8 Signs a New VP Won’t Work Out. And 3 Things Not to Worry So Much About.

Hiring a VP that doesn’t work out is tough. As hard as it is to really find even 1 great VP candidate you believe in … when in doubt, slow it down.

Because you how what’s even tougher? Keeping him or her on for more than a few months when it just isn’t going to work. Because the damage compounds. 

You fall further and further behind on the plan. You hire a bunch of folks that don’t perform. Morale suffers. Everyone gets a bit lost. So if you do make a mis-hire — and everyone does — at least course-correct quickly. Move him or her out within 90 days if you can (or if possible, move them into an IC role instead if you can). 

And remember, it’s your fault if they don’t work out. Most VPs with some success on their LinkedIn likely would thrive somewhere else (different stage, different product, different structure, etc). Just not at your company.

So let me outline the aspects of managers that in my experience has 95% of the time lead to them leaving/quitting/ washing out in 3–9 months. 

Some crystal-clear signs you made a senior mis-hire:

• Too defensive re: their poor performers. A great manager is highly aware and transparent re: who on their team is the best, mid-pack, and not performing. If they are too defensive about their non-performers, that’s a sign of a manager that can neither deliver nor scale. It’s OK if a VP stands behind a team member that isn’t performing for a cycle or two. That’s her call. But defending someone that can never meet plan is a sign of a VP that doesn’t know how to hire great people.
• Can’t meet deadlines. This may be OK in junior employees I guess. But never in a manager.  
• Won’t commit to a number. A number of leads. A revenue number. A number of story points. A number of hires. An NPS goal or a net retention goal. Mediocre VPs will often sort of acknowledge a goal … but they claim they can’t meet it due to not enough money, hires, features, etc. Yes, there never is enough. It may be a reason to debate the number. But that’s not a reason to not own a number. 
• Doesn’t understand the mission. This may be your fault as CEO, but if any leaders don’t get the mission you are on (or really anyone), it won’t work out. You can’t have VPs on a different mission than you.  
• Doesn’t want to grow. Anyone that doesn’t want to add new skills won’t work out in a startup < 200 employees or so. A VP of Sales that has only done inbound? Well, if she’s strong, she’ll want to learn to add outbound. Or build a field team. Or add an SMB team.  
• Too threatened by new VPs and leaders. This makes perfect sense in BigCos and with junior hires, but in start-ups, if a VP/Director/Manager is too threatened by a new hire / new role, something isn’t going to work out here. It’s OK for an AE to be a bit worried when you hire her boss, your first VP of Sales. It’s not OK for your head of marketing to be threatened by your new head of sales.  
• A “player”. If they talk too much about how amazing it was to work at DropBox, how terrific Stewart Butterfield was to work for … well that’s great. But that’s a derivative effect. Not the game itself.
• Can’t hire anyone great in first 30–60 days. All great managers can. Generally, they have 2-5 folks they want to bring on before they start. 
• Lack of 100% ownership and too many excuses. You already know this. If they don’t own something in their area, really, they own nothing.

When you see this behavior in your managers/directors/VPs, at least plan on the fact you’ll need to hire a replacement in a single-digit number of months.

Now the flip side is, some “negative” characteristics actually can be an asset in a start-up, up to a point. Here’s my list of things not to see as flags, more as areas you can help and backfill on as they grow, especially with stretch VPs:

• Frustrated with other leaders not delivering: Maybe OK. This just comes with ownership. If your VP of Sales is frustrated that your Head of Marketing won’t own an Opportunity Commit, that’s understandable. It’s your job as CEO to fix this, somehow. As you upgrade the team, this should fade a bit.
• Can only hire folks that are a junior version of themselves: Maybe OK at First. Yes, this is a sign of a new / green manager. But you can help them open their eyes to a more diverse set of backgrounds, experiences and hires. You need to start ASAP and early, though. By hire #3-#4 or so.  
• Mainly doing / focused on what they are good at. If you are a first-time VP of something, you won’t be great at everything. No one is. It’s OK if your stretch VP mainly focuses on the areas she’s great at … as long as she also takes accountability of the areas she is weak at. They will grow, and you are getting leverage here. Find a way to help backfill their weaknesses.

Now, these are things to quickly watch for after the hire. 

What are a few related tips to make sure you don’t make a mis-hire for a VP role in the first place?

• #1: Ask who she will bring with her. Review their LinkedIns and talk to their potential hires. This is especially important with a VP of Sales candidate, but should be true for any true VP. All true VPs know recruiting is job #1. So even if they are a stretch VP, they’ll have at least a handful of candidates ready to join them. Ask. Ask who they are. Ask why. And talk to at least 1 or 2. If the candidate doesn’t have any, or any good ones, to bring with him … that’s not a VP. More here.
• #2: Do a 60 Day Plan With Every VP Candidate as a Penultimate Step at Least. 60 day plans are wonderful vehicles to see if you are aligned and on the same page. Yes, they are work. So if you want, maybe don’t make the candidate do it for a screening meeting. But I find it great as a penultimate step, to make sure it’s a good fit for both sides. Before they sign the offer letter, have them put together a First 60 Days Plan and present to your entire senior team. That will not only highlight gaps, but make sure everyone is close enough to being on the same page to win together.   More here.
• #3: Don’t Hire a VP You Don’t Believe In. Just because your board loves her, the team thinks he’s great, etc. It’s hard enough to be a VP in a startup. If the CEO doesn’t believe in you — it’s basically impossible. So if your gut says don’t hire Mr. Perfect — don’t make that hire. More here.