Entrepreneur Conversations
Most owners learn to hire by hiring wrongly first
A small business is its people long before it is anything else, and the first few hires carry most of the weight. In this session a practising entrepreneur describes how they actually built a team: who came first, how they were found, what went well, what did not, and what changed in how the founder works. The room then asks what it wants to know.
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Hiring is where many owners meet their first expensive mistake, and few talk about it.
Most people who start a business have not managed anyone before. They hire in a hurry, often a friend or a relative, and learn what they should have asked only after the person has started. The cost of a wrong hire is more than money. It is time, trust and the other people on the team who notice.
Management books speak about teams in general terms. A founder can say what it was like to be the person making the decision with little time and no experience. They can describe the first hire, the first person who left, and the first time they had to say something difficult.
The session does not offer a method. It offers an honest account from one person, which the room can compare with its own situation.
What the speaker is briefed to be candid about
35 topics across 7 areas. Seven parts of building a team, taken in the order most owners meet them.
Working Alone FirstBefore there was anyone to hire.5
- What they did themselves, and when it became too much
- How they decided it was time to bring someone in
- What they were afraid of about hiring
- What they could and could not afford
- What they expected a first employee to do
The First HireUsually the most instructive one.5
- Who it was and how they were found
- Why that person, and what they hoped for
- How it went in the first months
- What they would ask differently now
- Whether it was a friend or relative, and how that shaped things
The speaker describes the experience in general terms and is asked not to identify former or current employees.
Finding and Choosing PeopleWithout a human resources department.5
The speaker describes their own practice and is not asked to give legal or compliance advice. Rules on employment differ by place and size, and the room is encouraged to check what applies to them.
- Where they look for people, and where they have stopped looking
- What they ask in an interview, and what they learned to notice
- What they check, and how
- How they decide between skill and attitude, and when each mattered
- What they do before and during a trial period
Training and TrustHow work was handed over.5
- How people were taught the work, and who taught it
- What was written down, and what lived only in the founder's head
- What was hard to hand over, and why
- How they learned to let someone make a mistake
- How much supervision turned out to be right
Pay, Roles and ExpectationsKept general, with no figures required.5
- How they thought about fairness in pay, without stating amounts
- How roles were explained at the start
- How expectations were set, and what happened when they were not
- What they changed as the team grew
- What they wish they had agreed in the first conversation
No salary figures are requested, and the speaker is not recommending what anyone should pay.
When It Did Not WorkWrong hires, difficult conversations and departures.5
- A hire or an arrangement that did not work, described without names
- When they first knew, and how long they waited
- What the difficult conversation was like
- What it did to the rest of the team
- What they now do sooner
Keeping People and Changing RoleWhat the founder learned about themselves.5
- Why people have stayed, and why people have left
- What the founder does now that they did not do alone
- The part of managing they find hardest
- How their own day changed as the team grew
- What they would tell a founder about to hire for the first time
What the founder prepares
- A short account of how the team came together, in order
- One hire that worked and one arrangement that did not, without names
- What they check or ask now that they did not at first
- A willingness to say that another owner might do it differently
What the room can ask
- How did you decide whether to hire a friend or relative?
- What did you get wrong with your first hire?
- How do you know someone is right in the first month?
- What do you do when a person is not working out?
- What do you handle yourself that you wish you could hand over?
How the session runs
The founder speaks for about fifteen minutes from a few notes, and the rest of the time goes to questions from the room. A facilitator keeps the conversation moving and can ask the first question if nobody does. Before the day, the speaker is briefed to describe their own practice without naming current or former employees, not to give legal advice, and not to promote their business or recruit from the audience. The length and the group are agreed with the host in advance.
What your students leave with
- A realistic account of how one small team was built, in order
- An idea of what a founder looks for in a first hire, and why
- A clearer view of the mistakes new employers commonly make
- Understanding of how a founder's own role changes as people join
- Questions to ask yourself before hiring the first person
- A sense of how a founder thinks about keeping good people
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.
Hear how a team is really built, including the hires that did not work.
Tell us who your students are and what stage they are at. Sessions are free for participants.