Skip to content
All posts

How to Be a Memorable Salesperson Part 6: Take Risks

In a research study with 530 B2B buyers, we gathered information about buyer experiences with sellers. In related research, we collected over 500 stories from sellers about their own personal best in selling.

Every single one of the sellers’ stories had something in common. Most of the buyer examples about preferred sellers suggested the same common ingredient, too.

In all these recollections of extraordinary sales and preferred sellers, there was an element of change required. There was an obstacle or a challenge that loomed large. What got remembered and appreciated was the sellers’ efforts to improve the situation.

So, how to be a memorable salesperson? Buyers notice when sellers take chances and are unafraid to try new things. In some of the buyer comments, the seller did not succeed. Nevertheless, those sellers’ efforts were remembered.

Related posts:

How Will Taking Risks Help Me Be a Memorable Salesperson?

Of course, we’re not talking about extreme risks or unnecessary ones. This isn’t about throwing caution to the wind.

Risks involve:0301 - tightrope-1

  • Trying a new way to connect with someone you can help.

  • Asking for help and admitting when you don’t know an answer.

  • Doing more than the bare minimum to show you care.

  • Not taking the easy “yes” if it’s not the right thing for the buyer.

  • Boldly asserting your opinion even if it may not be easy for someone else to hear.

  • Owning responsibility for errors made and taking swift actions to make it right.

  • Attending events or meetings where you don’t have all the answers and are there to learn.

  • Incremental changes that add up to innovations in how things are done.

  • Pushing back against policies or practices that no longer make sense.

  • Inviting feedback and remaining open to self-improvement.

These smaller risks can become part of your regular routines. They will build up your risk tolerance for times when a bigger risk looms large.

What makes a risk-taker memorable is that people admire in others what they are afraid to do themselves. Asking for feedback, for example, can be daunting. It makes you vulnerable. When a seller asks “What could I be doing differently that would make it easier to work with me?” buyers appreciate the opportunity to voice their concerns. And, just as important, they admire the seller who asked the question because they know it wasn’t an easy one to ask.

You’ll be memorable for taking the risk AND memorable for getting results from those risks.

What Can I Do to Step Outside My Comfort Zone With Buyers?

Don’t believe the myth that all sellers are fearless and somehow imbued with superior levels of confidence. Sales call reluctance, fear of rejection, and resistance to change are real struggles for many sellers. You’re not alone if the basic work of selling still seems risky to you.

Start by identifying what feels risky to you. Then take these preliminary steps to move through the risky situation. Do it over and over again until it doesn’t feel as risky.  

What You Fear or Feel
Is Risky

Baby Steps to Start

Cold calling and hearing another “no” when asking for a meeting Remember in sales that “no” often means “I don’t know enough to say yes.” Look for ways to provide more value and relevant information before asking for a meeting. And don’t forget that every seller hears a lot of “no’s” for every one “yes.”  
Meeting with someone and being rejected Put yourself in the buyer’s shoes. You say “no” to sellers, too. Why? It’s because you don’t see value in what they offer. It’s not personal. Remember that: It’s not about you.
Hearing an objection An objection is an invitation to provide more information. It represents a gap in the buyer’s understanding of what you’ve offered. Make the links between what they value and what you have to offer.
Making a presentation to a group No matter how large the audience, they are all just people. They are thinking about themselves more than they’re thinking about you. Talk about them and the spotlight will no longer be on you.
Not understanding what the buyer talks about You can’t know everything. No one expects you to. Instead of worrying about “looking stupid” plan to look curious and interested. When something comes up that you don’t know about, ask. Simply say “I’m not very familiar with ______. I’d really appreciate an explanation about it.”  Buyers don’t mind explaining. They do mind dealing with posers.
Being exposed for not having answers/info You’ll get questions from buyers that you don’t know how to answer. Don’t make stuff up. Record the question and go find the answer. Get back to the buyer in a timely manner. They won’t think less of you for not knowing. They’ll think more of you for taking the time to give them a solid, reliable response.
Asking for the sale Buyers are often confused when sellers don’t ask for the sale. You’re not doing them or yourself any favors when you offer something like “I’ll give you some time to think about this and call you in a week or so.” The time when they’re most likely to say “yes” is when the value is clear and compelling, when you’ve presented your solution effectively. ASK.


We often avoid risk because we are afraid of the consequences.

Have you considered that inaction – not taking the risk – also has consequences?

Wouldn’t you rather go down fighting? Wouldn’t you rather be able to look back and say “I gave it my all. I tried everything I possibly could”?

Wouldn’t it be nice to have a starting point for next time that is not the same as last time?  When you take risks and fail, you fail forward. You learn from the risk and the results. You become stronger from it because you acquire new information, new skills, and new confidence for the next time around.

Risk-takers become more confident because they know they can survive failure and even become better because of it. That, too, makes you more memorable.

How Can I Learn More About Taking Risks and Failing Forward?

The mindset and behaviors associated with getting outside your comfort zone and pushing beyond the status quo are more often associated with leadership than with selling. To work on these skills, you may want to explore books about being a leader. I’d recommend Learning Leadership by Jim Kouzes and Barry Posner or Stop Selling & Start Leading, the book I co-authored with them to bring leadership into sales.

You’ll also find a few webinars about this on The Sales Experts Channel. Take a look in the archives section called Sales Competencies for content that is inspiring, educational and related to challenging yourself in new ways.  

If you struggle greatly with risk-aversion, check out the work of Margie Worrell. Her videos and books will be gamechangers for you.

And don’t forget to work on additional ways you can become more memorable,:

  • Stick with this series to read more about buyer research and field observations with sellers.

  • Check out this video playlist on the People First PS YouTube Channel with more tips and research with buyers. There are 25 videos there, each one lasting just 3-5 minutes.

  • Read the book that started it all. DISCOVER Questions® Get You Connected is packed with ways you can make yourself more memorable to buyers. It was ahead of its time in bringing research with buyers directly to sellers.

Whatever you decide to do, make a commitment to become more memorable. Standing out in a crowded sea of sellers is a surefire strategy for boosting your sales success.

New Call-to-action

The CONNECT2Sell Blog has been discontinued as our focus has shifted to leadership at every level. Research with buyers demonstrates that buyers respond favorably when sellers show up as leaders. If you'd like to step into your full potential as a leader (and boost sales!), take a look at our free and affordable courses on