5 Habits of Successful Salespeople
Jake Dunlap
“My number one, most successful habit of top performers is to be creative and break stuff.”
Early in my career, I found that I had a thick skin and the “personality” for sales. I started out at a telemarketing company, after all. And you had to be able to roll off getting hung up on.
But a few years later, I really started to understand the sales process when I started at a company called CareerBuilder.
From the stages of telemarketing to sports sales to an AE to enterprise sales to management and leadership and some other things in between – there are five habits that I developed over my career that allowed me not only to be successful but accelerate success.
Throughout this session, I’ll give you real-world success stories from my own experiences and take a couple of really great questions from the crowd, such as: “What is the best way to manage up to leadership that sees being creative as a detriment?” and “How would you shape your week as a relatively new SDR targeting new business and looking to get promoted in the next four months?”
Three of the habits I’ll cover will help you see success in your current role, and two will help you manage your career to the next level. Let’s get into the specifics.
- Be creative and break stuff
- Utilize your team
- Be confident
- Create an 80/15/5 mindset
- Plan ahead for the next steps in your career
Recap: My 5 Habits of Successful Salespeople
The important bits:
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- 2:40 – The number one, most successful habit of top performers is to be creative and break stuff.
- 7:30 – Once you establish a baseline of success, something that works, then start to iterate and get creative.
- 9:24 – Great salespeople are great quarterbacks. They realize it’s not their job to play every position.
- 12:21 – Loop CS in early. The main reason that you lose deals is “no decision.” Your main competitor is not some other person. It’s “who’s going to own this?”
- 14:12 – There’s a difference between confidence and being cocky or arrogant. Confidence comes from preparation and knowledge.
- 15:00 – Don’t prep for the rose-colored glasses meeting – prep for the meeting where everything goes wrong.
- 17:53 – You should know more about your product and industry niche than the buyer.
- 19:00 – The 80/15/5 Mindset. In my daily and weekly activities, 80% of my time is spent on things that are going to impact the near term (2-3 weeks), 15% of my time is spent on things to impact the mid-term (1-3 months), and 5% of my time is spent on things that will make me more successful in 6 months to a year.
- 22:10 – Do things today to make the life of your future self easier.
- 23:20 – What to say to leadership when they won’t let you be creative.
- 26:43 – If you’re looking to get promoted, know that your manager doesn’t promote you. Your manager’s manager/boss promotes you.
- 33:33 – I didn’t get an MBA to put MBA on my LinkedIn profile. I went to learn.
- 36:03 – Do the work to round corners 2-3 years in advance. Do things today to make yourself sharper down the road.
Be creative and break stuff
The number one, most successful habit of top performers is to be creative and break stuff.
Let me give you an example. In my very first post-college job, I was at the Tampa Bay Rays, who at the time were the worst team in major league baseball. I was selling season tickets, premium tickets, and suites.
Back then, the inbound phone loop was basically a circle of us (an old-school version of the round robin). If my counterpart was on the phone and I wasn’t, the inbound call would skip him and come directly to me. At the end of the season, I looked at our CRM and did a scatter chart of every single inbound phone call that converted from the previous season. I found these spots right before lunch, 11:00 to 11:30, and later, from 2:00 to 2:30 and 4:00 to 4:30, when nobody called in.
So I thought, why don’t I make all my cold outbound calls during those times? Starting that next day, I’d start cranking my calls during those times because I knew statistically that people were less likely to call in then.
So then what happened? I was getting routed all the inbound calls because my counterparts were on the phone making outbound dials.
After two or three days of this, people started to notice and asked, “Jake, what are you doing? Why are you getting all the inbound calls?”
I pulled up my spreadsheet and showed them that I discovered these are the time slots where people are less likely to call inbound. I told them they were more than welcome to do the same, and statistically, they should be doing exactly what I’m doing.
Guess how many of them did it? None. Then about two or three weeks later, they changed the phone tree system.
That was when I started thinking about what I could test and what other creative things I could do to make my job easier.
First, though, you have to establish a baseline. Today this may manifest itself in A/B testing. Once you establish a baseline of success, something that works, then you can start to iterate. But you can’t test too many variables because then you won’t know why something worked.
So my number one habit of highly successful salespeople is not to be these crazy creatives that are always trying new things. You have to first start with a great baseline. And then test new things to get better.
Audience Question: “What is the best way to manage leadership that sees being creative as a detriment?”
Here’s what I’ve done in the past that has worked. I would go to my boss and say, “Hey, John, I already know that I’m good at executing the baseline.” (Note – First you have to earn the right to have the conversation. Once you to the baseline, then go to your boss.) “I have a few ideas for ways that I think can actually make us next-level successful. They won’t just impact me. I think they’ll help the entire team. So here’s what I’d like to do. I know that there are minimums that I need to do. I will do those, but I also want to use five to ten percent of my time to try a couple of new things. And if in three to four weeks, it’s not working, I’ll go back to a hundred percent of the other stuff. Does that work for you, John?“
I’ve never had a leader say no to this.
Utilize your team
The number two habit of successful salespeople is knowing how to utilize your team.
You don’t need to do it all, especially for any of you out there doing mid-market or enterprise sales. Great salespeople are great quarterbacks. They realize it’s not their job to play every position.
I think back to one of the successful moments early in my career, I was 29 in San Francisco, and our North American CEO said, “I just heard the CEO of Intel speak. Hit them up and set me up a meeting.”
It was a tall order to fill, but I reach out like I’m told, and do you think I tried to book the meeting with myself? No, I leveraged my CEO, and sure enough, a week later, we ended up getting a meeting with the VP of Talent Acquisition for Intel.
At this level, I didn’t try to set up meetings with just myself. I just set meetings for my leaders. The chances of me being able to hold my own as an enterprise rep with the VP of Talent Acquisition for Intel were very small – and the same in other cases.
All of you, your VP and CEO are happy to get on the phone and close a big deal. They are happy to fly out and meet with a VP of what could be a million-plus dollar account for you/them.
Another thing I learned is that the main reason we lose deals is “no decision.” Your main competitor is not some other person. It’s “who’s going to own this?”
So, why do companies get to that point?
After you put together your proposal or pitch, people get in a room together and say, “Who’s going to own this?” And then the person who was your main champion is thinking they have a lot on their plate, and they don’t want to own it. Maybe sometimes they’ll go to bat for you. Sometimes they won’t.
What I found is that when you bring the customer service team in early, they will be the ones to say, “We’re going to take care of this.”
Before all these people would get into a room and make their final decision, we’d say, “Let’s talk about go-live. The best part is our team will do all the work.” Then we’d walk our clients through the process. This doesn’t mean our team was actually going to do the work. It meant our team was going to own and project manage it.
Utilize your customer service team. Bring them to that call. Let your clients think, “I’m going to be taken care of. They’re going to make sure I’m successful.” So when they get in that meeting, there are no questions about ownership or people trying to push off ownership.
Be confident
If you’re thinking that you want to be more confident, but you don’t want to seem too cocky or arrogant, stop thinking they’re synonyms. I feel like so many people have this twisted. There’s a difference between confidence and being cocky.
For me, confidence comes from preparation and knowledge. Anyone who has worked with me can attest to this. I am a preparation monster. If we have a big meeting coming up, we are going to prep our faces off. We are going to role-play every scenario that could possibly happen. That way, when I get in the meeting, I’m free to execute. I’ve already thought about what could happen and am confident in our solution.
If you ever think in a meeting, “Ugh, I knew Larry was going to ask me that,” then why didn’t you prep for it? It actually shocks me how salespeople get into sales calls and are surprised by some question or objection they’ve heard many times before. Why are they surprised by it? Prepare for it. Expect it.
I don’t prep for the rose-colored glasses meeting. I prep for the meeting where everything goes wrong. I prep for the meeting with the most demanding buyers I will ever meet.
Confidence comes from my ability to be present. It comes from my preparation, research, and knowledge about the industry.
Another thing I want to point out is sounding confident. Don’t say things like, “Is now a good time?” or “I really appreciate you taking the time to meet me. I know you’re really busy.” It says that your time isn’t as valuable as theirs.
Instead, try this, “Hey, I’m excited for the conversation, John. I’ve done my research, and here’s what I understand, but I want to spend the first five or ten minutes to clarify. Each of our clients is different in terms of how they think about XYZ.”
Buyers are put off when they hear you sound desperate or overly thank them. As humans, we think that if someone over thanks us for their time, the chances are that it will not be a high-quality conversation.
You are the expert. You know more about your product and the industry niche than the buyer, or you shouldn’t be selling it. Go sell something you can do that with so you can have smart, confident conversations.
Create an 80/15/5 mindset
This next one, I think, will really impact your lives. It’s called the 80/15/5 mindset.
What does this mean?
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- 80% of my time is spent on things that will impact the near term. That could be the next few weeks, the next month, or six weeks.
- 15% of my time is spent on activities that will impact the midterm – about three to six months from now.
- 5% of my time is spent doing things that will make me more successful six months+ from now.
For example, we’re probably launching our startup sales school in September. At this point, it’s in the 15% bucket because I know it’s probably not going to really launch until October. So I’m spending an hour today planning for it. It will not impact anything now, but it could impact things in four or five months.
What’s a 5% activity? That might be my January 2023 goals. What are the things that I want to make sure that I have accomplished personally? I have an hour blocked out for that.
Let me tell you the recipe for disaster.
If you constantly spend 90 to 95% of your time on things for the present, you are guaranteeing your future will be horrific. I call this being on the hampster wheel.
You also need to think about the skills that you will need. If you’re not that good at executive conversations, then every week spend an hour talking to executives or understanding them more.
Plan ahead for the next steps in your career
When CareerBuilder opened up a program for me to get my MBA, I was a frontline sales manager at the time.
I didn’t need an MBA then, but I knew that if I wanted to get a better perspective and understand business better, I would.
Then, going into my third year at CareerBuilder, I started thinking, okay, what’s the next promotion for me?
The next role for me was probably an Area Vice President, and I would need enterprise sales experience. I knew that if I wanted to go and lead men and women who were 15 to 20 years older than me, I had to be able to walk the walk. I couldn’t just fake or conceptually say this is how you close an enterprise deal. So I left my management job and went back into the field for a year.
Here’s where this leads to.
At this point, I’d been with CareerBuilder for almost four years. I loved the company, but Glassdoor came knocking. There were 20 people at Glassdoor at the time, and nobody in sales. I interviewed and said these are the things I’ve done over the last three years to get here. I earned my MBA, I have enterprise sales experience, I have successful sales leadership experience, and a proven track record in sales.
They were in the late stages with a few other people, and I got the job because I started putting in the work years before.
My boss didn’t have to tell me to do this. Your company is not 100% responsible for your professional development. You are.
But you should find companies that will invest in you as CareerBuilder did.
I began to do the work to round corners two to three years in advance. I didn’t know that it would lead me to become a VP of sales at a company that became a unicorn. But I did know my own skill set. I knew where I was strong and where I was weak. And I started to do things to make myself sharper down the road.
So what’s your next, next step? What are the things that you’re going to do over the next X years? What do you actually want to do? Is this actually the right path for you? That is thinking two to three years ahead.
To recap the habits of successful salespeople
Number one, be creative and always start looking for the next thing.
Number two, utilize your team. It is not your job to get every single part of the sales process. I think of it as expert project management. Because once I know the players that are involved, I can then say, okay, we need Lucy on this call and Johnny on this call.
Number three, be confident when you talk to people. Make sure you sell a product that you care about so you can be confident.
Number four, the 80/15/ 5 mindset. 80% is spent on the now, 15% is spent on the next three to six months, and 5% is spent on the long term.
Number five, you have to start to think ahead. What are you doing today to prepare yourself? You have to start doing the little things now to be ready when the opportunity comes.
That’s it, do these five things, and I promise you, you’re going to be wildly, wildly, wildly successful.