A Sales Leader's First 90 Days: Preparing for Day One

By Hope Eyre on May 18, 2017

A few weeks ago, we published a blog for sales leaders embarking on new roles that launched our multi-part exploration of how leaders approach their first 90 days and what we can learn from their experiences. The topic was born from a startling statistic: The average tenure of a Sales VP working in the same role at the same company is incredibly brief – about 18 months.

This is the first of four articles that, together, will tackle what we believe are the top 90-day challenges facing sales leaders taking on a new role:

  1. Cutting down on the initial chaos
  2. Learning your new organization deeply within 30 days
  3. Obtaining early wins to establish momentum
  4. Assessing organizational alignment with Sales and setting longer-term strategy

Seasoned professionals may glance at this list and think, “thanks for pointing out the obvious.”

But here’s the thing.

Sales is a messy business full of messy human beings, each with his own capabilities, expectations, personal goals, learning style, and political agenda.

Understanding them, harnessing their unique power, and avoiding mishaps is no mean feat – regardless of how much experience you have or the size of the operation you assume.

High Stakes

Whether your team makes the company money or not will rest with you. And you’ll get about one fiscal quarter to prove you can do it to management’s expectations. As Michael Watkins points out in his book The First 90 Days, "The first few months is a strong predictor of overall success or failure in the job."1

Our goal is to give you practical tools, not just to avoid mistakes, but to capture more success faster in your first 90 days – perhaps from opportunity that isn’t visible at first glance precisely because there is chaos, because we make assumptions, and because we have to navigate in political and cultural environments that take time to understand and occasionally work against us.

After all, we’ve yet to meet a new Sales VP who told us his/her learning curve was gradual.

Challenge #1: Cutting Down on Transition Chaos

Our focus in this article is Challenge #1 – cutting down on the typical chaos that accompanies a role transition by spending personal time preparing well before your first day – notably by asking in advance for very specific information from your new employer (see our checklist).

The temptation to NOT do this as thoroughly as we’re recommending is overwhelming. You may be burned out from your old role, planning to take a vacation, moving to where your new job is based, or simply enjoying the opportunity to binge-watch Game of Thrones. Who among us wouldn’t?

But there are good reasons for putting in plenty of advanced effort, and they pay off significantly in cutting down on the initial chaos that creates what we call the fog of transition.

Here’s how:

  • It surfaces any risk that’s related to customers, star performers, revenue retention, impending high-value deals, or employee morale and crystalizes the immediate mitigation actions you’ll need to take
  • It accelerates your understanding of sales team composition, structure, and financial performance – the three areas you’ll make tactical decisions about first
  • It allows you to thoughtfully view all you’ve gleaned from interviews and research through the lens of this new information, then deliberately look for gaps that, if not filled, will almost certainly add to the fog of transition
  • You’re able to arrive on day one with a list of specific people or roles you want to interview (beyond your direct reports) and the questions you want to ask
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Six Sales Leader Transition Traps

This isn’t just a case of getting a jump on your first day to garner credibility (though that’s a side benefit).

Advanced preparation can avoid serious mistakes that sales leaders are more vulnerable to making in early days because they don’t know what they don’t know and – being messy humans – are prone to making more assumptions when faced with a steep learning curve.

Michael Watkins refers to these dangerous assumptions as “transition traps.”

In our experience, there are six “transition traps” into which new sales leaders are in danger of falling throughout the course of their first 90 days.

  1. Failing to secure your team because you've made assumptions about team morale, commitment, and job satisfaction
  2. Misjudging sellers or making hiring/firing decisions based on assumptions about the ideal seller capabilities required for their job
  3. Setting expectations that you’ll grow revenue by a specific percentage on a specific deadline without fully understanding, or more likely underestimating, the average sales cycle
  4. Failing to understand expectations for how your sales team should interact with business operations: product development, manufacturing and distribution, solution implementation, customer support, and marketing
  5. Not building the lateral or upper management relationships you'll to need to call on politically to "plow the road“ when your team encounters internal hurdles to closing deals
  6. Over-estimating your team’s capacity to absorb and sustain process changes you intend to implement, particularly those of the “I’ve always done it this way” variety

Let’s look at an example of one Sales VP who found himself in a difficult situation, because he made an eminently reasonable assumption that was entirely incorrect.

The Price of Making Assumptions - A Case Example

George had confidence in his ability to take over sales at his new employer, a maker of backpacks and outdoor-lifestyle luggage. And with good reason. He’s a 29-year veteran of the consumer packaged goods industry.

Two of his first employers were Newell Rubbermaid and The Thompson Company, maker of the WaterSeal brand. Both are well-known for their classical CPG training, and George was fortunate to have benefited from these programs early in his career.

From there he’d gone on to work for companies of varying sizes with varying degrees of formalized process, structure, and sales support. He’d always been successful. This would be his second job in the role of Sales VP, and he was looking forward to it.

Yes, he’d be working in a new category with new retailers in channels he wasn’t experienced with, but he was ready for that. A meticulous planner with a reputation for keeping cool under pressure, George started studying the luggage category and walking stores where his new employer’s products were sold well before his first day.

He used what he learned to ask questions, while still transitioning out of his previous company, to ensure he knew the situation he was walking into. They’d already told him that he would need to evaluate his sales team very quickly and make decisions about their ability to drive revenue. Performance, they felt, could be improved, and it was with this expectation that he’d accepted the job.

The Crucial Pivot Point

Almost immediately, it was clear to George that he’d have to make significant team changes. No problem. He understood the exact qualities that he wanted in high-performing sellers. His years of experience had formed a crystal clear picture. He gave the profile to HR, handled the attrition meetings with the current staff, and started interviewing.

By day 60 George was in the process of onboarding new team members, but there remained some degree of disorder that made him uncomfortable – not because he doubted his ability to get it under control, but because he felt he was missing something in the larger picture of the business.

He was, frankly, still onboarding himself – learning the categories, establishing internal relationships, and absorbing the culture, while simultaneously hiring new team members and constantly travelling to customers. The pace was fast; it was obstructing his vision and he knew it. Still, he persisted, reasoning that if he could just get the new team members on board, things would settle down, and he could step out of the trees to view the forest. Then, he would think about strategy.

The Reveal

Around day 90 the light bulb behind George’s discomfort came on. In hindsight, it was precisely because of his classical training that he made the assumption, and thus his mistake.

In all his years working in consumer products, brand managers made the decisions about what products to sell. They made them based on consumer insights, industry trends, competitor activities, and the needs of their top retailers. It’s typically a highly data-driven process.

Here, it was the sellers themselves who initiated new product designs based on needs and requests from their retailers.

The sellers would then work closely with actual designers to build them – in effect, giving almost every major retailer exclusive products made only for them. If the sellers didn’t develop their own products, they had nothing, or little, to sell.

Digging deeper, George now discovered the full breadth of what his sales team was expected to do: Product design, packaging, setups, costing – even occasionally communicating directly to factories in China. This hadn’t come up during his interviews, likely because the firm was so accustomed to operating this way that it simply hadn’t occurred to them that it was out of the ordinary.

George had hired several new sellers, people with excellent sales capabilities but with no experience in product design. Based on how things were run to-date, he appeared to have hired the wrong people.

90 days into his new position, George realized that he had inadvertently dried-up much of his own product pipeline in some key categories. The all-important back-to-school sales meetings were not that far away.

What was he going to do?

The Recovery

George fell into parts of two different sales leader transition traps:

  • Failing to understand early and fully how sales impacts the operational aspects of the business
  • Making hiring or attrition decisions based on an assumption of the seller capabilities required

“If I could go back in time and do it again, I would have asked them to describe the product development process in detail - from light bulb (concept) to shipping label. Then I would ask how the sales team was involved at every point in this process: What they’re responsible for, where they need to give input, how much actual control is in their hands, what the performance expectations are.”

George managed through his first selling season by relying largely on existing product development processes and the few sales team members operating effectively in the current structure. He then started advocating for a brand manager.

He also took steps to start creating a “core” set of product offerings that would be appropriate for multiple retailers and channels. This would vastly cut down on the unsustainably expensive practice of offering so much exclusivity.

He never dreamed that he’d be setting product strategy. It was not his wheelhouse; yet here he was, and the experience took its toll. “I felt like I couldn't bring anything I’d learned (from previous experience) to the table. It was as if I’d been a football player all my life, and you suddenly put a hockey stick in my hand and said ‘play’.”

What opportunities to drive revenue, increase efficiency, defeat competitors, and improve customer relationships had George missed because he fell into a transition trap that took enormous effort to climb out of? Constant vigilance against making the assumptions associated with these traps is, we believe, the best way to inoculate yourself.

Preparing for Day 1: Our Recommendation

Our recommendation for sales leaders taking on a new team is to onboard yourself by taking very specific steps to gather pragmatic information that the company should easily be able to provide you in advance (if they can’t, that in itself should be a red flag - see our checklist).

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“Leverage the quiet time between roles,” says David Cottingham, Vice President of Sales at RFIdeas. “You think you’ll have time once you start, but you won’t.”

You have three objectives in doing this:

First, identify any financial, customer or employee risk that may need immediate mitigation once you arrive

Second, cut down on the fog of transition by getting to the basics in advance: sales team composition (who’s who), structure (territory/customer segment assignments), and financial performance. Combine this with interview learnings and look for information gaps. Arrive on day one with a plan for who to interview and what questions to ask.

Third, be aware of the six sales leader transition traps and recognize where you’re vulnerable to falling into one.

In our next article of this series, Learn and Take Action for Early Wins, will explore the right information for sales leaders to learn in a short timeframe, then discuss how to use it to identify opportunities for early wins.

Note: While we lean heavily on the concepts of Watkins' book The First 90 Days, this is not a condensed rehash of his work, which we advise everyone to read. It is instead an addendum for sales leaders that address the unique challenges they face taking over the engines of revenue at a new company, division or group.

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Hope Eyre

Written by Hope Eyre

Hope Eyre is a sales effectiveness expert who takes a roll-up-the-sleeves approach to building winning sales organizations. She regularly works side by side with sales teams around account segmentation and planning and has helped numerous complex organizations rethink they way they serve their largest accounts. Hope’s specialties include sales transformation, sales capability development, leadership development/coaching and performance management. If “sticky” could be a word to describe a consultant, it would be a perfect descriptor for Hope, as clients like to keep her around.

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