Sales Leader's First 90 Days: Dig Deep to Determine Longer-Term Strategy (Post 3 of 4)

By Hope Eyre on Sep 25, 2017

9 Minute Estimated Read Time


This is a continuation our multi-part exploration of how sales leaders approach their first 90 days in a new role at either a new company or with a new sales team at their current company. 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 – only about 18 months.

So many of our clients have found themselves in new positions, after a relatively short tenure in their previous roles, that we wondered what we could learn from their experiences.

Article 3 of 4

In Article 1, we tackled onboarding yourself with your new company to prepare for day 1. Article 2 offers concrete steps for balancing the need for learning with the need to take the quick actions required to achieve early wins – what we call our “Secure & Get Right” method.

In this article, we’ll show you how to dig deep into the sales organization so you can systematically surface the knowledge you need to determine longer-term strategy. We’ll also use our discovery process to understand the all-important political and cultural landscape. Finally, we’ll begin building relationships with key influencers whom you will, sooner or later, have to rely on to ensure your team’s success.

SO FAR: You Should Have Accomplished…

By day 30, you have ideally onboarded yourself and learned your new organization well enough to take whatever decisive action is needed to net you the early wins so critical to establishing your credibility.

Depending on the sales situation you’ve inherited (start-up, turnaround, growth mode, etc.), you should also have:

  • Confirmed your management’s business priorities
  • Secured your team by guarding against the loss of high performers
  • Secured any at-risk customers from defecting to competitors
  • Taken initial steps to get your organizational structure and financials right, at least for the short term

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BOLO: Transition Traps #s 3 – 5

In days 30-60, Be On the LOokout specifically for transition traps 3 – 5:

  1. 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
  2. Failing to understand expectations for how your sales team should interact with business operations, including product development, manufacturing and distribution, solution implementation, customer support, and marketing
  3. 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

The other transition traps are important or course, but you’re more likely to encounter these three in your second month on the job.

It’s Time to Dig Deep

If you’ve read Articles 1 and 2, you are by now inured to our constant drumbeat of gathering information and learning. But so far we’ve advocated obtaining specific information at a semi-shallow level of detail because your first 30 days also demand decisive action, and there are only so many hours in a day.

But it’s now time to dig deep. You’re going to need to set a longer-term strategy as well as assess which aspects of your business may be out of alignment with each other or with the rest of the company, or with management’s priorities. You must also grasp the political and cultural aspects of your organization – ignore them at your peril.

Do Your Own Discovery

To do all this requires an extensive discovery effort. This isn’t the type of activity you can do from your office. The reports, presentations and other documents you’ve gathered so far are fine. And certainly you’ve learned from your initial interviews with your team.

But the type of information you need in order to fully understand your sales organization comes only from asking questions. A lot of them. You may, depending on the span of your responsibilities, need to delegate some of this effort. We, however, are big believers in having sales leaders roll up their sleeves and do as much discovery as possible for themselves.

First and foremost, you can’t learn the political or cultural landscape if you delegate discovery to others. You’ll hear nuances and patterns of knowledge that will help you distinguish between what’s important and what’s nice to know. And you’ll continually refine your facts, so you can consciously test whether you’ve reached truth or whether you’re inadvertently making decisions based on erroneous assumptions.

The Payoff is Political

But there’s another reason to do your own discovery.

You’ll get an excellent payoff in visibility with peers and upper management, which is crucial to succeeding in your first 90 days. As a sales leader you’ll be under a microscope, and in the absence of personal access to you, people will simply fill in the gaps with what they hear from others. Take this opportunity to control your own first impression.

That, however, pales in comparison to the credibility you’ll gain with the people you manage. And please, drive your discovery effort well beyond your direct reports. If this takes townhall style meetings and a month of travel, do it. You have a short window to use your relative ignorance for political advantage. Do not waste it. You will never be the new guy again.

You NEXT 30 Days Objectives

These, then, are your objectives for the next 30 days – the period between day 30 and day 60:

  1. Dig deep into your sale organization so you can determine longer-term strategy
  2. Actively look for instances of misalignment between the different aspects of your sales organization, and note them for later remedy (we’ll show you how)
  3. Identify those influencers who will be needed to ensure your team’s future success and begin building relationships with them
  4. Use your discovery efforts to political advantage with peers and upper management and to establish credibility with your team

And by all means, please re-clarify your management’s priorities and expectations to ensure they haven’t changed in the last 30 days.

Conducting Discovery: Our Recommended Question Bank

We’ve built our First 90 Days Question Bank with a deliberate eye toward developing longer-term strategy and fixing alignment issues. Therefore our discovery questions fall into one of four buckets:

  • Strategy & Structure
  • Process & Technology
  • Enablement & People
  • Management & Coaching

These cover all your sales bases, metaphorically speaking.

Keep in mind there are aspects of these areas that are best gleaned from reports (territory coverage, manager span of control, win/loss ratio, pipeline metrics, seller book-of-business assignments, compensation structures, etc.).

We focus our question bank on knowledge that cannot be gleaned from reports but rather requires human interaction. In our next article on determining longer-term strategy, we’ll talk about how to organize knowledge from both sources to ensure you’re seeing the big picture.

 Deep Discovery Question Bank

 Strategy & Structure

 Process & Tools

  • Describe our relationship with customers. Do they see us as strategic partners? Do they consult with us on their business issues? Or do they see us as a vendor who provides a product or service?
  • What's the biggest challenge facing the sales organization today? What is the cause? Is there anything preventing us from addressing it?
  • What's the biggest opportunity we have as a sales organization that we aren't exploiting today. What's it worth to us? What's preventing us from pursuing this opportunity
  • When we win a deal, why do we win? What do customers say about why they selected us? What differentiates us from our competitors?
  • When we lose a deal, why do we lose? What do customers say about why they did not select us (other than price)?
  • Have we optimized sales coverage against prioritized markets and customers? Do we have the right resources by market segment and across the customer lifecycle
  • If you were me, what would you focus on first?
  • How standard is our sales process? Is it custom to our group or is it standard across the company? Is this the right process for how our customers like to be sold to?
  • How disciplined are the sales team and front-line managers at executing the sales process consistently?
  • What tools does the sales team have to help it win (account or territory plans, win plans, deal qualification checklists, sales collateral, presentations, etc.).
  • What additional tools does the sale team need to be effective?
  • What supporting groups (marketing, sales operations, pricing, insights group, pursuit management, product management, subject matter experts) provide the most critical support to deals. Why is their support important? How well do we collaborate with them and use what they provide?
  • What is our CRM system? How disciplined are we at using it to manage the business.

 People & Enablement

 Management & Coaching

  • How clear are the roles and responsibilities of every member of the sales organization? How effectively do the different roles coordinate to win?
  • Does the sales team have the right skills to win effectively against our competitors? What skills need to be improved or enhanced and why?
  • How well do we articulate the business value of our offerings to customers? How well do we use data and insights to show that value?
  • Who are the best sellers in the organization? What do they do differently from everyone else that makes themselves successful?
  • What additional support does the sales team need to win deals? Is there anything they should STOP doing, START doing or CONTINUE doing better?
  • Tell me about the best day you ever had in your position. Tell me about the worst.
  • Do we have clear performance metrics (leading and lagging), and does the team know what they are and how their actions affect them?
  • Does the sales team know how the sales organization is performing at any given time?
  • Are we pursuing the right mix of new customer acquisition and current customer expansion to maximize revenue or strategic advantage?
  • Do front-line managers have a consistent cadence with their team to ensure they’re effectively managing their business?
  • Do front-line managers have a consistent coaching cadence with individual team members to drive performance and personal development?


Our suggestion: Choose your questions, determine who you want to interview and combine your findings with the hard data from reports so you can clearly see where you have gaps (such as skills gaps) or alignment issues (such as a compensation structure with incentives that conflict with the behavior expected by management).


Spotting Gaps and Alignment Issues – A Case Study

Candice Sherman ran into exactly these issues when her employer, communications and cloud services company Unify, was acquired by Atos, an €11.7B behemoth 10 times its size based in Bezons, France.

Suddenly under new management and engulfed in a very different culture, Candice found herself alone with little direction from the new company other than to instruct her sales team to keep selling their current line, but also start selling a “new bag” that included cyber security, big data and consulting service – areas where her team had little expertise.

Difficulty Gathering Knowledge and Building Needed Relationships

Candice wanted to make a plan for understanding the new company and getting aligned with management expectations and her peers on the Atos side, but the opportunities turned out to be limited.

It seemed she was going to be in the position of keeping morale and her team together without much support, at least in the short-term.

Absent clear guidance, she developed a vision for her team but struggled to find an audience for it. “It wasn’t that they didn’t care, they just had bigger fish to fry;” certainly a common situation for companies in the throes of a post-merger integration.

In the Absence of Clear Direction, Rely on Yourself

So Candice decided to execute an “I’ll do this until someone tells me to stop” management strategy. There was no budget to bring her team together to relay the vision, so she put it in motion virtually with “lunch and learns” (on the new bag) and frequent cadence calls to stay close to her team to ensure they felt supported.

She also spent time evaluating her seller’s skills to understand who would be successful selling the new bag and who might need additional help. Constant communication, she felt, was the key ingredient in her ability to keep the entire team together with almost no attrition for a full year after the acquisition.

Misalignment Surprise

The misalignment surprise hit when Candice realized her team’s updated compensation structure didn’t actually support a new directive from management to achieve quicker growth in recognized revenue, which was now far more emphasized a critical KPI. Sellers were getting paid when the sale was made, but no one had any incentive to drive the pace of product or services delivery so revenue could be recognized faster.

As in most companies, there tended to be a lag between the sale, or contract agreement, and when revenue could be recognized by the company from an accounting standpoint. This situation was exacerbated by the fact that Unify’s products and services tended to have an even longer revenue recognition cycle than Atos’s core services.

The situation was frustrating, but there was no point in getting ruffled. Candice brought the misalignment to management’s attention and asked “What would you like me to do differently?”

Candice went out of her way to emphasize her respect for the leadership team at Atos. “They are truly brilliant and I’m confident they’ll continue to execute their digital transformation strategy at high levels.”  But ultimately she elected to leave, having decided her preferences for managing her business were out of sync with the Atos culture.

Still, she took away valuable lessons in maintaining her credibility with the team. “I (kept) an open forum where they could share their frustrations.” And she let them know, “you've been heard, I understand, I will run that up the chain of command.” She might not be able to guarantee action, but that kind of honesty earned her their loyalty.

Identifying the Influencers Needed to Succeed

Whether Candice would have benefited over time from stronger relationships with the influencers from her acquiring company, we cannot say. Given the post-merger distractions at Atos, she did her best to make lemonade.

Her circumstances aside, we are strong advocates of making a deliberate plan to identify and schedule the time to build relationships with the influencers who have the ability to “plow the road” for your sales team.

What groups does your team rely on to drive a deal forward: Solution experts? Pricing strategists? Customer marketers? Product managers? Supply chain operations? Customer care? Who heads these teams and what do you know about their management priorities and incentives?

Sooner or later you’re going to need their assistance to drive a major deal to close or to retain a critical customer who’s about to defect to a competitor.

Therefore, We Have This Suggestion

Do what Rosalinde Torres suggests and anticipate what you’ll need from which influencers, then take steps to nurture these relationships. Your current preparedness on this front, she suggests, is reflected right in your calendar. “Who are you spending time with, on what topics? Where are you travelling?”

Look at your calendar. Do you have meetings with key influencers (or customers for that matter) on it? If not, figure out who you need to have strong relationships with and schedule those meetings.

Do it now. This isn’t a matter of being social, it’s a matter of risk mitigation.


Digging deep is a time consuming, sometimes strenuous, effort that many sales leaders are tempted to give less consideration to than is prudent. Occasionally they’re uncomfortable with the sheer volume of personal interaction required for this task. If you find yourself in this situation, find delegates to help you and remember two of Michael Watkins central tenets for working systematically through your first 90 days:

  • Small actions taken now have a huge impact later
  • Failure to create momentum in the first 90 days virtually guarantees an uphill battle for the rest of your tenure.

FIRST 90 DAYS TOOLBOX: Question Bank

Question Bank for Deep Discovery into the workings of your sales organization and your company’s culture and political landscape. Choose which questions apply to your situation, decide whom you need to interview and get out from behind your desk.

Article 4 (of 4)

See the final article in this series, where we’ll show you how to organize your key learnings and use them to build a roadmap that defines a longer-term sales strategy.  Or, to see the whole series with added detail in eBook form, download our Sales Leader's First 90 Days eBook here.

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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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