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.

Chapter 1: Relationship Selling - The Key to Your Sales Challenges

In today’s unpredictable and rapidly shifting markets, one of the most persistent challenges in sales is staying focused on adding value, not just making the sale. That’s where relationship selling comes in. While this concept isn’t new to most of us in sales, applying it effectively and consistently is where the real challenge lies.

Many organizations are striving to become more customer-focused. But how can advisors and sales professionals remain productive and assertive without sounding overly sales-driven?

The Power of Assertive Relationship Selling

Here’s the truth: Assertive salespeople, those who lead with confidence and care, win more business. These professionals are so committed to doing what’s right for their clients that they’re willing to risk the sale to help the customer make the best possible decision.

This is the essence of relationship selling: prioritizing the long-term relationship over the short-term win.

Assertiveness in sales isn’t about pressure, it’s about clarity, curiosity, and courage. When done well, your early conversations help qualify (or disqualify) prospects quickly and respectfully. That means less wasted time chasing people who will never buy, and more energy directed toward solving real problems for real buyers.

The Discovery Process: Ask Better, Sell Smarter

In those initial, assertive conversations, your goal is to uncover the prospect’s real pain:

• What problems are they facing?
• What have they done to try and solve them?
• How is their current provider performing?

These conversations aren’t just about gathering surface-level information. They’re about building insight, so you can determine whether a true, mutually beneficial relationship can form.

In our sales methodology, a qualified prospect must meet three key criteria:

1. They have a compelling reason to buy or make a change.
2. They have the resources and willingness to invest (time, money, effort).
3. They have the authority and readiness to make a decision, including financial decisions.

Bold Questions That Build Relationships

To discover whether a prospect qualifies, you need to ask bold, sometimes uncomfortable questions, questions that require assertiveness and emotional intelligence.

Here are a few examples:

• “How will you go about telling your current provider that you’re moving in a different direction?”
• “If funding is limited, how do you plan to address the problem?”
• “The budget you mentioned won’t achieve your goals. What would you be willing to compromise?”
• “What will you do if your partner isn’t on board with making this change?”

Imagine having the confidence to ask these questions regularly. What would happen?

You might fear losing opportunities, but in reality, you’d likely gain more meaningful ones. You’d eliminate indecision, shorten your sales cycle, and build trust by helping your prospects face their own obstacles head-on.

Final Thought

Relationship selling, when done with assertiveness and empathy, doesn’t just help you close more deals, it helps you close the right ones.

When you stop making presentations to people who can’t say “yes” and start focusing on those who are ready to move forward, your entire sales process becomes more efficient, more effective, and more rewarding.

So, if you’re facing challenges in your sales process, try this:
Be more assertive. Ask better questions. Focus on building real, lasting relationships. The results will speak for themselves.

Chapter 2: Build Lasting Relationships in Sales

If your goal is to retain and grow client relationships, you must consistently create a remarkable experience for your customers and prospects. Because if you’re not providing that superior experience, rest assured, your clients may start wondering, “Who else will?”

Ask Yourself These Key Questions:

To evaluate your customer relationship strategy, reflect on the following:

• What are you doing to keep your clients happy and satisfied?
• Are your clients referring others to your business?
• Is your organization delivering an exceptional experience at every touchpoint?
• Are you learning your clients’ wants, needs, and pain points, every single day?
• Are you under-promising and over-delivering?

What Can We Learn from Disney?

Think about a place where you wait in long lines, spend a lot of money, and still leave excited to tell others how great your experience was. For many, that’s Disney.

Disney has built decades of success by exceeding expectations and creating passionate brand advocates. In Inside the Magic Kingdom, author Tom Connellan outlines seven keys to Disney’s customer experience strategy. The biggest takeaway? Their “magic” isn’t random, it’s the result of a consistent, intentional process that dazzles.

Dazzling Experiences Aren’t Optional

To truly impress your clients:

• Your service must be predictable and consistent.
• Your clients must know what to expect and trust you to deliver.
• It can’t be a once-in-a-while thing, it must be how you do business, every day.

This doesn’t mean treating everyone the same. Your top 20% of clients should get a different level of attention than your bottom 20%, but everyone should get the basics done right, every time.

If you want to stand out from competitors and earn long-term loyalty, you need to go beyond service, you need to dazzle. Treat your advocates like family. It’s not extreme, it’s what separates memorable companies from forgettable ones.

Because in business, it’s always the little things that matter.

4 Strategies to Retain and Create Loyal Advocates:

1. Find out what they want
   Don’t guess, ask. Give clients a list of preferences and allow space for them to tell you what really matters.
2. Prioritize critical areas
   Clients won’t always tell you what’s wrong. Just like saying “It was fine” at a restaurant, they may avoid conflict. Dig deeper to find the real issues.
3. Identify their performance bar
   Where are they setting expectations? Don’t assume. Find out and then evaluate if you’re meeting or exceeding them.
4. Negotiate expectations
   If something doesn’t align with your process, say so. Don’t agree out of fear of losing a deal, because if expectations don’t align now, they won’t later either. That client is unlikely to become an advocate anyway.

Final Thought

This all assumes that you already have the business acumen to understand your clients’ industry, goals, and challenges. But even then, never assume you know what they expect, ask them.

That simple conversation can lead to extraordinary results: repeat business, strong referrals, and loyal client relationships that last.

Because when you understand expectations, exceed them, and stay consistent, your clients will not only stay, but they’ll also bring others with them.

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