Helping Your Team Overcome Their Fear of Failure in Sales

Sales Prospecting Tips for the Coach: The Reality of Prospecting

Here’s a sales prospecting tip for the coach: prospecting is not always fun. If you are a manager, you should not tell your people to “just pick up the phone and have fun with it.” They will know you don’t know what you’re talking about.

Fun is water skiing, snow skiing, swimming, hiking, going to a play or the opera, having a picnic, watching a ballgame, attending a family reunion, singing, playing guitar, enjoying an online or Xbox game, falling in love, dancing, going on a cruise, eating an amazing meal, getting a promotion, a raise, or recognition for a job well done. Those are fun activities!

Facing rejection, not talking to anyone, having people hang up or unsubscribe, being told not to call again, or having people lie or avoid you—those are not fun. Many prospects won’t return calls or emails and will say whatever it takes to get rid of a salesperson. Salespeople must also deal with people asking for free information or canceling appointments at the last minute. These are not fun activities.

Sales Prospecting Tips for the Coach: Teaching Resilience

If prospecting isn’t fun, then what is it? Here’s another sales prospecting tip for the coach: you must tell your team this:“You don’t have to like it; you just have to do it.” It’s called work for a reason.

Salespeople have to put a lot of preparation, thought, intellect, and skill into being successful at prospecting. Our sales evaluation partner, Objective Management Group, has found that the single biggest contributor to sales success is the ability to be rejection-proof. Even with skill, technique, scripts, and preparation, if salespeople can’t handle rejection and the emotional roller coaster of prospecting, they’ll struggle and fail more often than they succeed.

Rejection-proof salespeople recover quickly from setbacks. They get back on the phone immediately, learn from mistakes, and keep going.

Additional Sales Prospecting Tips for the Coach

• Hire hunters. Use a sales-specific evaluation to ensure you’re bringing in the right people.

• Provide leads, even if you charge for them. Stop trying to make non-hunters into hunters.

• Inspect what you expect. Hold your team accountable for consistent prospecting activity.

• Offer training and coaching to help them prospect effectively in today’s environment.

• Role-play phone calls and first meetings in every sales meeting to keep skills sharp.

• Equip them with prospecting strategies and tools that help them stand out from competitors.

If your salespeople have a solid phone approach and don’t sound like everyone else, they’ll have a chance. Help them uncover the root causes of their prospecting challenges, like beliefs or need for approval, and then coach them through it. With practice and preparation, their phone conversations can become as natural as breathing.

The bottom line: sales prospecting isn’t about having fun, it’s about getting the job done so that salespeople have solid appointments that lead to real opportunities and closed business. That’s where the fun begins.

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FAQ: Sales Prospecting Tips for the Coach

Q: What is the best sales prospecting tip for a sales coach?
A: Teach your team that prospecting isn’t about enjoyment—it’s about discipline. Consistency, accountability, and resilience are key.

Q: How can a coach help salespeople overcome rejection?
A: Encourage quick recovery after rejection and role-play real scenarios during team meetings. Building emotional toughness is essential.

Q: What should a sales manager focus on during coaching sessions?
A: Focus on helping your team develop strong prospecting habits, use targeted messaging, and stay accountable for daily outreach goals.

Q: Can prospecting ever be fun?
A: It can be, once your team sees results. Success in booking quality appointments and closing deals turns the hard work into something enjoyable.

In 2002, Marie Guion-Johnson’s 41-year-old husband, Rob, died after going into cardiac arrest while swimming. That experience led Guion-Johnson to start the company Aum Cardiovascular and invent the CADence, a small device that doctors hold over a patient’s chest to detect blockages often missed by other tests. At the end of the article, the interviewer asked, “What does the company’s name mean?” Aum is an ancient Sanskrit symbol that refers to a low humming sound, the same sound heard from a diseased coronary artery. But when she’s asked by potential financial backers, she says it means “assets under management.” That got me thinking about sales managers and their assets—people.

As a sales VP or manager, your only asset is your people. You don’t own equipment, buildings, or other capital. You don’t really own the people either, but the company has placed its trust in you to manage the assets it has invested in. And, believe it or not, some of those “assets” have also placed their trust in you. So, how are you doing?

What “assets under management” means for sales leaders

If you were to look at your people as an investment portfolio, are you getting the ROI you expected or should expect based on the investment of time, money, and effort? As a total portfolio, you may be exceeding your objectives, but what about the individual assets? How are you doing with each of the team members you’ve recruited, hired, and onboarded? Unlike your personal investments, where you probably have an investment or money manager, you are the one managing this portfolio. Are you doing the things you should be doing to maximize the return?

5 Must-Dos to Maximize your Assets Under Management

1. Honest assessment of individual holdings: First, don’t treat them all the same. The bond isn’t supposed to perform like your growth fund or equity holding. But is it performing as expected? If not, why not?

2. Assess the “why not.” Looking only at the return, pipeline, or sales results isn’t enough. You have to get beyond the symptoms (not calling enough, not converting effort into opportunity, not closing) and uncover the root causes of underperformance.

3. Have the fierce conversation (not aggressive, not punitive) about current performance versus expectations. Use data and your recruiting file in this discussion: “This is what I’m getting” (show effort and results data) versus “This is what I thought I hired” (show the résumé, interview notes, and contract). Then ask, “Did I make a hiring mistake?”

4. Agree on the problem. Ask questions rather than telling them what you see as missing in their effort or execution. Just like in selling, if you get the person to recognize and verbalize the issues or challenges, they own them. When the discussion ends, ask, “Is this where you want to be?” (They’ll say no.) Then ask, “Are you sure?” (They’ll say yes.) Finally, “Does this mean you’re willing to do everything possible to succeed?” (They’ll say yes, assuming they pass the intelligence test.)

5. Develop a disciplined approach to get them back on track. Create a plan with specific times for activity, clear behaviors to inspect, details about joint work, and scheduled coaching meetings. All of this should help the person you believed would be a superstar get back on track for success. 

Catch Issues Early

Here’s the kicker: you must recognize and address these problems as early as possible. Do not be satisfied with making progress, trending in the right direction, or thinking they haven’t hit their stride yet. Don’t make excuses for lack of effort or execution. Identify the problems early, address them, take corrective action, or, as you would with an underperforming asset, sell.

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FAQ: Sales Team Performance Management

What is sales team performance management?
It is the ongoing process of setting expectations, inspecting effort and execution, coaching to behaviors, and measuring outcomes so the team delivers predictable results.

How often should I review individual performance?
Weekly for activity and pipeline movement, monthly for conversion ratios and skill focus, quarterly for role fit and long-term development.

What data should I inspect beyond closed deals?
Prospecting blocks completed, first meetings set and kept, second meetings advanced, proposal-to-close ratios, average deal size, cycle time, and calendar discipline.

How do I handle a persistently underperforming rep?
Use a time-bound improvement plan with clear metrics and support. If behavior and results do not change, reassign or exit quickly to protect the portfolio.

How is this different from micromanagement?
Micromanagement fixes tasks. Performance management clarifies outcomes, inspects leading indicators, and coaches skills while preserving autonomy and accountability.

What Makes a Successful Salesperson?

Let’s start by evaluating what makes a successful salesperson. We recently asked the participants of a workshop to identify and share the habits they believed contributed to the success of their best salespeople. Below are some of the common habits identified:

• Develops great relationships
• Networks regularly
• Practices good time management
• Gets to decision makers
• Is selective in prospecting
• Provides exceptional customer service

Then we asked them to talk about the flip side of the list—those habits that inhibited or hurt a salesperson’s ability to close more business. Below are some of the habits they identified:

• Sells on price
• Inconsistent prospecting
• Procrastinates
• Presents to the wrong people
• Does not fully qualify prospects
• Poor prioritization
• Is too comfortable

These desired sales behaviors provide insights into which habits are most important for sales leadership in developing and motivating salespeople.

The Role of Sales Management Habits in Leadership

We partner with and utilize the most recognized sales evaluation in the industry by Objective Management Group. To avoid guessing about what contributes to effective sales management habits, here are the core competencies taken from their sales management evaluation below. Take a moment to review the list and reflect on how effective you are in these areas.

This comprehensive list of competencies has layers of effective sales management habits beneath it. Let’s focus solely on the skills of a great coach—one of the most critical roles of an effective sales leader—as managers should be spending at least 50% of their time coaching.

Coaching Habits That Drive Sales Growth

Here is a list of skills and habits necessary for successful sales coaching:

•  Consistently coaches
• Has a passion for coaching
• Debriefs sales calls effectively
• Stays in the moment
• Asks enough quality questions
• Does not need approval from salespeople
• Handles joint calls effectively
• Does not rescue salespeople
• Implements and coaches the execution of a consistent sales process
• Is effective at getting commitments
• Coaches to improve skill and change behavior
• Knows how and why people buy

It’s not enough to just have the skill. For managers to be successful at building a sales team for growth, they must be in the habit of using those skills. One of the most important sales management habits is scheduling coaching time on the calendar with a focus on improving skills, not just coaching a deal at hand.

Building Extraordinary Sales Managers

Being an extraordinary sales manager is challenging and time-consuming. It requires attention to detail, the ability to have tough conversations with those who are not meeting their numbers, the desire and commitment to grow yourself and your salespeople, consistent activity, and patience.

The rewards: like the coach of a winning team or conductor of an extraordinary symphony, you have the ability to positively affect the success and lives of your salespeople and company by cultivating effective sales management habits.

Frequently Asked Questions About Sales Management Habits

1. What are sales management habits?
Sales management habits are the consistent behaviors, routines, and practices that sales leaders use to coach, manage, and develop their teams. These habits shape performance, accountability, and long-term sales growth.

2. Why are sales management habits important?
Strong sales management habits create structure, improve coaching effectiveness, and ensure that sales teams are consistently meeting and exceeding goals. Without these habits, performance often becomes inconsistent and results unpredictable.

3. What are examples of effective sales management habits?
Examples include regularly coaching salespeople, setting clear expectations, holding team members accountable, tracking performance metrics, and investing time in skill development.

4. How can I improve my sales management habits?
Start by scheduling consistent coaching sessions, reviewing sales activities instead of only results, and developing systems that support recruiting, performance management, and accountability.

5. How much time should managers spend coaching as part of sales management habits?
Industry best practices suggest that managers should spend at least 50% of their time coaching. This habit ensures skill development, behavior change, and stronger sales outcomes.

The obvious way to measure sales performance is by results. If a salesperson is hitting or exceeding goal, that looks good on the surface. But what about the majority of your team who are not? Numbers alone tell you what is happening, but not why. That’s where a sales skills assessment comes in.

Key Data Points in a Sales Skills Assessment

To get a true picture of performance, you need to go beyond outcomes and evaluate behaviors, skills, and effort. Consider these areas:

• Critical ratios

  • Effort: Are they making dials, networking, and using LinkedIn effectively?

  • Effectiveness: What do ratios tell you? For example, if only 10% of conversations result in an appointment, is that good enough?

• Observation

  • Joint calls: Are they following the company sales process?

  • Execution of sales fundamentals: Are they asking enough of the right questions, weaving in stories and analogies, listening actively, and digging deeper to understand client problems?

• Role-playing

  • Do they understand and demonstrate your sales process?

  • Can they articulate what consultative, client-focused selling really means?

  • Do they show the same skills in a practice setting that you expect in the field?

• Pipeline and activity data

  • Is the pipeline growing in volume and reliability?

  • How does their performance rank compared to peers?

  • Are they putting in enough effort to create opportunities for success?

The Honest Question: Would You Buy from This Salesperson?

An effective way to evaluate skills is to role-play or observe live selling situations and then ask yourself one honest question: Would I buy from this salesperson?

Your answer will likely fall into one of four categories:

1. I would not buy from this person. In fact, I’d love to compete against them.

2. I would not buy from them right now based on what I just saw or heard.

3. I’m undecided. I need more information or more time to make up my mind.

4. I would buy from this person. They engaged me, uncovered problems I need to address, and made me think about changing vendors or spending money I hadn’t planned to.

One client recently held a sales meeting with an hour of role-play around a single sales step. At the end, a product specialist remarked, “With the exception of two people, I don’t believe I would buy from anyone else I saw in that one hour.” That is the kind of courageous, honest feedback that defines a true sales skills assessment.

What Sales Leaders Must Bring to the Table

Performance management is not just about observing your team. It also requires the right mindset and habits as a leader:

• Supportive coaching beliefs – If you think people will only perform well if they like you, you’re in trouble.

• Resilience to rejection – You must be willing to tell someone the hard truth, even if it stings.

• Understanding of desire and commitment – If a salesperson isn’t fully committed, you’ll find yourself addressing the same problems repeatedly.

• Data analysis skills – Without digging into the right data, coaching is guesswork.

• Time allocation – If you’re not doing ride-alongs or role-plays, you’re missing two non-negotiable assessment opportunities.

The Bottom Line

Effective sales leaders know that an honest sales skills assessment must be done regularly. Ask yourself: Would I buy from this salesperson? The answer will drive deeper, more actionable coaching conversations. While it may be uncomfortable, and you may even lose someone along the way, it often inspires salespeople to sharpen their skills and elevate their performance.

FAQ: Sales Skills Assessment

What is a sales skills assessment?
It is a structured evaluation of a salesperson’s behaviors, effort, and skills beyond just sales results. It helps identify why someone is or isn’t performing.

Why is a sales skills assessment important?
Because results alone don’t show the root cause. Assessments uncover gaps in effort, execution, and understanding that you can address through coaching.

How often should sales leaders conduct a sales skills assessment?
Regularly. Role-plays, ride-alongs, and data reviews should be ongoing, not just once or twice a year.

What are common areas to measure in a sales skills assessment?
Critical activity ratios, joint call performance, role-play ability, pipeline strength, and sales activity levels.

How can a sales skills assessment improve results?
By identifying specific skill gaps, leaders can coach more effectively, leading to stronger pipelines, higher conversion ratios, and better long-term performance.