Sales leaders’ top challenges – and how to beat them

Sales leaders’ top challenges – and how to beat them

You were a greatsalesperson. Now you’re a goodsales leader.

Wouldn’t it be good to be great again?

Whether you’re a new sales leader or a veteran, you likely face the same struggles.

Yep, the same.

Why? Because the leadership part of the job is what keeps managers up at night. The people and process issues dig deeper and linger longer than any sales slump.

Now this will help – the eight biggest challenges sales leaders face and how to consistently stay ahead of or eliminate them.

Challenge 1: Expectations

Issue: This could be the mother of all challenges for sales leaders (any leader, for that matter). You expect salespeople to perform, behave and respond in certain ways. Same goes for colleagues and the C-Suite: You expect one thing – and are disappointed or frustrated when expectations aren’t met.

The problems usually arise because leaders don’t clearly communicate their expectations. So salespeople can’t ask for direction, counter with their outlook or even declare a willingness to get it done.

Best practice: Be clear when you give formal or informal directions on the outcome you expect. Be even clearer if you expect the result to be achieved in an exact way. Then, most importantly, ask salespeople to restate the goal and what’s expected.

Challenge 2: Communication

Issue: No one listens to me! Most managers feel that way, especially when things go wrong. But the problem often lies in a failure to recognize and speak to different communication styles.

People listen, process and comprehend information differently based on many factors, including: life and work experience, education, age and level of authority.

Best practice: Never assume people understand you. In fact, always assume they don’t understand on your first communication. Even when everyone is busy, you want to invite clarifying questions for important topics. Almost always, follow up on important information and expectations through other communication channels – for instance, a detailed email after a group announcement or a text after a sales coaching session.

Challenge 3: Coaching

Issue: The challenges in coaching run the gamut – from not enough time to do it to a reluctant audience receiving it. But the biggest obstacle for most sales leaders is execution – what to coach and how to address it effectively.

In a formal or organic coaching situation, leaders often take one of two approaches: 1) I’ll do it for you now and you just do it like this from now on, or 2) Oh come on, you can do better than that!

Neither work well because you’re either shouldering the weight of the issue or blowing it off.

Best practice: Developing salespeople could be the most important part of a leader’s job. When they do well, you do well. Rather than tell them what to do, help them discover ways to tackle different challenges. Resist the temptation to step in or away, and probe with questions and direction like this:

  • I noticed you did X when the prospect did Y. Can you tell me why?
  • How has that worked for you in the past?
  • What are other approaches you might consider?

Challenge 4: Change

Issue: Sales leaders are used to facing and handling constant change in technology, economy and industry conditions. The challenge here is helping a sales team prepare for and navigate the chaos.

Best practice: Experts agree: Successful sales managers calmly face the storm ahead, adjust through the challenges and embrace the changes. How? Most expect more of themselves than they do their team. Then they encourage the team to push through. They often come early or stay late to strategize with individual salespeople and the whole group to adapt and overcome the challenge.

Challenge 5: Motivation

Issue: Many sales leaders figure their salespeople are motivated by the same thing they were in that position – be it money, prestige or a desire to move into management. So they base incentives and motivation tactics on a single desire.

But one salesperson’s drive to attain a bigger bank account is another’s desire to make an impact in the industry. Sales leaders who don’t figure out what motivates individual reps struggle with low morale, misguided competitiveness and turnover.

Best practice: Dollars and rewards are only part of the equation. Successful sales leaders regularly sit and talk with salespeople about a lot more than numbers, goals, hits and misses. Find out why they got into this work and why they stay in it. Ask what they love and hate about the job. Ask what they feel their natural strengths are and where they’d like to expend the most energy. Most importantly, keep asking: What motivates them today will likely change.

Challenge 6: Data

Issue: Oh, the things you know, thanks to data! The challenge is having and knowing too much. Many sales leaders get buried in data and analysis, trying to figure the reason behind every number they follow. Or they might track too much, too little or the wrong things. Then they draw wrong conclusions and make irrelevant decisions based on bad data.

Sure, some say numbers don’t lie. But numbers can help hide the truths you don’t want to believe.

Best practice: Analyze the data you use to analyze performance. Regularly ask if the numbers you gather are just nice to know or actual indicators of improving or declining performance. If you don’t gather relevant, quality data, you can’t diagnose problems in the sales process, individual performance issues and improvements.

Challenge 7: Alignment

Issue: Many leaders struggle to gain Sales and Marketing alignment. But it’s a fallacy to believe that’s the only alignment problem in organizations today. Sales and Marketing don’t operate – and complain of misalignment – in their own vacuum anymore. Sales leaders need to keep their teams in line with people in almost every function – from development to delivery – to keep customers happy.

Best practice: It’s nearly impossible to meet and share information with every facet of an organization. The best approach to universal alignment: common goals. Sales, Marketing and every other moving part need tasks clearly outlined so nothing overlaps or falls through the cracks. This only works when everyone shares a common goal – for instance, increase customer satisfaction 12%, double customer acquisition this year, win the highest industry award, reduce customer turnover to zero next year, ISO certification, etc. Then leaders set and maintain course by consistently and continually driving home the goal.

Challenge 8: Time

Issue: Many people think they’re busy as sales reps. Then they step into management and wish they had all that time again! Sales leaders often spend so much time and energy on their sales team, they end up doing management work and meeting demands after hours. They give up professional development (and sometimes even personal interests) in the pursuit to help everyone win.

Problem is, very few win when a sales leader struggles to manage time.

Best practice: The most successful sales leaders find their time is best spent sharing more than doing. They let go of more and more tasks, and use more time to coach, strategize and plan. Leaders also focus seriously on learning. They find mentors, attend training, read in-depth and ask for help in understanding anything that can have an impact on sales performance. By guiding others to perform more effectively, they end up performing tasks less and coaching more. Equally important: The best disconnect from work and maintain healthy habits and relationships outside of the office.

By showing salespeople that personal and professional development, plus disconnecting, are important, the best sales leaders set a high bar for salespeople.


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