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Questions Your Sales Leader Wants To Ask But Won't

For some sales leaders approaching you, the CEO, can be nerve-wracking. They may think some questions are better left unsaid, either because they "should" know the answer but don't, or because they are nervous about how you'll react, or they may think it's a dumb question.

However, to build a strong company culture, you should have an environment of open communication and trust. After all, you want your employees to feel you are approachable, right? That they can trust you?

Below are seven questions your sales leader wants to ask but won't.

Which Direction Now?

As an owner, you're likely part of a CEO peer group like Vistage, Allied Executives, The CEO Roundtable, or Entrepreneurs Organization. Between meetings, books, articles, the media, and more, you probably hear all sorts of great ideas, solutions, new methods to try, etc. When you do not see results fast enough, you rely on those new ideas and go back to your sales leader and tell them what you heard or read. You say to your sales leader that it would be a good thing to try or investigate.

A lot of CEOs are visionaries. They are great at coming up with ideas and sales leaders know it.  But they also want to know which idea you want to pursue now. Because last month you did the same thing after your CEO meeting, and now this new idea may or may not fit into what the sales leader is already doing, based on last month’s direction. Your sales leader is having a difficult time constantly changing direction and has zero time to react. So which direction do you want them to pursue?

Is It Okay for Me to Say No?

You're the boss; you have a million things going on all at once, right? It would help if your team made sure your ideas are executed. So, when you ask someone to do something, you would like it if they said yes and implemented right away, correct?

Your sales leader knows saying yes to your requests at work is a no-brainer. It ensures that they are relevant and have high engagement. It shows you can depend on them, and they are eager to be involved. However, your sales leader is also juggling a million different things like their 1-on-1's, reporting, coaching, analyzing, setting sales targets, etc.

So with those other tasks, your sales leader wants to know if it's okay to say no to your request if they can’t get to it right away, or if it doesn’t fit in with what they are currently doing. Instead, you may want to consider what is the appropriate priority for your request.

What Level of Authority Do I Have?

Authority in an organization is the power, right, or permission to act. It is the ability to control the outcome. It is what a sales leader can do without asking you first. Your sales leader wants to know if they can approve pricing, move cubicles around, hire/let people go, change the strategy, etc. with or without your permission.

The two common situations that happen a lot are:

  • The sales leader will do something but you as the CEO will want to know why they did not ask about it first.
  • The sales leader will wait three weeks for you to have the time to talk about a minor thing, and then you will want to know why they are even asking you about it.

Right from the get-go, you need to clarify what responsibilities the sales leader can do without you, can tell you about, has to ask you about, or needs to involve you. So, what can your sales leader do without your permission?

We have an Ask/Do/Tell tool that can help you clarify some of this with your sales leader. Let us know you are interested by emailing us at info@pivotaladvisors.com

What Information Do You Look at Every Day?

You are continually looking at reports, trends, numbers, financials, etc. But what is it that drives your company? What information do you find valuable every day? Your sales leader wants to know how best they can benefit you. Do you want to see daily sales reports or daily/weekly product trends? Let them know what is most helpful to you.

What Does "Be More Strategic" Even Mean?

When you tell your sales leader, they need to be more strategic; they aren't exactly sure what you mean. Do you want them to set the strategy? Or do a competitive analysis? Or what? More than likely, you want your sales leader to analyze the market and business trends, then come to you with solutions and plans. Be specific if you want them to be forward-thinking.

When you say, "be more strategic", you may think that it is obvious what you are asking. You hired them with "strategic" in mind, but in actuality, they are coaching deals. You have to set expectations early on about "being strategic." When you are hiring, let them know you want someone to bring you a plan to market trends.

If you want more on hiring the correct sales leader, check out our blog, "Did You Hire The Right Sales Leader?"

What Do I Need to Do to Move Up?

Some salespeople want to reach sales leader status, and some sales leaders want to climb higher. During your sales leader’s annual review do you hear things like "I want to grow," or "I'm looking to advance my career"? These are key examples of someone who does indeed want to move "up the ladder," but they may not know how best to do that.

You can encourage them to get specific certifications, have them shadow the role they are interested in, or promote virtual training and learning. You can do many things to help them if you notice your sales leader wants to advance yet does not come out right and say it.

What Is Your End Game with the Business?

The time has come; you have run your business successfully for 35 years, and now you want to golf for a living. What about your company? Your sales leader wants to know if you are planning to retire and hire someone else to take over the company, or planning to sell the company, or are you planning to make it employee-owned? More importantly, your sales leader wants to know how they fit into your end plan.

Chances are your sales leader does not want you to retire, but they know you will eventually and do not want to come off as nosey.

All These Questions, What Do You Do?

Now you have seven questions that your sales leader wants to ask but won't. What do you do? Open communication by setting up a meeting to discuss these and other questions your sales leader may have. Start with your expectations of their role. Find out what they need from you. Explore what they want out of the company. Talk about where you see the company going.

Meet up quarterly to keep going over role expectations and continue to be honest and transparent with them. How are they performing? How are you investing in them? Set up an "ask, do, tell" meeting on the level of authority. Let them know where they can improve and give them tools to do just that.

Talking through these questions and any others with your sales leader on a quarterly basis will help build a stronger, more trusting relationship. Which leads to improved morale and efficiency.

About Gary Braun

Gary is a founder and co-owner of Pivotal Advisors. He has worked for 20+ years as a salesperson and sales leader. Gary has been a guest speaker for many groups such as Vistage, Allied Executives, CEO Roundtable, Sales Management Association, and more. If you want to find out more about Gary check out his profile here.
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