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How To Avoid Hiring The Wrong Person For Your Startup


by Nathaniel Koloc


“He sounded so capable in the interview!”






“I just don’t know what happened. It seemed like she had exactly the right experience we were looking for!”


“The whole team loved him, so we just went with it.”


Perhaps you’ve uttered these words yourself, or heard them from a hiring manager who is experiencing frustration and buyer’s remorse when a new hire turns out to be a dud. Hiring someone who fails to meet expectations is a huge headache, especially when it was your job to vet them in the first place.


But there are ways of making sure that you don’t get snowed by someone who is good at making a first impression, but bad at delivering results. Here are the key things to do when hiring that’ll guarantee you never hire a dud again:


1. Make them show, not tell.

After your initial screen of incoming candidates, you should have everyone that you are seriously considering do a trial task that is representative of the work that they’ll be doing if hired. The point here isn’t to get free work done from candidates, it’s to see what they will actually do when presented with certain goals and constraints.


Choose something that takes two to three hours, requires a familiarity with relevant skills, networks, or industry knowledge, and will force them to draw upon resources that they’ll have at their disposal while working for you. Simulate a mini version of their work as closely as possible.


If I were hiring a director of development, I may ask them to a) identify a likely funder of my organization, and b) outline a proposal to see how they organized their approach. If I were hiring a manager of partnerships, I would have them a) identify three new organizations that they think would make good partners for me, and b) ask them to show me how they’d make first contact with these organizations.


Tell the candidates they can ask you questions as they are working on the trial. Good people will nail the project, but great people will hit it out of the park after clarifying a few things with you and asking for guidance on key points.


Have all of the candidates do the same task, so that you’re comparing apples to apples. You’ll find that only the most motivated candidates do the task, and you’ll immediately see who is more thorough and puts time into it. You’ll also see whose judgment is most aligned with your actual work. You can teach skills, but judgment is hard. Design the task to show how good their judgment is.


2. Be painfully thorough.

Everyone likes to ask things like, “What would you do in this situation?” or “How do you think we should face this challenge?” These questions show insight into how a candidate thinks and reacts to your organization’s realities.


Far less popular are the simple, boring, background questions – the grungy details of their past work – that actually illustrate what they’ve been able to accomplish. By the time someone is a finalist under consideration, you should be able to answer each of the following questions for, at the very least, their last three jobs:

  • What were they hired to do?
  • What resources were they given to work with?
  • What challenges did they face?
  • What outcomes did they create, or what accomplishments did they achieve?
  • Why did they leave that role?

If you ask these questions to your top two or three finalists, you will get a much better sense of which of them has actually accomplished more relevant things.


Yes, this takes time. Yes, it can get boring. But until you have a clear sense of these things, you don’t really know what you’re dealing with in their history. It’s easy to assume things about someone’s past; it’s harder to take the time to uncover those details. This is critical information.


3. Be consistent.

Whatever your interview process, make sure it is consistent across all incoming candidates. Choose your interview questions wisely, and seek help on this if you aren’t sure what to ask. Once you have the questions, you should develop a basic rubric – even if it is qualitative – so that scores are at least mostly consistent across interviewers and across candidates.


When you are narrowing in on finalists, you should have them interview with your entire team (if it’s small enough), or at least everyone they will be working with closely. Make sure you give your team members specific, unique questions and rubrics to use, otherwise they’ll likely ask repetitive questions and re-run the same conversations with the candidate over and over – which limits your ability to get new insights and further evaluate how good of a fit that candidate would be.


4. Resist optimism.

The biggest mistake the hiring managers make is being optimistic, hoping that this candidate is “the one” and not objectively trying to determine if they really have the skills and background required to do the job. Making idle small talk, using favorite “oddball” questions (e.g. “If you were a kitchen appliance, which one would you be?”), and spending too much time selling them on the opportunity are all unhelpful things that hiring managers do when they are clouded by optimism and eagerness to hire.


And the opposite isn’t smart, either. Using hardball questions, intimidation tactics, and giving trick questions or tests are equally unhelpful.


The best approach is to be calm, measured, balanced, and consistent. Your gut reaction to people is relevant, but is not substitute for measured due diligence. Take your time and be thorough – you’ll thank yourself later!


NathanielKolocavatarNathaniel Koloc is co-founder and CEO at ReWork, a Colorado-based start-up that connects talented professionals to hiring managers at for-impact companies. Nathaniel is an 2011 Unreasonable Fellow and a member of the YEC.




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