Flaky People in Start-Ups

A friend recently asked me, “How do you deal with flaky people when you’re in start-up mode?”

My answer: Don’t.

When you’re just starting up a new business, the people you choose will be absolutely critical to your long-term success. These are the seed people, the grandparents of your business, the ones who will set the pace for generations to come.

A start-up requires an incredible amount of work. It’s not for the faint of heart. A flaky person is not someone with a strong heart—at least, not for your business. Why would you want someone who only cares half-heartedly about success?

There are exceptions, of course. Perhaps that person’s skills are extremely rare. Or that person is already loaded with prior commitments. What do you do then?

Then it becomes a matter of motivation and task management. I’ve already written about motivation. Here are some tips on managing the tasks of a flaky person.

(In this definition, a “flaky” person is one who is unreliable, may not complete tasks on time, and may even forget some of those tasks.)

  • Be clear and direct about expectations. Put them in writing (an email is fine).
  • Get that person’s buy-in on tasks. Have that person agree (verbally or in writing) to the tasks.
  • Set clear timelines and deadlines. Make this schedule visible to the person.
  • Communicate often, even to the point of over-communicating. Repeat the tasks and deadlines.
  • Hold regular, predictable, and frequent checkpoints. The checkpoints can be short and succinct.
  • Give feedback immediately to the person, especially if performance is an issue.
  • Have a back-up plan for an alternate resource.

In my opinion, working with a flaky person in a new business is very, very risky. Personally, I wouldn’t do it. But if you have no choice, hopefully these guidelines can help. Good luck!

Author: Mike Lee

An idealistic realist, humanistic technologist & constant student.

5 thoughts on “Flaky People in Start-Ups”

  1. Thank you for posting this. I don’t think people realize how important it is to be honest in starting a business. I seem to attract the flakiest people, and have had to learn to really speak the truth up front. I just had a guy go behind my back and find another partner for an agreement that I reluctantly agreed upon only verbally, to create a GOOD website for him. I always got kind of a flaky feel from him. And had asked him to sign a contract. I should have known by his initial reaction, and by the fact that he is a real estate agent, that he just wasn’t thinking in the same reality as I am. I will never believe in the ability or the desire to change peoples minds to do better business with them. They either know exactly what is fair and realistic, or they don’t.

    Thanks again!

    Have a good one.


  2. Hey Cale, I’m sorry that happened to you.

    Something similar happened to a friend of mine too – a business partner went behind his back, stole his idea, and pursued it with another partner. That kind of thing is inexcusable. It’s such a small industry that it’s practically suicide to do something like that.

    I’ve always kind of believed that what goes around, comes around. Integrity is really important in business; those that lack it aren’t going to be in business for long.

  3. I’m just finding out how flaky one of new hires is. He had pretty good resume and was even recommended! You’re absolutely right about half-hearted people. Avoid them at all costs.

  4. I’m sorry to hear you had to deal with a flaky new hire. I’ve always believed in a probation period for new hires for this very reason. I hope you guys are able to sort it out, or get him out. Good luck.

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