The art, science, and labor of recruiting: Assessing a potential candidate

Assessing a potential candidate

There are several competencies you will want to consider in key employees: content / knowledge, cultural fit, hiring competencies, motivation, work-style, leadership, values and past performance.


(i) Assessing Domain Knowledge

Test the candidate’s general industry knowledge and their breadth of industry knowledge. It’s important to find those candidates with their finger on the pulse and who are truly curious about the space they operate in. Consider asking:

  • What do they think of other companies’ strategy in the industry? 
  • What do they think of other great companies outside the industry? This shows breadth.
  • What magazines/blogs /news sources do you read regularly? Test to see if they can prove it with real stories. If you are looking for someone broad, then you want someone who reads broadly and has lots of stories and examples that are relevant to topics you bring up. This question can be very useful both within a candidate’s domain and outside it.
  • Describe a problem in their functional area of expertise: What would they do? When? How long do they take to get to decide? Who would they ask for help? 


(ii) Assessing Cultural Fit

Although it’s difficult to determine in a functional interview, the ability to have fun with a team is critical to enhanced teamwork and probability of success. Anecdotal history of a person versus the “fabric” of a person is different and getting to the latter is hard. Consider:

  • How did they respond in a crisis?
  • How much “heart” do they have when things get tough?
  • What’s the best team you’ve been a part of and why?
  • How much energy do they have?
  • How much passion do they have?

It is critical to determine whether the answers to these questions complement your team and their skills and abilities.


(iii) Assessing Ability to Hire and Build Teams

Hiring skills are usually far more important in a leadership role than characteristics such as domain experience. So, it’s crucial to address the candidate’s ability to assess other people and to assess how they think about the team they may build if they were to take the job. Again, specific examples of candidates will get you a better assessment and if they can’t think of specific candidates it should show you a lot.

Can they come up with candidate ideas? Do they apply old models of looking for recruiters, organizational charts, and needs, or do they think of a new situation and get creative?

Every management candidate should be a great recruiter, 
no matter what their area of expertise.

How do you get a clear sense of a candidate’s hiring credentials? Consider asking some of the following questions:  

  • Who is the best manager they have worked with and why? Triangulate with your own perceptions of this person, if applicable or use it to level set the candidate.
  • Who is the best technologist that they have worked with? Triangulate with your own perceptions of this person, if applicable or use it to level set the candidate.
  • What do they look for in a potential new hire for these types of positions or prioritize in key hires?
  • What is their “model” hire for a position? This answer reveals a lot about what the candidate considers a star hire and what he values in himself and others. Consider whether it is consistent with what you want.
  • What do they look for or prioritize in a candidate or in each job they had?
  • Who was their best hire in each job? Best hires and how a candidate recruited them shows you the style, process and bar they set in recruiting. “A” players hire “A” players while “B” players hire “C” players.
  • Who was the most difficult hire they made? In recruiting, I often say a “no” is a “maybe” and a “maybe” is a “yes.” I look for candidates who are aggressive recruiters and team builders – and don’t take “no” for an answer from great candidates.
  • How much new hiring did they do?
  • What kinds of questions do they ask potential new hires when they are recruiting? This answer shows what they value.

Try to assess the type of recruiter a candidate is: Maniacal (good)? Creative (good)? Is their style of hiring similar to your own or different? Are they process-oriented? Do they depend solely on HR or recruiters (bad)? Are they aggressive? How good a salesman are they for new hires? How aggressive, persistent or imaginative is the candidate? Try and assess how much they pursue superstars, especially ones who already know them.

Anybody who is passionate about great people has great recruiting stories to share. Look for specific examples or “battle stories” from candidates. 

Perhaps they pursued somebody despite the odds or despite turndowns“To get my candidate, I parked in a London Hotel for a week and met the candidate every evening after his day job” or “I flew to Chicago under the excuse of ‘I am here already, can we have dinner’ to get a CEO interested in a job.”

Always probe for creativity and imagination in the candidate’s hiring mentality. Ask “who would you bring along?”  The question isn’t solely related to their previous company, but other people in the industry that they’ve been impressed by. A “why” combined with a “who” reveals what they value about their team and how open-minded or creative they can be.

Furthermore, consider where the candidate primarily hired from; mostly internal hiring is not a good sign (although in some big companies it is normal); mostly using recruiters is also not a good sign; a good network is a good sign. How persistent are they in recruiting? Do they just call a recruiter (bad sign) or have broad network or lots of followers?


(iv) Assessing Motivation, Thoughtfulness and Critical Thinking

Earlier in the document, I mentioned the importance of non-functional requirements. But how exactly can you assess them in a “sterile” interview environment?

Firstly, notice how well the candidate prepared for the interview. How well informed they are. Did they review the company website, research competitors or scan the media for relevant stories? Ask boldly:

What do they like about your company? What don’t they like or what worries them? 

Their answer should provide some insight into how interested the candidate is, how much pre-research they have done and whether they are action-oriented. Remember you may need to sell a candidate first and get them interested or excited before the take a keen interest in selling themselves to you.

  • Ask what they look for and what they worry about in various direct and related businesses? Evaluate their answers – were they thoughtful and based on reality or “bluffed,” for the sake of the interview. 
  • What are they most proud of in each job they had? Evaluate level setting and their “standards”. One can understand a lot about the motivation, quality and standards a candidate sets for themselves from the stories they share. Look for contributions beyond their own job function. Are the standards compatible with what you are looking for? Note that it is important, no matter what area you are trying to investigate, to look for what the candidate “shows” as well as “tells.”
  • Have they jumped to new areas? New companies? How risk-averse are they? Examples: some guys explain they were entrepreneurial inside a big company but have been there for 20 years! The flip side, changing jobs every two years is not good either.


  • How many hard questions the candidate asked about your company? A very good sign because you don’t want a “yes man”.
  • How hard did they probe you? This reveals how thoughtful and critical-thinking they are versus how much they “follow the conventional wisdom.” Many executives don’t like to hear about critiques of their company or strategy. Instead of being defensive, listening to a great critique can be very useful, even if you don’t hire the candidate.
  • What is quality of their questions? How insightful are they about your business and about their business? 

Beyond answers, there are some additional signs offered by all candidates if you have the acuity to look for them[1]:

  • Body language. Did they look at you? Open or closed stance? Animated or dead hands? What are their feet saying? Which way do they point? Eyes? Eyebrows?
  • Distract in middle of question: is the candidate focused enough to return to original question (especially if original question is important)?
  • Ask for action items after the meetings (send me x or y!) and look for level of follow-up; how detailed? How motivated? How much did they pay attention to details and revisit key points in the follow-up?
  • In companies, executives don’t always have the luxury to spend weeks creating a “follow-up” document: test the candidate’s ability to think on their feet. Ask:
  • What would they do in the first 90/180 days? Get an immediate answer but also ask for a thoughtful answer as a follow up item. Determine what they are able to produce with a week for research, diligence, and follow-up questions.


(v) Assessing Values

A candidate’s perception of the role that work plays in their life is crucial. Entrepreneurial environments need passionate, dedicated, curious people. Having said that, it’s important not to “cue” a candidate into values questions because people tend to have studied the right answers. Get a sense of a candidate’s values and desires by asking indirect and subtle questions:

  • If this role wasn’t around what would they ideally look for? Assess the quality of their answer and determine their other options. Are the jobs they are considering ones you would value and are they consistent with the candidate’s answers on what they are looking for? 
  • What other jobs are they considering? Why? Determine what they really value versus what they say they value and assess whether the two are consistent.
  • What other roles are they / have they considered? Which ones did they like? Why? Judge quality of thinking and understanding of opportunities, both others and yours.
  • Which roles did they turn downWhy? Assess the quality of thinking and their personality/orientation.

Is the candidate in demand?

Good candidates will be sought by multiple organizations.


(vi) Assessing Work-Style

Entrepreneurial leaders can’t shy away from tough decisions and challenging situations. You need people who are totally committed to making the company a success. Find out:

  • What is the hardest they’ve ever worked? Hardest job? Do they fire people when they need to? How much do they care about the firings? The content and the delivery of these stories are helpful in characterizing people.
  • How do they handle a crisis? What crisis or difficult situations have they been in? What did they do?
  • When have they fired people or motivated people, and what are the stories behind them? What are their greatest achievements in each job? This shows a lot about priorities and personality – especially if they’re willing to admit mistake
  • Describe a problem they’ve had. What did they do? What would they choose as a do-over in each job? How long did they take to get to a decision? Who did they / would they ask for help?
  • How much do they know areas that they did not directly work on? Look for openness and curiosity – it reveals how much they might contribute outside their area. This can be important for startups and its value is often grossly underestimated.
  • If they could have any job, which startup would they work for? Why?


How good is the candidate at evaluating opportunities? Ask them:

  • What business opportunity would you pursue if you got $10 MM to invest in one startup? This represents the quality of their thinking and ambition they can bring to your team and should be consistent with what they value and the other jobs they are considering. Is this what you need/want?
  • In which popular segment of opportunities, if any, would you defy conventional wisdom and stay away from investing? This shows independence and thoughtfulness regarding investment.


How can you test their imagination?

  • What would be a game changer in their current job/business? Assess their ability to look beyond conventional wisdom.
  • How would they define the job they would pursue if the current position was not open? What if their position was open at their favorite startup? More detail and more exciting ideas say something about the candidate and what they value, think about, etc, whereas answers with no detail behind them is a bad sign. “I will think about it and get back to you” is ok, as it shows a more thoughtful person.
  • How do they answer questions they don’t know answers to? Pay attention to whether they make up an answer versus be thoughtful.
  • How well do they think on the fly in new areas? Find out whether they focus on key questions to find out about (good sign) versus just blurt out answers (bad sign)
  • How do they make decisions? How do they make critical decisions in each job? Discover whether a consistent pattern emerges.
  • Do they take responsibility for failures? Why did it happen? Accountability is key.
  • How local or global is their thinking?
  • When have they shown leadership in a non-obvious situation? Determine how subtle or sophisticated can they be.


What do you think about their judgment?

  • How did they work with “hard to handle” people?
  • When did they make a bold decision? What do they consider bold?
  • Are they driven by gut instinct or process? Do they know when to use each?
  • Are they able to make both process-oriented and rapid-fire decisions?
  • Who is the best person they have worked with at a variety of levels (e.g., CEO, CFO)? Why? This informs you what they value.


(vii) Assessing Past Performance

Judging a candidate in each of their past roles is hard. All too often, I hear “I did well” or “the circumstances were bad,” or “I was working with a bad strategy/boss” etc.

How do you get to the story behind the story?

How do you keep your biases from interfering with this assessment (as the receiver can be just as biased/error prone as the sender)? Consider these areas of exploration:

  • Discuss frustration or satisfaction with each situation or job they’ve been involved with. Reasons for change indicate what is important to the candidate. Try to get to the truth about why a candidate did not like or was not liked in their previous role. This approach needs subtlety/indirect questioning in questions to get to honest answers.
  • Look for hints of what a candidate’s superiors thought of them. What do they think of the boss? Who got promoted and who was given greater responsibility? Why not this candidate? Getting promoted is usually good but can be bad, depending upon that situation and your requirements.
  • What was the career trajectory of the peers who the candidate admired? What does that say about the candidate? How did candidate work with peers they admired or did not admire?
  • How many people can the candidate get to follow them? This may signal how good they are or how good a team leader they are (which are different things and appropriate at different stages of a company). The best reference for a person is through team members following them to a subsequent job or a boss pulling them into a new job. A candidate who did not bring a lot of team members along to a new job probably is not well liked or did not build a great team under them. I ask the question “who did you hire into your new job?” for each position a candidate held.
  • How much ownership do they take or do they follow the blame game?


The track record of a candidate is generally obvious. There is valuable learning from being part of success but a separate learning from what a candidate accomplished versus what others around him accomplished or where the candidate got lucky being at the right place at the right time. Remember, you are looking to determine what role the candidate played in a success while also determining how much they learned from that success. Again look for “show” not “tell.” What specific examples can they give you about their contributions (can this be verified by references?) and their learnings? Remember that success has many fathers! 


(viii) Assessing Leadership Competency

Consider the following leadership competencies when asking questions:




(ix) And It’s Not Just About The Candidate…

You’re not there to simply ask questions and review answers. In addition to your evaluation, you need to sell. The interest-level of a candidate is directly tied to how much you sell the opportunity. You cannot delay the sales-pitch until after the interview! You want to know how a candidate behaves when they are really interested, trying hard and really want the job.

And then there’s the tricky problem of perceived seniority. How do you conduct an interview with a much more experienced person? It is hard for a young entrepreneur to interview somebody many years their senior. You need to sell while evaluating them AND be respectful to get their defenses down. Keep in mind it is not easy to be interviewed by a less experienced and much younger person. Try not to make a candidate feel interviewed. Try to make them feel like you are selling them on an opportunity. Be sure to think about questions that are appropriate for somebody with their experience, background and biases.

Above all: be sensitive.

Also remember that you’ll sometimes have to sell the opportunity before you actually interview a candidate – they may not be interested (yet)!

If you decide to progress to a second interview, do it after some reference checking. Try to probe into questions raised by the referrers and confirm key suspicions by asking about the same thing in a different way.

[1] Navarro, Joe, and Marvin Karlins. What Every BODY Is Saying: An Ex-FBI Agent’s Guide to Speed-reading People. New York, NY: Collins Living, 2008. Print.
[1] Allaire, Jeremy. “How to Shape the DNA of a Young Company.” Interview by Adam Bryant. The New York Times 22 Jan. 2011, Business sec. Web. <>.
[2] Khosla, Vinod. “Gene Pool Engineering.” Khosla Ventures. 1 Oct. 2012. Web. < /gene-pool-engineering-for-entrepreneurs>.
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