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  • Writer's pictureMichael Clements

Why are outbound sales so hard and what to do about it?

Updated: Sep 9, 2019

Who do I call? What do I say? What if they say yes? If they say no then what do I say? Yes, these are all very valid questions and concerns when engaged in outbound selling. I can empathize, as I once too did not know the answers to these questions. In this article, we will discuss some of the top reasons why cold calling is difficult. Plus we’ll give you suggestions and action items to move your calls further along in the sales conversation and will ultimately lead to more sales.

1) It goes against human conditioning

Anyone who has had a job that incorporates outbound prospecting knows all too well the anxieties that come with learning the craft. From a young age, we were told to not to talk to strangers, not to interrupt, to raise our hands when we would like to speak, to wait our turn in line, and the list goes on and on. Cold calling goes against all this human conditioning. Its uncomfortable and it creates angst and fear; which is not a state that bodes well for success.

Solution: We need to re-frame our thinking around our outreach. First, you chose to call this prospect for a specific reason: your product or solution helps companies just like theirs improve X, Y, and Z. You are calling because you believe you can deliver value to move this prospect to a better place. Even on the toughest days, remember that! One way to reconfirm the why of your outreach is to regularly listen or read through your company’s testimonials. Remembering on every call that your service or product helps companies just like the one you are calling will increase your confidence. I still remember from early in my career a call back voicemail I received after leaving a prospect a voicemail about my company's services, “Hey Mike, thanks for your voicemail. Yes, I would like to set up a time to discuss your software further, give me a call when you can, thanks”. I listened to that voicemail repeatedly to start my days during my first few months as a business development rep (BDR). So please always keep in mind that you are calling for a good reason and these efforts do convert to more qualified opportunities. Be sure to focus on your wins and the value you provide and with practice and good techniques the results will be well worth overcoming the fear.

2) People are busy

It’s 2019 and people are busier than ever. They have more and more people vying for their attention, and there are ever more channels for our prospects to be bombarded with information. We can seem like a speck of dust in the daily tornado of advertising for C-suite executives. Add gatekeepers, direct to voicemail options, and canned rebuttals such as “I am stepping into a meeting, can you call me back” or even better yet, “ok, can you send some material to and we will get back to you?"

Solution: There are a few tips to note here:

  • Your pitch and initial rebuttal handling must be airtight.

  • Accept that you are an interruption so expect and pre plan for a rebuttal or two, and understand that tone and confidence are critical to move into a sales conversation.

The pitch has to be rehearsed and role-played. We all know pro athletes practice more than they play and they never start a game without a warm-up. Well, sales executives are the pro athletes of the corporate sales world. Things happen within split seconds during a live conversation so being well prepared and warmed up will dramatically improve your chances of winning the prospects confidence. Role-playing goes for your top rebuttals as well. Common rebuttals such as; “we have a vendor for that,” “we do that in house,” “Call me back later,” “there’s no way we can afford your solution,” all need to be prepared for and practiced until your responses become automatic. Overcoming rebuttals is such an important component of successful outreach that I will devote a separate blog to that specific skill set and technique.

3) Lack of process

Ok, you re-framed your thinking, practiced your pitch, and got through to your ideal customer profile (ICP), and the call went well. There’s definitely potential for a future conversation, good job! Now here is another area where breakdowns occur. If you are in professional sales, you may have a key performance indicator (KPI) upwards of 250-500 calls a week into over 150 accounts or more. You must have a system and a repeatable process to track all your outreach to be successful. Without a process, leads are destined to fall through the cracks. Additionally, most sales reps don’t use just one channel as phone, email, video email, and social are all typically baked into a robust outbound sales approach. It is simply not possible to remember all of your account statuses without a sales process (also known as sales cadence).

Solution: Implement processes to support and enable sales reps to more easily track and manage their outreach - ultimately, leading to more conversations and qualified opportunities. An example cadence is shown below (by no means the rule, just merely illustrated as an example).

Day 1 (Monday): Email/Call/Voicemail (referencing email)

Day 3 (Wednesday): Call/Email (referencing past voicemail or email)

Day 5 (Friday): Video Email (referencing previous outreach)

Day 8 (Tuesday): Call/Voicemail (referencing video email)

Day 9 (Thursday): Social connect and message (referencing video email)

Day 14 (Monday): Call/Voicemail/Email (referencing the channels of outreach)

The importance of process leads to our next point; leveraging technology and tools to be able to execute a dynamic and personalized sales process at scale.

4) Lack of tools to get the job done

CRM and other sales enabling technologies should become as close to you as your best friends. They are critical in creating and sustaining highly personalized specific outreach at scale. You need to know all the details of your opportunities at a click of a few buttons. Some examples include: company name, industry, location, website url, employees, titles, numbers, emails, was contact made and with who, what was said, what pain did they reveal they are hoping to solve, what parts of your offer were they receptive to, what are the next steps, when was the callback or demo scheduled for, who else in the organization needs to be involved to come to a decision on these types of initiatives, and the list goes on.

Solution: You need a customized tech stack. Each company's stack should be tailored to the organization's needs. In a separate blog I will overview some of the common sales enablement apps and tools available on the market today.

5) Unrealistic expectations

One of the biggest deterrents to success I see on the front lines when it comes to sales is not understanding how important and empowering outbound is to consistent quota achievement. Some people even argue that ‘cold calling is dead’ - fair enough, if that is what they believe. No question that new channels such as social have emerged and some gurus are quick to discredit traditional selling channels (although, you still need an outbound approach when using social). That said, my most profitable channel (aside from inbound leads or referrals) is hands down outbound calls. Think about it - once you hone your skills on the phone you no longer have to wait for prospects to come to you, you can go to them! Sales pros can potentially double (or more) their pipeline by adopting an outbound program. Not to mention the improvements in communication, messaging, and overcoming of fear which boosts self-confidence, self-worth, and further improves performance in many aspects of both sales and life.

Solution: Understand the numbers. Depending on the industry, you will have different conversion rates. From my personal experience in SaaS, I convert around 10% of my calls to a conversation. My conversion to next steps (follow-up call or demo) from these initial conversations is about 15-30%. I provide this range as some days 25 calls leads to 2 demos and some days 150 calls converts to nothing. To put it more simply, if you make 100 dials into a decently curated list, you can expect to have 10 conversations and book 1.5 to 3 meetings. These numbers are hard to digest for many and even were for myself when I first started committing to making them. But think about this; if you can make 50 dials a day (realistically about 2-3 hours) with our previous math that is another 10 SQL’s a month! With an average deal size of say $10K, we are talking an additional $100,000 of pipeline a month, over $1,000,000 a year! This addition to the pipe is on top of the inbound, social, and referral leads you would be working already. (A side note: the metrics above do not include leveraging newly available technology, such as auto-dialers, that can increase your call output by 10x or more.)

6) Fear outweighs skill

When I first became a business development rep (BDR) I didn’t know much. It was rough. I even contemplated quitting after 3 months because the pain of what I considered consistent failure at the time was eating at my self-worth and it seemed to have no end in sight. But the fact of the matter was that I was learning like crazy every day! I was improving at mapping organizations, locating my ICP, getting past the gatekeeper, opening a conversation, using persona-based value props, piquing interest, asking compelling questions, spinning to demos, and booking meetings with key executives or the whole selection committee. It did take me a few months to get to a place where I could book meetings consistently, but that is why I am so passionate about helping other salespeople, I have been there and know you can do it too! We don’t know what we don’t know and we, for sure, often don’t know what we are capable of. Sales and outreach are not taught in school, and as we mentioned in point one, it goes against our conditioning, and frankly, it's hard work with much rejection and adversity to overcome. Just keep in mind that additional $1M in pipeline as you chip away :)

Solution: Frameworks, scripts, role-play (pitch and rebuttals), recordings, practice time and reviews.

Frameworks and scripts are similar but not identical:

  • The framework, to me, is the mental attitude, strategy, and agenda that we go into the call with. It is the understanding of who, why, and what.

  • The script is the delivery. I tend to leave my scripts somewhat open-ended. I currently use a script that is only a few sentences long. I use it to open a conversation with a strong intro, clear value proposition, and a call to action. Once I have engaged, I have had the most success doing just that, engaging in real-time and having a business conversation. New sales reps can have more than a skeleton script for support, and as they get comfortable with the offer and industry, they can scale down the script.

  • Role-play is a must. Role-playing my intro and rebuttals took me from green and hesitant to prepared and confident. This preparation helped with my pace, tone, and allowed me to get loose and have some fun, leading to significant increases in conversions.

  • Recordings are truly where you can dig into the details of your call. If you are not recording your calls, demos, and all sales interactions possible, you will reach a plateau. You sound different than you might think and the sales conversation likely went different than you recall. Things happen too fast, and there are so many situations to remember within a day, week, and month. Recordings will help you realize where you lost engagement, where you stumbled with your delivery, or where you missed a cue from the prospect that you could have used to dive deeper to reveal more pain, etc.

  • Lastly, like becoming an expert in anything, practice, persistence, and patience is essential. You likely won’t be where you want to be within a few days or even a few months. But with constant laser focus and ongoing refinements you will be leaps and bounds ahead of where you would be if you do not adopt a review process for your outreach.

I hope these tips help you in your pursuit of sales excellence. Feel free to reach out and connect with me on LinkedIn or contact me directly at 604.999.0724 /


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