You’re going to hire the wrong executive

Executive hiring is hard. You’re going to get it wrong. Here’s why.

 1257 words • 6 min read

Congratulations—your startup is scaling, and it’s time to hire that VP of Marketing or VP of Sales to take things to the next level.

Unfortunately, you’re going to get it wrong. Your first executive won’t be the right fit and you’ll have to part ways. This isn’t uncommon—my experience is that >50% of executive hires don’t work out.

There are a variety of reasons why, but here are a few of the common places it goes awry:

They don’t have the necessary experience

Generally, when hiring an executive, you’re either hiring the person who’s done it before and asking them to do it again, or you’re hiring the up-and-comer who hasn’t done it before, but who was the key lieutenant of someone who has (so they saw it happen, even if they weren’t in charge of it themselves).

Sometimes, you can’t get either of those people to engage with you. Your startup is too early, and they want you to call them when it’s actually working. With no other option, you hire the best salesperson you know (a friend of a friend), give her the title of VP Sales, and hope it works out.

Setting aside the danger of giving out the title, this is a risky strategy. The job of running the sales org is very different than the job of being the top sales representative, and you typically end up getting less than a year of good productivity from the person before the company’s needs outgrow them.

They haven’t seen this part of the journey before

Sometimes you hire someone super-seasoned whose resume just blows you away. They ran North America sales at Salesforce for five years! And they want to work for me??

They’re an expert, they’re well-respected, they’re charismatic. Seems perfect, right?

But running sales at a public company is nothing like running sales at an early-stage startup. There’s a huge difference between “I was the person who wrote the playbook that worked” and “The playbook was written by my 3x predecessor. I inherited a playbook that worked, and I optimized it.” Your startup requires the former.

And this isn’t just about public companies. This is true within substages of the startup: getting from $1m to $10m is totally different than $10m to $50m, which is in turn different than $50m to $100m. The things you care about adding at $50m are the exact wrong things to worry about when you’re only at $3m, and vice versa.

You can miss here by going “too seasoned” and you can also miss here by going “not seasoned enough.”

They copy-and-paste their previous playbook

If you hire a veteran marketing leader from a product-led growth company, you’re getting a bunch of expertise on marketing for product-led growth businesses. That’s great if that’s what your business is. But if you’re a sales- or marketing-driven business, what you really need is expertise in paid ads, SDRs, etc.—and your executive, despite being super-smart, will unintentionally lead you astray by recreating the playbook that worked for them previously.

The worst part is: the techniques that worked for them in the past are not only dependent on their business model, they’re even dependent on very specific attributes of the buyer, the sales cycle, the sales amount, and the product.

So it’s very rare that the exact same strategy from somewhere else will happen to work super-well for you.

They don’t actually want to do the work

Startups are a slog. Being an executive at a startup is a slog. Once they’ve put in the blood, sweat, and tears to figure out how to take the company from $10m to $50m, they’re probably pretty burnt out on that phase of the journey, and they’re enjoying reaping the benefit of all the machinery they built to get there.

In some cases, they may think you’re excited to do it again—but in practice, what they actually want to do is to fast-forward to that $50m point. The way this manifests is an aversion to actually getting in the weeds.

If your new executive’s first move at your startup is “I need to hire these three people,” it’s not going to work out. It instead needs to be “I need to get my hands dirty to figure out what’s really going on here.”

You just get unlucky

Sometimes it’s not the executive’s fault at all. Sometimes there’s something wrong with your company: you didn’t really have product-market fit, you’re starting to max out the addressable market in your initial niche, or you just weren’t ready.

Regardless of whose fault it is, when the business is not doing well, you’re much more likely to turn over your executives, either because you want them to leave, or because they bail for something that feels more successful.

Of course, it gets worse…

Normally, when you have an underperforming employee, you’re quick to identify it and correct the issue. If you can’t solve the problem, you gracefully and efficiently part ways, and try again with someone else.

This is much harder with your executives.

When it isn’t working, the root question you need to ask is: is the strategy bad, or is the execution bad? If the strategy is bad—change the strategy. If the execution is bad—well, you probably need to replace the people. (If your sales team’s execution isn’t what it should be, in addition to being your problem, it’s definitely your VP Sales’s problem.)

The first problem is: you’re slow to realize that things aren’t working, because you’re not very close to the machine anymore—you’ve delegated a bunch of work to your executive.

Once you get a whiff of something not working, you doubt yourself, and you’re in denial about it. They know way more about this field than you do, right?. So surely they’re doing this right—or at the very least, they’re doing it better than you could.

The worst part is that you’re blinded by how smart they are. But of course they’re smart! You had a rigorous hiring process. You spent a bunch of time with the candidate, and so did your cofounders. If this person were not smart and charismatic, they never would have passed your process.

I’ve experienced this firsthand on a number of occasions, and this phenomenon isn’t unique to me. Here’s a quote from Larry Ellison in “Softwar,” about an executive he’d hired:

Ellison also had a genuine respect for Walker’s intellect, which blinded him to his other faults. “I like very smart people, and Walker’s very smart. In those days, whenever I was defending somebody, my defense would be to point out how smart they were. Geoff Squire wasn’t impressed by this argument. He said, ‘Yes, Larry, he’s very smart, but can he do his fucking job?’ I just stared at Geoff and said nothing, but I was thinking, ‘Oh, God. He’s right. Brilliance is not enough.’ ”

All of this ultimately causes you to be slower to react when a change needs to be made, to the business’s detriment.

Wrapping it up

Executive hiring is hard. You’re probably going to get it wrong. That’s OK.

The best way to derisk the hire is to avoid the mistakes above. Do they have the right expertise for this size, stage, and shape of company? Do they actually want to do the job? Are you ready for them?

And then once they’re in seat, give them free rein to do what needs to be done—but don’t use it as an excuse to abdicate responsibility. Good luck!