Do You Run a Sales Team or Just a Group of People Who Report to You?

By Rachel Cavallo

Whenever I work with a group of salespeople, I notice one prevailing theme.  They love to interact with each other and share ideas.  When we give salespeople an activity that involves sharing their experiences and asking for feedback from their peers, the level of engagement and enthusiasm skyrockets... especially when teams are dispersed and are working remotely and virtually. To build on that, most surveys that we receive post sales training show that the sellers want more opportunities to share with and learn from their peers.

If sellers love collaboration and learning from each other, shouldn't sales leaders be running their teams to foster these dynamics?

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Are You an “Operational” Sales Leader?

By Masami Middleton

As sales consultants, we often say that great sales leaders demonstrate three things consistently: 1) They are great sellers, 2) They are great coaches, and 3) They are great operators.

Sadly, top sellers promoted to sales managers do not magically demonstrate all three. This is why we see and talk regularly about the “Peter Principle” in sales, where sales leaders "rise to their level of incompetence".

Of these three traits, which do you think is most lacking?  Most would probably debate between traits #2 and #3.  Let’s look at it from the manager’s point of view:

  • Great Seller: “I am a great seller, that’s why I got promoted - duh.”
  • Great Coach: “I have good relationships with my team; I can teach them how to be successful.” (Red flag – what made you successful does not necessarily make everyone successful.)
  • Great Operator: “What do you mean by ‘operator’?” (Red flag - Not many are thinking about how to run a winning sales team.)

We have written a lot about issue #2, on sales coaching.

In this blog, we focus on trait #3, on successfully operating a sales team. (Which by default improves your sales coaching impact).

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Top 10 Account Planning Mistakes to Avoid

By Masami Middleton

In B2B sales, driving revenue from existing accounts is far easier than landing net new customers. With so much opportunity available, why do mature sales organizations still “wing it” with their Account Planning process?

According to CEB/Gartner research, only 28% of sales leaders believe their account management channels meet their cross-selling and account growth targets. Thoughtful, intentional account plans provide real strategic insight and actionable game plans for account teams to meet growth targets. For sales managers, account plans provide an excellent foundation for consistent coaching conversations, insight into forecasts, and an overall way of staying engaged with customer activity.

Account Planning is the process of determining the best way to grow and add value to existing accounts. While many organizations engage in both Account Planning and Territory Planning (systematically determining how to optimize impact over a portfolio of accounts), the purpose of this post is to explore the deep dive Account Planning process to dissect one account at a time.

If your team is currently digging into Account Planning (or about to), here are 10 common mistakes to avoid.

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Sales Leaders: What’s Your Plan for the Next 90 Days?

By Hope Eyre

A couple of years ago we published an e-book called A Sales Leader’s First 90 Days. It was inspired by the classic Michael Watkins book, but tailored specifically for Sales VPs, SVPs and CROs who had recently taken over a new organization. (For broader context on our Sales Leader's First 90 Days program, check out our introductory blog.)

Since so many companies have either re-organized or are in the midst of doing so, we find many of our "First 90 Days" principles relevant as established sales leaders plan their next 90 days.

We’ve condensed 90-day lessons into four key questions sales leaders can ask themselves as their companies undergo shifting strategies. Which of these challenges pertain to you and how can you address them in the next 90 days?

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Sales Leaders: Assess Skills Gaps Now to Avoid Pipeline Issues Later

By Hope Eyre

We suspected this would happen, and then we got confirmation from the Sales Ops team at our largest client.

“Some of our best sellers have become some of our worst,” they said.

The client was describing a subset of sellers who had historically been star performers based on the strength of their relationships; especially those who had relied heavily on face-to-face socializing.

“It’s the ones who never had to lean into any technology, because they were successful without it,” the lament continued. Pipelines already under stress were absolutely going to be affected.

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CSO, CRO, VP of Sales: Which Leader Fits Your Company? Which Fits You?

By Masami Middleton

As sales consultants, we encounter sales leaders with a variety of fancy acronyms in their titles. In addition to the SVPs/EVPs of Sales, the sales leader landscape also includes CROs, CSOs, and CGOs. While these titles imply a distinction in roles, to most people, it’s just alphabet soup. 

What’s the difference between a Chief Sales Officer (CSO) and a Chief Revenue Officer (CRO) or Chief Growth Officer (CGO)? From the CEO or board member perspective, which role does your business need? For a sales leader, which role is the best fit with your capabilities?

The easiest way to distinguish between these roles is to compare their scope of responsibility, core objectives, and what defines success. Appointing a “heavy hitter” to a CSO, CRO or CGO role, rather than a VP of Sales, indicates the need for a greater span of oversight from a strategic, revenue generation, and customer lifecycle perspective.

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Talking to Your Sales Team: Do it More Often, Starting Now

By Hope Eyre

If you manage sellers, frontline sales managers or indeed anyone, you understand they’re under stress, apprehensive, and craving any type of normalcy until actual normalcy returns.

Most sales leaders we talk to are currently in break/fix mode: Some are having to shrink their organizations or reduce pay. Most are trying to figure out how to help customers whose businesses or entire industries have been upended.

All are worried about the health and safety of their teams in addition to working hard to help sellers quickly become accomplished in a virtual environment. The key to managing much of this lies in how you’re communicating with your team while stress is running high.

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How Do Sales Leaders Stay Credible and Legitimate?

By Hope Eyre

There’s this TED talk I like by General Stanley McChrystal called “Listen, Learn… then Lead.” We assign it as homework in our Leadership Academy, a 6-module program we’ve run for years at individual clients to ready their next generation managers for leadership positions across a variety of functions.

General McChrystal (who knew he was funny?) has several poignant messages delivered compellingly against the backdrop of combat, but his key takeaway is this: Leaders are good when they’re willing to learn.

“How," he asks, "does a leader stay credible and legitimate when they haven’t done what the people (they’re) leading are doing?”

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Why Newly Promoted Sales Leaders Rise to Their Level of Incompetence

By Kelsey Peusch

Whether you are a successful top performer seeking a senior management position or you’re already a senior Sales Leader looking to hand pick your next protégé, there is something you should know. It’s been statistically proven that the best sales representatives won’t make the best sales leaders.


All too often we encounter sales leadership teams yearning for the skills and structure required to elevate their team’s performance. We are talking about sophisticated, highly educated, teams of men and women, the majority of which were top performers in their respective organizations.

The jarring realization, one we must often share with our clients, is that the skills required to be a high performing seller are different than the skills required to lead high performing sales teams. Seems obvious, no? Unfortunately, we see organizations seeking to retain top talent by rewarding them with upward mobility with little regard to skill set.

This anomaly is known as The Peter Principle which presupposes this fact: “If organizations promote the best people at their current jobs, then organizations will inevitably promote people until they’re no longer good at their jobs. In other words, organizations manage careers so that everyone ‘rises to the level of their incompetence’. ”

Sales is no different and here is the proof.

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Boosting Sales Coaching Creativity: 3 Techniques to Reinforce Basic Selling Skills

By David Szen

I spend a lot of time with sales leaders and my hat goes off to the hours they work and pressures they accept in their role. Their job is a hard and often thankless one dealing with complex client, employee, organizational, competitive, and financial pressures.

Sales leaders have a great capacity to reinforce essential selling skills in their teams, but all too often, the day-to-day demands get in the way. While dealing with daily pressures and fire drills, many of their reps are stumbling on fundamental selling skills. The ones I hear a lot about are: 1) discovery/questioning skills, 2) navigating and answering the tough questions, and 3) delivering relevant and powerful value messages.

Here are three techniques to put the creativity back into coaching and develop these key selling skills amongst your team.

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