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Andrew Sykes: These Are Proven Habits for Successful Salespeople

Which habits make the biggest difference in your life and at work?

What are the traps that keep us from becoming true masters of these habits?

Why is empathic listing a key selling skill?

On a recent episode of the Reveal podcast, we connected with Andrew Sykes, CEO of Habits at Work, for answers to these and other questions that are top of mind for revenue leaders.

Key Points to Remember

  1. Deliberate practice with feedback can make the difference between doing things pretty well, and doing things at a level of mastery.
  2. We tend to satisfice—to do things until we’re good enough to get by, and then we stop trying to improve. 
  3. Most sales training is quickly forgotten, seldom implemented, and therefore makes no impact. 
  4. Empathic listening is paying attention to another human being using your entire body, all your senses.
  5. Asking smart questions makes you look more intelligent, increases credibility, and boosts trust.

True Mastery

There’s this big gap between people’s knowledge and their behavior. We tend to say knowledge is power. But what I’ve noticed is everyone has bad habits. Almost everyone has had those bad habits for a while and they know what it looks like to quit those habits. They just haven’t done so yet. 

So what we realized is that there needs to be some deep thinking about the first question, which is, “How do you change habits?” And then the second question of course is, “Which habits should you create that will make the biggest difference in your life and at work?”

And so we started that research project, which was to figure out for people in sales and customer success, what are the habits that distinguish the extraordinary from the merely good? And in the end we came up with this list of 12. We don’t claim that it’s exhaustive or the be-all and end-all, but it is backed by a lot of research and personal experience. 

Most people relate to these habits as completely obvious. They are things like posing the right questions, and listening empathically, and telling stories—many of the things that we as salespeople know to do. 

But like so many things in life, there’s a difference between doing things pretty well and doing things at a level of mastery. And so we are in the business of helping people not only create these habits, but through deliberate practice with feedback, to turn those habits from good into extraordinary.

We think we’re in the business—as sellers and as customer success executives—of helping people make progress in their lives. And what better way to do that than through the art of conversation.

The “Good Enough” Trap

I think there are a number of traps. But the first one is that our minds are so sharp, that as soon as we understand the need for change, we almost tell ourselves that we’ve created the change. So we intellectualize things and assume that the job is done. 

I think the more important issue is we tend to satisfice. And what I mean by that is we do things until we’re good enough to get by, and then we stop trying to improve. 

And my favorite example of that is learning to drive a car. If I asked you to rate yourself on a scale of one to 10 in terms of your driving ability, how good a driver would you say you are?

Most people I ask this question to say seven, eight, or nine. Every now and then someone says 11. And then I say, “What I didn’t do is define the scale. So if a NASCAR driver is a 10, would you still rate yourself as an eight or even above a five?” And most people’s response is, “I guess not.” Because there’s an enormous gap between day-to-day drivers and the real professionals. 

And an interesting question for us is, “What explains that gap?” And we think there are three things. Number one—when we were three weeks into driving good enough to get from A to B, we say to ourselves, “I’ve got this.” And from that point on, we started to drive from A to B on automatic, gaining experience but not necessarily improving. When I look back on my own driving ability, I am no better today than I was when I was 25. In fact, maybe worse because bad habits creep in over time. 

Professional drivers didn’t say, “I’ve got this.” They say, “I want to be great at this!” And as a consequence, they practice with the intention of getting better. They hire coaches to give them the right kinds of performance feedback. And it’s not time in the car but what they’re doing with that time that explains the performance. 

If we bring that back into the work environment, just think about how little time we each get to spend practicing our skills versus using them. Listening is a great example. In the last year, how much time have you set aside to practice listening, versus listening during a meeting or during a sales conversation in order to get a job done? And the answer for most people is not much if any. And that’s why I think we carry on being happy with good enough instead of becoming true masters of these habits.

In our view, unconscious experience is the enemy of mastery…intentional or deliberate practice is the genesis of genius.

Data Breakout—Listening Skills

With so much focus on listening empathically, it only felt right to listen to the data around the concept. 

A study cited in Business Communication: Strategies and Skills found that while most people believe that they have above-average listening skills, the average person listens with only about 25% efficiency. 

Imagine only hearing one-fourth of the words spoken to you every day. Or in other words, “imagine hearing fourth day” (that was 25% of the previous sentence).

Other research shows that only about 10% of us are effective listeners, and it’s mostly because we tend to listen as a form of “waiting to speak” vs truly to understand.  

Practicing the Fundamentals

I think that it’s useful to practice each of the 12 habits, and then to practice putting them together. The analogy I love is martial arts. If you think about learning something like Kung Fu, you spend hours, weeks, and months practicing punches. And then separately kicks. And then separately blocks, and rolls, or whatever the moves are. And at some point you get to start to put these things together into moves. 

And the same is true of sales. At the bottom of it is a set of habits that make you really powerful, if and only if you can put them together into conversations that create these different futures. 

All of those things that we know as the moves of a seller—at the bottom of it all, they’re like the Lego blocks from which great performance is built. And those are the things I would practice—the fundamentals rather than these sophisticated sales moves. 

And we’ve seen the same thing in sales training. We consider ourselves the anti-training company in the sense that most sales training, even when it’s phenomenal, is quickly forgotten, seldom implemented, and therefore makes no impact. 

So our view is, instead of trying to teach people elaborate sales processes and fancy techniques, just work on the fundamentals, and then trust that they’ll put them together really well. 

The three [habits] that are critical…the habit of posing the right questions, the habit of listening empathically to the answers you get, and then be able to share compelling stories that inspire customers to buy and take the steps that you want them to. 

Empathic Listening

We define empathic listening as “paying attention to another human being using your entire body, all your senses.” Yes, of course your ears because you need to hear what’s being said. But with your eyes, pay attention to what’s not being said—the way people are feeling, their body language, their facial expressions—so that you allow yourself the opportunity to feel what they feel, see what they see. And with that, then attend to what you think they need.

Because in the end, what’s the purpose of listening? It’s to enable us to serve other people. And so much of what is said in a sales conversation is said to hide what people are feeling. If a customer’s feeling like they don’t trust you, they’ll say a bunch of things that prevent you from learning what they really care about, or what the real issue is that they’re dealing with.

But if you’re just prepared to be silent, which is the first step in empathic listening, to pay full attention with your whole body, which is the second step, and then recreate what you heard—“What I heard you say is A,B, and C. But importantly, what I think you feel is frustration or maybe irritation. And if that’s correct, what I think really matters to you is having a great relationship with your customers or with your children.”

And if you can relate to people at these three levels of listening—that we recall what’s said, what people feel below it, and what really matters to them underneath it all—the response you’ll get back is, “You really get me, you understand me, you have a sense of the whole world I’m living.”

And I think that’s the ultimate goal of empathic listening. For someone else to say, “You just understand completely.” And given that relationship, why wouldn’t I ask you for help in solving my business problems?


I encourage people to take every sales skill imaginable, and test it out on the people that you love. Because what’s the difference between helping customers make progress in their lives, and helping friends and family make progress in their lives? I think the answer is “not much.”

The Power of Questions

We have this story in our heads that “if I ask a question, I’m going to reveal my ignorance and therefore I’ll look bad,” where the research says exactly the opposite is true. You look more intelligent. You’re more likable because you give people the opportunity to speak about the thing they love the most—themselves. 

And what a great outcome [it is] that questions lead to a credibility and a trust boost. I’ve come to summarize that research by saying, “Sometimes having all the answers is not the best answer.”

Questions are an expression of caring, because you care to learn, you care to listen, you care to be curious about someone’s life, work, and challenges.

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