This guest post was written by Dan Sincavage, the Co-Founder and Chief Strategy Officer of Tenfold.
To navigate the world of sales, you’ve got to be flexible. Time-tested techniques aren’t so tested anymore when the person applying them doesn’t account for the context. And when it comes to context, the business landscape has changed drastically in the last decade or so. Of course, this is not to say that these time-tested gems are useless now but the difference is, these days, you’re required to recognize the nature of challenges and be open to new ways of approaching situations. In this post, we gathered 21 out-of-the-box tips from sales coaches, business leaders, influencers and thought leaders from all over on how to deal with the different challenges that sales professionals face on the daily.

Focus on the second sale

Set your eyes on the referral potential of your prospects and near-close deals. For many companies, the bulk of their business come from retained clients and referrals. Prospects who found your company through a colleague, friend or associate have a higher chance of actually purchasing. Same applies to those who have friends who vouch for you. Ask yourself: Will this be such a satisfactory experience that my customer will buy from me again or tell his friends?”
Work hard on each customer. They’re worth more than their contract size.  

Write down objections

When at a face-to-face presentation for a prospect, you need to play your strongest cards. You’re genuinely interested in what they have to say–but how do you show it? Write it down. When they object or ask questions about your product that you don’t have a quick, solid, and sure answer to, note it down. This gives you time to think as well. Of course, answer their questions and objections by putting forth benefits that are closest to or mimic their eventual use case.

Flex your empathy muscle: Use “feel, felt, found”

When a prospect shoots you with a strong objection, don’t recoil. And, definitely, don’t retort. Keep your calm and show empathy by using feel, felt, found in your response.
I understand how you feel. A lot of my present customers felt the same way. But when they found out how much time they saved by using our product, they were amazed. – Barry Farber
Then ask for an appointment.   Out-Of-The-Box-Sales-Tips-to-End-Deal-Drought  

Stay out of the friendzone

It might sound like a good idea to be chummy with your prospect to get to their good side. However, there’s a flipside to that. Think of your friends. They’re comfortable to dilly dally. They stall out on plans and have no issues with flipping their decisions on you. Obviously, you don’t want your prospects to act like this. So, hold off being friends until the deal closes. Adam Townsend says, “ Never try and make the prospect a friend until the deal closes, you are only making it easier for the prospect to stall, to be vague and excusing their unresponsiveness. Friends are forgiving. Business partners aren’t.”

Cancel meetings not in line with your current goals

Filling up your calendar with meetings that start one after the other is bad for a variety of reasons. There’s stress, the frustration that comes with not making schedules happen, and so on. You need to cross off things that are not a priority right now. Accept it. Do it. You have to empty your plate a bit so you can finish your food. You don’t want to waste opportunities by half-assing.

How about painting?

Most people process visuals better. To put this to your advantage doesn’t really require you to be a Da Vinci! You just need to know how to paint a picture with your words.
The best route to take is to find something in ordinary life to compare the feature to–something that’s relatable to your prospect. When the customer can see how this can work for them IN THEIR MIND – they are sold! – Kim Duke

Go even deeper

It’s a must for prospectors to know what their leads’ struggles are. For complex B2B sales, being acquainted with the intimate details is very important. To best communicate with your prospect, you need to rely on the information you’ve gathered. This way, you can simplify the communication and get right to the heart of the matter. What are their biggest earners? How do they drive revenue best?

Focus on yourself

Okay, before you think I’m out of my mind, hear me out. Sell yourself, not your products.
Understand that your differentiator when positioning yourself to clients isn’t products, it’s you. Not only should superior service be your trademark, but you can also distinguish yourself by company culture. – Mark Sokol

Aim extreme

Do you always accomplish your goals? You might be under-challenging yourself. Skip or get the easier goals out of the way. The purpose of setting goals is to challenge yourself. How to qualify goals?
  1. Challenging but achievable.
  2. Aligned with your career and personal desires.
  3. Fits the core priorities of your current client or company.

Sales leaders: Ask your subordinates

Running out of ideas? Send out a mass email to your subordinates down to the floor. They can be phone reps, field reps, SDRs. Send an email to everyone asking for at least three creative ideas for a certain sales situation. For example, ask them for three cold call opening lines, or door-opening ideas. Compile the list and have someone lay it out on a snazzy PDF. Send it out to everyone. It’s a good push for people to do something new and also a good way to get everyone involved and be team players.

Don’t guess just to appear knowledgeable

Don’t guess. If a prospect has a question you don’t know, it’s okay to say you have to check first. Here’s the tip from TerraCycle CEO Tom Szaky, “If you don’t know the answer, do not guess: People will ask you tough questions, and you may not always know the answer. The person asking you may be testing you, knowing the answer full well. And if you fumble, it’s very hard to rebuild credibility. Do not guess.”

Use props

Want to shake up your demo? Use props. Now before you complain that it’s overly 90s, don’t underestimate the power of doing what’s unexpected. Too many presentations are already boring–differentiate yourself.

Bring food to the table

Struggling to get face time with a decision maker? It’s time to do something really out of the box. Literally bring food. Make sure to bring something irresistible!
Tell the receptionist that you’d be happy to send the food to the office, but would prefer if you could get 10 minutes while they eat. They always feel too guilty to take the food and run. –Adrian Miller

Play hard to get

B2B buyers are so used to salespeople sales tactics bordering on desperation that jogging up the script could work wonders. MarketReach Founder Amanda Puppo shares, “Customers tend to expect pushy, one-dimensional salespeople. Break that mold. Just when the client seems to be at an intractable crossroad, throw down something like, “This really may not be right for you,” or “I’m not quite sure that you’re in the right place now for what I’m offering.” Doing this could help you do a soft-reset on a deadlocked sales call, and even push your prospect towards finally making the decision.

Appeal to the ego

Who doesn’t like to be reminded of their power? Challenging decision makers’ position by asking them if they have the power to make the decision can work toward your way. New York health coach Ellen Reach shares a tip. Here’s a closing spiel she uses for decision-makers, “Some people make things happen. Some people watch things happen, and some people wonder what happened. Which one are you?” Of course, as with any out-of-the-box tip, tread lightly.

Offer yourself as a conference speaker

This works best for small businesspeople who are experts in their niche. First off, hopefully, you’re part of a local group like a chamber of commerce, a meetup group, or even a local mastermind. If not, don’t worry, this tip is still applicable.
By speaking, you position yourself as an expert, validate your credibility and increase your company’s visibility. – Scott Ginsberg

P.S. it

Here’s a tip for emails. Use the P.S. It’s a tool that very few salespeople take advantage of. Emails are a tough nut to crack. And I’m not talking about just cold emails. Sure, cold emails are the pits, but they continue to produce results for many organizations. A lot of professionals focus on getting their emails opened and even answered. The question now is how do we make sure of the email efficiently to communicate the message we have and get the response we want/ You’d be surprised how effective using P.S. for your most important message is. It’s often the first (or sometimes, only!) part of the email most recipients would read.

Get used to waiting

There’s a certain intensity that comes with working in sales. However, a huge part of why we’re always waiting is that in the middle of these waiting times, we often have very limited time to get through to our prospects. It may be a limit to their time, a strict communication policy for cold calls, and so on. Long waiting times can throw you off; it’s true. You fidget and anticipate. During this time, sometimes our minds play tricks on us–makes us think of worst case scenarios or make us more stressed than we should already be. The call comes back or you get called to the office suddenly, and now your energy is all over the place.
Be prepared for waiting. Inevitably, there will be times you are stuck waiting–whether it be for a client or a train. Be prepared for these moments by always having something ready to do. – Jessica Helinski


Stressed out? Nothing good coming out of your calls? You need something to make you feel a bit better. It doesn’t have to be a huge thing–try a random act of kindness. You’ll help someone else and you also feel positive in return. Not sure what to do? Pay for someone else’s lunch? Bring treats to the sales floor and share? Or you can even go try doing it online. Send someone a meal for the night or cross off an item on their Amazon wishlist.
Attitude is contagious. Random acts of kindness help brighten anybody’s day. The person on the receiving end will be pleasantly surprised that you went out of your way and in return, you’ll feel positive from helping another. – Jeff Boss

Schedule your worries

It’s so easy for worrying to take up the majority of our day. There are many ways to cope with stressful situations. And, honestly, worrying might not be the best choice but we all do it. As a result, our productivity drops, we become more stressed, and we don’t even get to begin solving the challenges that stress us out in the first place. To spend more time solving rather than worrying, schedule it. Schedule your worrying. Give it half an hour a day or even a whole hour! Spend it just worrying. Write your worries down. Pour everything into that one hour. You feel like an hour is too much just to stress over a prospect that implied they don’t like your product? Well look back to the past few days of stress and examine how many hours you’ve lost to worrying. What? You’re welcome. Out-Of-The-Box-Sales-Tips-to-End-Deal-Drought