What I learned about why people buy after interviewing 30 Basecamp customers

My grandma’s toaster was terrible.

Only one side worked, the coils were dim, and it suffered from premature popping.

But despite its many shortcomings, I was never able to sell my grandma a new toaster.

See if you can figure out why.

Here’s why I told my grandma to buy a new toaster:

  • Faster. Dark toast in 2 minutes vs. 7
  • Cheap: Only $30
  • Better: Two pieces of dark toast

And here’s why my grandma didn’t buy a new toaster

  • Slower. The hassle of learning a new TUI (toaster-user interface)
  • Unnecessary expense (money doesn’t grow on trees ya know)
  • Not better: She only eats one piece of toast and likes her toast light.

So why didn’t grandma buy? After all, my reasons made sense, right?

You can’t tell people why they should buy.

At every turn my toaster opportunity was doomed to fail. That’s because I was telling my grandma my reasons for getting a new toaster.

But no matter how good my reasons where they weren’t Grandma’s reasons.

People buy for their reasons, not yours.

Buyers vs. seller’s point of view

Yet most sales conversations are based on the salesperson’s point of view rather than the buyer’s point of view.

For example, here’s the structure of a typical sales conversation:

Build rapport, discovery needs, qualify, present solution, get commitments, follow up, close the sale

The intent is to move prospects through a sales funnel. But “move through the funnel” energy causes prospects to retreat because it’s different from how they buy (more on that later) and often feels “salesy”.

If your prospect feels like they’re being “sold” or “manipulated” they won’t tell you what’s really going on in their mind which can really gunk up a pipeline with stalled opportunities.

But if your sales conversations create an environment where your prospects feel safe and not sold to, they’ll relax and tell you the truth about their situation. Get more truth and you’ll spend spend less time hoping and chasing.

But how do you create environments that foster truthful conversations when a) only 3%* of people consider salespeople trustworthy? and b) sales reps are hard wired to progress people through sales funnels?

And what do truthful conversation sound like anyway? And how do you have one? (Spoiler alert . . . they are based on the buyers point of view, not the sellers.)

(*a conservative estimate)

The Jobs to be Done Interview

I learned what truthful conversations felt like when I interviewed 30 Basecamp customers using something called the Jobs-To-Be-Done framework (JTBD). And it forever changed my approach to having sales conversations.

The JTBD framework is an interview technique that lets you travel back in time and observe the circumstances that caused people to buy.

For example, here’s the timeline of circumstances that caused the CEO of a digital agency to buy Basecamp.

The Timeline

January: 2 clients. Uses whiteboard to manage projects.

February: 4 clients. Brings on a remote project manager. Switches to Excel & email.

March: 8 clients. Hires 2 more remote employees.

April: Things slip through the cracks. Files aren’t in one place. Clients complain.

May: Tried Asana. Low adoption. Switches back to Excel and email.

June: Lands high profile client. Wants to be more buttoned up. Tries Basecamp.

July: Fast adoption. Buys Basecamp. Everything in on place. Clients are happier.

To buy or not to buy: push & pull vs. anxiety & habit

What took the CEO so long to buy Basecamp?

Let’s look at why the CEO didn’t buy Basecamp in February:

  • Their struggle or “push” wasn’t intense. They were making progress with Excel.
  • There wasn’t a strong force “pulling” them towards something better.
  • There would have been “anxiety” around learning a new process (cost and time)
  • Excel and email (their habit) was comfortable.

In February “anxiety & habit” were stronger forces than “push & pull” so they didn’t switch to something else.

If this was expressed as a line of code, it would look something like this:

IF anxiety & habit > push and pull THEN don’t switch ELSE switch

Now let’s fast forward and look at why they bought in July

  • The “push” or struggle became more intense because things started falling through the cracks. Then, clients complained. Then they got more clients. And more employees. And finally, more work.
  • There were stronger forces “pulling” them towards something better (Asana & eventually Basecamp).
  • Their “anxiety” lessened when they tried Basecamp because it was adopted quickly.
  • They broke their Excel habit when they tried Basecamp because it was easy to make progress.

In August, the push and pull was greater than anxiety & habit so they switched.

How JTBD insights become revenue

JTBD interviews force you to look at your product through the eyes of the “jobs” your customer needs to get done.

For instance, here are some of the jobs people hired Basecamp to do:

  • “Get everyone on the same page.”
  • “Put everything in one place.”
  • “Feel more connected and aware of what is going on in the office when I’m away.”
  • “Stop drowning in an endless chain of email.”

Armed with these insights, Basecamp could use the customer’s language in their marketing messages to attract similar customers. You can see what this looks like on Basecamp’s website.

Using JTBD to have more truthful sales conversations

One of the first things I noticed about JTBD was how quickly customers opened up and “got real” about their circumstances and struggles. You could feel their emotion and energy. It was as if I’d been their friend for 5 years.

JTBD interviews were the opposite of how my sales conversations felt.

Now I know what you’re thinking. These were customers not prospects. So of course, conversations felt more chill and relaxed. There was no sales pressure. No expectations. No quota to hit.

That’s all true.

But I was beginning to wonder. What if I used the JTBD interview technique to create an environment where prospects felt safe. What if I “showed up” merely to interview and guide not to move people through a funnel. Would a conversation like that clear out the gunk in the pipeline and stop the chasing?

The purpose of a JTBD sales conversation

The sole purpose of a JTBD sales conversation is to know the prospect’s truth which is:

  1. “Yes, I am open to continuing the conversation, sharing more to see if we’re a fit and possibly learning about your offering.”
  2. “No I am not interested right now.”

Your goal isn’t to move people through a funnel. Or get to schedule a next step. This is a pretty drastic mental shift. But my hypothesis is by leaving the “funnel” energy behind, you’ll create a safer environment leading to more truth. More truth equals less gunk in the pipeline.

A guide to start your Jobs to Be Done sales interview

Part 1: The warm up

Research shows that starting conversations with just 5 minutes of authentic and genuine small talk begins to build trust. (Trust is something that builds over time, but here’s where it starts.)

Here are a few warm up questions:

  • I noticed that you climbed Mt. Kilimanjaro (topic the other person is interested in). Why on earth Lisa?
  • Impressive client roster you folks have. What makes you such a badass VP of Sales Bob? (find out what makes your prospect special).
  • What was the best part of your weekend? Do anything that would make me jealous? Do tell (story your prospect can tell)
  • What are looking forward to this week?
  • Never been to Colorado. Why is it amazing?

I read somewhere that you should think of warm up questions like a metal detector. Go through them until your prospect starts going “beep, beep, beep”. Then get even more curious by following up with something like:

  • “Really?”
  • “Tell me more.”
  • “What do you mean?”

One caveat. If you’re not genuinely curious about the person you’re speaking with, skip this step. Prospect can smell “fake curiosity”.

Part 2: The preamble

Confirm time

Lisa, I believe we have 30 minutes carved out. Does that still work for you?

Share agenda

What I find works best is if I take just 60 seconds tell you how we help CEO’s of digital agencies be more awesome.

Then I’d like to turn the tables and take 10 minutes or so to interview you so I can learn about your situation.

Based on your responses I’ll give you some guidance if I think I can help you get what you want.

After that you can decide if it makes sense to continue the conversation. And it’s perfectly OK if the answer is no.

Lisa, that’s what I was hoping to do today. Anything else you’d like to cover?

Your 60 second story

So, hi again. I’m Josh. And I’m a sales consultant who helps CEO’s of digital agencies between 1–5 million in revenue get more of the clients they want to work with. I’m different because, I not only provide the strategy, technology and process but also the specific words to use in your outreach campaigns, sales conversations and pitches.

Transition to interview

So, that should give you a sense of how we help, but more importantly I’d like ask you a few questions about your situation so I can best guide you if I can. At certain times, I may dive deep and ask you detailed questions about a situation. There are no right or wrong answers. You can think of it like we’re filming a documentary and we trying to get all the details right.

How does that sound? Great. Let’s begin.

Part 3: The interview

Find the motivation

  • Option 1: What changed at ACME that prompted you to jump on a call today?
  • Option 2: Typically, people talk to us because they want to feel more connected and aware of what’s going on in the office when they’re away or they want to make their teams more self sufficient. Do any of those resonate with you?
  • When did you first start thinking about that?
  • What triggered you to start thinking about it?

Understand where they’ve been

  • What have you tried?

Find out where they want to be

  • Tell me what better looks like 6 months from now.
  • What does a home run look like?

Understand motivation for switching (if any)

  • Why not just keep doing what you’re doing?
  • Why not do this in house rather than hiring a consultant?
  • Is there any urgency around this? Why?

Part 4: Summarize

Thanks for being so open about your situation. Let me take a moment to see if I understand.

The reason you decided to chat today is . . .

Where you want to be tomorrow is . . .

You’ve tried . . .

Am I tracking?

Part 5: Recommend

Three paths:

  1. Anxiety & habit > push and pull. Or their challenges don’t ladder to your offering. Part ways. “Based on my current understand I don’t think we can help you now because . . .”
  2. You know something else that can help. Point them in the right direction. “We can’t help you because . . . but I know another firm that can. If you’d like I can make an introduction.”
  3. Sounds like a fit. Ask permission to continue the conversation. ” Based on my current understanding, we might be fit. Would you be open to seeing how we might help you . . . (what they want to move away from or towards?)”

Part 6: Have the appropriate sales conversation

Once you’ve completed the interview, you should be able to identify where your prospect is on the timeline:

Satisfied: “I’m making progress. I’m very satisfied.”

First thought: “What we’re doing isn’t working as well anymore.”

Event #1: “That event that just happened (hired remote employees) made things worse.”

Actively looking: “I’m going to invest some time and see what’s out there.”

Event #2: “We need to act quickly. The high profile client we’re about to bring on will have higher expectations.”

Deciding: “I’ve narrowed it down to a few options.”

Buying: “I’ve committed to purchasing.”

Your conversation will vary based on where your prospect is in the timeline.

Here are a few scenarios:


This is the no-pitch zone. You have two option here:

  • Circle back in a few months in case circumstances change.
  • Educate prospects on what’s possible.

Educate prospects on a better tomorrow

A great example of educating people on what’s possible is Basecamp’s Way to Work Workshop. Prospects get to spend the afternoon with Jason Fried and see behind the curtain — how Basecamp communicates internally, how they decide what to do, how they divvy up work, etc. In other words, people get to see how they could be more awesome in the future. This forges a strong emotional connection between the “teacher” and the “student”.

“You will attract way more buyers if you are offering to teach them something of value then you will ever attract by simply trying to sell them your product or service.” — Chet Holmes

But what if you’re not Jason Fried?

What can you make your prospects smarter about? How can you show them what a better tomorrow looks like during a sales conversation if they’re “satisfied”?

Instead of a deck or demo, put together a few slides that show your prospects what’s possible.

Here are few examples:

A step by step process for getting “sh*t” done

How remote software teams resolve conflict

Then ask, “so, what do you think?”. Then be quite.

First Thought

These prospects realize they’re struggling but may not be ready to do anything about it. You can waist a lot of time here if you don’t know the right question to ask.

Here’s a question you can ask that will give you a sense of how open your prospect is to changing:

“On a scale of 1–10, ten being ready now 1 being not ready, how ready are you to try try something new?”

Most people will respond with something greater than a 1, which means they have some motivation. Now you want to find out more about their motivation. So follow up with:

“Why didn’t you choose a lower number?”

This might seem counter intuitive but phrasing the question in a “negative” way will allow your prospect to find their own reasons for change. Studies have shown that people are more likely to act for their own reasons not someone else’s reasons. The idea behind this question to to help people find their own reason for taking action. (Instant Influence, Michael Pantalon)


If your prospect is deciding, your conversation might sound like this:

Since you mentioned your struggling with getting everyone on the same page, let me show you how we do that.


Do you think this would give you what you want?

How does that compare to how you’re doing things today?

Part 7: Find out how/if they want to proceed


Lisa, where would you like to go from here?

This question gives people autonomy. And autonomy lowers sales pressure because it gives people the freedom to choose the next step (if any).

If the prospect says they need to speak with their boss you could ask:

Would it make sense to connect after you’ve spoken with Jill?

Other clients at this stage have found it helpful to pull in IT because of the technical questions that come up. Do you think that make sense for you folks?

The idea is to ask questions that give people the freedom to choose the next step or slow down. Whenever I’ve forcefully dictated a next step prospects usually end up canceling. You can’t make someone do something they don’t want to do. (Plus dictating next steps feels sorta “icky”.) These questions slow things down and allow the prospect to move forward on their timeline. Pressure is created when you’re going faster than your prospect wants to move.

If your prospect doesn’t agree to an advance, they might not be ready for change right now. Not a problem. This helps you waste less time chasing.

Above all, check how you “show up”

While interviewing prospects, it’s helpful to think of yourself as a documentary film maker rather than a salesperson trying to get a next step. Be genuinely curious. Your prospects will feel your “safe” energy and will be more open to reveal the truth about their struggles, anxieties and what a better tomorrow looks like. And spend less time chasing.



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