new org chart for the department, one with 45 people on it instead of the 20-25 who were currently there. I believed the department was understaffed but was surprised to see the magnitude of the ask. When I pushed back in general, the response I got was “I plan to overspend and overdeliver.” Hmm, ok. I don’t mind that, although a more detailed plan might be useful.  

Then I pushed back on a specific hire, pointing to a box in the org chart with a title that didn’t make sense to me. The response I got was “Yeah, I’m not entirely sure what that person does either, but I know I need that, trust me.” Yikes. 

There are two reasons why The Playbook is mythical. 

The first reason there’s no such thing as a Playbook for executives is that every situation is different. No two companies are identical in terms of offering or culture or structure. Even within the same industry, no two competitive landscapes are the same at different points in time. If life as a senior executive were as simple as following a Playbook, people would make a zillion dollars off publishing Playbooks, and senior executive jobs would be easier to do, and no one would get fired from them.

Now, I’m not saying there isn’t value in analogous experience. There is! But when hiring an executive, you’re not solely looking for someone who claims to know all the answers based on previous experience. That is a recipe for blindly following a pattern that might or might not exist. The value in the analogous experience is in knowing what things worked, sure, but more importantly in knowing when they worked, why they worked, under what conditions they worked, what alternatives were considered, and what things fell apart on the road to success. A Playbook is only useful if it can be applied thoughtfully and flexibly to new situations.

The second reason there’s no such thing as a Playbook when it comes to hiring executives is that the person who might have written the Playbook is actually not available for your job. Most CEOs start a search by saying, “I want to hire the person who took XYZ Famous Company from where I am today to 10x where I am today.” The problem with that is simple. That person is no longer available to you. They have made a ton of money, and they have moved beyond your job in their career progression. What you want is the person who worked for that person, or even one more layer down…or the person who that person WAS before they took the job at XYZ Famous Company. Those people are much harder to find. And when you find them, they don’t have the Playbook. They may have seen a couple chapters of it, but that’s about all.

In the end, the department I referenced above was more successful, but not because of adherence to the new exec’s entire Playbook. The Playbook got the department out over its skis – we overspent, but we did not overdeliver. The new exec ended up leaving the company before they could implement a lot, and that person’s successor ended up refocusing and rightsizing the department. That said, the best thing the department got out of the exec with the Playbook was their successor, which was huge — one element of a strong exec’s Playbook is how to build a machine as opposed to just playing whack-a-mole and solving problems haphazardly.

(Note – I am using the singular they in this and in other posts now, as Brad. Mahendra, and I chose to do in Startup Boards. I don’t love it, but it seems to be becoming the standard for gender neutral writing, plus it helps mask identities as well when I write posts like this.)