When you should bring in the heavy hitters - Raw Signal Group

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Photo by Jacob Moseholt.

By Melissa Nightingale

The VCs on your board are up in your shit. It’s been 6 months since they not-so-subtly suggested that you get some more senior talent around the table. At first, it was a gentle discussion about scale and the impact the people who have been there/done that can have on a growing team.

Sometime around the 3 month mark, it turned into introductions and coffees that you didn’t ask for. And now, around 6 months, it’s no longer a suggestion. You can show up to the next board meeting without the role closed but it’s going to be pretty uncomfortable.

“I wouldn’t take this job.”

The line goes quiet.

“Did I lose you?”

“No, no,” he says. “I’m still here. Just thinking.”

The recruiter at the other end of the phone is a friend. He’s asking about a role that we both know I won’t take. Smart recruiters ask for advice, even when they know they aren’t going to make a sale. If the role is a dud, he wants to know what he can do to make it more compelling.

I continue: “I wouldn’t take this role because it’s so clear that the CEO doesn’t want to hire for it. This has all the markings of a board-initiated role. I wouldn’t take it in it’s current form and here’s the kicker, you probably shouldn’t hire anyone who would.”

He sighs. “That’s what I was worried about. Thanks.”

“Good luck,” I say. Trying to end on an up-note.

Minister Without Portfolio

The job description is utter crap. It reads like someone said, “Go hire a senior person” without any thought for why or what that person will do once hired. This is nothing new as I’ve spent a career reading through poorly thought out roles — both for my own hires and for others. But this one is particularly crappy.

The title is C-level and while it will look impressive on a business card, the title and the responsibilities don’t line up. When I dig into the parts about what this person will do, the impact they’ll have, and how the company will measure success, it’s pretty hollow.

Startups and scale-ups have notoriously light job descriptions and senior roles are no exception. But there are some clear markers that a role is bullshit. Truly senior people can spot these markers a mile away, regardless of what the job title says.

This is one of those roles. It’s an unwinnable position. While the company may convince someone to take it for a compelling title and salary, the odds of them closing anyone good are low.

Letting Go of Your Baby

In the earliest days of starting up, you and your co-founder made all the decisions. You didn’t need a framework for other senior people. You were the most senior members of the team and all of the highest level decision-making belonged to you.

Now you’re like a first time parent trying to drop off your baby at daycare. You come with a laundry list of instructions about how to do the job. You recognize that these people are full time experts on kids. But you are the world’s foremost authority on your kid.

This should be a natural union. Except…

You are optimizing for the individual.

They are optimizing for the collective.

You are optimizing for rightness.

They are optimizing for scale.

You don’t want to be prescriptive, per se. You have learned that prescriptive is code for micro-manager and you are certain you don’t want to be that. It’s not that you don’t feel the crunch of trying to do everything yourself and falling short on all areas. You most certainly do.

It’s just that you know an awful lot about the business, having built it from the ground up. You have a clear vision of what you’re trying to build going forward. You want people who can extend your capabilities in service of that vision.

The problem is that most senior hires are motivated by an opportunity to have real and lasting impact. If you are not looking for people to modify, stretch, or alter your vision, you might want to rethink that senior role. Even if you are able to close someone, it’s unlikely they’ll stick around for long.

Bring in the Professionals

You shouldn’t get strong-armed into hiring a very senior team before you’re ready. It’s bad for you as the founder and it burns the senior hires you may want to work with eventually. To top it off, the recruiting process is already lengthy and expensive.

So when should a founder look to up-level their team? Here are three questions that will help you know when it’s time to invest in seasoned/senior talent:

Are you tired?

It’s ok. We’re all tired. The question you want to ask yourself is: Are you tired because you’re up all night solving problems that other people have already solved?

In the early days, founder roles let you do a little bit of everything. That can be fun but can also start to feel like a massive weight. You don’t need to have all the answers. If you’re hung up on...