When you should bring in the heavy hitters

heavy hitters

The VCs on your board are up in your shit. It’s been six 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 three-month mark, it turned into introductions and coffees that you didn’t ask for. And now, around six 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 its 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.

Every startup struggles with executive hires.

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.

ask an investor

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 okay. 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 problems that are well understood across the industry, seasoned executive hires should make a big difference in your ability to sleep at night.

Are you okay with decisions being made in your absence?

We all want to say yes to this. It’s a bit of a straw-man. What kind of autocratic monster would say no to this? But take a moment to really think about how this one makes you feel. Sit with the anxiety of someone making a call and telling you about it after the fact. Starting to get twitchy?
Good. Let’s reframe the question…

Are you clear on which decisions can be made in your absence?

If you’re tired, struggling with delegation and honest dialogue, the recruiting process will only magnify those issues.

Very few leaders are comfortable with all decisions being made in their absence. Usually, it starts as a subset of decisions that you want to delegate, and that’s how you hired staff in the first place. The risk for junior roles tends to be low. While your interns might accidentally pull the company offline for a few hours, they are unlikely to tank the business entirely. With senior hires, delegation is a much higher stakes game.

The best way to calm your anxiety around this is to establish a shared understanding of objectives in the first place. We talked about a founder’s vision and clarity. Is that clarity of vision shared throughout the organization? Is it written down somewhere? Are your senior staff operating with the same core assumptions in mind? Do they know which decisions are free and clear and which ones they need to bring you in on?

Can we be honest?

This is a we question. It doesn’t count if only you as the boss are able to be honest. And it doesn’t count if I, as a senior member of your team, are honest with you but you aren’t honest in return. This one has to be bidirectional.

How comfortable are you with the idea of radical candor? Can you commit to mutual respect and ongoing honest dialogue for your senior team? Can you tell your people when you think they’re fucking up? Can you help them get out of their own way?

If you answered yes to all of the above, it’s time to dust off that senior job description again.

You’re in good company

Every startup struggles with executive hires. These folks are leaders from the moment they come in the door. They are the people who will impact your corporate culture on day one, and they set the tone for so much of how your business operates. It’s natural to want to get it right.

Bring senior hires in too early and you risk over-staffing — either with too much process or big solutions that don’t fit the scope of your business. Bring senior hires in too late, and you suffer the difficult-to-quantify opportunity costs of slower growth and strategic missteps.

If you and your board are talking about “upleveling the team” and “bringing in some heavy hitters,” know that the best version can be amazing. There is magic in a well-functioning executive team where people are working together to scale the business.

If you’re tired, struggling with delegation and honest dialogue, the recruiting process will only magnify those issues. The good news is that there’s a fix for the sleepless nights. There are answers to the problems you don’t know how to solve. And there are people who treat direct communication as a non-negotiable, both for themselves and for you.

There are loads of senior folks out there who can’t wait to help. Let them.

This article was syndicated with permission from The Co-Pour


Melissa Nightingale

Melissa Nightingale is a founder and partner at Raw Signal Group. She is co-editor of The Co-pour and co-author of a book about modern leadership (coming fall 2017). Melissa’s been a startup warrior since the first dotcom boom and has the branded t-shirt collection to prove it. She has held senior leadership roles in marketing, pr, and strategy at several fast paced startups, including Wattpad, Edmodo, and Mozilla. Melissa moved to Toronto after more than a decade of working in senior tech roles in Silicon Valley. She is gradually adjusting to seasons.

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