There is zero doubt that being professionally and appropriately funny as can help your cause with prospects. Most prospects (like most people) have enough serious things going on in their life. They could use a smile or chuckle in their day. Of course, your use of humor must come at the right time and be received in the right way.

I see three key takeaways from comedians:

1. Preparation – We know that pre-call planning is important, which I define as you knowing the questions you will ask the prospect (and how they will likely respond), and also you knowing the questions the prospect will likely ask you (and how you will respond). If you watch a good comedian, you will see hours of preparation that went into their act. They would never get up on stage and wing it. Everything is planned. Just like a Navy SEAL, they plan their dive, and they dive their plan.
   
   
2. Storytelling – Any good joke is a story that builds to the delivery of the punchline. The story that tells the joke is building to that moment. The best jokes allow you to put yourself into the story and experience all the emotions that are typically present in a good joke. Great salespeople do the same thing. They present a story that allows the prospect to see themselves in the story… living with the same problems… finding and implementing solutions that solve those problems.
   
   
3. Embrace Failure – Most comedians started off not being as funny as they would eventually become… they had more than a few nights when they were met with a lukewarm reaction from a tough crowd. Perhaps they were even booed off a stage along the way. But they did not quit… they just kept going as they learned from their mistakes, and they chased improvement. When I am asked about the most important attribute that great sales performers possess, my answer is always relentless effort. They just keep showing up. They just keep making dials. They just keep going out to see people. It is hard to keep someone down when they keep showing up to work.

So, there you go… the next time you watch a comedian, ask yourself what you can copy into “your act.” After all, your sales success in 2025 is no laughing matter!

Think about it: What do you need your salespeople to do in the field? Most leaders would say: sell consultatively to build long-lasting relationships. What better way to build that competency with your sales team than to demonstrate it with consultative coaching?

According to Google’s AI tool, “Consultative sales coaching is a type of training that helps sales teams learn how to understand their customers' needs and offer solutions.” Isn’t that exactly what you want your people to do in the field? Think about the individuals on your team and those who consistently produce beyond the expected. There is something more than just their skills that drives their behavior and success. There is the Will to do whatever it takes to achieve their goals and the skill to execute.

Consider this example:

• A lower-performing salesperson without developed consultative skills will present earlier in the sales process than is prudent, before learning about the prospect's problems, consequences, and reasons for buying from them. They likely receive many "think-it-overs" from their prospects after presenting, and their pipeline is full of unqualified prospects.
• A high-performing consultative salesperson uncovers compelling reasons for prospects and customers to buy from them by using active listening skills to ask good, tough, and timely questions. And they do not present solutions until they have a deep understanding of the problems and know that the prospect both must and will fix the problems.

Now let’s apply this to consultative sales coaching:

• A non-consultative sales coach will typically not spend enough or any time debriefing with their salespeople on key meetings. They do not have established coaching hours on their schedule, and they do not know the personal goals of their salespeople, so they do not really know what motivates them. When they talk to a salesperson about how a prospect or client meeting went, they are likely to tell them what to do instead of asking consultative questions like, “What did they say when you asked them what their current provider has done to help them fix the problem?” or “What did they say when you asked them how long the problem had been going on?”
• Sales managers with consultative sales coaching skills will ask many questions and help the salesperson understand what they have not yet uncovered about the opportunity. They demonstrate consultative conversations with their coaching.

Consultative sales coaching matters because it is personal, based on the salesperson’s situation, drive, hopes, and dreams. Sales coaching is crucial for every organization because salespeople who report to a manager with strong consultative coaching skills tend to have 26% more closable late-stage opportunities.

Most sales coaches move up through their company because they are good producers and, because of that, are adept at selling themselves. However, they may not be as skilled at coaching their salespeople. Sales managers need a coaching system so they know when and how to intentionally and effectively coach their salespeople.

Here are the 9 Skills in our Consultative Coaching Skill Development Plan below and the link will take you to a landing page with 9 short audio clips to help you build your skills.

1. Debriefs effectively after significant calls
2. Effective on joint calls
3. Asks quality questions of their salespeople
4. Understands the impact of a salesperson’s Sales DNA
5. Can demonstrate an effective sales system
6. Is effective at getting commitments from salespeople
7. Consistently coaches skills and behaviors
8. Understands the impact of a salesperson’s Will to Sell
9. Is effective at onboarding new salespeople

Find out more about how to be a consultative sales coach here.

My observation of salespeople is that they desperately want to live at the value end of the equation but when push comes to shove, they tend to slide over to the price side to push deals across the finish line.

4 Key Differences

Seth Godin calls discounting price the “race to the bottom.” He has said it is a race you can’t win and that it is a race you don’t want to win. Here are four keys to having success selling value and staying out of the race to the bottom:

1. You must have table pounding conviction in the value that you and your firm provide. You can’t think it might be true. You must know it.
2. You must remember that value it is never meant to be communicated. It is meant to be demonstrated. Said differently, you can’t be going around talking about value and telling prospects how good you and your company might be. You must demonstrate it by having conversations with your prospects that your competition is not having. Remember, if you must tell people how good you are, there is a chance you are not all that good!
3. You must be willing to walk away when your prospect makes it clear that their buying decision is going to come down to price. I have a name for prospects like that – I call them “nonbelievers.” They do not believe in, nor do they have any appreciation for the value you bring to the table. Why spend a ton of time with nonbelievers?
4. Finally, none of the above will work unless you prospect with the appropriate intensity. You must take a “Seven Eleven” approach to hunting, meaning you are always open and working to fill the top of the funnel. It is hard to walk away from an opportunity if you don’t have another opportunity to walk towards.

And no offense to Walmart by the way. It is a fine place to shop. Just don’t try to sell like they do. It is hard to “out Walmart” Walmart!

 

These three qualifying questions will help salespeople sort all of their new business opportunities into two piles. Over on the left is a pile of opportunities that they want to go after. They believe they've got a good shot at winning the business because they are in their niche and in their market, so in the sweet spot. And over here on the right is another pile of opportunities. These opportunities are opportunities that they should walk on by. They're good folks, good men, good women, good businesses, but they are unlikely to leave the provider they're using today and move the business to their firm. 

The problem is of course, weak pipelines make cowards of us all. If there's not much or anything in their pipeline, then salespeople will be content to talk and work with whatever comes their way. It is the equivalent of going grocery shopping when hungry, everything looks good and almost everything makes its way into the shopping cart. So, let's start by looking at these three qualifying questions that will help engage more of the right prospects.  

3 Questions to Ask if You Want to Engage with the Right Prospects

Question #1: Do I want to win this business? 

The question every salesperson must ask themselves is, do I want to win that deal? Do I want that business? Do I want this firm or these people as a client or a customer? Are they going to be easy to work with? Are they going to be loyal to me? Are they going to be a believer in our value proposition? Are they going to have the wandering eye when every other firm offers a cheaper option? Do I want the privilege of working with them? 

That is one of the best things about a career in sales. You get to pick your clients.

 Question #2: Can I win this business?

The answer to this question is largely a function of whether or not the incumbent relationship is breakable. A salesperson must consider, can I win it? They can't win unless there are two things present at the same time. The prospect has a problem, a challenge, an issue that they have to fix. They’ve got to be in front of a company or an individual that has a problem that they absolutely have to fix. They're not kicking the tires. It has become a priority that they have to fix. 

And secondly, they have to be able to leave the incumbent provider. They have to be able, at the end of the sales process, to do what some would consider to be very tough. Does the problem hurt that much or would they rather live with it? The prospect always wants to avoid that difficult conversation of calling Mary or Matt at the current provider and saying, you're done. We're moving over here to another company. A salesperson can't win the business unless they have a prospect with a problem they have to fix. And they're willing to say, Bye-Bye to the incumbent.  

Question #3: How do I win this business?  

Question 3 is a matter of sales methodology and sales strategy. When a prospect says to a salesperson, “I've enjoyed our conversation. I'd love to see you put into writing what you think you can do for us.” That request might be fine, but let’s discuss the evolution of an opportunity. The prospect must have a compelling problem that must be fixed and be willing to leave their current provider. Two steps in the sales process.  But a salesperson must find out if they have the capacity to deal with it – meaning do they have the time, money and resources to take action.  And then a salesperson must make darn sure they are in front of the decision makers and if not, how and when can they meet with them. The how about engaging with prospects is the great pipeline cleaner.  Strong salespeople know that the best time to lose a prospect is today. There are more steps to this stage-based sales process, more than can be covered today.

Bonus Questions:

Another unwritten rule is that salespeople must get very good at talking their prospect’s love language. Their love language revolves around the problems they're having and the potential you have to solve them. What are the future growth opportunities that they might see? That's what they think about all the time. Any executive, any owner of a company, the men and women who put their sweat equity into building something - they're concerned about a lot of things. But at the top of their list are the problems and the things that threaten their business today. And as they look down the horizon around the corner into the next quarter or the next fiscal year, what are the potential opportunities that they would like to seize or take advantage of? These are the questions that will help you engage with prospects. 

In summary, all salespeople are going to lose deals they probably should have won. But there's one thing that is inexcusable and that is not being properly prepared for a sales conversation. That is not a matter of skill, that is a matter of discipline and being accountable and making the decision to pre-call. One way to engage with more of the right prospects is to have a prospect scorecard. A prospect scorecard will put a little bit of logic and methodology to the process.

 

 

 

 

The traditional perspective on cross-selling, if we were in discussion at a training session, would likely involve me asking the participants why we should engage in it. Common responses would revolve around increasing sales, driving market penetration, and enhancing customer loyalty to fend off competition. While these reasons may hold some truth, let’s shift the focus to this question: where is the emphasis placed?

The traditional rationale centers on the benefits to the company – more sales, increased market share, and customer retention. However, there’s a notable absence of consideration for the customer. This observation holds true in our experiences at Anthony Cole Training Group, where, despite our 30 years of engagement in this conversation nationwide, rarely does anyone express that cross-selling and up-selling strategies should occur because they genuinely are in the client’s best interest.

As sales leader, you should lead the charge to adopt an approach that will foster comfort for you and your team and also elevate the quality of the relationships you have built with your customers over time. To achieve this, we must entertain the possibility that the most compelling reason to broach the topic of relationship expansion with a client is the potential benefit to their best interests. It could be that your client is struggling with a problem they need assistance in solving. Here are ten keys to helping your team with client expansion, a much better term for cross-selling or up-selling:

1. Remember the focus is on the client, not you or your company
2. Take a consultative approach
3. Demonstrate empathy
4. Be curious and ask the right questions (takes practice)
5. Engage in active listening
6. Ask if they need your help
7. Be their guide
8. Make it your goal to take care of the whole client
9. Focus on stewardship instead of selling
10. Guide them to make sound decisions

You will encounter doubt and skepticism, no doubt. Your salespeople will likely think but not share the following:

• If I ask for other business, they might think I’m greedy
• I’ll ask for other business after I’ve proven I can do a good job for them
• I’ve already asked them - they said they aren’t interested
• I can’t ask for other business because it might jeopardize my current relationship
• They already have a relationship with someone else that does that for them

If your team truly believes that they are stewards for their clients, many of these objections fall away. After all, by its very definition, stewardship is the job of taking care of something that has been entrusted to you. We will often coach salespeople to “think like the CEO” and ask CEO-like questions. Understanding the bigger picture that the prospect is operating from is always additive. A consultative approach to this will involve asking questions about growth goals of the company or retirement goals for the individual. What is keeping them up at night or getting in their way of reaching their plans? Understanding the environment and industry your prospect or client is operating in is essential. Remember the word “entrusted”.  As you reflect on your team’s success or challenges in the areas of cross-selling and up-selling strategies, have they earned the trust and operated as a steward for their clients? Let’s eradicate the term cross-selling and focus on relationship expansion and serving the whole customer.