The sales process can get mentally frustrating. It could break the strongest and send one on a thought spiral that keeps tightening as one goes down!
It shouldn’t be like this. But it happens to a lot of us who work in the sales and GTM teams.
And here’s why—whenever you hit a roadblock you start thinking that it’s happening to you alone or that this failure is specific to you. What adds fuel to the fire is the constant success stories across platforms like LinkedIn where almost everyone is 2xing their quota, closing million-dollar deals, and going to the Maldives for a vacay!
Hey, I feel you, and that’s why I’m making an attempt to make sure you shouldn’t feel that you’re the only one “struggling” or “failing” among other “successful” people.
I bring to you seven personal narratives of top sales leaders on the rejections they faced, the confusion they had regarding their role and future, and something that made them feel bad but still they carried on.
So, without further ado, let’s begin!
Charlotte Johnson – Account Executive, Salesloft
Want to hear something funny…
I was reaching out to a prospect for over 3 months.
(let’s call him Boris)
Didn’t answer the phone, didn’t engage with my emails & didn’t reply to my LinkedIn messages.
But I know I personalize my outreach and send relevant content and frankly, I know this process works.
So of course continued reaching out.
Once “Boris” got to the end of my personalized tier 1 cadence he went in my nurture one.
Again I know has useful & relevant content throughout.
Luckily this is effortless for me to do as Salesloft allows me to personalize at scale and nurture those who I just can’t seem to get a response from.
But you could see how most people would probably give up after reaching out the first few times, right?
No engagement so they clearly aren’t interested….
Boris replied to me 5 months after I first entered him into my cadence.
And guess what? He has seen all of my outreach & enjoyed it.
But the timing wasn’t right & now it is.
You’re probably thinking where am I getting with this story?
No, I’m not here to gloat about booking Boris in 5 months after first adding him into my cadence as frankly, this happens a lot.
Timing isn’t right for a lot of our prospects but when it is right I’m the one they go to because have been actively staying engaged with personalized & relevant content.
I’m here to remind you that just because someone isn’t engaging with your LinkedIn messages or emails or calls, doesn’t mean you should stop using a certain channel or even give up.
Because chances are, if you’re personalizing & sending useful & relevant content then they have probably seen it but maybe just timing is bad.
We can’t control timing but we can control reaching out consistently.
So keep going for when the timing is good! 💪🏽
John Barrows – CEO at JBarrows Sales Training
This is NOT a post where I’m going to rip someone apart or call them out in public. This is meant to learn from so it can stop happening as much as it does in our Predictable Revenue going-through-the-motions sales world we all live in. This happens every day and all day in our space and it needs to stop.
02/24/22 – SDR from CompanyX starts a cadence with me. The first sentences on a few were “personalized” with something about my blog/podcast which was better than most (good job). One of the e-mails commented on a trip I went on to the Amazon Jungle which showed some extra effort so I responded and agreed to meet with them but set a clear expectation about my interests: “We’re not looking to invest in any new tools but I’d be open to checking out what you have to see if it’s something I might be able to recommend to clients.” By the way, the tool was about lead generation, list building, nurturing, and outbound prospecting which is exactly what we train on.
04/04/22 – SDR/AE transition e-mail sent with context for both me and the AE (good job) but positions it as me wanting to learn about cold prospecting and outreach which is not what I said (didn’t listen). Admittedly I should have responded to clarify but I let it slide.
05/31 – after 2 reschedules (my fault) and persistence by the SDR to reschedule (great job) I had the meeting today. The AE got on the call and did the typical “Thanks for jumping on the call today. I’d like to learn more about your business and what your GTM strategy is so we can find a way to help.” I asked if the SDR had set the expectation that this was more of a partner call vs. a sales call and if they had done ANY prep or research before jumping on with me. The AE awkwardly said yes while fumbling to look at our website trying to articulate their understanding of us but then went back into their canned pitch about wanting to learn more about me and our GTM strategy. It was painfully obvious they had done zero prep and the expectations for the call were way off so I stopped the conversation, expressed my frustration with him/them for not respecting my time enough to even do the most basic of prep, and gave some feedback on how to do this better next time and got off the phone 5 minutes after it started.
People, THIS HAS TO STOP! It happens every day, all day, and it’s embarrassing to our positions/roles, our companies, and the overall profession of Sales. If the SDR had actually listened and set the correct expectations instead of just trying to get the meeting and the AE had looked at our website for more than 2 minutes this wouldn’t have happened. This is also management’s fault for most likely tracking QUANTITY metrics over QUALITY metrics.
Listening, setting clear expectations, and doing 5 minutes of research would have prevented all of this. You don’t have to be a sales genius to give a shit.
Mattia Schaper – Founder, SDRs of Germany
In the first year of my career, I realized that sales is a long game.
And that patience isn’t my strong suit.
I was prospecting this big German retailer for an entire year – sent millions of emails and calls, recorded videos and every time I saw one of their physical stores I took selfies in front of the storefront and sent it to them on LinkedIn. Never got a response back – it was driving me crazy.
In my last working week for the company, I had to admit that I failed. While preparing my account handover, I was even thinking of not mentioning that account because I didn’t want my colleague to see all the failed attempts.
And then I got an email.
They were sorry it took them so long, they had to sort out some internal stuff before meeting me but they were ready now.
For the whole year, I was so frustrated, but that email made me feel like the queen of the world 😂
Niraj Kapur – Managing Director, Everybody Works In Sales
How Long Do You Chase A Client For?
One of my favorite podcasts is Sales Influence by Victor Antonio he’s a powerful motivational speaker and Sales Influence is one of the world’s top sales podcasts.
I wanted to appear on this podcast and share my story, tips, and advice since there are so many people who don’t know how to sell and I wanted to help them sell better.
❌ Rejection 1 – I contacted Victor after my good friend Daniel Disney did a terrific interview. Heard nothing.
❌ Rejection 2 – I sent my interview from another podcast I had appeared on to show the quality I could deliver to his listeners. Heard nothing.
❌ Rejection 3 – I recorded a video giving topic ideas for his podcast. Heard nothing.
❌ Rejection 4 – I promoted the Sales Influence podcast and tagged Victor. He said thanks and no mention of me being a guest.
Most people would have given up. This mattered to me so I wasn’t quitting.
☑️ I heard Victor talk about his love of Samurai. So I Googled Samurai and Business, found several articles, read them, and sent Victor the best one.
☑️ He contacted me to be on his podcast.
It’s the best episode I’ve done out of 180 podcast interviews. Sales insight, advice, techniques, mistakes, and lessons learned. Here are the lessons learned from this experience:
💪 Don’t give up too quickly. Most people do.
✌️ Be creative.
👍 Give massive value
😃 Enjoy the process and learn from it
🏅 No doesn’t mean no forever, it often means “not right now” or “try harder.”
Kyle Coleman – SVP, Marketing, Clari
I was the youngest person at my startup, thinking I had to be perfect to compensate for my lack of experience.
Adding to that pressure was the person sitting directly to my right — the co-founder of Netflix, Marc Randolph.
🤖 I tiptoed on cold calls, staying as close to script as possible.
🤫 I stayed quiet in meetings, diligently taking notes but not contributing to the conversation.
😬 Basically, because I was so focused on not making mistakes, I wasn’t doing my job.
This was not lost on Marc, and he pulled me aside one day:
😎 “Relax, be yourself. We hired you for a reason.”
He told me that not only was it okay to fail, but it was also expected. And that the important part was how you react to failures and shortcomings.
The pressure I was putting on myself lifted, and I started having fun again.
✊ 9 years later, it’s hard to overestimate the impact his words had on me.
If this is you, young buck, take Marc’s advice. Be yourself, try new things, learn from failure, and force yourself to grow.
Holly Allen – Head of Sales Development, Thrive
I remember when I was an SDR at G2, and I had my quarterly review with a couple of senior people.
It was pretty early on in my SDR career and I was saying I really wanted to be a top performer.
One of them asked me “who is the top performing SDR in the US, and what are they doing to be the top performer?”
I couldn’t answer the question because I didn’t know, and I felt really stupid.
How could I say I wanted to be a top performer, but I didn’t know who the top performers were and what they were doing?
How was I meant to know what I needed to do to get there?
So my top tip for SDRs, who want to be the best – look at what the top performers in your business are doing.
Are they doing 100 calls a day? Do 120.
Are they sending 150 voice notes a day? Send 180.
Do what your top performers do and add on 20%.
Daniel Disney – Speaker, Trainer, Author
A sales rep once told me that their sales manager made them go all the way back to a prospect because they didn’t close the deal during the first meeting…
It was the first meeting with the prospect
They had a good chat, built a good rapport and there was a real interest in the product
The lady had said she wanted to discuss it with her husband when he got back, but was confident he would be happy
The sales rep went back to the office, feeling pretty strong about this opportunity
When they got in they were confronted straight away by their sales manager…
“Did you close the deal???”
They told their manager the story, initially feeling that it went well
“Why didn’t you close it? You should have closed it.” they shouted
They then demanded that the sales rep go all the way back there RIGHT AWAY to close the deal
Under immense pressure (and being a young new sales rep), the sales rep went back
After then putting pressure on the prospect, she reminded them that she wanted to speak to her husband, but had now lost all confidence in the sales rep and company
The opportunity was instantly lost
And she probably told her friends about the bad experience with that company as well
Pressure doesn’t work in sales
It doesn’t work on salespeople and it doesn’t work on prospects or customers
Don’t try to force people to buy
Don’t force your sales reps into doing it
Guide and support them through the process
Sometimes people aren’t ready to buy
Look after them until they are
Pressure doesn’t sell, helping does
So We’re Saying
Sales is hard.
The work trips, business dinners, incentives, and the hustle looks glamorous. But that’s not what every single day looks like.
The highs are really high and the lows are heartbreakingly low. There are rejections, and moments of frustration, but that’s exactly what makes the process so rewarding in the end.
I hope these narratives gave you the strength to carry on in case you’re having one of those “bad sales days”.