Entrepreneur Conversations
Failure is easier to admire from a distance than to describe honestly
Many talks treat failure as a stepping stone with a lesson on the other side. This session asks a founder for something plainer: what they decided, what went wrong, what it cost them and other people, and what they would check now. The aim is not to make failure look attractive. It is to let the room learn from one real account.
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Failure stories are common, and most of them are shorter and tidier than the events were.
A story of failure told on a stage tends to move quickly to its lesson. The decisions, the dates and the people affected fall away, and what remains is a line that sounds wise and is hard to use. A room that wants to learn needs the detail the line leaves out.
The conversation also needs care. A failure can mean a closed business, a debt, staff who lost work, a strained family or a long period of low confidence. The speaker is asked to describe it truthfully and to be fair about the cost, without turning it into a performance or into a case for taking risks lightly.
The session does not claim that failure is good or that it leads to success. It offers one honest account, which the room can examine and ask about.
What the speaker is briefed to be candid about
35 topics across 7 areas. Seven parts of the account, told in the order it happened.
What Was Being AttemptedThe business, venture or project at the time.5
- What it was, in plain words, and who it was for
- Why they believed it would work
- What they had in place: money, people, customers, experience
- What they were confident about, and what they were avoiding
- What others around them thought
When It Started to Go WrongThe first signs, with hindsight set aside.5
- The earliest sign, and when it appeared
- What they made of it at the time
- Why it was explained away or put off
- Who raised a concern, and what was done about it
- What they could have checked and did not
Speakers are asked what was known then, not what is obvious now.
The Decisions Along the WayWhere the account becomes specific.5
A fair account names the founder's own share first. The speaker is asked not to blame named partners, employees or customers, who are not there to reply.
- Two or three decisions that mattered, and the reasoning behind each
- What the alternatives were
- Which decisions they would still make
- Which were wrong, and how they found out
- What was in their control, and what was not
The CostTo the founder and to other people.5
- What it cost in money, in broad terms and with no figures required
- What it cost in time, health and confidence
- Who else was affected, such as staff, suppliers, customers, lenders and family
- What was done for them, and what could not be done
- How long the effects lasted
This part is not skipped. Hearing only about the founder's feelings is not an honest account.
Carrying On or ClosingHow the decision was made.5
- How they decided whether to continue, change course or close
- Who they spoke to, and who they should have spoken to sooner
- What the process of closing or restarting involved, in practice
- What they would do differently in that stretch
- What it took to begin working again
What Went Wrong and Whose It WasSeparating the causes.5
- What was a decision of theirs
- What was outside their control, such as the market, a customer or events
- What they did not know and could have found out
- What they now think the real cause was, and whether they are sure
- What they are still uncertain about
What They Do Differently NowHabits, not slogans.5
- What they check regularly that they used to ignore
- Who they talk to before big decisions
- How they limit what they can lose
- What they would say to somebody facing the same choice
- What they would not want listeners to take from the story
What the founder prepares
- A plain, ordered account of one real setback, with dates and decisions
- A clear statement of what it cost, including to other people
- The warning signs they now watch for
- No blame on named individuals and no claim that failure is a qualification
What the room can ask
- When did you first suspect something was wrong?
- What did you do with that suspicion?
- Who did you tell, and who did you wish you had told sooner?
- What happened to the people who worked with you?
- What would you check now, before the same kind of decision?
How the session runs
The founder describes the setback in order for about fifteen minutes, and the rest of the time goes to questions. Before the day, the speaker is briefed to describe what happened and what it cost, not to reach for a moral, and not to name or blame individuals. Questions can be asked aloud, on paper or sent to the host in advance, and a facilitator keeps the discussion respectful and practical. Because the subject can be personal, the speaker may decline any question, and the facilitator will move on without comment. The length and the group are agreed with the host beforehand.
What your students leave with
- A sequence of decisions and events, not a moral, from one real setback
- The ability to tell apart a founder's choices, bad luck and missing information
- An understanding of the costs of failure, including those borne by others
- A few early warning signs to watch for in your own work
- Questions to put to any founder who describes a failure
- A fairer, less romantic view of risk
Scheduled sessions
Nothing scheduled yet
Sessions are arranged with a college once a date is agreed. Ask us and we will find the right person for it.
A student rather than a college? See what is coming up, or ask your placement team to host this.
Learn from one real account of what went wrong, and what it cost.
Tell us who your students are and what stage they are at. Sessions are free for participants.