What is a poke the bear cold email?
A poke the bear cold email asks one neutral question about a problem the reader may not know they have, and leaves the pitch out. Josh Braun, who teaches selling through books, courses and workshops, set the idea out in Ditch the Pitch. Poke the Bear, published on joshbraun.com on 12 August 2021. The question Braun tells sellers to start from: "What do you know that your prospect might not know that can hurt them?"
Braun sets two kinds of question side by side:
- Leading questions push the prospect towards the answer the seller wants, such as asking whether they would be interested in making more money. Braun says these put prospects on the defensive, because prospects know they are being boxed in.
- Neutral questions get the prospect to think differently about their current solution. In a 9 October 2021 post, Braun calls them illumination questions and says they don't prompt a desired response: the prospect is left to make up their own mind.
Braun's examples each point at a risk inside the reader's current way of working, without naming the product: a buyer who may be overcharged for shipping, a company that runs motor vehicle record checks every quarter and may miss violations between checks, a company hiring salespeople whose good interviews may still turn into bad sales hires.
What should replace the meeting request?
A question. Braun's Cold Email CTAs (19 November 2021) lists asking for time as the thing not to do, with examples such as offering two time slots or asking for a quick 15-minute conversation this week or next. The thing to do instead is to poke the bear: end on a question that gets prospects to think differently about their current solution. In 8 Reasons Why Prospects Aren’t Responding to Your Cold Emails (14 October 2021), asking for time is reason five, and Braun's replacement for a request for 30 minutes on Friday is two words: "Worth exploring?"
Here is how Braun's own posts treat each way of ending a cold email:
| How the email ends | Braun's advice | Braun post, date |
|---|---|---|
| Ask for a time slot or a quick call | Don't | Cold Email CTAs, 19 Nov 2021 |
| End on the poke-the-bear question | Do | Cold Email CTAs, 19 Nov 2021 |
| A two-word interest check | Gauge interest before asking for time | 8 Reasons, 14 Oct 2021 |
| Ask whether an email exchange makes sense | A low-friction ask that gauges interest instead of assuming it | Let's Write a Good Cold Email, 21 Sep 2021 |
| Ask for 20 minutes to hear a different perspective on a goal the prospect has | How to word it when you do ask for a meeting | How to Ask For a Meeting, 25 Dec 2021 |
Three of the four posts say not to ask for time in a cold email, and two of them say to gauge interest first. When Braun does ask for a meeting, in the 25 December 2021 post, the request is framed around what the prospect wants: a different perspective on a goal they already have.
How do you write a poke-the-bear question?
Start from how the prospect does the job today, then find what that way of working can cost them. These five steps follow Braun's posts.
Write down the current way
Braun's Poke the Bear Generator page (15 June 2025) shows an example output: a persona and a solution go in, and out come the job to be done, two current methods, the new way and five questions. Do the same for your buyer on one page.
Name the cost of doing nothing
In Pitching vs. Poking (18 August 2021), Braun compares two cold call scripts for the same product. One is focused on what the product is; the other on the cost of inaction. Write one sentence on what the current way costs when it fails.
Pick a question shape
Four shapes appear in Braun's posts. How do you know... asks about a hidden risk. Just out of curiosity, how are you... follows a short problem statement in Braun's poke-the-bear cold call script. If you don't mind me asking, how are you currently... gives the prospect an out; Braun suggests it for cold calls in a 20 October 2021 post. The generator's questions list the current methods and the new way side by side and ask which one the prospect uses.
Check it is neutral
If the question has an obvious right answer, it is a leading question. Remove any wording that assumes they have the problem or tells them how to feel about it.
Cut the email to five lines
Braun's Crispy Cold Emails (17 August 2021) lists five lines or less as one mark of a good cold email. Open with something you noticed about the prospect and move your name to the end, as Braun suggests in a 15 August 2021 post. Our cold email opening lines give you starting points.
Three poke-the-bear versions for a small B2B product
The product, names and emails below are made up for this post to show the method. They are labelled examples; none is a real email from a real company. The product: a tool that tracks domain, SSL certificate and hosting renewals for every client website a web agency looks after. The reader: the founder of a 15-person agency.
That draft describes the product, leans on the kind of generic save-time line Braun's 8 Reasons post marks as generic, and asks for time. Three rewrites, one per question shape:
Each version ends on the question, as Braun's CTA post suggests, and none asks for a call. If Jordan replies, that is the moment to explain what the tool does.
How to A/B test the three versions
Change one thing, the question and the line that sets it up, and hold everything else fixed. This test plan is ours: Braun's posts give the method and don't include a test design.
| Part of the test | What to do |
|---|---|
| Audience | One segment, such as web agencies with 5 to 50 staff, split at random into three equal groups |
| What changes | Only the poke-the-bear question and the line that sets it up. Same subject line, sender, signature and send days |
| How many | At least 100 people per version. At 100 sends, each reply moves the reply rate by one percentage point |
| What to count | Positive replies (interested, or asking a question back) per person emailed, 14 days after the first email. Log negative replies and unsubscribes separately |
| Follow-ups | The same follow-up for all three groups, or compare replies to the first email only |
| Decision | Keep the version with the most positive replies, write a new challenger and run again |
Small numbers mislead. If version A gets four positive replies and version B gets three, treat it as a tie and keep sending. Our rule of thumb: wait until the leading version has at least ten positive replies before you call a winner.
If you send through Siela's AI SDR, the first email is your own template, sent with each person's name, company and title filled in, and each run's leads are saved in their own CRM group. To keep the subject line identical across all three, pick one from our cold email subject lines.
Which mistakes turn a poke back into a pitch?
Here are five, each drawn from a Braun post, with a fix:
- A leading question. If the question only has one sensible answer, rewrite it as a how question about their current way.
- Generic gains. Braun's 24 November 2021 post says saving money is such an overused promise that it puts prospects straight into resistance, and suggests naming a specific loss instead. Braun links this to loss aversion: people tend to prefer avoiding losses to acquiring equivalent gains.
- Talking about yourself. The 8 Reasons post flags an I-to-you ratio of 7:1 and lines about what you do instead of what the prospect can do.
- Too long for a phone. The same post asks whether you can read your email on your phone without scrolling.
- Bumping the thread. In the 15 August 2021 post, Braun says bumping an email to the top of the inbox often reminds people why they didn't reply. Make one chess move per email instead: each follow-up raises another problem you solve. More in our guide to following up without being annoying.
Frequently asked questions
What does poke the bear mean in sales?
In Josh Braun's sales training, poking the bear means asking a neutral question that gets a prospect to think differently about their current solution, usually about a risk or cost they haven't noticed. Braun pairs it with ditching the pitch, and Braun's 2021 cold email posts say to gauge interest before asking for time. The joshbraun.com post that sets out the idea, Ditch the Pitch. Poke the Bear, is dated 12 August 2021.
Is poke the bear the same as asking a leading question?
No. Braun treats them as opposites. A leading question nudges the prospect towards the answer the seller wants, and Braun says prospects get defensive because they can tell. A poke-the-bear question is neutral: it asks how the prospect handles something today, or how they know a risk isn't happening, and leaves them to draw their own conclusion.
Should a poke the bear cold email ask for a meeting?
Not at first, going by Braun's 2021 posts on cold email calls to action. They say not to ask for time and to gauge interest first, either by ending on the poke-the-bear question or with a short interest check. When you do ask for a meeting, Braun frames it around what the prospect gets, such as a different perspective on a goal they have.
Can you poke the bear in a follow-up email?
Yes. Braun's advice on follow-ups is to avoid bumping the original email, which often reminds people why they didn't reply, and to show another way you might help instead. Each follow-up can poke at a different problem your product solves, one per email, which Braun calls making one chess move per email.
How many emails do you need to A/B test a poke the bear question?
Braun's posts give no number. Our rule of thumb is at least 100 people per version from the same segment, sent in the same week, and no winner until the leading version has at least ten positive replies. At 100 sends, one reply moves the reply rate by a full percentage point, so small gaps are mostly noise.
Sources
- Josh Braun: Ditch the Pitch. Poke the Bear (published 12 Aug 2021 (page metadata))
- Josh Braun: Cold Email CTAs (published 19 Nov 2021 (page metadata))
- Josh Braun: 8 Reasons Why Prospects Aren't Responding to Your Cold Emails (published 14 Oct 2021 (page metadata))
- Josh Braun: Do You Ask Questions That Make Prospects B.S. Meter Go Off? (published 9 Oct 2021 (page metadata))
- Josh Braun: How to Ask For a Meeting (published 25 Dec 2021 (page metadata))
- Josh Braun: Let's Write a Good Cold Email (published 21 Sep 2021 (page metadata))
- Josh Braun: Pitching vs. Poking (published 18 Aug 2021 (page metadata))
- Josh Braun: Poke the Bear Generator (published 15 Jun 2025 (page metadata))
- Josh Braun: How Uncover Problems Without Prospects Feeling Defensive (published 20 Oct 2021 (page metadata))
- Josh Braun: Crispy Cold Emails (published 17 Aug 2021 (page metadata))
- Josh Braun: Stay Away From These Four Phrases In Cold Emails (published 15 Aug 2021 (page metadata))
- Josh Braun: 95% of Salespeople Don't Need to Overcome Objections, They Need to Poke the Bear (published 24 Nov 2021 (page metadata))
- Josh Braun: About (checked 20 Oct 2026)