10 Questions to Make the Right Hire

I recently led a Founder’s Leadership Roundtable at Galvanize to discuss and brainstorm solutions to the challenges that startups regularly face. The business mix was across industries – cybersecurity, enterprise solutions, sports and entertainment data analytics, travel and healthcare – with companies at varying growth stages from pre-launch to post-seed early stage growth.  The business founders also had diverse backgrounds from new leaders to those with extensive financial experience and a three-time CTO co-founder.  Here is some learning and insight from the different perspectives as it relates to finding a co-founder and building out a team.


Several founders expressed challenges around evaluating how to bring in a technical co-founder to avoid or mitigate potential disasters around making a poor match.  We explored the factors that help make the right hiring decisions, including doing comprehensive vetting up front to make sure that you are in sync with your potential mate (I mean co-worker) before getting hitched.  In fact, we all noticed the corollaries between founders and spouses – co-founders are like work-spouses, since you can spend as much, if not more, time working with them than with family or significant others.  An ideal scenario would be to build a long-term match made in heaven without entering into a shotgun wedding that is likely to end in divorce and pain.  Here are suggestions to help you successfully navigate your co-founder and new staff selection review process.


The quality of the questions you ask initially can determine the quality of the candidate you get and the overall fit of your match.  Here are important areas to explore with any potential new hires:

  1. What do you want to work on? Use this to uncover the type of work they actually want to do, so you can assess if your role aligns with their interests.
  2. What do you care about? Discover what motivates them – is it equity, money or experience?  Consider this factor to understand their expectations and make sure you find a person for your team who wants the same things as you.
  3. What values are important to you in a company that you work for? This will help you to assess overall cultural fit – do they share your vision for the company and how it will operate.  Are you both trying to change the world or do you only care about an early exit and maximizing growth to make a lot of money?  Ideally your priorities will be similar.
  4. How much do you understand about our business sector? Having relevant experience can be very important, particularly in specific cases, like enterprise solutions, where technologists may need specific expertise for the role.
  5. What are your strengths? For engineers, do they have the skill set that you are looking for and will need for your solution?  While a great attitude can be important and finding a well-rounded player can be useful, there are times when you need a very specific type of expertise to move your business forward.  Know the difference.
  6. How will you help us to increase revenues? Co-founders should have a sense of your business growth drivers and consider this an important part of their job.
  7. What are you afraid of or what concerns do you have about joining our team? Leave this open-ended for them to share any bad experiences they may have had in the past.  Are they gun-shy?  It can be helpful to understand any concerns they might have, anticipate potential risks and uncover possible red flags before they become problems.  Look for possible triggers they might have that cause a stronger than expected reaction.
  8. How can we best prepare you to join our organization? Have them lay out for you what information, resources or other insights they might need to help make onboarding smoother and what they hope to accomplish in the short-term.
  9. Describe your ideal working relationship. How do they do their best work?  Do they like to work independently (many developers prefer to work on their own) or are they willing to collaborate?  This is important to know if you like brainstorming and want someone to bounce ideas off of.  Understanding working styles can save a lot of aggravation down the road to know how you both will work together.
  10. How open are you to feedback? This question is for both the candidate and you.  If you ask them for input on your strategy or current website design, for example, are you willing to listen to their feedback and incorporate their ideas or are you just looking for someone to come in and execute on your vision.


If the initial business concept is your idea, acknowledge how you can structure a role for new co-founders that gives them skin in the game, but also recognizes different contributions.  Contracts are a whole separate discussion, and can be important like pre-nups, but we’ll save that for another time.  While founders often have vision, passion and a single-minded focus on bringing their idea to life, it’s also important to be open to new ideas.  If you are bringing in co-founders, then you need to be able to listen to their ideas, value additional involvement and be willing to receive input from others – without these qualities, it is unlikely that you will be able to retain colleagues or grow your business successfully.

I hope these questions are helpful in allowing you to assess potential candidates who are likely to become long-term partners.  Also keep in mind that as your business grows, the team that may have been critical for where you are now at the beginning of your startup may not be the skill set that you need to have in the organization as you look to scale and expand the business.  Make sure that you align the talent with the needs of your organization for your company’s current stage of growth.

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