I think we all want to ask good, if not great, questions in a job interview. They show the interviewer your interest, skills, knowledge, and abilities. They also help you figure out if you want to work there. There are plenty of websites and experts that give you advice on what to ask a potential employer. For instance, here are a few examples of questions to ask:

1. What skills and experiences would make an ideal candidate?

2. What is the single largest problem facing your staff and would I be in a position to help you solve this problem?

3. What have you enjoyed most about working here?

4. What constitutes success at this position and this firm or nonprofit?

While these are good, these types of questions have never been fully satisfying to me as the answer to any one question may not be representative of the reality you face when you start working there. An example to drive home this point is what I learned about how to interview prospects for Product/Market fit by asking great questions the right way. It is not only the question you ask but the way you ask that is critical.

For instance, if you ask someone what kind of movies s/he likes to go to, s/he may answer “Spotlight” or “Boyhood” or “12 Years a Slave”. However, if you ask what movies s/he went to in the past few months, s/he may be more likely say, “Warcraft” or “Central Intelligence” or “The Conjuring 2”. 

If we went with the aspirational first set, then we would think our friend had a certain type of taste in movies and likely get the wrong impression. The second set represents a different direction altogether. The needs are more likely ascertained by asking questions about what they do versus what they aspire to or what the answer they think will be acceptable to you. In lieu of actually observing behavior which is not always possible, asking questions of current or past behavior is the next best option.

It is in this spirit that I offer you a set of 10 questions to pick from that hopefully give you insight into the company to help you make your decision. I have compiled these after and over a 30-year career starting in inside sales up through being a GM, VP, WW Sales, CMO for a $120MM company and finally a trained business growth advisor and neuroscience geek.

I hope they are useful to you.

  1. What are the company’s core values? What are some of the ways you keep them alive within the organization?  Look to see if the senior team has created a set of rules to live by. This can give you a sense of whether they are top down in their thinking where a few people make all or most of the decisions or they are more likely to push authority closer to where the information and knowledge are so necessary decisions can be made quickly based upon pre-determined guidelines. Keeping them alive is key. Are there posters on the walls highlighting a person that embodies a particular Core Value, can they talk about the last time they rewarded someone for living a Core Value, etc.?
  2. Can you explain to me the process you go through when making critical decisions? Ask for an example.  This can have many answers. Look for the difference between a leader that believes s/he already knows the right answer and steers/persuades the team towards that versus one that knows the direction and/or destination they are headed and has created a process to find the optimal path or sets of paths to reach it. These managers will seek different perspectives and may even split the group up to research and defend certain possibilities and set up a devil’s advocate contingency to find the best answer. S/he may already have something in mind but is open to being persuaded by others versus the other way around. 
  3. Why did you start the company?  (Best asked of Founder but others may know) Look for core purpose here. The “why” of the business. The answer should line up with your ideals, values, and expectations. The answer should pull you toward wanting to be part of this company. Did s/he start this business to solve a problem, does s/he love the customer more than the current idea? This is especially key for startups. I believe that one of the main reasons why most startups fail is they fall in love with their idea and not with the customer whose problem(s) they are supposed to be solving. Another reason why many companies fail or falter is that they have forgotten the main reason they started the company in the first place. Please see previous blog post for more info here.
  4. What is the company’s strategy? If I were to ask a few others in the company, how consistent might the answers be? The second question is more useful than the first as most folks will give you some answer to the first question. You may also want to ask this of several folks to compare how closely they are related. Again, you are looking to see what type of organization you are looking to join. If they are good at communicating important items like strategy simply and coherently that anyone in the company can articulate then they are more likely to value their employees and are great at communicating in general.
  5. How do you bridge the gap between strategy and execution?  This will likely be a surprising question but it is interesting to see how it is handled. You will have to judge for yourself whether or not the answer is good enough for you as there is no perfect answer. If someone has a great answer to this or really any reasonable answer showing how he or she has thought this through, take that job! These are the kind of people you want to work with! There is a great book on the topic – Strategy that Works.
  6. Please describe your team to me.  Look for title and function versus capabilities/assets. If they go into a job description and title versus the value each member brings to the team/company they are more likely to see less value in the individual and care more about the bottom line or the individual role. This may reveal how they view others. This may reveal how they review “team”. Possibly how others are there to serve their needs or the needs of the company versus how they create an environment where everyone is valued. Where his or her job as a leader is to create a safe environment to facilitate input from everyone and to find ways to make everyone around them better.
  7. Describe to me a typical weekly management/team meeting.  Look for status updates versus problem-solving, discussion, debate, and resolutions. Do they make decisions during the meeting? Are they likely to call someone in to clarify a point to move things forward? Great management teams use this time together to get things done and do not end the meeting until they accomplish what they set out to accomplish at the beginning of the meeting. This meeting should be more like a spirited game of hockey versus a hushed game of golf.
  8. How do you leverage your core competencies to grow your business? Great companies leverage their distinct capabilities and are able to grow in unique but powerful ways. They typically value teams over departments and are less “siloed”. They scale and solve more problems for more customers because they leverage fundamental capabilities that apply across any customer base, division, etc. Having this “capabilities” approach allows these companies to find the next growth curve well before the existing one begins to tail off. Another blog post (~11,000 companies born each hour! …..) goes into more detail here based upon recent research.
  9. How often do you get feedback or request input from the team that is 2,3 or more layers below? Ask for an example how this feedback affected an important change or decision. Do they value employees that are closer to the customer and the market dynamics or are they more about making decisions on high with little to no input from others? You can also see if they are a flatter organization versus hierarchical.
  10. How would you describe your change/improvement management process? It is unlikely that the company has one but this shows how willing the leaders are to invite input from anyone and everyone. If the company does have one, then this would be a place to work for those who want to learn leadership skills and be valued as a contributor to the ultimate success of the company.

I hope this was useful. If you have other great questions that you ask, please put share them with me along with your rationale for asking them. I would love to learn other great questions.

Be Exceptional!


If you found this post useful, please sign up at the top right of the page to receive my twice monthly blog posts.

Published by Bill Flynn

Gazelles Member Advisor and early stage startup specialist with a proven track record with 16 Boston-based startups (9 to date with 5 successful outcomes, advisor to 7 others); SMB to Fortune 500 companies. 20+ years of Senior Sales, Marketing and GM experience in industries including mobile advertising, security, digital advertising, e-commerce and IT. Core Competencies: Player/Coach, Metrics-driven, Execution-based philosophy, Life-long learner


Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.

%d bloggers like this: