Red Flags of Poor Sales Leadership

Creating and maintaining a quality sales leadership team is often like attempting to navigate a minefield. You may think your leadership team is on good footing, you may even start to feel cautiously optimistic about hitting your goals - only to have that missed forecast bomb blow your legs off seemingly out of nowhere.  

What are some advance warning signs that poor sales leadership is putting your sales team at risk to underperform or worse, decimate your organization? 

Here are the first 5 to look out for...

1. Practice? We’re talking about practice?

Unless you’ve hired Allen Iverson to lead your sales organization, then yes, we definitely should be talking about practice for your reps. 

If you have a sales leader who has failed to build in role playing exercises as part of their continuous skills training for the team, then you have a sales leader who has not only failed at the basics, but has put your sales team at risk for underperformance and attrition. 

Reps may find role playing uncomfortable and awkward at first, but sales is a performance based profession and as such, building a routine and culture of practice is required to achieve consistently successful performance. 

If you have a sales leader that is massively undervaluing (and if they are not running scheduled practice sessions then they are) what consistent practice will do over time, how would you expect your reps not to massively undervalue training as well? 

Consider that your main competitor's sales team has a daily practice schedule, while your sales team practices weekly, if that. Best case compared to your team with a non-formalized weekly practice schedule, that's 4 extra practice sessions per week, 16 per month and 192 EXTRA practice sessions per year that your main competitor’s sales team is doing. 

Which team would you bet on to outperform and outpace over the long term?

2. Bodies Before Messaging

Throwing bodies at pipeline creation is a passion of many sales leaders with access to a hiring budget. You’ll see them extremely excited on LinkedIn, proudly proclaiming, “I’m hiring!”. However, without a significant focus on the rubber meets the road details like prospect messaging your organization could hire hundreds of reps and not only fail spectacularly but quite expensively as well. Bonus! 

We’ve heard sales leaders say a lot of crazy things, but one we’ll always remember is a VP of Sales who was wonderfully transparent about his complete lack of pipeline while asserting that prospect messaging wasn’t going to be the critical first step in his reps’ sales process. In fact, he told us, he didn’t even consider messaging as a part of the sales process. OK.  

Once hired, what will all these folks be saying on the phone and via email? What messaging will they be trained with? Any sales leader who doesn’t understand the critical role that messaging is going to play in your sales process, has either been away from the frontlines of pipeline building for too long or is just incompetent. Either way, it’s not good.  

If you’re a B2B company that needs to build pipeline and your VP or SVP of Sales’ first move is to hire a Sales Director, a BDR manager, a BDR Operations manager and a team of on-premise BDRs before anyone, let alone this so-called “sales leader”, has written word one of a call script - you might as well start lighting money on fire.

3. One Trick Pony Sales Methodology

Sales methodologies can be useful when properly learned and deployed, but overreliance on a singular method or a singular aspect of any method is the sign of someone who will struggle to effectively manage the overall deal process to a closed-won status.

Two critical sales skills are the ability to both lead and Sherpa the buyer’s journey as well as manage the overall sales process. Salespeople who could use improvement in this skill set often attempt to compensate by becoming fervent devotees of one particular sales methodology or, in the most extreme cases, one defining aspect of the methodology. 

We once observed the sales process of an SVP who relied so heavily on the questioning style taught in the book Let's Get Real or Let's Not Play, that his conversational style was painstakingly pedantic. As such, any sales cycle he involved himself in stretched infinitely as multiple meetings with prospects occurred with no forward guidance and the prospects defaulting into leading the sales process themselves. 

If you observe your sales team scrambling to run demos at the last minute, this is a sign that there is a leadership vacuum occurring in the sales process and the prospects are in control of the sales process AKA the inmates are running the asylum. 

4. Reps’ Time Is Their Time (To Waste)

Whether the issue is constantly missed or rescheduled 1:1s, a last-minute Louie style booking of team meetings, QBRs and distributing agendas, a lack of formalized team practice drills and process, failure to protect the team’s time at the end of the quarter or even worse, actively assigning administrative projects at that time - all of those realities indicate a sales leader who does not respect their reps’ time. 

Or worse yet, a sales leader who does not understand that efficient time management is crucial to not only their team’s success, but to the health and longevity of the company.

More concerningly, it indicates a sales leader who has seemingly forgotten that the base of your company’s revenue generating team consists of nothing more than your reps’ skills and their time. 

All the sales enablement and tech in the world is useless if reps’ are not empowered to manage their time like high achievement professionals. If your reps’ manager is not respecting their time, what behavior is being modeled for them?

5. Data Analysis, Say What?

Beyond basic quota attainment or progress to plan, most sales teams have KPIs or various categories of metrics that they are also measured by. The measurement of sales team activities such as calls, emails and prospect meetings, data entry frequency and quality of the data, forecasting accuracy, rates of conversion, length of sales cycle and other deal related metrics typically fall under the purview of the sales leader to monitor and manage. 

With no shortage of sales related applications in most companies’ tech stacks, collecting this kind of data on a per rep basis has never been easier. However, you might be surprised to read that many sales leaders never do any analysis other than stack ranking their reps. 

Most tools in the modern sales team tech stack come with analytics capabilities and reporting functions built in, so plenty of sales leaders simply build a few nice looking team dashboards and leave it at that. 

What these sales leaders should be doing is using the basic stack rank data as a guide that leads them to uncover the info they need to train the team on proven best practices. The KPI dashboards do play a vital role, they are the trailheads that leaders should be starting at, on their hike to the top of the quota crushing sales team mountain. 

Basic KPIs will identify which reps’ data the team leader should be analyzing to identify patterns or key indicators of success. What are the top reps saying, writing and doing that is keeping them at the top of the board? 

Hint : it’s not just how many cold calls they are logging every day, or how many emails they are sending. It’s the content and copywriting they are deploying, the questions they are asking, the turns of phrase and dialogue they are using in their sales performance.

For example, listening to a rep’s call recordings shouldn’t be about identifying how many times the rep says, “um” or “like”, the real value there is being able to identify what the top reps are saying on calls and demos that connects with prospects and successfully engages them while continuing to guide them through their buying journey. 

So take a look at your sales team’s KPIs - do you have just a bunch of nice looking dashboards or do you have nice looking dashboards AND a sales leader with actionable insights and proven best practices to continuously train the team on?