"Sell me this pen." That might just be the best sales one-liner in history.

It's a favorite for sales professionals from used car salespeople to Wall Street wolves. And for good reason — it's an exciting, accessible way to test a salesperson's fundamentals. How someone responds to those four words can tell you a lot about how — and how well — a candidate is going to sell.

Why Ask a Sales Candidate to "Sell Me This Pen"?

Over the last 10 years, I have seen many sales leaders use this question as part of their interview process to whittle out the "can-dos" from the "can-nots." There are generally three standard responses to this question — each of which illustrates one of the three selling styles typically used by salespeople.

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The Value-Added Approach

The first of the three is known as value-added selling, where a candidate attempts to create interest by highlighting the various features of the product that make it desirable. They may say something like:

  • "This pen is gold — that positions you as a person of value to your peers."
  • "This pen has refillable ink cartridges, so you'll never need to buy a new one."
  • "Compared to other pens, this pen is very smooth and comfortable to hold."

The majority of people without selling experience will utilize this method. That figures; it's probably the most straightforward. But that's not to say that everyone who takes this route is inexperienced. Even those who have received thorough sales training may succumb to the pressure of an interview and lead with comments along these lines.

The problem with value-based selling is that you show zero knowledge of what the buyer feels is important to them. You're making blind inferences with your assertions of value. To put it bluntly, you're shooting in the dark. If you're lucky, one of your guesses will stick, but this approach just doesn't cut it in one of my interviews.

The Solution-Based Approach

The next evolution in this method is solution-based selling. This is when a candidate successfully asks me questions about what I look for in a pen and if I have any problems with my current one. Then, they build the case that this pen will solve my needs.

  • "What is the most important thing for you when it comes to buying a pen?"
  • "What color pen are you in the market for?"
  • "What were the strengths and weaknesses of the last pen you owned?"

Candidates with an enterprise sales background normally demonstrate a strength in this area. However, many of them still hit a roadblock when the questions they ask lead to a conclusion where the customer needs a solution they can't offer.

For instance, you can find out a customer is in the market for a pen, but they may need a red one when you're only selling black. Plus, there's no guarantee a buyer will keep answering your questions. They might not even have any interest in talking about their problems with someone they don't know.

The solution-based approach is better than the value-added one, but there's still a good chance it'll take you nowhere. That's why I always look for reps who demonstrate the third technique.

The Problem-Creation Approach

Problem creation — without question the best way to "sell me this pen."

Instead of asking open questions, reps who use this tactic establish a clear "ladder" for buyers to follow using questions which make them concerned about problems they didn't even know about in the first place.

With this approach, the buyer arrives at a pre-set conclusion which the sales representative has orchestrated. This is the best possible outcome. Any rep who can successfully take this route has the kind of grip on the sales process every hiring manager wants to see.

That being said, this outcome is a rarity. Reps who can successfully use the problem creation method aren't easy to come by.

How HubSpot Sales Reps and Partners Respond to "Sell Me This Pen"

We asked a few HubSpot sales reps and HubSpot partners how they would respond to this interview prompt. Here's what they had to say.

Sarina Kowaguchi, Inbound Growth Specialist, North America, SMB, HubSpot

For me, it always comes down to knowing your prospect and custom-tailoring your sales approach based on their specific needs and goals. You can't sell a person the benefits of your pen without any context. If you pitch them benefits that they don't care about, you're just throwing pasta at the wall hoping something will stick.

Additionally, if they aren't experiencing any frustrations with their current pen situation or don't have ambitions to improve their current state, you may be trying to sell something to a person who will never buy.


Before I even begin pitching my product, I would ask my prospect questions along the lines of:

  • Why are you in the market for a new pen (or why aren"t you in the market for a new pen)?

  • What kind of pens do you currently use?

  • In what scenarios are you using their pens and are there any pain points associated with your current pen choice?

  • What does an ideal pen look like to you?

  • Are you evaluating any other potential pens?

Information is everything — when you have enough data or insight about how a prospect thinks and what they are looking for, it helps you sell the value of your product in a way that is relevant to them.

Sharen Murnaghan, Channel Account Specialist, Dublin, Solutions Partner Program HubSpot

When I worked in Yellow Pages, we were taught that the sales process was "the logical thought process a buyer (prospect) goes through before making a positive decision to buy". I believe this still holds true — the most successful salespeople think differently. These salespeople want to collaborate with their prospects to enable them to make this positive decision to buy. These salespeople want to create opportunities for the buyer to solve problems they didn't even know they had.

So when a salesperson is asked to "sell me this pen," typically they will respond with one of the following approaches.

The first approach is value-based, meaning they will focus on creating interest in the benefits of the pen.

"This pen has refillable ink cartridges, so you'll never need to buy a new one."

"Compared to other pens, this pen is very smooth and comfortable to hold."

The second approach is solutions-based — these salespeople will focus on the features of the pen and hope that they hit on a solution it might solve.

"What color pen are you in the market for?"

"What were the strengths and weaknesses of the last pen you owned?"

A third approach, which I believe is most impactful, is based on identifying a problem for your prospect and positioning the offer as the solution. Salespeople who do this are often successful because they think differently.

They see the sales process as a collaborative process that both buyers and sellers go through together to help the buyer to make that positive decision to buy. These salespeople create insights and ideas with their prospects so that the prospect will realize a problem they didn't even know they had.

Once the problem is realized, this salesperson will collaboratively work with that prospect through their logical thought process and present an opportunity to them that will solve the problem.

"When you get married, how will you want the thank you cards to look when you sign them?"

"When delivering your presentation to the board, how would you like your 'pointer' to represent you?"

Tim Jones, Founder & CEO of Eternal Works, HubSpot Solutions Partner in Virginia Beach, USA

In the days when I went in for interviews, I'd take a notepad and pen to take notes.

If someone asked me to "sell me this pen" today, I'd ask to see the pen.

Then I'd take a few seconds to examine it, scribble something down on my notepad as if I were taking the pen for a test drive.

Finally, I'd ask the person to write down a few things they look for when buying a pen. As they go to reach for the pen, I'd say, "So you're obviously admitting you need a pen right now; would you like this pen? It might be for sale."

Rajathurai Nagarajah, Senior Business Development Manager, Tank Utility

Raj, uses the use case approach:

"(Prospect name), when"s the last time you used a pen? Oh, this morning? But you mistakenly snapped it due to all your at-home workouts paying off? Ugh, it was your favorite pen because of its flashlight and multi-ink features? Well, there are several pens, we offer — flashlight pens of all styles that have been trusted by people since 1982.

Would you be interested in learning more?"

Mintis Hankerson, HubSpot Sales Manager SMB, NA

In 2020, customers care most about efficiency and convenience. To sell anything in 2020 I would ask about current state vs. future desired state. Gap selling is how things are sold today. Customers want a sales rep to identify apparent gaps and consult them on how to fill them.

Buyers need to know the impact of filling the gap and the quantifiable pain that investing in a solution will resolve. If I were to sell a pen today, I would ask:

"I'd love to hear how you are using your pen today versus how you would like your pen to serve you in the future?"

"How are you taking notes today? How much time do you spend taking notes?"

"What are your greatest pain points in the way you use your pen today?"

Based on how your prospect answers these questions, you can then position the pen as a solution to the pain points and gaps in their current experience and then highlight how this pen is going to be the difference-maker to help achieve the desired future state.

If a prospect is content with their current pen experience, that is when the consultative part of your job starts. Talk about how other people are able to perform better because their pens serve them and help them work efficiently.

How to Answer "Sell Me This Pen"

When I first started asking this question, I noticed that it drew a number of cliché or pre-prepared responses. It makes sense though. I would say a solid majority of the sales community knows this example at this point. That's why I started bringing a pair of sunglasses to my interviews.

I would keep them next to my notepad and the candidate's resume as they presented. At one stage in the interview — normally toward the end — I would place my iPhone carefully on the middle of the table and say, "Sell me these sunglasses."

I would get a number of responses, most of which would fall into one of two buckets:

  • Value-based selling: The candidate would try to sell me on all the exciting features these sunglasses had to offer. They'd emphasize something like the glasses' polarized lenses or high-brow brand name.
  • Solution-based selling: The candidate asks me questions about my daily life to see if the product could potentially solve any of these for me, such as, "Do you have trouble seeing while driving?" or "Do you like to go to the beach?"

None of these candidates were nailing the question. In fact, it took a full 34 interviews before I found the unicorn.

After I asked this candidate to sell me my sunglasses, they sat there in silence and didn't ask any questions. Seeing the iPhone, they simply turned on the flashlight, shone in my eyes, and said, "How would you like some sunglasses now?"

Needless to say, they got the job, and I know I made the right call. They went on to be one of my highest performers and most loyal employees.

That's the kind of mentality you need to bring to the table if you really want to "sell me this pen." Get me thinking of a problem I didn't even know I had: a problem that only "this pen" can solve. If you can do that — and do it compellingly — you're the kind of salesperson hiring managers are after.

The moral of the story? A good salesperson can solve a problem a buyer can see, but a great one can solve a problem a buyer didn't know they had.

Editor's note: This post was originally published in March 23, 2017 and has been updated for comprehensiveness.

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Originally published Jul 7, 2020 12:45:00 PM, updated July 07 2020

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Sales Hiring