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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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.

Why Sales Accountability Matters

Most companies want accountability but focus on the wrong metrics. They track closed sales as the main measurement. The problem is that closed sales are lagging indicators. Looking only at closes is like driving while staring in the rearview mirror. You see what has already happened, but you miss the predictive activity that drives future success.

Instead, we need to measure forward-looking metrics such as:

• Prospecting dials made

• Appointments set

• Appointments kept

• Second meetings scheduled

Tracking these activities gives sales leaders critical ratios, such as dials to first appointments or dials to closed sales. With this data, you can set intelligent goals and begin to coach true sales accountability.

Coaching at Every Step of the Process

Effective managers track and inspect each step of the sales process, from initial calls to proposals and closes. When you hold salespeople accountable for activity, you gain the ability to predict outcomes with much greater accuracy.

For example, if Jane typically averages 15 calls for every closed deal, but she is only making 10 calls, it is no surprise she is missing her goals. Without accountability to her ratios, she cannot improve.

The Role of Consequences in Accountability

Tracking numbers only works if the data is used to hold people accountable to promised goals. This requires tough conversations. Ask each salesperson:

“What will happen if you do not reach this goal? What are the consequences if you don’t achieve Extraordinary?”

This shifts responsibility back to the salesperson. If Bill shrugs and says, “Maybe next month,” you may not have the right person in the role. If he is serious, he will connect his missed goals to personal consequences such as financial strain or delayed family plans.

Eliminating Excuses in Sales

Excuses are one of the biggest barriers to accountability. In Objective Management Group’s assessments, about 66% of salespeople admit to making excuses for poor performance. They blame the company, the competition, or the market instead of taking ownership. Left unchecked, this mindset lowers standards across the organization.

Consider this example: Jane misses her call goal because she was busy handling operational issues. She blames the company. Your response should be, “Jane, if I did not let you use that as an excuse, what would you have done differently?”

This question forces her to think through the problem and identify what must change. It removes the option of excuse-making and reinforces accountability.

Building a No-Excuses Culture

Sales accountability is a full-time job. Excuses will always surface in new forms, so train yourself to recognize them and respond consistently. Practice using the critical accountability question:

“If I did not let you use that excuse, what would you have done differently?”

Use it often and you will notice how quickly it changes the tone of conversations. Over time, it helps create a culture where salespeople own their results, and managers can coach to meaningful behaviors instead of debating excuses.

FAQ: Sales Accountability

What is sales accountability?
Sales accountability is the practice of tracking and inspecting key sales activities, then holding salespeople responsible for meeting their promised goals and activity levels.

Why is sales accountability important?
It creates predictability in sales results, eliminates excuse-making, and ensures salespeople focus on the right activities that drive revenue.

What metrics should managers track for sales accountability?
Instead of only tracking closed deals, managers should monitor calls made, appointments set and kept, second meetings, proposals, and conversion ratios.

How can managers address excuses from salespeople?
By using the accountability question: “If I did not let you use that as an excuse, what would you have done differently?” This shifts responsibility back to the salesperson.

How does sales accountability improve sales performance?
When salespeople know they will be held to activity standards and ratios, they adjust behaviors proactively. This increases consistency, accuracy in forecasting, and overall sales growth.

Why Sales Habits Matter

As an educator by degree, I learned early on that behaviors and habits are shaped by rewards and consequences. Developing effective sales habits follows the same pattern.

• Good habits contribute to the achievement of your goals and objectives.

• Bad habits take you further away from those goals.

• Consistency depends on your level of commitment. If you are serious about long-term success, good sales habits stick.

• Lack of consistency often signals a lack of true commitment.

• Winning is a habit. Unfortunately, so is losing.

Often the habits that matter most do not feel urgent. Exercising, eating well, getting enough sleep, prospecting, or blogging may not demand your immediate attention. But they quickly become urgent when a crisis hits, such as a health scare or being placed on a performance improvement plan.

Your sales habits are a direct reflection of your commitments.

5 Steps to Better Sales Habits

If you want to improve your results, here are five steps to building better sales habits:

1. Identify goals and objectives that are non-negotiable.

2. Create a detailed plan to achieve those goals.

3. Use a system to track your progress and the activities that lead to success.

4. Inspect what you expect. Regularly evaluate whether you are on track.

5. Find an accountability partner who cares enough to hold you responsible.

Developing strong sales habits takes discipline, but the rewards are worth it. When you focus on building consistency, your actions align with your goals and long-term success follows.

Frequently Asked Questions about Sales Habits

1. What are sales habits?
Sales habits are the consistent actions and behaviors that help salespeople reach their goals. Examples include prospecting daily, following up with leads, and tracking pipeline activity.

2. Why are sales habits important for success?
Strong sales habits create discipline and consistency. They keep salespeople focused on the activities that drive results, even when motivation fades.

3. How long does it take to build new sales habits?
It often takes several weeks of consistent effort to form a new habit. The key is commitment and accountability to stay on track until the behavior becomes routine.

4. What are examples of bad sales habits?
Bad sales habits include inconsistent follow-up, failing to track activity, avoiding prospecting, and letting distractions replace high-value selling tasks.

5. How can I stay consistent with good sales habits?
Use a clear plan, track progress daily, and partner with an accountability coach or manager. Commitment to long-term goals helps make sales habits stick.