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The Intricacies of Bringing in External Leadership

If your sales organization is growing fast, you’ll reach a point where the need for leadership surpasses the amount of in-house people who can actually fill those roles. When this happens, you’ll need to look externally for the best managers. 

Don’t just hire, prepare 

There’s a lot more to this process than simply hiring the best person for the job. You also have to set expectations with your existing team and be upfront about how you’re looking to fill the role externally. Sales teams can be tribal. If you catch them by surprise with a new manager, they’ll resent them, making the ramp period much tougher for everyone. 

There are two main reasons to bring in outside knowledge and experience:

  1. You want to inject new ideas and expertise into the company because your sales team has been resting on its laurels. It’s time to move to the next level.
  2. Your company is growing faster than the available talent can accommodate

Before you start interviewing, explain to your reps why you’re looking externally and help them understand the rationale behind your decision. Your company might be going through a hiring blitz at the moment, making it a good time to bring in more managers. Or perhaps you have a team of super senior people that need more support than can be provided in-house. 

This is a delicate moment. You need to hire someone, but your team is not happy about how you’re doing it. They probably think it should be one of them. You must manage through this and get everyone over this hump. 

Know what you’re looking for

Next, create an ideal hiring scorecard or profile. Hone in on what management at THIS company looks like today. Your objectives will look different if you’re an early stage startup or a later stage company. Identify what’s unique about your sales process and team. Look for these traits when you meet with candidates. 

For example, you might work in a high velocity, high process organization selling to inbound leads. Your team is very transactionally with big pipelines and a machine-oriented sales process. In this case, you want someone who has the operational chops and experience for this type of environment. 

Don’t bring in someone who’s used to managing reps that each have 1 or 2 big deals a year. The same goes for the inverse. If you have a team of senior sellers who close $200K deals a couple times a year, don’t bring in someone with only transactional experience. The role won’t be a fit for the new hire, the reps, or the company goals.

Address the cultural tax

Hiring externally will trigger an “immune response.” Just like with our bodies, if you’re healthy, you’ll have a strong immune response to something new entering your body. The stronger the sales team, the stronger their rejection. 

I call this the cultural tax. It’s what you pay to your team when you don’t promote from within. That’s why it's important to put a lot of thought into hiring right. A mishire can lead to your best sellers feeling slighted and leaving the business.

As the VP of Sales, your role is to manage this immune response across the team including reps, managers, and even across departments. I was once brought into the company to be a true sales leader and move the focus away from just customer success. There was an aversion to how I started doing things. Fortunately, my boss did a good job of shielding me from the initial growing pains. Here’s how.

5 steps for a smooth transition

  1. Point blank, call the issue out 

This new manager will do things differently. Tell your reps that you need their buy-in during the ramping process that will likely take 6 months. Ask them to do everything they can to help your new manager be successful over this time. After that, if the manager still doesn’t fit, then you won’t keep them on. 

Additionally, if the manager is going to take over work from someone else, you really need to get that other person onboard early in the process. Otherwise, they may just dump a ton of work on the new person without any guidance or, conversely, they won’t want to give up their legos to someone new.

  1. Prepare the manager for the cultural implications 

This is especially important if the new manager will be responsible for reps who had also interviewed for this job. They aren’t going to be happy. The best thing a manager did for me, when I was a new manager, was to prepare me with this information so I knew I was walking into a minefield. 

  1. Ask externally hired managers to lean into their strengths

In today’s modern sales world, every company has different strategies and processes. If a new manager goes from healthcare to fintech, it’s going to take them some time to adjust. 

New managers are set up for failure if they try to become experts in the business too fast. Reign them in. If they came from a process driven environment, have them focus on processes, rather than closing deals. 

This builds the manager's confidence, plus it shows reps that the manager can add value immediately.  You don’t want to put them in a position to publicly embarrass themselves when they get something wrong early on. 

  1. Set up a 30/60/90 ramp plan and set expectations

Call out the specifics of what you want to see while the new hire ramps up. As an example, you may want them to be able to close a deal by the end of month 1. They should be able to put together a QBR for their team by month 2. They need to be able to contribute in leadership meetings by month 3. Be really specific about it. 

Give your new hire a codified and documented ramp program. I don’t recommend that the VP of Sales is involved in ramping. Instead, tell the new manager that they need to go learn specific things listed in a syllabus, like speaking with 3 people from marketing about your demand generation engine.

→ Click here for a 30/60/90 ramp plan template for a Director of Sales ←

  1. You alone will decide if a new manager is working out or not

Don’t rely too heavily on feedback from your reps. 9 out of 10 times their immune response will judge the new leader too soon. Plus, your expectations for this new hire will be different from your rep’s expectations. Externally hired managers are under more scrutiny because of the cultural tax. 

Until the manager is culturally embedded and all set, they’ll probably get the cold shoulder from people. Trust me, I’ve been there, and it kinda sucks. So try and recognize what this will feel like for the new manager. Personally, I go to lunch with my new leaders every day until they have a close enough relationship with someone else who they can have lunch with. Once this happens, I take a step back. 

Start on the right foot when hiring externally

Preparing your reps for upcoming changes is crucial, especially if they’re eying the new manager role as a chance at an internal promotion. You may choose an external candidate, but it doesn't mean that you don’t value their work or want them to move up in their career in the future. By also preparing your new manager for any cultural taxes, you’ll ensure a smooth transition as you grow your team and reach new heights.

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