Sales Problems Most People Hate Admitting to

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Sales is frequently far from glamorous. There are moments of glory, (I see you President’s club in the Bahamas), but the bulk of our days are far from idyllic. Updating the CRM, forecasting with leadership, client calls, and the bottomless emails can blur together faster than you can order “blue light filtering” glasses on Amazon. Yet most helpful articles, guides, and webinars focus on key themes which, while impactful, ignore the random little things that can make our days so much… “fun.” Yep, the sales problems and solutions most people hate admitting to are the ones we seem to ignore.

Our goal here today is to address situations that are commonly ignored in “best practice” articles because while every rep will likely face these at some point it may only be once or twice a year (or in their career). But just because you may not experience these this week doesn’t mean you shouldn’t be ready! If you’ve lived through the situations below – Enjoy the reminders of when this happened to you. If you haven’t experienced any of these yet, now when you do, you’ll know you’re not alone!

Sales Problems and Solutions

That call took 30 minutes! The prospect would…not…stop…talking

99% of a sales rep’s life is trying to pull information out of prospective clients the same way teachers pull details about cheating from a trio of students who submitted the same paper. But every once in a while, you will meet Jim or Sally. They haven’t spoken to anyone all day and just had a cup of coffee. They’re THRILLED to talk to you about anything except your product. How do you avoid wasting time without being rude?

Pro Tip: This is the one time you should deploy a “Yes/No” question! The limited number of answers allows you to limit their response and immediately pivot to “moving this conversation to email out of respect for your time.” It’s much easier to choose when to engage over email!

I have a prospect who *really* wants to buy, but they’re not a good fit or are below our minimum deal threshold.

sales problems and solutions

Ouch, this one hurts…”It’s free money, ” your brain says. “We can’t do it,” your boss says. The truth of the matter is that many companies need a certain threshold for each deal to ensure deployment, onboarding, and sale process costs are covered. If it doesn’t meet that threshold, you’re not just giving the product away for free but also your time and your colleagues’ time.

Pro Tip: Try phrasing your response like this, “We’ve learned from our customers that it’s impossible to see enough ROI on our product below X deal size. Can I recommend you take a look at these other products that will probably be a better fit? I’d hate to see you end up with a product that isn’t the right fit!”

I lost my laptop/My laptop was stolen/I spilled kombucha on my laptop!

Sadly, unfortunate accidents occur in life. There are legends of laptops stolen out of locked trunks, taken on weekend getaways only to become the victim of their partners’ exploded shampoo bottle and even ones that walked away from the middle of corporate headquarters. Company property will get damaged either through accident or wear and tear. Situations like this are planned for and it’s built into operating budgets. The good news is there’s only one thing to do – and as long as it doesn’t become a pattern you have nothing to worry about as long as you follow this simple pro-tip.

Pro Tip: Own up, notify IT immediately, and be ready for some gentle ribbing/jokes. Companies generally have insurance for situations like this, and as long as there wasn’t gross incompetence, it can’t really hurt you.

My boss wants me to go on this business trip (or buy something) and front the cost on a credit card. However, I don’t have enough money to pay for it and still pay rent while waiting for reimbursement.

This situation is all too common sadly, especially early in sales careers. It’s one thing to go from San Francisco to Topeka for a week where the flight/hotel could be under $2000 for the week; it’s another thing altogether to go to NYC for a week when a hotel alone is likely $2000. It’s easy for management to forget the days when they didn’t have a high credit limit or lived paycheck to paycheck.Regardless, companies don’t issue corporate cards to early career sales reps, leaving you to fend for yourself or face the embarrassment of revealing your financial situation to your boss. At the same time, it is legal for companies to require reps to cover all travel costs up front and submit for reimbursement. When you’re interviewing make sure to ask about travel and expense reporting policies. (Another variant of this is who should pay for your training – your employer or you? This was a particularly interesting discussion on INSIDE inside sales with Andy Paul!)

Pro Tip: If you’re in this situation, I’m sorry. However, there are some actions you can take. Start with reading your company handbook or any documentation around expenses and expense reporting. Know your rights according to your company and country. If you do all your homework and still end up in this situation, tread lightly. Utilize your network and advisors to figure out how to broach the topic with your manager or HR. But in general…try to build up your finances where you can eat a standard business trip knowing you’ll get it back within 90 days. There are a ton of resources to help with financial planning. While you may have learned a lot in school, managing a budget is rarely included so sometimes you need to ask for help.

My call volume is low because I’ve been stuck in training and meetings all day!

sales challenges

Wait…you can’t make 80 dials a day and attend four hours of meetings? All sales reps have to balance training, note-keeping, client-facing activity, and prospecting. Some days start with a team meeting, which turns into back-to-back client calls, then a mandatory “Lunch and Learn.” Then, your boss Slacks you at 2 pm asking, “WHY HAVEN’T YOU MADE ANY DIALS TODAY?!” What’s a busy rep to do?

Pro Tip: Proactively communicate with your boss. If you have clear activity goals, check your calendar the night before and make sure you have time to complete them. If you don’t have enough time, let your boss know BEFORE you miss. That way, they can either tell you what meetings to skip to hit your goals or give you a “pass” for the day.

Learn from Your Experiences

One of the best things about sales is that no two days are the same. It can be routine, but it is never boring. (The buyers won’t let that happen.) While it’s never fun to admit when things go wrong or when you got yourself into an embarrassing situation, doing so is the best way for your team to thrive. Be brave. Be vulnerable. Learn from your mistakes (and the mistakes of others).

What did I miss? What situations have you noticed your whole circle experienced and laughed about over a beer? Would you handle the above differently? Tell us what you think and maybe we’ll add a part two!

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